10 Night: Rome -> San Gimignano -> Florence -> Venice Itinerary

As your itinerary points out, you only have a single full day in both San Gimignano and Venice. To me, that's not enough time in either and too many hotel changes for such a short trip. I would cut out San Gim, maybe do it as a day trip from Florence, and add those nights to two of the other cities.

Donna

You mention wanting an experience outside of major cities. I would suggest choosing a town that's easier to get to than San Gimignano. Orvieto is a possibility, an hour outside of Rome by train, so you could do it as a day trip or as an overnight on the way to your next stop. And unlike San Gimignano, Orvieto is on a train route. I believe it will also present you with better opportunities for two of your interests – art and food.

And there are many other options that are easier to get to than San Gimignano. Assisi is a particular favorite of mine, although I would do it as an overnight between Rome and Florence.

My other thought is that you really only have 9 full days on the ground, with 4 stops. That's a lot of moving around. Much of your arrival day will be hampered by arrival logistics and jet lag. Also, Figure you will lose at least a half day each time you change locations, and possibly a full day to get to a place without good transit options. I would drop at least one of the stops.

Marc: Remember that every time you move from city to city, you lose a day's time. And your first and last days on a trip are wasted recovering from the flight over and getting to the airport, going thru security and waiting for the departure. The cities you want to visit are great European cities, and you want to allot sufficient time to see them properly.
In the case of flying out of Venice Marco Polo Airport, travelers transfer flights at other larger gateway European airports.

If you've not made your flight arrangements, a better itinerary might be:
Tue 5/17 - Depart Boston You can fly on Norwegian Air Shuttle 1 way for $322 into Rome.
Wed 5/18 - Arrive in Rome at 12pm. Rest up the remainder of the day.
Thur 5/19 - Rome
Fri 5/20 - Rome
Sat 5/21 - Rome
Sun 5/22 - Rome-Florence on an afternoon train
Mon 5/23 - Florence
Tue 5/24 - Florence--rent a car and visit San Gimignano and Volterra, or San Gimignano and Siena. Or day trip to Sienna on bus.
Wed 5/25 - Florence -> Venice afternoon train
Thur 5/26-Venice
Fri 5/27-Venice
Sat 5/28 -Depart Venice at 2:00 p.m. on Norwegian Air Shuttle for $289.70

$612 is an extremely favorable round trip airfare, especially when you consider Italy is more expensive to fly to than most other European countries. I hope that fits your schedule better, as being flexible is often a big money saver. I'm glad to picnic on Norwegian Air Shuttle's brand new Boeing 787's to save 1/2 of a legacy air carrier's airfare.

Agree with others - Try to fly into Venice and out of Rome. Most flights leaving Venice are very early in the AM, and it takes a bit of time to get to the airport. Also, when you fly into Venice, it is more relaxing when you arrive and you have a chance to get over jet lag.

San G is better off done as a day trip, I would add the days to another city, but stick with only the 3 (Venice, Florence, and Rome) so you don't have the travel time and hotel changes. There are plenty of smaller towns to be seen by day trips, as previously mentioned.

Thank you everyone for your responses, this is very helpful! We will likely spend our nights in these three cities.

I'm sure everyone has different opinions but any thoughts on how you would break down across these three? We've been thinking that since one of our Rome days will be a wash due to travel to perhaps do 4 nights in Rome, 3 nights in Florence, and 3 nights in Venice with a day trip/tour to Tuscany between Rome and Florence or out of Florence.

Would be curious to hear any differing opinions on this breakdown.

I also forgot to mention, we already booked out trip into Rome and out of Venice...

Me personally I like Siena over Florence. You could always stay in Siena and take trips around Tuscany including a 1 hr bus ride to Florence for the day. Perhaps something like....

Tue 5/17 - Depart Boston
Wed 5/18 - Arrive in Rome at 12pm.
Thur 5/19 - Rome
Fri 5/20 - Rome
Sat 5/21 - Rome
Sun 5/22 - Rome to Siena
Mon 5/23 - Daytrip via Bus to Florence, return to Siena at night
Tue 5/24 - Daytrip via Bus to San Gimignano, return to Siena at night
Wed 5/25 - Siena- Venice afternoon train
Thur 5/26-Venice
Fri 5/27-Venice
Sat 5/28 -Depart Venice

For ease of logistics I would suggest Siena over San Gimignano.
Stay 2 nights in Florence, and 3 in Venice, but be smart with your train times.
On the 25th make an afternoon bus excursion to San Gimignano from Siena.

Thurs 5/19 - Arrive in Rome at 12pm
Fri 5/20 - Rome
Sat 5/21 - Rome
Sun 5/22 (am) - Rome -> Florence
Mon 5/23 - Florence
Tues 5/24 (pm) - Florence -> Siena
Wed 5/25 - Siena (afternoon bus excursion to San Gimignano)
Thurs 5/26 - Siena -> Venice
Fri 5/27 - Venice
Sat 5/28 - Venice
Sun 5/29 - Depart Venice in AM