Travel Advice: Italy Travel Itinerary

I recently received an email from a reader named Charlie who is planning his first trip to Italy and looking for some itinerary advice.

Here is an excerpt:

Dear Vagabondress,

My wife and I are planning a trip to Italy the end of September and early October.  Our mission is 2 fold.  Attend a wedding of some dear friends of mine (Italian women, French man) on 9 Oct just outside of Milan and see some of the wonderful sights and history of Italy.   I can project about 10 days in Italy (2 other days to travel there and back) for a total of 12.

This is my 1^st time to Italy and of course, I want to see it all, but due to time and $$$, I will not be able to see everything.  Should we just focus on a northern Italy adventure (Venice, Florence, Tuscany, …) or see as many cities as we can stand starting in Rome and making our way north to Milan?  The latter I’m not too crazy about, but I could do it if it were necessary.   We love to travel (long distance) but we would rather not pack up every day or night just so we can say we’ve been there.

We are considering flying into Milan from Wash Dc on arrive on 29^th of Sept.   Travel to Florence (see below) same day to start our trip.

Day 1:  San Gimignano (stay here several nights as a base) and taking day trips in the region to….include Pisa, Lucca, Florence…?

Day 4 Venice:  2  days

Day 6 or 7 open at this time

We have to be in the Milan area by Friday, Oct 8^th to meet up with the wedding party etc.

Since then, we’ve chatted a bit more, and he gave me some more details. Turns out he’s very open to Rome as well!

Here is my advice for you, Charlie:

1) Try not to leave out Rome! Rome is a fantastic city, and it would be a shame if your first trip to Italy didn’t include it.  Include at least two full days in Rome.  There are so many sites.

2) San Gimignano might not be the best base for you. It’s a beautiful Tuscan hill town, and the boar dishes are sublime, but it’s very far from other major destinations.  If you and your wife are renting a car, though, and don’t mind long distances, it could work.

Plot out the places in Tuscany that you’d like to visit.  (Hint: Pisa and Lucca can be done together. You don’t need much time in Pisa.)  Then find a town for your base that is in a relatively central location.

Personally, I would stay in Florence — the city center, natch — and take the train and bus to towns each day.  The trains are frequent and efficient — plus, you don’t want a car in central Florence!  I think this could work out nicely, since you could spend the morning at Florence museums like the Uffizi, then take off for an afternoon in a nearby Tuscan town.

3) Venice can be done in one day. I know I’ll get a lot of flak for this, and I do, but Venice is absolutely doable in one day, provided you leave early in the morning.  It’s a three-hour train journey from Florence.  Ideally, two days would be best.

Keep in mind that many final trains home from Venice leave in the late afternoon.

4) Don’t bother sightseeing in Milan. Get there in time for the wedding festivities, of course.  But compared to Rome, Florence, Venice and the hill towns of Tuscany, Milan doesn’t have many must-sees.  You’ve got precious little time; use it elsewhere.

Here’s my itinerary for you:

Weds 9/29: Fly to Rome in the evening.

Thurs 9/30: Arrive in Rome. Enjoy some light sightseeing.

Fri 10/1: Rome.

Sat 10/2: Split your day between Rome and the train to Florence.  Just make sure you arrive in time for a bistecca fiorentina!

Sun 10/3: Florence sightseeing.

Mon 10/4: Visit some Tuscan hill towns.  Return to Florence at night.

Tues 10/5: Visit more Tuscan hill towns.  Return to Florence at night.

Weds 10/6: Final day in Florence — use it however you’d like.

Thurs 10/7: Early train to Venice.  Sightseeing all day in Venice.

Fri 10/8: Train from Venice to Milan; arrive in time for the wedding festivities.

Sat 10/9: Wedding day in the village outside Milan.

Sun 10/10: Fly home.

Now, that’s with Florence as your Tuscan base.  You could alter this itinerary to have a base somewhere in Tuscany, but I’d recommend you spend the final night in Florence so that you can get an early train to Venice (likely via Bologna).

Just know this — this is a rushed itinerary.  You and your wife need to decide what would be best for the two of you — would you come back feeling like you needed a vacation to recover from your vacation?  Or would you feel terrible if you didn’t visit a certain destination?

If you feel like you’d rather cut a destination in favor of having a relaxing trip, read the guidebooks, do some research, and decide what’s best for you.  That’s because everyone, myself included, would give you a different opinion. But this is your vacation!

Good luck, Charlie!  Hope you enjoy your time in Italy.  May it be the first trip of many!

Have any advice? Where would you go if you had ten days in Italy? Please share!