Can I do this myself? First time to Italy.

Although it may seem daunting, you can absolutely do this yourself, especially given that you’re starting early and have the locations determined. We don’t have the experience in Sicily, so I’ll let others give advice on those travels, but once you have flights decided, you just start filling in with your accommodations, tours and activities, food and the like based on your research and forum recommendations. Start with a good book like Rick Steves Italy. You’re not alone with the help of Forum Friends!

Agree with Fraubarr - this is a can do!

Yes, you can absolutely do this! That said, it would probably be helpful if you shared your general ideas and/or itinerary with the group so those who have taken similar trips can provide advice and suggestions to make the trip easier.

You can absolutely plan this on your own. In addition to the information you’ve already gathered, you will get lots of useful details for planning from a Rick Steves guidebook and Google Maps. You can use a spreadsheet to layout a basic itinerary with hotels, sites, and restaurants and modify it as you go along. For hotels I use Booking.com as it allows you to filter for price, amenities, etc.

For simplicity, consider the possibility of dropping the Sicily piece for this trip to spend more time in Florence and Rome or possibly adding another city between Florence and Rome. Sicily could be a separate trip on its own for another time.

Rick Steves guidebooks provide details in train travel between cities, purchasing tickets, etc.

Have fun planning!

Yes, been planning trips abroad on my own since the 70’s. Used to do it by reading Fromm’s Europe on $5 A Day.

Now use the internet for research proving you can teach an old dog new tricks.

Italy is very doable on your own. I’ve been there at least 5 times. For years a friend had a home in Oriveto. Since sold as they now live back in CA. Will you be relying on public transport? Time of year?

Check out Timeout Magazine on Line, same with Nat Geo and Conde Naste, research accomodations (VRBO, Air BnB’s, hotels ) Research airlines.

For me planning is part of the excitement of travel.

Hi. I want to share some AI things about this. AI is quite advanced nowadays and can think of things we might overlook, but compared to humans, it lacks a bit of human touch and personal experiences that AI can't fully capture.

So, to help improve how you use AI, I usually like to add this prompt: 'Before answering my questions, you need to ask me questions, one at a time, until you have 99% confidence you understand my needs, then output the answer.' This really helps refine your planning and improve the output.

However, in most cases, you can definitely come to the Rick's to ask questions, because human answers can never be replaced by AI. Hope this helps. XD

Hello ndlaw2k, and welcome to the forum,

You absolutely can plan your own European vacation. I've been doing it since before email and the web (Rick used to have a form letter to fax to hotels inquiring about reservations) and it is so much easier now.

My first tip is count nights, not days, and create a spreadsheet or a list with each night and where you are sleeping. This makes sure you are reserving something for every night and have all nights covered. Then you can fill in travel details for the travel days on those days you travel and what you want to see that day. Keep in mind 3 nights somewhere si 2 full days with days of travel either side.

Be careful of European days being marked the reverse of American dates so 15/2/2027 not 2/15/2027. The calendar on the reservation site will act the same but it's something to be careful about. Also be careful with 16:00 being 4:00pm and 6:00pm - it's a mental error that's easy to make if you're not used to military time. Trains run on 24 time not am/pm. Most of the rest of everyday Italy uses 12 hour but trains, museums, and places that hate ambiguity will be on 24 time.

Get guidebooks for the places you want to see. A good guidebook will save you time, money and missing something you really wanted to see but didn't know, or have details. about. Rick has good hotel guidelines and restaurant recommendations. These I lean on the internet more for places to eat and drink as they are constantly updated but having a solid recommendation when you are vacationed out is a great thing. If you use Rick's books read his reviews carefully. One of the things I like about his work is there a lot of subtext embedded in his reviews and observations and if you read him carefully you can learn a lot about a place. Booking.com is great resource for searching but I always then try to book directly with the hotel I've selected if I can. Rome2Rio is a good starting point for general questions "How long does it take to get to Bologna from Florence? How about Milan?" and broad searches but always confirm any information you are counting on with the actual source.

Now the only criticism I'm going to make of your plan is with 11 days you don't have time to do Sicily. Sicily requires two flights and needs at least a week - better two weeks - all by itself. With Florence and Rome you might have time for 1 city in Sicily but the two flights are going to take up way too much time out of a tight schedule. With 11 nights I would pick a 3rd mainland city or add some planned day trips to your two city schedule to see some other cities. Rome, Florence, Venice is classic first Italy trip for a reason, but you don't have to do Venice if you're not interested. (It's on of my favorite cities.)

Set a schedule, break your stay into chunks for easier planning, ask for advice and help on the various pieces put together a plan. In the end there is no way to learn or get better at then to go and do it. There will be issues, probelms and misunderstandings along with amazing moments and revelations. As with anything the more you do it the more you learn and easier it gets, but without a first trip you'll never know.

Happy travels,
=Tod

PS "AI" aggregates (some would say plagiarizes) the combined postings of the internet but it had no actual experience or intention. I will always be more interested in a personal personal experiences when it comes to travel than the average of 1,000 websites, ads and blogs.

I've never used a travel agent, but from what I've seen from other people that I know who use them, they tend to book their customers into hotels that provide them a commission; that's part of how they make their money. This would limit your hotel options.
And I agree with the other posters, the two of you should be able to plan a lovely trip that is way the two of you want it to be. As you've already seen, there are plenty of experienced travelers on this forum who will be happy to help. I've been lucky enough to visit Florence and Rome a number for times, and Sicily for one special trip.

If you care to share your cities and days in Sicily, I can provide some input. We visited about eight years ago, spending two weeks there, and I loved the many layers of history in Sicily. My spouse and I are (especially me) very interested in ancient history, and also love mosaics. So they were the focus of our trip; we chose to skip places that other people might feel are must-sees. And, in a choice that others might not make, we spent a day with a private guide visiting Morgantina and the museum in Aidone, which houses the "Venus of Morgantina" sculpture. That Venus was bought by the J Getty Museum, but eventually repatriated to Italy.

create a spreadsheet or a list with each night and where you are
sleeping.

That is a very good way to do it. I like to put every activity (hotel, transport, sight-seeing, etc.) into a calendar. That way I can easily see if anything overlap, that should not overlap. It is VERY important to use the correct (local) timezones, to avoid confusion - Especially long flights where the start and the end are in different timezones.

A "trick" I use, is to add the address of activities to the item in the calendar. Then I can just click on the address to open Google Maps on that address and get a route (walk, public transport, or car) to find it. Very handy in a foreign city, but I also use it at home.

You find out your way of doing it.

Have a wonderful vacation.

Welcome! Yes, you will be able to plan this without a travel agent or AI. A few tips that I have found helpful:

a) Go to your public library or bookstore and take a look at the travel books for Italy. I'm old school, so after I determine which ones may be helpful, then I make a purchase. I use a highlighter to mark things that are helpful or interesting, and I giv my husband a different colored highlighter to do the same. When we leave for our trip, I cut out the pages of the book and take those along, rather than carrying an entire book.

b) I start looking for accommodations by using the filters on Booking.com and I also read reviews online. Chat with friends for input on places they hqve stayed. ALWAYS book direct with the hotel; read cancellation policies and dates very carefully.

c) For Italy, the Trenitalia website and app is very easy to use. Again, book direct with the provider, not a third party site. Do the same for things you want to visit such as the Vatican, Colosseum etc. Some of the ticketing sites for those look official, but they are not. Google the Man in Seat 61 for advice on train travel.

Once you have your plan more in place, or have more questions, come back to the Forum. Happy planning!

With Florence and Rome you might have time for 1 city in Sicily but the two flights are going to take up way too much time out of a tight schedule.

Well, maybe they could fly into Pisa and out of Palermo. They could take an high speed train from Florence to Rome and a domestic flight from Rome to Sicily. This way, by Flying home from Palermo, they'd avoid backtracking to Rome.

Sicily is way bigger and more diverse than most Americans think, but a 3-nights trip should be enough to get an idea.

Such a great response already. Thank you!

A little more info -- I was looking at Rome, Florence, and one other city (Venice, Sorrento), but my wife is set on going to Sicily b/c that is where her ancestors are from. I know it requires a flight (train or ferry is too long even overnight). We are looking at Ortigia. We can get a flight back to the States from Catania, so no flight back to Rome required. In other words, my wife has spoken, so this is the lineup. Haha. Prob 4 nights Rome, 3 Florence, 4 Sicily. I know that is on the aggressive side, but we'll do our best to breathe and take it in.

Dates are also locked 3/17-3/29. That last 2 days are Easter and Easter Monday, which are obviously big holidays in Italy. Agents I have contacted say it won't be a problem (Easter Monday is the flight out), but I won't expect a big excursion to be available on Easter. I've used tripmasters and AI and can basically replicate what the travel agents have given me if need be.

Keep the advice and encouragement coming! Thanks again.

You can do this, but ditch the agents—they don’t seem to be of any real help. And be very careful about AI. I see errors with it all the time—since it basically just hoovered up the internet, that is to be expected. Most of your question can still be answered by a basic web search, as original sources (like the train system website, etc.) are best.

Have you considered just enjoying Sicily? It would still be a short trip, but not all the time and money lost to transit. You can always go back!

Planning a trip may seem daunting but it's really very easy. Don't use AI for trip planning. The information is just not reliable. There are numerous threads citing ridiculous examples. The technology just isn't there yet for this sort of application.
Instead, use videos and guidebooks for inspiration, hotel websites and hotel aggregators for lodging, and this forum and related guidebooks for recommended guides and activities.

Three bases is fine for an 11 day trip. IMO however, Sicily deserves a lot more time that may not really work with your other two cities on 11-day itinerary. If you could expand your trip, you could amortize the really expensive airline tickets over more days and make Sicily work. Sicily can be a lot cheaper than your other destinations so let's say 4 days in Palermo costs you the same as 3 days in Rome.

Trains and public transit are generally a great way to get around in Italy. Is a driver more convenient? Sure. But aside from being an expensive luxury (for folks without mobility issues) you miss out on experiencing a slice of normal Italian life. I like those aspects of travel so I don't mind taking a bus or a metro.

People have different budgets but we spend a lot less on your Italy trips. I am pretty selective about lodging in some ways but ultimately I have to remind myself that it's just someplace I sleep and get ready for the real adventure of being out and about. I'm sure a €400 hotel room is nice but I purposely will never find out. I'm at the point in my life where I need a comfortable mattress and a bit of quiet. I don't need to pay extra for a view that I can get for free while walking the street the next morning.

Pack light. It's liberating. One bag; either a backpack or a small to medium roller and a shared small daypack for your water bottle, guidebook and extra phone battery

Consider skipping Florence this trip and add the 3 nights to Sicily. Seven nights in Sicily would allow you to see the east side of the island reasonably well.

When we went to Sicily we flew into Rome first and spent two nights. We had been to Rome before. That allowed us to take an inexpensive Ryan Air flight to Catania.

You also could easily spend your entire trip in Sicily.

We have visited Italy many times and $14K for a tour of 11 days seems high for two persons.

Here is a Gate 1 Travel tour of Italy that is 11 days and costs $3299 per person. Air fare not included.
https://www.gate1travel.com/tour/italy-tours-11dencit27.aspx
It doesn't include Sicily, but here is one for Sicily:

Here is a 12 day tour of Sicily and Malta for $2129 pp.
https://www.gate1travel.com/tour/italy-tours-12daffsicmt27.aspx

Here is a Road Scholar tour of Tuscany and Umbria that we took last year, it was great. Cost is $3949 pp.
It is 12 days.

https://www.roadscholar.org/find-an-adventure/22977/The-Hidden-Medieval-Villages-of-Tuscany-and-Umbria

Shop around before your choose.

Yes, you can do this trip yourselves. Here’s some helpful hints:

• Have the Trenitalia app loaded on each of your phones. It’s extremely handy for purchasing train tickets. The cities are in Italian - Roma, Firenze
• When you cross the streets in Rome, do it intentionally & check for Vespas. I exaggerate my hand motion slightly and don’t hesitate or pause- keep moving forward. Or cross with a group of people.
• Have ApplePay loaded on your phone to pay. I never pull out a credit card anymore.
• Wear a money belt, so you don’t lose your passport or credit card/ATM. It’s worn under your clothes and you access it in your hotel room or a bathroom.
• Look up some “Italian tourist words” on YouTube and learn them.
• Restaurants are wonderful! But this thankfully is also not the US restaurants. You won’t be rushed or interrupted by “Is everything good?” questions. Food is very local if you get away from the touristy restaurants. Eat after 7pm and walk a few blocks away from sites. Be sure to greet them in Italian and ask on the menu which dishes are their local ones. I have never been disappointed, and they appreciate that you care about their local food.
  

Have a great time! …and very special that your wife has family history there!

If Sicily it is, why not go all in?? Sicily is wonderful and easy to navigate independently. Only a few days there will likely leave you feeling sad that you did not stay longer and explore further. When we went, we flew to Rome and then directly to Catania, picked up a car and took off on our own, ending in Palermo. From there we flew back to Rome and spent three days before heading home. At the time Rome seemed like a must do but, in retrospect, we wish we had used that time to extend our stay in Sicily.

The only thing that worries me is the "connective tissue" between each of these pieces. Like a recommended guide or driver for a day; or a hidden special experience we'll miss.

If your wife has spent time researching her ancestry and knows the specific villages her ancestors are from then it may be worthwhile hiring a local guide to take you to them. I'm guessing this is why you mentioned Ortigia. GetYourGuide / Viator / Tours by Locals are some starting places or do a web search for guides. Depending how long ago your wife's ancestors left there may be cousins still there. Contacting the village's commune (town hall) or parish church before going can be valuable — many small Sicilian towns have someone who knows old families or can pull up civil records on request and your guide will be able to speak with them if you go to see the records.

I would not rely on AI to plan the trip, not without a lot of verification since AI happily lies. Get the Rick Steves Italy and Sicily books or ones by some other brand. They will recommend museums, guided tours, and hotels. A 2-star hotel in Italy is fine and often has private bathrooms (check the ones you look at), a 3-star is a bit more comfortable and will have private bathrooms. If you don't care about price then the 4-star will of course be great. My guess is a few hours of your time planning the entire trip will save you up to $5,000.

Late March last year is when we were in Sicily --- it's just a perfect time to go! Florence and Rome will be much, much more stuffed with tourists. If you are able to rent a car, even better, but I know that people here on the forum have gotten all around Sicily by public transportation. Yep, with 11 nights, I'm voting for simplifying your trip logistics and staying in Sicily the whole time, or maybe with a couple days in Rome.

Here's my trip report, not so much for the specific places, but just to give you a taste of what a trip to Sicily can be like at Easter: https://community.ricksteves.com/travel-forum/italy/sicily-spring-2025

Lots of great advice here. Travel agents will steer you to the places where they will make a commission.

You can do this if you have the time to do the research. I build three pages in an Excel spreadsheet -- one for a calendar view for planning, one in a chronological format for the details, and one for all the references (passport info, Global Entry info, frequent flyer info, web sites, etc.).

The trains are great in Italy. They are on-time, clean, and efficient. https://www.trenitalia.com/en.html. Creating a profile with them will help when booking multiple train trips. Pay attention to total travel times noted and avoid the local trains, taking the high-speed Frecciarossa trains whenever possible. We travel Business class on the trains and paying a few Euros for seat assignments is a great value.

The Sicily advice is correct. It is a trip unto itself. Spend more time in Rome and Florence. If you have AMEX, they can provide great assistance on airline flights and hotel recommendations.

You have already received a lot of good advice. I agree that 11 nights for your destination cities is a lot. When you travel from one city to another consider most of your sight seeing for the day gone. It takes time to get out of your hotel, get to the train station with enough time to be sure you are a bit early and don't have to rush to find your way around an unfamiliar station with signage in a foreign language. Then when you arrive , it's finding your way out of the station, getting to your new hotel and getting settled. Finally you can get out and about to do XYZ for the remainder of the day in the new location.

Read different guide books on Italy as each has a different take on places and how to do things. The RS guides are very detailed are worth your time to read in detail. Successful travel is doing lots and lots of reading ( travel, books, travel sites, etc) and planning about the places you want to go to and sites your want to see.

Make a chart/table /spreadsheet with your detailed notes and keep a copy on your phone and/or print it out, as back up.

I've never used a private guide but others will chime in with advice. The RS books often have a few guide recommendations for notable cities.

Are you certain that the direct flights from the US to Catania are available in March? I would also compare pries, because in recent years when I have looked at direct flights to both Catania and to Bari, they (operated by Delta) are much more expensive than flights on ITA connecting in Rome.

My opinion and mine alone, is that going all the way to Sicly for only three days is not a good plan. And perhaps your wife's ancestral home is on the other side of the island...

I have used private drivers in Sicily so could give you names if you like...when you are ready..that's worked out very well for me.

I would never consider using a travel agent who does not give you the names of hotels in advance. And US-based agents might know well certain hotels but they are not likely to be very helpful about getting from place to place by bus or train.

If you are looking for upscale hotels, you could check to see if they are part of the Virtuoso network; you book with a Vurtuoso agent and will get free breakfasts, possible room upgrades, and other benefits that you would not receive if you booked direct with the hotel....

I would go to Sicily first. The weather might be better in Sicily than in the north earlier in March. Also it is always best to return from an airport that will offer the most options to the US, and that is Rome.
Catania is the closest airport to Syracuse (Ortigia). Coming back from Sicily to the US is a convoluted endeavor. There are no non stop flights from Sicily to the US in winter and therefore you’d need to connect to a European hub and flights to the US depart in the morning, so it would require a very early wake up. Consider also that if the Mt. Etna volcano decides to act up, they close the Catania airport for safety reasons.
Then, after Sicily, I would fly from Catania to Florence. Both Volotea airlines and Vueling airlines have non stop flights from Catania to Florence.
Take the fast train to Rome (90 min trip) and come back to the US from Rome.
Be aware that you are going to Italy at a time when Daylight Saving has not kicked in yet (Italy, like the rest of Europe, changes the time on the last Sunday of March), so it gets dark sooner. March is generally cool but not cold, however the weather in March is not settled yet and is unpredictable, and the chance of rain may be high.
3 nights in Florence and 4 nights in Rome are appropriate. Sicily needs at least a couple of weeks but if all you want is Syracuse, then you can do it in 4 nights.
You don’t have time for other cities unless you prolong your vacation. That’s already a lot of real estate you are covering in just 11 nights.