Planning with a travel agency vs. alone

I don’t know much about Perrillo other than their tours. I didn’t know they did private tours.

Rick Steves does small group tours (24-28) and hubby and I find that we enjoyed every tour we’ve done with him. Do you object to doing a group tour?

We’ve used other tour operators also, and had no issues with them except the “optional” extras that add to the costs. We’ve also traveled independently.
Are you traveling to Italy? When are you traveling?

Take a look at Booking.com for hotels where you don’t have to pay upfront. Do you have a guide book?

On this forum you can read RS trip planning, train ticket purchases, and more. Click on the three lines in upper left corner to find his information.

Give us more info about when, where and your interests, and many will help you with planning.

Sure u can do it yourself but u say u do not know how. Well perhaps u can interview other travel agents to find one u trust. Or consider taking a small group guided tour to your area of interest.

Why do you think you can't get travel insurance unless you use a travel agency?

Thes are two very reliable companies offering a variety of plans.

https://www.insuremytrip.com

https://www.travelguard.com

Please tell us where you want to go, we're all travelers on the forum, very willing to help.
But to help you we need more info.

Perillo Tours spends a lot of money advertising as we see their commercials. If you retain them, you’ll help them pay for all that advertising.

I don’t see why you can’t plan your own trip. It is such fun to do so. I’ve been planning my European trips since I was 22 years old. No internet back then. It is much easier now.

We started with a first trip I’m 2010 all planned with Rick Steves’ books. He lays out logistics like no one else. How to buy train tickets, when to rent a car, etc. We pick our lodging through other sources but read what Rick has to say about locations. You can do it!!

Where do you want to go, when and for how long?

The internet has essentially put the travel agency industry out of a job. Many of those remaining and successful are selling cruises. Perillo is in the business of brokering guided tours which is a completely other business. Rick Steves is another great tour company selling and organizing their own tours. But guided tours come at a price.
I have been traveling to Europe since 1970, and my first trip was my only guided tour. Planning the trip is often the most fun of the trip, especially since we travel on a budget in order to travel twice as often. And although I do a great job planning and executing our trips, there will be a time in our lives that we will be going on guided tours.
Individual travel comes with a little anxiety, especially when things don't work out as planned. Those traveling on their own need to carry a phone/tablet/computer that allows them to make reservations on the fly. And it helps to have some ingenuity, knowledge of info online and basic knowledge of where you're going.

Yes, they're selling you a service you could do yourself if you knew how and wanted to take the time.........but that's hardly the point. You could figure it out and make it happen, but it would take research and time. The question is, do you want to invest that research and time, or do you want to pay someone to do it for you and save you the time and trouble.

Some people love researching and planning, and other people hate it. I don't know which you are. I personally love it, and put together my own 4 week trip to Italy last fall that, including day trips and not including flights, involved 7 train trips, 2 bus trips, 1 hotel, 4 short term rental apartments and 4 half-day walking tours. It was great fun to plan, and I had a great time. Other people wouldn't feel comfortable or enjoy that type of planning. Only you know which you are.

"The internet has essentially put the travel agency industry out of a job."

That hasn't been the case in this area. The travel agents are still in business and seem to be thriving.

garrayhyd,

You can absolutely plan the trip yourself, although it's a lot of work compared to taking a tour.

If this is your first trip to Italy, you might consider a Rick Steves tour, as they take care of all the details and the guides are exceptional. I find that I learn more about the history and culture of a country with a tour, and the smaller groups on RS tours have been great.

I tend to use a combination of a tour along with self guided travel before and/or after the tour on many of my trips. On the self guided portion, I use the relevant Rick Steves guidebook to plan hotels, sightseeing etc. I generally plan my flights using the airline websites and then have the international flights booked by a licensed travel agent. I've found that there's a significant benefit in having the long haul flights booked with a travel agent and I will always use that method! I book European budget flights on my own. If I decide to buy cancellation or baggage insurance for a particular trip, I get that from the travel agent at the same time. I have to use a separate agency for travel medical insurance, so I arrange that myself.

Regarding rail or other transportation in Europe, you can easily do that yourself using the rail network websites or online resellers such as www.trainline.com or others. A good site to check rail trips all over Europe is the Bahn.de (German rail) website, although they only sell tickets for trains originating in Germany (with some exceptions).

Another great resource is the group on this forum. If you could share more details of the trip you're planning, I'm sure the well travelled group here could offer a lot of great suggestions that would help to make your trip a reality.

More information would be helpful.

I agree with the others....do you enjoy researching? If you do, this will be fun, but much less stressful if you are allowing yourself time. When is your trip?

I planned our own first Italy trip in 2015. Our first European trip! Yes, I was nervous, but Had almost a year to plan. You can do it, and this forum, plus the TripAdvisor forum, plus RS guidebooks will help you do!

Ther is a step-by step process I think. After you decide your dates and cities (the forum can help with that itinerary), then you book air. Then research and book hotels in each city (cancellable rate, will always be higher), then research and book tours (they are typically cancellable).

I buy insurance within 14 days of my air, to get the pre-existing condition coverage. Travelguard and Allianz are 2 good ones. You can add up air, hotel, tours (even if you haven’t prepaid) as much as you want. We can talk insurance if you decide to do it on your own.

Forums can help answer train questions, link where to purchase train tickets and when. I’ve had forums members on both boards link what the train monitor looks like for departures/arrivals and ecpkain it because I was nervous as to how they looked.

You will want to go back to Europe. By doing this yourself this first time, it will give you confidence and understanding when you are there, and subsequent visits to other countries.

Any advice? Perillo definitely has experience, but I am not sure if
they are selling me a service I can do myself,

Yep, they are absolutely selling you a service you can do yourself, and as far as "experience" goes, you'll find a wealth of that right here on the forums!! Add a good guidebook or two and you've got all the tools you need to build a great adventure! :O)

Travel agencies have their benefits for people too busy to plan their own trips or simply don't care to put the time/effort it takes to do that. Escorted group tours have their benefits for folks who enjoy the social aspect, having many details such as transport, hotel reservations, some meals and attraction tickets, etc. taken care of for them, and the peace of mind of having a pro at hand 24/7. There's no wrong choice unless it's wrong for YOU.

One word of caution regarding agencies which do customized plans? I'd be cautious to research them carefully as there are "experts" out there who've never set foot in the countries they are touting travel services for.

That said, and as you can see from posts above mine, many of us successfully plan and execute our own trips. The benefits there include (usually) saving $, being able to do exactly what we wish to, for as long or short a time as we wish to, and without doing that in a group, although some of us also book guided tours of just specific attractions such as, say, the Colosseum/Forum/Palatine or Vatican Museums. You just have to be willing to put in the time and effort.

Booking hotels in Europe is generally no more difficult than booking them in the States Booking.com is popular with many of us, and many hotels have their own websites in English these days. Some travelers are big on Airbnbs; a common resource as well, although I usually recommend accommodations with 24/7 desk services for nervous newbies abroad.

Lastly, and as you've also read in previous posts, you certainly can buy your own trip insurance. We haven't, and wouldn't, leave the country without it.

Sorry for the additional post but looking back at your forum history, I'm a little confused? It looks as if you are well along with an independent plan for your trip, and even indicated (gigi's thread) back in December that you were no longer working with Perillo for cost reasons? It also looks as if you've already booked at least one airbnb (in Florence). So it's curious, given the work you've already done, that the agency-versus-no-agency question would arise at this point? IMHO, it would be a BIG waste of $ for the potentially few details yet to wrap up.

You intend to depart the 3rd week in June, and the destinations you list are Florence, Sorrento/Amalfi and Rome. These are all VERY easy to do on your own via public transit; there are tons of threads which cover the "hows" as well as info in Rick's guidebooks. We're also here to answer any questions regarding transport.

We have lived in Europe (Germany) for 4 years and traveled by bus tours, rail, car, rental car and do it yourself.

For a first time European trip, a tour might be best, but not absolutely necessary. If you do it yourself, you need to plan every step of your trip and travel.

I have checked Perillio tours and they seem expensive to me. You would be paying more to go on their tour than doing it yourself.
Also, other tour companies can offer you a budget, but great tour.
Check out Gate 1.

Do your research on tours and if you don't want a tour, then plan your trip carefully, it is not hard.
You don't need to pay upfront for hotels or B&Bs, but you can pay upfront and save. Use Kayak.com to check for best deal, or TripAdvisor.com
Then book directly with hotel. Tours (day tours) can be purchased in advance. Check Viator.com if you can't find local tours.

Trip insurance is a good idea, especially if you are a Senior and have a medical issue. Make sure you get medical evacuation coverage.

Thank you everyone! It feels like I have personal trainers on this forum :) I have done a lot of it myself. I have an Itinerary and I know what tours I want to do on each day - although the first skeleton of an itinerary came from Perillo. I'm planning 13 nights in total in the end of June. I do NOT want to go on a group tour. I am using miles and purchased my flights that way. I dislike big buses and masses of people being shuffled from tourist trap to tourist trap. So, Perillo does have a custom independent travel consultant that puts this together based on your needs. This being said, they did agree to allow me to use an Airbnb in Florence and Rome while they pick up Sorrento. I chose a hotel and thought it was all good, then they inform me I didn't cancel my Expedia and they never were able to pick up the request directly. Therefore, I now don't have a sea view room. So...of course I feel like I messed up and now am looking for an alternative. The Grand Hotel de la Ville looks nice and probably the closest option, but their price is over $400 per night once all the taxes are thrown in.

I will be flying into Rome, then need a transfer to the main station to take a train to Florence where I have already booked an Airbnb within a 5 minute walk of the station. I know which tours I want there - except I am not sold on the Tuscan wine and olive oil trip. Not sure if I want Chianti, since we are not necessarily fans of Chianti. We will be in Florence for 5 nights.

Then we take the train to Naples and need a transfer to Sorrento. I have the tours planned, although our agent suggested Pompeii on the way back to Naples before we go to Rome. Haven't decided on that yet. Also need the transfer back. I'm sure I can ask the hotel for transfers.

Then train to Rome - I have an Airbnb scheduled and can set up tours there easily. Then transfer to the airport the day of the flight. I am just nervous about train tickets and buying them in advance. What if I am delayed somewhere and miss the train? It's pretty expensive for a family of 4. Also, how do I know how long it will take me to get from Rome Airport between getting my luggage and then taking a taxi to the main station? I wouldn't even know how to figure out which high speed train time I need. That's really what is stressing me out about all of this.

I do both independent travel and guided tours are both are great experiences. Just so you know for the future, Rick Steves tours do not match your stereotypical description in the post above. They are 1/2 the size of traditional tour groups and don’t do tourist trap/shopping stops.

Many people don’t buy train tickets in advance for their arrival day. They wait and purchase after arrival.

Hi Kathy,

Yes...I had given up on Perillo because I felt like it was really expensive. I got Airbnb's and was well under way - until I hit a wall with my train travel and now the Hotel Regina Sorrento room issue because I didn't confirm properly. I'm just frustrated :(

First, all is not lost. Second, you're on the right track. Third (and most important!), stop and smell the roses!

That first day, I believe you can take a direct train from Rome Fiumicino airport to Florence Santa Maria Novella (SMN) station. Uh, much easier if you haven't packed your whole house into many suitcases, so in RS parlance, 'pack light, pack right'! Really, it's that important!

Five nights in Florence is just right, and if you're staying 5 minutes away from SMN station, you're within walking distance to almost everything. Book times at Uffizi and Accademia but leave time to wander--it's all there, on your own time. A nice cheap day trip by bus to the neighboring hilltown of Fiesole would be cool. Private tours of Chianti are pricey--they're very cool but if you're OK with Florence, why go? There's plenty right there in front of you.

Train Florence to Naples is simple. Yes, to save big bucks--up to 65%--book early on Trenitalia. Get on the site and mess around with their website wonkiness, book mock trips (looking at stops and time between stops--that will tell you whether it's high-speed or not) without firing in--you can do it. The tickets you book (probably needs to be done 90 days in advance at least) will be non-refundable, but the overall savings make it worth the risk in my opinion. Read up on how it's done--I save digital copies on my phone & iPad and fail-safe it with hard printed copies--Yes, I'm quite anal-retentive about this aspect!

Whatever place you find in Sorrento--and book as soon as possible, as you're finding out, lodging is finite there (and expensive!)--unless you want to take the gritty Circumvesuviana commuter train (it's OK, real cheap but a pain if you've got bags)--you'll want to set up transport direct from Naples Centrale station to your Sorrento hotel. They can help set that up for you. It won't be cheap, around 100 Euro.

Leaving Sorrento, however, I would take the Circumvesuviana (daytime, you'll have the lay of the land by then) to Naples Centrale, and you will have already booked your train leg to Rome. You will need a taxi from Roma Termini station to your AirBnB, don't mess with the bus! From there, you're home free. One thing about Roma, my favorite city on the planet: you're cheating yourself if you don't take time to just wander, chill, and take this city in rather run from tour to tour. We stayed a week at an apartment without booking anything, and now I want to do it for a month.

Good luck with your planning!

Thanks all. I am definitely not doing a tour. I don't like being on someone else's time schedule. I don't like buses and it's just not for me. I do like having some things done for me - like the train and transfers as well as the insurance. I will check out the link for insurance so at least I can cover that. Maybe the train company can help me. I'm going to call the hotel directly to see if they may have cancellations between now and June in a sea view room. Ugh.

Your homeowners insurance company usually has a link to a travel insurance outlet that they recommend. We do it each time, and only get insurance for the total amount from air, lodging (only the non-refundable part) and then non-refundable train travel. As I recall, $5000 of travel insurance costs about $150. Peace of mind to me.

Another option for Sorrento to Rome is on Italo, another Italian rail company. They operate a bus from Sorrento to Naples, then high-speed train Naples to Rome, all on one ticket. Right now tickets are only available until June 12 but you can play with bookings to get comfortable with the website, italotreno.it. Early June trips for Sorrento to Rome are about €34. If you are willing and interested in investing your time, you CAN plan this trip on your own (with a good guidebook and the RS Forum!).

I don't like buses and it's just not for me. I do like having some
things done for me - like the train and transfers as well as the
insurance.

Understand that some destinations can be easier to get to by bus (not a TOUR bus) than by train. Siena (from Florence) is one of those, as well as Naples airport>Sorrento or reverse. And regardless whether you book your own "fast" trains from Rome>Florence, Florence>Naples and Naples>Rome, etc. or they're booked for you, if you miss the one you're reserved for, you are almost always still on the hook for the price or at least a good % of it. There are some exceptions if you change your ticket BEFORE your train has departed but it depends on the type of ticket you purchased. Anyway, an agency or train company is not going to be of any help if you miss your train so just plan on showing up on the time. If you want to save some serious money, you're going to want to pre-book the least expensive economy tickets, and those are almost always non-changeable and non-refundable, or at least not for the full price of the ticket.

There no reason you can't book all of your trains in advance with the exception of Rome> Florence arrival day. There are only two Trenitala trains daily which depart from Fiumicino airport directly to SM Novella in Florence so timing for either of them may not work with your plane's arrival time. Italo trains do not service the airport. You can either take the Leonardo Express train into Termini station in Rome and then a "fast" train - either Trenitalia or Italo - from there to Florence, or take a cab to Termini: price to Termini for the 4 of you will by express train or cab will be about the same. Either way you do it, this journey is the one I wouldn't pre-book a "fast" train for lest your flight be seriously delayed or even cancelled: I'd bite the bullet and pay the base day-of price when you get there.

Now, some folks give themselves a wide enough time margin to risk buying arrival-day tickets in advance if they can get them for a price worth willing to eat the cost of if seriously delayed or cancelled That's an option as well.

But my point again is that just because an agency booked your tickets, they are not responsible for the price consequences of missing trains nor booking you onto new trains, make sense? Italian trains are great - we love 'em - and are not difficult to figure out with some pre-reading.

Rick Steves offers a consulting service, if asking here doesn't suit your needs:
https://www.ricksteves.com/travel-help/plan-your-trip-with-our-expert-consultants

Has anyone ever heard of this? I got an email and am wondering if this is a good option. Thank all of you for all your help. I think I am going to try to do it on my own. Now...if anyone has any great experiences with a wine tour out of Florence, let me know. Perillo had a wine and olive tour in Chianti, but couldn't tell me which wineries they visit. I wasn't comfortable with this. My son and daughter don't drink wine (22 & 19). But they would go for the experience. We are not fans of Chianti wine, so was looking for other options.

I also need to tell you about RailAid! I highly suggest adding it to your cart when booking train tickets. This service can provide peace of mind if there is an issue catching your next train.

As always, we’re here to help!

Contact us 24/7 by email at info@italiarail.com, or toll-free by phone at (877) 375-7245 Monday through Friday, 9 a.m. to 9 p.m. ET, and 9 a.m. to 5 p.m. on Saturday and Sunday.

Thank you for choosing ItaliaRail, and I hope your vacation in Italy is everything you dream of!

Pretty sure most of us on this thread do not book our tickets through 3rd-party Italiarail, and read the terms and conditions carefully as the thing doesn't cover missed trains for just any random reason at all. Not something I'd buy but maybe others feel differently.

It's just so much easier just to be on time for your trains - or just buy on the spot if you don't care about the cost - than go through all the stuff involved with the redemption process?

Yes, I understand that we can just arrive at the train station and buy a ticket, however, we were warned because it is high season, that this would not be easy last minute. I would prefer first class as well. I just don't want to arrive at the train station with family and luggage in tow after an 8 hour flight to find that there are no seats available to Florence. That's why I am concerned.

https://www.seat61.com/Italy-trains.htm

This site I found has the best information concerning European trains. Absorb it, and parlay it with Rick's info.

IMHO regarding first-class carriages (on trains) in Italy? It's not necessary to spend the extra $. 2nd class (or Smart, if booking Italo trains) is perfectly safe and comfortable; way more comfortable than coach airline seats.

Throwing that out as you seem somewhat concerned about budget for this trip. Naples>Rome, especially, is only about an hour by fast trains; not nearly enough time in seats to pay a premium for them.

IMHO regarding first-class carriages (on trains) in Italy? It's not
necessary to spend the extra $. 2nd class (or Smart, if booking Italo
trains) is perfectly safe and comfortable; way more comfortable than
coach airline seats.

Throwing that out as you seem somewhat concerned about budget for this
trip. Naples>Rome, especially, is only about an hour by fast trains;
not nearly enough time in seats to pay a premium for them.

At the risk of disagreeing witchoo, Kate, and invoking your temper...:))...

On Trenitalia, if you want to guarantee 4 reserved seats facing each other, you may have to opt for 1st class. I'll be reading a lot more about this to investigate in the next few months as we will be traveling to Europe spring 2021 with another couple for the first time--previous 3 trips it was just wife & myself. But we'll be booking early for train legs Munich/Innsbruck (actually Hall in Tirol), Innsbruck/Verona, Verona/Florence, Florence/Rome.

And although they aren't l-o-n-g legs (except a 4 hour trip over the Alps to Verona--we've done it and it's breathtaking!), I think as long as we can get the deep discounts, 1st class might be the best choice, even though it's always been 2nd class in the past, which in itself is perfectly fine and better than what we have in the States. I'm a cheap-a** but think a little more room & amenities might be in order this time!

gaarhyd-

How do you eat an elephant? One bite at a time.
Honestly you are making this way more complicated than it actually is.

It would be very helpful if you would post your complete itinerary as it is now. Give us exact dates, exact arrival/departure times.
Tell us what is booked and what still needs booking.
Tell us what you really need help with- is it booking train tix, booking tours, booking lodging, purchasing insurance?
All the answers are right here. if you have not already- buy the RS Italy book- everything you need to know is in it. Very simple to understand.
Amazon usually less than the RS price and faster shipping as well.

I looked back thru your previous posts and don’t see where you actually laid out your itinerary. It’s hard to help when we only have bits and pieces.
Perhaps start a new post and share all those details?

As for companies like Perillo- they make their money by booking tours, lodging, etc thru resellers that give them a commission- so it’s not really the best use of your money. All of those things are so easy to do yourself.
As someone mentioned above you could be dealing with an agent who has never even been to Italy- most of us here have been to Italy, many of us have been multiple times. We plan our own trips because we enjoy the planning as much as the travel. IOW- we know things and are never intentionally going to steer you wrong,
Looks like you are visiting Rome- Florence- Sorrento which is about the simplest/most straight forward itinerary to figure out.

Travel insurance- you mentioned you are using points for airfare- so there will be no refund there you would just get the points back if you cancel I assume.
Don’t book anything that is not refundable- lodging, tours

Why pay someone to book travel insurance when you can simply go to one of the highly recommended sights listed above- choose the plan that suits your needs. You will want coverage for trip cancellation/interruption, theft/loss, any medical emergencies and most specifically for Medical evacuation. Check your own health insurance to see if they cover anything- most do not. If you are on Medicare- you will need medical coverage, as Medicare is not valid in Europe.
If you miss a train- you are not getting an insurance refund on that. If you purchase train tix in advance add that to the trip cost you are insuring. You would get a refund if your trip is canceled for an accepted reason. Read the fine print!
We purchase travel insurance when we purchase our airfare, as that is usually non refundable for us.

Trains in Italy are very nice- there is no reason at all to pay extra for first class. There is hardly a difference at all and your trips are only about 2 hours long. Purchase form the actual TRAIN company not a reseller like ItaliaRail.
https://www.italotreno.it/en
https://www.trenitalia.com/en.html
I like Trenitalia.
If you are worried about trains being sold out- which is actually not something you should worry about- there are dozens of trains a day.
You will need to use the Italian names for station
(Roma Termini, Firenze SM Novella, Napoli Centrale)
If you feel better buying your arrival day ticket from Rome to Florence ahead of time then allow more than the time you think you will need to get to Termini- I’d guess 4 hours or so from flight arrival time. You do not need to purchase Leonardo Express tix in advance- no benefit at all, not even sure its possible- it is just like walking and buying a metro/subway ticket.
If you get to Termini and have time to spare- grab a bite to eat- or pick up food to take on train, use the bathroom, use the ATM,

If you’d rather take a cab to Termini- the fixed rate is 48€. Leonardo tix are 14€ (x 4 is actually more than a cab, I’d take a cab)
Go outside the terminal and get in the taxi line- it is well organized. Hand the driver “TERMINI" on a piece of paper along with your 48€ (or you can round top to 50€ although not necessary)

cont.

Tours- there are lots of highly recommended well reviewed tour companies listed on this forum- just search. We have done many of Walks of Italy- there are excellent. If you book more than 1 tour, you get a discount, they also offer a RS discount -email them. They are reliable and legit. There are others.
https://www.walksofitaly.com
In one of your posts you mentioned Sistine chapel- I can recommend Walks of Italy Pristine Sistine. Worth every penny.
You mention Uffizi- you will need to book those tix ahead of time. Search forum for that info- or ASK,
You mentioned above a "wine and olive oil tour”- thru Perillo so I don’t know which company that would be- but remember Perillo is making a commission on that and may well inflate actual price. You even say it's not exactly what you want. Look around, find the tour that suits your needs-Book it yourself. Walks of Italy- again- has a great Tuscany day tour.

If you want a guided visit to Pompeii or Capri take a look at Mondo Guides- we were extremely pleased with the tour, the guide, the price.
www.sharedtours.com

Sorrento and a sea view. You can see the sea from almost everywhere in Sorrento. How long are you actually going to be IN your room looking at the sea view? Does the hotel have a roof terrace or other outdoor space you can sit to see their sea view? Really- wouldn't worry about that one either. Availability in Sorrento is only going to get less and prices are only going to go up.

Go to www.booking.com, set your filters and see what you can find. Read the reviews. I’d bet 90% of the hotels in Sorrento list on booking.com. You might then check the hotel’s actual website to see if you find a better rate- sometimes you do- sometimes you don’t. Book accordingly
booking.com is perfectly reliable and legit.

If you are still unsure- then I’d recommend using the RS planning services linked above. At least you can be sure they know what they are doing.

Christine - you are AMAZING! I just can't believe all the valuable information I am getting! I do have Rick Steve's guidebook. I feel okay with most of the tours. We are going to pass on Uffizi because none of us are art fans and we feel like we will see a lot of other art in Rome and Accademia. The actual tour of Tuscany is the one that I can't decide. I contacted Roberto's tours, but saw some negative reviews about his personality. I also wasn't sure about going to a family vineyard. It seems like we would only see some small vineyard and not the experiences we would want for our first time in Tuscany. I will check out your other links.

I am going to give up on Perillo. There are just too many things they couldn't do for me. If I have to do a bunch myself, why bother paying the premium!

As far as insurance, I have to pay the Airbnb and hotels in advance, so they would be a loss. The tours also would need to be booked, but not sure of cancellation costs. For a family of 4, I figure about $10K of coverage is needed since we aren't paying for flights.

Here is my Itinerary BTW....
SATURDAY, JUNE 20, 2020 DEPARTURE JFK AIRPORT
SUNDAY, JUNE 21, 2020 10:50 - ARRIVAL – ROME-FIUMICINO AIRPORT
Transfer to Rome Termini.

Transfer to Florence via Frecce train (1.5 hours)
Local taxi pick up at Train station in Florence to Airbnb (or walk 5 min)

ACCOMMODATIONS
Airbnb June 21 – June 26, 2020. ( 5 nights )
Arrive appx. 2:30 pm

MONDAY, JUNE 22, 2020 GROUP TOUR - TUSCANY WINE AND OLIVE OIL TRAIL
TUESDAY, JUNE 23, 2020 Best of Florence Tour with Accademia
WEDNESDAY, JUNE 24, 2020 Relax a.m. FLORENCE COOKING CLASS WITH OLTRARNO FOOD TOUR
THURSDAY, JUNE 25, 2020 Pisa Private 3 Hour Tour followed by Frescu Mozzarella Experience
FRIDAY, JUNE 26, 2020 Late morning transfer to Sorrento
--- ACCOMMODATIONS--- Hotel Regina Sorrento – June 26 – June 30, 2020 (4 Nights)
SATURDAY, JUNE 27, 2020 Capri Excursion in Private Boat
SUNDAY, JUNE 28, 2020 Pompeii tour or free day

MONDAY, JUNE 29, 2020 Private Amalfi Coast drive - 8 Hours
TUESDAY, JUNE 30, 2020 Afternoon/Evening transfer from Sorrento to Rome
-----ACCOMMODATIONS--- Trastevere Airbnb June 30 –July 4, 2020. (4 nights)
WEDNESDAY, JULY 1, 2020 Colosseum/Segway Tour?
THURSDAY, JULY 2, 2020 Vatican Museums
FRIDAY, JULY 3, 2020 Trastevere Food Tour – 10:45 a.m. departure – 4 hours
SATURDAY, JULY 4, 202O Departure to New York

As far as insurance, I have to pay the Airbnb and hotels in advance,
so they would be a loss. The tours also would need to be booked, but
not sure of cancellation costs. For a family of 4, I figure about $10K
of coverage is needed since we aren't paying for flights.

IF your trip is canceled or interrupted for a valid reason as indicated in whatever insurance policy you chose- - then yes you would be reimbursed for those upfront payments as long as you get your insurance now- add up all the things that are prepaid- that is the amount of insurance you need- your "trip cost".

Pretty sure Walks of Italy tours are refundable - read their policies. I actually think I did once cancel one of their tours. It's been a while
The Trastevere food tour- also add that into your insurance coverage amount- if that is with Eating Europe- those tours are refundable (I know this for sure because I just had to cancel one we had booked with them in Portugal)

OK-
If you feel you must get train tix for your arrival day trip to Florence- book a train no earlier than 3 pm. (Check the direct trains- I know there are only 2/day from FCO- not sure if one of those works time wise for you)
No way will you be in Florence by 2:30 with a 10:50 arrival. It takes time to deplane, passport control can take a while- allow at least 1.5 hours plus time it takes to walk thru airport etc, luggage is usually there by the time you get thru passport then there might be a short wait at taxi stand- it's about 30-40 min drive to Termini- if no traffic.
Just my guess but if all goes well/on time you could be at Termini by about 2-2:30? That gives you time to find your track- they don't even put those up on board til just a few min before departure time.

Taxis will be right outside SM Novella station- no need to prebook. Write or print your lodging address on a piece of paper/index card and hand it to the driver. Florence is small- cost shouldn't be much more than 10-15 euros. I'd keep that address card handy- for all travelers to carry- nice in case you need to get directions home :)

You are really doing a LOT of tours. Might be nice to just have a day where you can wander at will.

You can purchase your train to Naples as soon as they are on sale since you know that's the day you are going.
You do know that you will have to catch the local Circumvesuviana from Naples to Sorrento right?

Same for tix Naples to Rome. Again Circumvesuviana gets you from Sorrento to Napoli Central (and Pompeii)

If you need links for anything - just holler.

ETA:
Also going to throw this out there-
Just because everybody else goes to Vatican Museum doesn't mean you must. Yes the Sistine is breathtaking. The museums are a mob scene I am an art/history lover and COULD NOT WAIT to get out of there- not sure I will ever go back.
There are plenty of other fun/interesting things to do in Rome. Just as you gave up Uffizi- it is OK to give up Vatican. You can certainly just go to St Peters without doing the whole crazy mob at Sistine/Vatican.

TBH I think Borghese Gallery is more of a must do-the sculptures there are simply jaw dropping. And the nice thing is your visit is limited to just 2 hours so it's easy to fit in. Maybe rent bikes in the park there afterwards? Just a thought.
Tix must be booked in advance.

For Galleria Borghese in Rome use this site to purchase tickets.
http://galleriaborghese.beniculturali.it/en/visita/visit-the-galleria-borghese

For Florence Museums
http://www.b-ticket.com/b-Ticket/uffizi/default_eng.aspx

Vatican Museum
https://biglietteriamusei.vatican.va/musei/tickets/do?weblang=en&do

I'm so happy to see you taking all this great advice. I was in Italy three times this past Nov. and Dec. and am writing a book on how to travel to the Holy Land (I took two cruises out of Rome and stayed there for several days at three different time periods.) I have two recommendations to add on. I'm going to gift you with some info from the first draft of my book for Pompeii:

As we planned our trip to Pompeii in Naples, we considered several options: a ship excursion, taking the train, etc., but then discovered a relatively new option: the Naples City Sightseeing Bus. This company is well known for their Hop on Hop off bus tours, but this is a specially designated bus for a direct trip to Pompeii. Many reported the train was dingy, congested, and a haven for pickpockets, so CSB was a great alternative.
The company defines your trip as Race 1, Race 2, or Race 3, and you are to leave and return at the time assigned for your “race.” In the low season, there are only two races, and ours was the first, leaving at 9:40 AM.
We purchased the tickets online before our trip, and the company sent a voucher by email. We walked from the ship on the main pathway and visually located Castel Nuovo on the left. We walked past the Castel, and the City Sightseeing Booth was on the left. We redeemed our voucher for the tickets, boarded the bus, and it took off on time. The narrated trip was perhaps 45 minutes.
The bus drops off the passengers by the International Tourism Office, and you walk through the souvenir areas to find the Pompeii ticket office.
We used Rick Steve’s audio app and written info from his book since the map from the site was way too complicated.
The entrance, Porta Marina, had been a harbor before Vesuvius blew and filled it with volcanic debris in 79 AD. Five miles to the north is Mount Vesuvius. When it blew, Pompeiians had no idea they were living under a volcano. It had not erupted for 1,200 years! The ash, which buried the entire city, helped to save it from the sixth-century barbarians who plundered other towns.
Pompeii’s streets were once quite sophisticated. These original basalt stepping-stones let pedestrians cross without getting their sandals wet when the streets were flooded with water to clean them. You can still see the well-worn ruts from the chariots. The sidewalks were paved with bits of broken pots and studded with selective bits of white marble to help people get around in the dark, either by moonlight or with the help of lamps.
The Forum was Pompeii’s commercial, religious, and political center. Pompeii’s citizens gathered here to shop, talk politicians, and socialize. Business took place in the important buildings that lined the piazza. The Temple of Jupiter, dedicated to the supreme god of the Roman pantheon, dominates the Forum.
The Basilica was the first-century palace of justice. The big central hall is flanked by rows of columns marking off narrower side aisles. Frescoes and mosaics were all over Pompeii.
Via Abbondanza was Pompeii’s main street and is lined with shops, bars, and restaurants.
The Fish and Produce Market now holds casts of Pompeiians eerily captured in their last moments. There are many collections of pottery and other artifacts in this market display. The casts of people were quite dramatic, and there was a sad one of a young child who died immediately after the volcanic eruption.
The Baths of the Forum had six public baths with hot, warm, or cold baths. In the caldarium or steam bathroom, the double floor was heated from below.
A “Fast Food Joint” was right across the street from the baths. Most ancient Romans didn’t cook at home for themselves, so these “take out” restaurants were commonplace. The holes in the counters held the pots of food.
The House of the Tragic Poet is a typical Roman style home with two family-owned shops. In the entryway is the famous “Beware of the Dog” mosaic. A richly frescoed dining room is off the garden. Part two in next post.

Pompeii continued. The House of the Vettii is Pompeii’s best-preserved home once owned by two wealthy merchant brothers. The prominent picture of a huge erection probably maybe wasn’t meant to be pornographic. Note the goldsmith scale, indicating that only with a balance of fertility and money can you have an abundance. The Romans were all about abundance and decadence.
The Bakery and Mill show a brick oven and stubby stone towers that are grinders shaped like an hourglass. A wooden apparatus with two horizontal arms allowed the later to be turned by either human or animal power. The grain was poured into the upper hollow of the catillus, and ground flour came out the bottom. Many carbonized loaves of bread were found here during excavation. Each neighborhood had a bakery like this.
The Brothel or Lupanare was a simple place with beds and pillows made of stone. It contained ten cubicles that have small panels of erotic scenes.
Our guide in Corinth told us the word prostitute comes from the practice of temple prostitution, where the women stood in front of (pro) the temple statues. Pro+ statues= prostitute. Most prostitutes in Pompeii were of Greek or Eastern origin, and they were required to pay taxes for their services under the decadent emperor Caligula.
The Theater sat 5,000 people in three sets of seats. The square stones above the cheap seats once supported a canvas rooftop.
There are about eighteen Christian crosses carved into masonry throughout Pompeii, which proves Christians were there during that time. In 61 A.D., during a visit to the nearby harbor town in Puteoli, the Apostle Paul also mentioned the presence of a Christian community there, thirty miles west of Pompeii. Acts 28:13-14.
“From there, we set sail and arrived at Rhegium. The next day the south wind came up, and on the following day, we reached Puteoli. 14 There we found some brothers and sisters who invited us to spend a week with them. And so we came to Rome.”
There is also a Vivit Cross and an inscription in Insula 1.13 and the Meges Stamp Rigi in Pompeii, which reads “Audi Christianos” or “Listen to the Christians.” It was roped off, so we couldn’t see it.
Herculaneum
How about a trip to Herculaneum and Mount Vesuvius? Many people say that Herculaneum is better preserved and more manageable than Pompeii. Of course, Pompeii is the most famous, but its sister site benefited from its more recent discovery and careful restoration. Pompeii suffered because of the bad behavior of early tourists.
The City Sightseeing Bus also has a route for that trip, so check it out at https://www.city-sightseeing.it/en/naples/
You can also take the train to Herculaneum, but that requires either a long walk or a taxi to the train station, Porta Nolana. The walk from the Ercolano Scavi station to the ruins at Herculaneum is one-half mile, gently downhill in more or less a straight line down Via IV.

Also, consider a visit to Ostia Antica. Really, it is larger than Pompeii and a wonderful way to spend a day. There are usually very few tourists there. Rick Steves highly recommends it. We stayed in Ostia on the coast and took the train to Ostia Antica. If you want directions, I'll be happy to supply them.

My husband and I (ages 75 and 68) have travelled to Italy twice and I planned each trip fully myself. I find that to be a really fun part of the trip itself! We use Expedia and Booking.com and reserve cancellable rooms only in case something happens or I find a place I'd rather we stay. I always read the reviews and consider the location, proximity to train station, etc. Train travel in Italy is super easy to use and there is no need to fear it. I print out a rail map of Italy with all the cities listed and map out my itinerary. I use a printed calendar with big squares to write in and go from there with a logical route to match the itinerary. Each time I reserve a room, I write it in the calendar, and print off any information about that place and the confirmation. Any railway tickets purchased in advance are also printed out, times noted on the calendar. I put the printed information for each day (or each group of days when staying put for a while) in page protectors, then put those in a flexible loose-leaf binder. I did not pre-purchase train tickets for the first leg of the trip in case of potential delay, but the train station at FCO is easy to find and the kiosk for purchase of tickets is easy to use. Or you can pre-arrange a taxi to take you to Rome. We never had any problems and have travelled extensively throughout Italy. We do not like to be held to restrictions of tour group travel. If we want to just stay near our room until noon, or even for a day to rest, we can do it. Each trip was over three weeks in length - the total cost of the first trip, including air fare, was under $8,000 and the second trip around $6,000 for two people (I got a really good deal on tickets that time!). Most tours are more than that for only nine or ten days. While we don't stay at the "Ritz", each accommodation was nice, clean and enjoyable. I liked having everything for each stay together, printed out, in the binder. I knew where to find hotel information and train tickets. Then I would move each day to the back of the binder as we travelled. I also made notes of how to get to the lodging, or to events/tours, so I was always comfortable about what we were doing. The only thing was, if I would have gotten separated from my husband he would have been lost for sure!!! haha LOL We always said he would stay wherever he was and I would look for him, because he wouldn't have a clue where he was or where he was supposed to be going!!! We can't wait to go again. Hope something here helps! Don't be scared, just be thorough.

Side note on Pompeii (which I know you're still debating)? This is the map and 142-page info leaflet in English produced by the Board of Cultural Heritage of Pompeii. It's a great source of info for the visitor, and can be downloaded for free to browse before the trip and to use as a guide during a visit..

http://pompeiisites.org/wp-content/uploads/A-Guide-to-the-Pompeii-Excavations-2.pdf

It's from this page of the scavi's official website:
http://pompeiisites.org/en/visiting-info/map-and-guide-to-the-excavations/

On Trenitalia, if you want to guarantee 4 reserved seats facing each other, you may have to opt for 1st class.

That is incorrect. Last trip I booked tickets for my family (4 + my sister) on Trenitalia. We only traveled 2nd class Super Economy tickets. I had reserved seats and I got to select my seats—no additional fee. I am in the process of booking tickets for our next trip and this is still the case.

Seat61.com has actual photos of 1st and 2nd class Trenitalia. Check it out.