Flying Boston to Italy First Timers

First time classic:

Land in Venice (VCE)

Venice 3 nights
Florence 3 nights
Rome 3-4 nights

Depart from Rome-Fiumicino (FCO)

If you don't have good flights options to VCE, you can go in and out of Rome, but go straight to either Florence or Venice upon landing (2 hr to Florence, 4 to Venice by train), so you save a hotel change. Leave Rome (your departure city) for last.

Knowing which month would sway me as to whether I visited "the big three" or Rome and the Amalfi coast. There is no rule you have to do the cities on your first trip. What do you want to do? With 9 days, open jaw flights are certainly the best option.

If you have not traveled much internationally, Naples is considered a more difficult place to start whereas Rome/Florence/Venice are easier. Here is a great thread by a regular forum contributor about their recent visit to Naples.

https://community.ricksteves.com/travel-forum/italy/naples-37d335fd-e698-4f57-bb81-3ff2e28c1176

Flying into Venice and out of Rome is pretty much an ideal plan, and I think you'll have no trouble finding flights from Boston with only one connection each way. Use the "multi-city" search option with your preferred airline or search engine.

Thanks for these great replies! Looking at late April leaving for home first weekend in May.

That's a lovely time for year, but it could be a tad cool on the Amalfi coast, certainly no swimming.

I agree. So next time to the AC. Thinking Tuscany day tour out of Florence. Maybe CT for a day or just do Florence?

Jack: also from Boston area.
Based on your original post you understand it well given your timeframe you can do:
Venice, Florence, Rome OR
Rome & Amalfi Coast (I would prefer to not stay in Naples and spend more time on the actual Amalfi Coast than in the city but many like staying there so opinions vary)

Flying open jaw like you are thinking of is the perfect solution with either to save time and backtracking.

Both are great vacations, I have done both ways ; well didn't include Rome when I did Venice/Florence and instead included other things in the north but same otherwise.

In terms of possible Direct Flights ; Rome will be your only option so no way to avoid a layover if Naples is your departure or Venice is your arrival city). If you hate layovers I could see some logic in backtracking to Rome so you can have a direct R/T flight from Boston.

To your more recent post: With your time if you want to do one of those tour groups for a day to get a taste of other Tuscan towns you could do that from Florence assuming you are OK rushing a bit in Florence.
I don't think CT is a good day trip (even in better weather time of year it is too far) ; and you definitely don't have time for 2 day trips ; when would you actually see Florence ; which takes 2 days to see the highlights of.

Personally as a daytrip from Florence I prefer Siena ; does not give you any countryside viewing nor sights of multiple towns but you would not be rushed around and have enough time to actually visited Siena properly by dedicating a full day to it, it is much different than Florence and equally impressive. Also very easy to do this as a day trip on public transit.

Usually 3 nights is really only 2 full days
Keep in mind before any day trips at all out of any of these cities: Florence would be best with 3 nights/ 2 full days, Rome with 4 nights / 3 full days and Venice best with 3 nights (2 full days)
That is with no day trips and is 10 nights ; more than you have so you are already rushing a little add in day trips and you are rushing a lot.

Siena sounds great. I am assuming it's classic Tuscany experience. I see your from Boston. Any airline recommendations? Lufthansa seems appropriate right now.

Lufthansa I have not taken but have heard is a nice flight to Europe.
I am not that partial to one airline over any other really. On the way I am so happy to be on vacation I am not bothered by being cramped in like cattle and happy to be fed anything.

I usually try to find a sale or see where I can use frequent flyer mileage to go (often with Chase points)
I believe your only direct flight to Rome options is Alitalia. I could be wrong but think the flight is sold by other airlines like Delta but the actual flight is Alitalia. Would prefer that flight direct vs. anything else with a layover in another European city first personally but only if the cost is not way out of proportion.

Siena is medieval which gives it a different look from Florence, the buildings are all siena brown color and looks for the most part unchanged ; very easy to be there and picture yourself back hundreds of years ;
Very easy to walk ; as a day trip you basically visit the Duomo which is more impressive than the one in Florence surprisingly and then walk one road from the Duomo complex which is filled with shops to the main Campo piazza which is one of the collest piazzas anywhere in the world and a great place to meander, have lunch and just hang out.

The town has more of a laid back feel than Florence, Rome or Venice.
The lack of cars in town (other than taxis) makes it really pleasant.
A few places to climb up for a great view of the town and surrounding countryside (Bell Tower in the Piazza or the Duomo campagnille)

To me Classic Tuscany are more the smaller hill top towns with farm lands and winery surrounding them. Siena is more of a city than that and in town you are not that close to any beautiful country sides, in that respect it is similar to Florence.

Open jaw is the way to go for sure. I prefer flying into Venice, home from Rome as Venice is a much more relaxed introduction to Italy especially when jet lagged the first day. Try looking at flights into Milan if Venice flights are not ideal or expensive. It's about 2 hours by train and easy to do. I think I saved $400 per person flying into Milan the last time I went. If you decide to see Venice Florence and Rome on this first trip I would try to work in some Italian countryside/Siena rather than going all the way over to the CT. You will spend less time traveling and more time enjoying.

I always fly out of Boston to Europe. I have flown BA, Swiss and Lufthansa. I like either Lufthansa or Swiss for Venice or Florence due to layovers and connection times.
I am one of the folks that does not really care for Rome so I would stay north. (I did like the AC though). For me, I would cut the trip down to Venice (4 nights) then Florence (4 nights). Fly out of Florence or Milan (if Milan add 1 night in Milan prior to flight home).. I don't think there are any direct flights from Milan to Boston via Lufthansa or Swiss Air but am not certain. Flying out of Florence is VERY easy since it is a small airport. I think you could find more than enough to do with 3 full days in Venice. Take the train to Florence. If you get bored with the city, take day trips to Sienna or Lucca. Day trip via tour to Chianti region. Lots to do/see in just these two cities, IMHO and would be a relaxing trip with no rushing to and fro. But that is me. Depends on your travel style.

One other thing I wanted to mention:
I think many people are turned off of Venice because of how they approach the city. Here is the typical scenario.... fly into Venice jet lagged and brain dead. Figure out how to get to hotel. If by bus or taxi, still need to figure out how to get to hotel via vaparetto, by foot, or water taxi. If using Alilaguna, still have same problem once you reach your stop.
One of the charms of Venice is the lack of roads and the "block" design typical if US cities but it also makes navigating the allies/canals to your hotel a potentially daunting task. Once you are there, you will see countless people dragging luggage with map or phone in hand, trying to find their hotel.
So, hotel selection is critical. Get very good instructions on how to get to your hotel. To me it is worth the cost of arranging (through your hotel if possible) either a porter to get you to your hotel or arrange a water taxi pick-up, or select a hotel very near a vaparetto stop. After my first visit I did not need to do this but I certainly wished I had for my first trip. And, bring a very good map (I have Streetwise map which I understand is no longer available), map app, etc.
Don't be put off by this post....Venice is magical.

Lisa said it: if flying into Venezia is not convenient, or has a long layover in Milano, take the train from Milano to Venezia Santa Lucia station. You can relax once you are on the train, perhaps not so much waiting for a connecting flight.

A daytrip to Siena is great (an overnight would be better), but plan to stay as late as possible; like many towns, it has a different character once the majority of daytrippers leave.

End your trip in Roma and fly out of FCO.

I just about always take BA to Europe from Boston. There are day flights, which I prefer, but most do the overnight flight to Heathrow and then switch to the European flight. (I prefer to fly to Heathrow on the day flight, stay overnight at the airport, and then get the European flight, but that's my odd way.) I have yet to have a BA flight that required me to change terminals as they have Terminal 5 (unless they fool you and put you on American Airlines, but you can catch that when you pick your flight.) Fly into Venice, not out, as a flight out would be at what I consider an ungodly early hour. Then, fly out of Milan at the end of your stay. I would do 3 nights(2 days) in Venice, 4 nights(3 days) in Florence, and 2 nights(1 day) in Milan. Contrary to others, I think there is quite a bit to see in Milan, but if you disagree, you can make a day trip to Lake Como. Also, after several trips, I have been unable to pull myself from Florence to see the Tuscan countryside, but Florence is a great base for that. I would suggest staying north for your first trip, but I'm not a Rome fan.

On a different note, we once did RT Rome, but only stayed in Rome on each end...my step daughter wanted to see St. Peters, hence our start. So we trained to Florence and spent half our week there, and then trained to Sorrento, and spent the second half there. It was February. Each daughter had picked their location. Florence (Room with a View) and Pompeii (and Amalfi coast). So that is an option as well. However, this wouldn't be my first choice, but we had a lovely time. I had already been to Florence, Venice and Rome...

The suggestions you've received are good ones particularly the open jaw flights. The suggestion of 3 nights in Venice, Florence and Rome is reasonable. Also, the comment about finding your hotel in Venice is no joke. This said, I would add only two thoughts to perhaps consider.

First: Unless you specifically want to lodge in the three cities, you might want to consider lodging in a nearby town (particularly in the case of Venice you might consider Padua or Vicenza). Lodging and meals in Venice will be more costly and the smaller towns will be less touristy (particularly in April). In the case of Florence, you might consider Fiesole or Empoli, and for Rome maybe Tivoli. Trains are frequent and each trip is brief (less than 1 hour). An 8 day rail pass is about $180 per person (second class). You could travel as many times as you desire within the 8 days. This is about all the transportation you’d need, other than perhaps a taxi or two in Rome.

Second: If you opt for a train pass, you could not only visit Venice from Padua, but also Vicenza or Verona, from Fiesole not only Florence but a day trip to Sienna, Pisa or the Cinque Terre, and from Tivoli in addition to Rome, spend time in Tivoli ( Hadrian’s Villa, Villa d’Este).

Thank you. Lots to consider. Enjoying all of the input. working on Venice hotels first and then off to Florence.

Venice is not that expensive. Like everything else in life, "it depends." I've always stayed in the lower-priced Dorsoduro area. Cannareggio should also be considered. Both are well-located (nothing is really far in this small city - you can walk the length of it in a hour. . . . if you don't get lost), and have good, low-priced restaurants, cafes and lodging. Cannareggio is closer to the train station, so more convenient from the airport. Dorsoduro is quieter, more residential.

Lately I have been flying Lufthansa or Swiss (same company) to Italy a lot since my home airport (SFO) is a United/Lufthansa hub and I have lots of UA mileage. But in general I'm open to all airliners if prices are decent and routing convenient.

From BOS you might also consider Air Lingus (via DUB). They fly to both Rome FCO and Venice VCE (but not to Florence) and have good options (and prices) out to BOS. See what you can find on a multi-city (open jaw) option on Kayak.com

Okay great helpers. Here's my latest thoughts after digesting opinions, from here and elsewhere, along with other considerations. All of the help has been well received and only confirms that there will be future trips to discover the other areas, Amalfi Coast, Capri, Sorrento, etc., preferably during season.

Trip early May
1. Fly non-stop in and out of Rome from Boston
2. 2 nights in Rome
3. Head to Florence for several nights to explore, relax and as a base for Northern travel with a possible night in Venice.
4. Tour Tuscany, Cinque Terre day trip, as a compromise for not going to Amalfi Coast.
5. Back to Rome for departure.

Thoughts appreciated.
Jack

Trip early May
1. Fly non-stop in and out of Rome from Boston
2. 2 nights in Rome
3. Head to Florence for several nights to explore, relax and as a base for Northern travel with a possible night in Venice.
4. Tour Tuscany, Cinque Terre day trip, as a compromise for not going to Amalfi Coast.
5. Back to Rome for departure.

I am not understanding the number of days, but if you arrive early in Rome, I'd consider heading to Florence that day so you can put all of your Rome time together at the end (depends on departure time of course, but you could avoid a one-night stay at the end that way). enjoy!

My husband and I don't like layovers. So when booking our flights for our April Italy trip, our guiding principle with choosing airports was to have the shortest flight coming BACK to the U.S. When the trip is over, the trip is over, and we're ready to get home!

Because of that, we chose to end our trip in Rome since I found several direct flights back to the U.S. when departing FCO. Our plan is this:

Going there: MSN-DET-AMS-VCE (layovers in Detroit and Amsterdam)
Going home: FCO-ATL-MSN (layover in Atlanta)

We live near the MSN airport, so we choose to use it because it's so convenient with getting to/from our house. It's a smaller airport, so we always expect layovers at bigger U.S. airports. But hey, we have a 15 minute drive home! :-)

PS: Forgot to mention that we're flying Delta and KLM. The AMS-VCE leg is KLM; everything else is Delta.

Assuming you fly in and out of Rome, you should go to Florence immediately upon landing (there is a train every 20 min. and it takes 90 min.).

If you decide to include Venice in your itinerary (let's say 2 nights). Do so after Florence. Then after Venice you'd go down to Rome (3h45 min by train).

Since Rome is your departure city, you should leave all your Rome nights at the end of your trip.

The above strategy saves you one hotel change (hotel changes are time wasters. The fewer you have, the better it is).

One night in Venice is not enough. Venice is unlike any other city in the world. I think there is a reason why Rick Steves and so many people on this Forum recommend 3 nights in Vence, Florence, and Rome. Definitely stay in Venice and not outside of Venice. Venice is magical in the mornings and evenings after the cruise ships depart.