Italy - 30th Anniversary Trip Assistance! 1st trip to Europe/Italy

Looks like a great itinerary to me. Personally I'd skip Cinque Terre in favor of another town/city like Pisa or Bologna, but that's just me. For the Florence and Tuscany area, since you want to see several different places you might consider hiring a private driver for a day instead of renting your own car or trying to get to all your destinations on public transport.

Should you add more days? Well, if you ask me there's never enough time to enjoy Italy! You be the judge and weigh how long you can afford to be away from home.

I would definitely rent a car while in Tuscany, so consider staying outside of the city because you can’t drive into Florence. Perhaps an Agriturismo.

Since the Amalfi Coast is high in your list, I would not skip it this trip. Sicily is really its own trip. It’s a huge island and not easy to get to, so it is it’s own destination.

I would skip the CT and remove a night from Venice, and then add another night if you can all on the AC. Make it to the Amalfi Coast! It’s so amazing. This would fit after Florence/Tuscany and then have Rome as your final destination. We love Ravello! So many amazing views, hiking the path of the gods, seafood, etc.

SueRN,

As this is your first trip to both Europe and Italy, my first suggestion would be to read Europe Through The Back Door prior to your trip. That will provide you with a lot of good information on how to travel well in Europe. You'll need to get up to speed on things like accessing money, travelling with electronic gadgets, avoiding pickpockets, etc. Also suggested would be to pack along a copy of the RS Italy 2019 guidebook (available now).

A few thought's about your Itinerary.....

I'd suggest adding days to your trip if possible. You'll be travelling a considerable distance to get to Europe, so may as well make the trip worthwhile (especially considering the occasion). I'd consider a slightly different order of cities......

• Venice - 4 nights is probably good, especially as you'll need some time to recover from jet lag.
• Florence - you might add one night to Florence as it's a great "home base" for Tuscany and easy to take day trips to Siena, Lucca or other locations. There's also lots to see in Florence.
• Cinque Terre - if possible, I'd suggest adding one night here too. Keep in mind that two nights is only about a day and a half of touring so wouldn't allow much time to see the five towns. It's also a great place to practice Il dolce far niente and just chill and enjoy a glass of Vino and some excellent Pesto in the area where it was invented. Book accommodations as soon as you've finalized the details, as rooms book up quickly. Have you decided which of the five towns to stay in? Each of us here have a preference, and I prefer to stay in Monterosso, which is the largest of the five towns and has the greatest number of hotels, restaurants, etc. and the best beaches of the five. You'll likely have to contend with crowds during the daytime in May, but I don't find that to be a problem.
• Montepulciano, Pienza and some of the other small towns in the Tuscany area - you could certainly rent a car in La Spezia but there are some potentially expensive caveats to be aware of when renting cars in Italy. More information below.
• Rome - You might return the car when you're finished visiting small towns in Tuscany, and take the train to Rome. Orvieto is a good location to return cars as it's only about an hour from Rome by train, although as I recall Hertz is the only agency there.

When renting cars in Italy, note that each driver listed on the rental form must have the compulsory International Driver's Permit, which is used in conjunction with your home D.L. These are easily available at any AAA / CAA office for a small fee, and are valid for one year. Failure to produce an IDP if requested can result in hefty fines on the spot! You'll also have to be vigilant to avoid the dreaded ZTL (limited traffic) zones which now exist in many Italian towns. Do NOT drive in Florence! Each pass through one of these will result in hefty fines, which you may not know about until several months after you return home.

There are also some important things to know when using trains and other public transit in Italy. If you need more information on that, post another note.

Congratulations on your upcoming anniversary, and good luck with your planning!

Your trip looks great. If possible, add a night to Rome and 2 nights to Florence/Tuscany. Adding these 3 days will allow you to enjoy this trip at a a more enjoyable pace.

You'll save some time if you change your path slightly.

4 N Venice.

Train to Florence 2H05m

3 N Florence. http://mobile.hotellascaletta.it Nice hotel great staff.

Rent car and drive to my favorite spot in Tuscany. http://www.borgorapale.it. 1H 15m
Everything you wish to visit is under an hours drive from here. This property has been in the family for over 300 years. They're great hosts and speak english. Download their PDF. Lots of great info.

3 N Tuscany.

Drive to La Spezia, 2H 35m, drop car, train to CT village of choice.

2 N Cinque Terre.

Train CT-Rome 3H 45m

4 N Rome.

We usually rent apartments, but as this is your first trip, you may be more comfortable with the availability of a hotel desk if you have questions.
In Venice, stay within walking distance of a vaporetto dock. In Rome, friends have stayed here. http://www.hotelnordnuovaroma.it/en/

Have fun planning.

Edit: additional info on the ZTLs Ken mentioned above and driving in Italy in their PDF.
https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones

More days? As many as you can get! My personal preference would be 4 days in Florence PLUS some time in Siena and Tuscany (4 trips to Italy and haven't been to Cinque Terre yet -- maybe next time.)

Also, when you mention starting on May 1, I hope that's your flight departure date, not your arrival in Italy since May 1 is a major holiday with lots of sights closed.

We just returned from our anniversary trip to Italy. We loved Cinque Terre and highly recommend you take a day off Venice and add it to Cinque Terre. We loved the hiking there, the small town vibe (as opposed to bustling city like Florence). We traveled everywhere by train, flew into Venice out of Bologna.

In Venice we stayed at Hotel Flora and loved the location, service, and breakfast there.

In Cinque Terre we stayed in the town of Monterosso and stayed at hotel Marina. Can not say enough good things about this hotel and the family that runs it.

Have a great trip! This board was a wealth of information for me when I was doing my planning.

Hello Sue and happy anniversary! I would suggest skipping CT, as in May the area is very crowded and spend more time in the Tuscan region, especially since you mentioned the towns of Siena, Montepulciano and Pienza. Siena itself is worth an entire day and Montepulciano and Pienza can be done as another day. Just driving in the area, you should stop when you see a vineyard or two or three that interests you. Rome is crazy and busy, but really worth more than 3 nights, as the history, architecture and art are amazing and while you are there, visit Vatican City. The museum and the vatican itself is an entire day. You could fly into Venezia and out of Rome (multi city on the website) and this alleviates back tracking. If you are staying in Tuscany and driving, make sure you get a IDP (international driving permit) at AAA, as the law changed a few years ago and now it is mandatory. Also, check this forum about ways to avoid ZTL's and finding parking prior to leaving your place. Good luck!

Another hello, Sue, and congrats on your upcoming anniversary!

I'll definitely agree with the others that Venice>Florence> CT> Rome is a better itinerary order as well as flying into Venice and out of Rome. I'll also agree that Rome needs another day: lots of interesting ground to cover in that one!

I'll throw out an alternative to renting a car for other parts of Tuscany? There are some day trips from Florence that are easily done by public transport, such as Fiesole, Siena, Lucca and Arezzo. While I won't discourage renting a car, and understand that not all of these are on your wish list, it's another option? Anyway, should you decide to make Florence a base and optimize the trains/bus, I'd add more days to that one and sacrifice the CT if necessary (but hope you don't have to). Sometimes the fewer details to get one's head around on a maiden voyage, such as the ins and outs of driving/parking in Italy, the better? :O)

BTW, we loved Florence but I'm also an art geek so there's THAT. The art...oh lordy.

A wise decision to save the Amalfi and Naples area for the next adventure. That deserves some time that you'll be hard pressed to fit in on this one.

Yes, the CT promises to be very busy in May, and Monterosso would be my vote as well for the same reasons Ken listed. As he also mentioned, hotels in that area fill quickly and far in advance so once you get a plan down, put the giddyup on reservations. You can get suggestions from the gang here when the time comes.

Congratulations on your anniversary, Sue! And welcome to this forum! I have found this forum to be an invaluable source of wisdom and good advice. I've traveled to Italy at least 10 times in the last 20 years - lost track - and am so excited for you that this is your first time to that gorgeous, delicious, friendly land. My thoughts: 1. Re. renting a car: Read LOTS about it, and know all of the warnings and also good reasons to rent. There is a lot on this forum. Also quickly go get RS's Italy book if you don't already have it (Octavia Bookstore, uptown, near Whole Foods often has it in stock). RS gives a lot of good info on car rental locations, etc. I last rented at Hertz (I believe) in Orvieto, both picking up and returning. It was a great location, close to the train station. From there, sis-in-law and I made Montepulciano our home base for a few days in Tuscany. 2. If you decide not to rent, how about taking a day trip out of Florence with a small group tour to several of the villages &/or vineyards? Tours by Roberto is a great experience (Roberto is on a number of Rick's TV shows about Tuscany. Excellent website). Or, Walkabout Florence does a tour of several vineyards and a couple of towns that Good Friend and I greatly enjoyed this past January. 3. Highly recommend Montepulciano as a home base if you decide to rent a car! It is well located for days trips throughout Tuscany, including Montalcino, Pienza, and Siena. It's a lovely town. Twice I've stayed at the Politian Apartments there (good website), which was great! Wonderful hosts, great location at the "top of town" with easy parking right outside the apartments. 4. Your itinerary - with suggested tweaks - looks good to me 5. Staying in Venice: What's your budget? Hotel Al Ponte Mocenigo is my current favorite. It's a straight shot - no bridges - from the San Stae vaporetto stop, 4 stops from the train station. Or Pensione Guerrato (lots of Rick's groups stay there, but many more stairs inside the hotel, and some have shared baths. Check what floor you would be on!). 5. Booking.com makes it very easy to see lots of photos, read reviews of hotels. Although I've stayed in them several times, I've generally stayed away from Airbnb's for a couple of reasons: Have to arrange to meet host at or near a specified time ("call when you get on the vaporetto", etc.), AND usually no possibility of checking in early and leaving luggage, and no possibility of leaving luggage after checkout, for retrieval later in the day. Some people love Airbnb's but these hassles don't make it worth it for me. (The Politian Apartments above are run more like a hotel, with luggage arrangements more flexible.) 6. The Cinque Terre area is quite beautiful; I stayed in Riomaggiore about 12 years ago for 3 nights. However, as noted by others, the area is getting so crowded, that you would need to be very strategic about your visit, and be prepared for the crowds. Do a "search" on this forum for "Cinque Terre" and read what a stay there currently entails. Finally: 7. I'm also in New Orleans, and work at Touro Infirmary. Private message me if you would like to have coffee, whatever, sometime for more conversation about Italy. The planning is at least half the fun!!!

Given this is your first time to Europe, especially Italy celebrating your 30th, I’ll suggest the obvious and perhaps the simplest solution ... the RS 17 day Best of Italy. On our 48th Anniversay we took this tour. We had traveled a good part of Europe on our own, plus two other RS tours at that time. The “first time” is fraught with learning experiences that can make some days hectic and somewhat non-productive. The RS tour is an excellent travel school. We had a spectacular diner on Lake Como and were grandly treated by our hotel when they knew of our celebration diner. We added days on to start and end the trip. Enjoy the celebration, come again when educated and trained on traveling on your own. We have sighed up for a 4th RS tour to celebrate our 50th next year. At 73 I’ll leave the driving to someone else. You’ve got some good on-your-own experiences ahead of you in any case.

My wife and I did a trip very similar to the one you're planning for our first trip to Italy several years back, except we did 5 nights in Sorrento instead of Cinque Terre (Venice -> Florence -> Rome -> Sorrento).

If you DO decide to hit the Amalfi Coast instead of CT, Sorrento is a great base if you on exploring the Campania region in addition to AC, since it's on the Circumvesuviana train line which connects to Naples, Pompeii & Herculaneum, plus you can catch bus or ferry service to Positano & Amalfi, or a ferry to Capri. The Path of the Gods hike from Agerola to Nocelle is almost worth the AC trip alone. Plus, the high speed train from Rome to Naples is only 1hr, with the Circumvesuviana to Sorrento adding another hour. There is also a Artecard Tutta la Regione pass you can buy which allows you access to all the major sites/museums in Campania for 34 euro. Also, you may want to consider flying out of Naples instead of Rome if the price isn't too much more, as it will save you considerable travel time on your last day, and the international terminal at the airport there is surprisingly nice. Make sure to stop for a pizza at Gino Sorbillo and sfogliatella at Attanasio on your way.

As for the rest of your itinerary, I agree with others that you should budget an extra night in Venice to allow for the jet lag to wear off. Then, at least 3 nights in Florence, especially if you are into art & history as there is so much to see and do there, and also considering the half day or so you will lose traveling there. You may want to consider more nights if you want to do any day trips via train to Pisa and/or Lucca, or Arezzo/Cortona. Bologna is also only a 35 min. train ride from Florence via the high-speed train, which is a foodie paradise if that's your thing. We did the Walkabout 1-day tour of Siena, San Gimignano and Pisa (w/ a stop at an organic Tuscan farm for lunch) which was pretty awesome.

I would then rent a car in town (most rental agencies rent near the train station, although I've heard on these forums that Hertz has another office in Oltrarno). Then, spend another 3 nights (or more?) at a base somewhere near Sienna which would be a good central location for seeing all the most famous spots in Tuscany (Siena San Gimignano, Volterra, and Chianti region in the north, Val d'Orcia in the south), or base near Montepulciano if you want to focus on Val d'Orcia and maybe hop over into Umbria to check out some hill towns there.

Ken's advice on dropping the car in Orvieto and hopping a train is solid if you don't want to deal with driving into Rome (plus Orvieto is an amazing hill town and worth at least a day stop in its own right), but as long as you have good directions to the rental car office it's actually not that bad. We dropped a car near Termini Station after our time in Tuscany, with directions we printed out before our trip without too much trouble. I am always pro-driving where possible as it saves the hassle valuable vacation time that come with mixing transit types. Definitely also second his advice on reading up on avoiding the ZTL's, and driving in Italy in general. Be sure to print out a page with the European traffic signage and tape it to your dashboard. Also, once you've figured out how many days you will be travelling via train, see about purchasing a Trenitalia (Interrail?) pass, which allows you X days of travel for a set price.

Hope you have an amazing trip, no matter where you end up it will be an unforgettable experience. Ciao!

I so appreciate all the responses and great information everyone has provided. I now need to absorb all this information, do more research and really get my plans in action. I may be back in touch with some additional questions. Thanks again, Susan

Five trips to Tuscany and we have always rented a car. I can’t imagine exploring the hill towns without one. We rent through AutoEurope.
We parked our car the whole time we stayed in the Cinque Terre, 3 nights.
I would skip the Cinque Terre with your itinerary, stay those two nights in Florence, see David and Uffizi, four nights in more rural Tuscany.

I have never rented a car in Europe, but I find it very odd advice to discourage car rental in Tuscany. When people say they want to see "Tuscany" rather than just "Florence", "Siena", or "Pisa", they're usually thinking about small hill towns, many of which have no train service. Although you can probably reach all of the most likely destinations by bus, you cannot get to very many of them in one day that way. Tiny towns, though charming, can often be fully seen in a very few hours. Not too many visitors have such long vacations that they are willing to devote a full day to the bus gymnastics required to see two such small towns in a single day. I once managed to squeeze three towns (not Tuscan) into one day, and I felt as if I had won the lottery.

Andrew, I don't think anyone implied that they should drive a car into Florence or Siena, as most cities - and even smaller hill towns - have a ZTL in their histroric center. For example, I merely suggested that they could pick up a car on their way out of Florence. As long as you follow the rental office's instructions (while having researched the ZTL & bus lane signage beforehand), it's not too difficult. And with a minimum of pre-travel research, one can easily figure out where to park just outside most historic centers (for example, parking at the Stadio in Siena).

That aside, I think it's nearly essential to rent a car if you are going to see small towns in Tuscany as were OP's stated intentions. As acraven stated, many towns are not reachable by train, and even if you figure out the bus route it might be so convoluted that you lose half the day in transit. Plus, seeing Tuscany is all about exploration - seeing a dirt road in the countryside and turning down it to see where it leads, or passing a nice-looking cafe and stopping in - and doing it at your own pace. Being on a bus timetable would not only limit your destination, but also dictate your day.

One other alternative would be to hire a private driver for the day to take you around the countryside, stop where your want to stop, and provide interesting background info about where you are. This will allow you to sit back and enjoy the scenery without the stress of driving in unfamiliar territory, plus if you like to drink it would allow you to sample as much wine as you like. Obviously, this is a very expensive option, but if you opted against renting a car, maybe hire a driver for the days when you want to explore the smaller towns, and hit the bigger towns that are easily accessible by bus or train on other days.

And with a car, staying at an agriturismo or country house becomes much easier.

Right. I don't know as most of us would strictly advise against a rental for Tuscany. It really comes down to where one wants to go, where one wants to stay, and personal comfort level/style? List the pros and cons of each option to decide. Personally, we love the trains as they usually (but not always) dump you off in the middle of a city/town or at least reasonably close to where we want to be. Want to have a few glasses of wine with a day-trip dinner? No problem: hop the train to go home. They also allow both of us to enjoy the scenery versus eyes on the road, and we don't have to think about parking and ZTLs. As we wouldn't ever leave luggage unattended in a rental, we wouldn't do any sightseeing between location moves, either.

Does relying on public transport limit some of the places we might go? Yes. As said above, very small towns can often only be efficiently accessed by car, and it's almost a necessity if wishing to stay at an agriturismo. Still, we're not agriturismo types so no problem there, and there are plenty of locations accessible by decent public transit we still want explore so there's our list of deciding factors. Yours may be very different so go with with YOUR heart's desire for this trip. With some advance homework, lots of folks rent for day tripping the countryside and do just fine.

Whatever you decide, you'll get lots of help from the gang here! :O)

Ciao Susan,

We just returned from our first trip to Italy, we were celebrating our 25th, and are in our late 40's. We too were torn over visiting the Cinque Terre or the Amalfi Coast. I would agree with the above reply that said, if you've always wanted to see the AC do it. Sicily is indeed a good place to do on its own. I have friends that are from there, and know several who have visited, and that is the advice they give. The way that I ended up organizing our trip was by choosing our "must see's" aided by Rick's book of course ;) I generally chose the three diamond attractions, and tried to plan enough time to see the ones we liked. Along with some recuperation time in Tuscany and Amalfi. We flew in and out of Rome as it fit our budget better, but wished we could have done an open jaw flight. We rented a car in Rome, and immediately drove to Amalfi. We stayed in Positano at an Air BnB with a beautiful view. The next day we drove to Pompeii, which we loved! On the way back we stopped in Sorrento for dinner, which was very nice. The following day we took the bus into the heart of Positano, the buses are crowded! We enjoyed the day, with shopping, a stroll down the beach, an appertivo, and dinner. Next, we drove down the coast to Amalfi, where we had pizza on the square with a singing waiter, and then toured the church. We continued up the coast to Ravello, and toured the gardens as the sun set. I think the most amazing views of the AC are at Conca dei Marini. So many people say not to drive the AC, but I am glad that we did, it made our trip. If you have experienced big city driving along with mountain driving here in the US and are not a nervous driver, I think it's fine. The roads are well lit, there are guard rails, and mainly a low rock wall along the entire drive. The worst part is trying to pass the buses, which is when you are thankful you rented a small car! lol. As far as renting a car, do it ahead of time here in the U.S. or I hear it costs much more in Italy. Also, purchase insurance with your policy here in the U.S. and do not accept the one they offer you at time of pick up, it costs as much as the car! From Amalfi, we went to Florence, and stayed at an Air BnB named the Pitti Apartment, the owners name is Marco. It was exceptionally clean, and located just across the river in Oltrarno, everything was a 15-20min walk. From there, we left for Tuscany and stayed in Montepulciano, at Villa Nottola an Agritourismo, they had a very nice tour, and were kind people. However, I would say that I enjoyed the Chianti Region more, and I know that is a matter of opinion, but for us the views were just amazing, the olive groves and vineyards were so well laid out, it all just looked a little more polished, if that makes sense. Also, we found that more of those wineries were set up for walk in tastings, which we prefer, though I would say to schedule at least one tour ahead of time. We loved the Ricasoli Vineyard, with the castle and the view of Siena, it's to die for. Also, Veranzzano Winery was very nice. In Montepulciano we would recommend Nottola and Avignonese. For a rustic experience, Palazzo Vecchio was very nice too and they do cooking classes, but call ahead if you can. I would definitely recommend driving Tuscany. We loved exploring the hill towns as well! From there we went to Venice, where we dropped off our car. We stayed for two nights, and unless there is a lot that you absolutely want to do, I would borrow time from there, maybe cutting it back to three nights. Remember it is usually cooler there as well. From there, we took the train back to Rome where we stayed three nights on the Via del Corso. I was surprised how much we liked Rome, and how many sights we were able to see in a short time. We were able to walk everywhere. I would highly recommend buying your tickets to the sights you want to visit ahead of time. Also, take a tour of the Vatican, it was very good! Dianne

I have been several weeks since I have posted so hopefully this post will be seen. I've been going through travel books, searching online and exploring some varied flight options. While I am enjoying the planning process I'm driving myself a little crazy and finding it difficult to make final decisions where open jaw flight arrangements and itinerary details are concerned. In reference to my original post, I think I'd like to stay in the AC area along with Venice, Florence and Tuscany area and Rome - rather than stay in CT for this trip. I will not be able to travel back to Italy very often and don't really know if I will ever get back so I want to see the AC area this visit. I understand I need to make decisions quickly as my travel dates are 6 months out and my open jaw flight details need to be secured but I an trying to determine the most efficient plan of how to arrange my travel itinerary for each area. So I am planning on travel dates beginning May 1, arriving in Italy for the first night on May 2. I will travel back home on May 18 or 19th so I will have 16 or 17 nights for this trip. We love city travel but also coastal travel as well.

Possible itinerary could be:

4 N Venice
2 N FLorence
3 N Tuscany area stay likely with a car
3N Rome
4N Sorrento and/or AC area
1 N left over...

Please let me know any advise you can offer on how I should plan the progression of my trip and on how I should arrange my flight arrangements considering the areas I'd like to visit.

Thanks for your input:)

Sue, you're going to want to stay in the city of departure the night before an international flight. You might consider a Venice> Florence> Tuscany> AC> Rome order? That way you could fly into Venice and out of Rome, and tack that extra night to Rome as well: 4 nights is really nice for covering all there's to see in that one.

Otherwise, look at flying home from Naples? Head to the city for a one-night stay after your stay in Sorrento/AC, and see the archeological museum in the afternoon. That's a good one to do if you intend to visit Pompeii earlier in the week.

Hi Sue
Just wanted to share our experience. We took our first trip to Italy in 2014- did 17 nights as well- now we are planning our 2nd trip for May 2019, our 40th- and now that I think about it I guess our 2014 was for our 35th!

Here is what we did

1. Fly into Venice- 3 nights- this was the right amount of time for us to get over jet lag, see the major sights, vaporetto to Burano etc. Loved Venice and are going back in May. We were anxious to get going and see more of Italy.
   We stayed at Hotel Ala - which was the perfect choice. Literally steps from SM Giglio Vaporetto stop and the alilaguna boat from airport dropped us right there. No bridges to cross. As we were checking out a RS tour was checking in so I guess we chose wisely.

2. Train to Florence- 3 nights. I think 3 nights is needed here- our problem was juggling the museum open/closed days some are closed on Mon. some on Tues- we arrived on a Sunday. Loved Florence and will return on our future 3rd trip to Italy.
   3 nights is really just 2.5 days- if art is not your thing I guess you could get away with less but…it’s Florence-- the art!!

3. Picked up rental car at a Hertz location just outside ZTL. Drove to Siena with some stops on the way. Driving was much easier than we thought. Not a problem at all.
   2 nights in Siena- I was very very careful to choose hotels that had parking and easy access, avoiding ZTLs etc. If you’d like recommendations let me know. We liked Siena and the Duomo (with tiled floor uncovered at the time) is a must see. But it was not our favorite hill town.

4. Drove to Montepulciano- 2 nights- with stops in Montalcino and a few other places on the way. LOVED Montepulciano and would return in a heartbeat. The charm to us was the mornings and evenings in the hill towns, thus the reason we changed hotels for 2 night stays- we wanted to be in diff places for the evenings.
   Spent a day driving around- Pienza was a highlight as we were there for a Pecorino Festival we were unaware of. (Plus it is a “flat” hill town- a welcome relief after Siena/Montepulciano).

5. Drove to Assisi- 2 nights. Another highlight. Took a short drive to Spello on 2nd day

6. Dropped car in Spoleto- took train to Rome- 5 nights.
   We were surprised at how much we loved Rome. There are so many major sights there that take time to visit, we are also returning here next May. I think it needs at least 4 nights for a first visit.

Anyway- since you want Amalfi and will probably be flying home from Rome- put Rome last- you need to be there for your flight.

I’d try this:
Venice 3
Florence 3
Tuscany hill town- 3
(or 2 in Tuscany, 1 in Orvieto- to drop your car before heading south).
Sorrento- 4 just go all the way thru Rome/Naples
Rome 4

Thank you Kathy.

I loved Verona- its history, beauty, and easily doable from Venice- the Arena is older than the Colosseum in Rome!! Lovely shops, restaurants, piazza, and a great restaurant to celebrate your Anniversary is a hidden gem called
http://www.osteriailbertoldo.com/
I had the best meal ever its family run and you need a reservation.

Happy Travels💫✨

You're welcome, Sue. You're going to have a wonderful trip! :O)

Christine H - I would love to know about the lodging recommendations in the Tuscany area you mentioned that has parking if we rent a car.

Hi Sue

In Siena we stayed here:
https://www.palazzoravizza.com
We were given very explicit directions of how to drive into town, checked in and dropped our bags then drove back around the hotel and down the hill to their own gated parking lot. Walked back up a short path and re-entered thru back of hotel. It was a very nice hotel- the terrace and views were fabulous- and it was just steps from the historic center.

There were quite a few others we considered in Siena that also had easy parking/access.
I used booking .com and filtered for parking.

In Montepulciano we stayed here:
https://twitter.com/kylegriffin1/status/1059624097217478661
It was absolutely lovely. Parking was down below the wall, hotel owned spots- we then walked up a path right into the center and steps to the hotel. Very easy to come and go on our day trips.

We also considered an agriturismo- this one:
http://www.agriturismomarciano.it
But in the end decided we wanted to experience the towns in the evenings/mornings.

Hope that helps

That helps greatly! I have a question about flight/layover and customs... I am trying to solidify my travel arrangements with arriving in Venice and returning home through Rome Or Naples as I am aiming to see Venice, Florence/Tuscany/ Rome/AC with a departure on May 1st and return back home on May 18 (these dates are flexlible) and of course seeing varying layover times. I am flying from New Orleans to Europe and wondering how much time for a layover I need when I arrive to Europe in order to get through Customs if I have a connecting flight in Europe? Any advise/experience is appreciated.

When you arrive in Europe you will just go thru passport control as you enter Schengen. (You will go thru Customs on your return to US)
If your flights are all booked on same airline, your baggage should be checked thru to your final destination.

Others may have more to add but I would say anywhere around 60-90 min is enough. The airlines are usually pretty good about getting their connecting passengers thru the airport to their next departure gate.

We have actually always flown TO Europe on a direct non stop flight -last trip we had to fly home from Nice thru Paris and the way AirFrance moved the connecting passengers thru the terminals, etc was really amazing, very smooth and no worries about missing connection.

You've received tons of great advise already, so I'll just add this:
Less is more. Perhaps visit fewer places and spend more time enjoying the places you do visit.
For me, Italy is so much more enjoyable when I take the time to settle into one place for several days or a week at a time.

Our recent trip was to four cities in two weeks. That felt too rushed for us; we'll definitely take it slower on our next trip!

You are concerned about passport control not customs entering Europe. Walk through Nothing to Declare door (customs) when exiting from baggage claim. You will declare what you bought and are bringing home from Europe when you return to the US Customs. On my recent trip passport control in London and Rome was very fast,10 minutes, much better than I remember in the past. Don't know what your entry city will be.
We liked staying in Venice in the Dorsoduoro and Cannareggio neighborhoods but you really can't go wrong. Avoid staying in San Marco area due to crowds..
Yes, you should rent a car for Tuscany. It is beautiful, rural mostly with lovely villages and towns in different areas. Get an IDP at AAA before you leave.
More days is always better. The long flights and large expense both ways make it better to stay longer if possible.
You are wise to save Sicily and the Amalfi Coast for a separate trip.

Thanks for all the great advise!