11-Night Tuscany Honeymoon In September


New member

I'm trying to plan our honeymoon in Tuscany, but am having some trouble deciding on an itinerary. We will be there 11 nights in September. Here are my questions for those Tuscany experts out there.

1) Flying into Venice vs. Rome: We are trying to decide if it makes more sense to fly into Venice and out of Rome or book flights roundtrip in and out of Rome. While Venice is beautiful/romantic, my opinion is that it's only worth two nights. I'm wondering if it's too out of the way for such a short time, as I don't want to waste too much time traveling from point A to point B during our trip. I realize it's personal preference, but would you recommend Venice or Rome for 2-3 days? As it will be our first stop and we will be jetlagged, we are mostly looking to relax, do some casual sightseeing and of course eat some good Italian food :).

2) Number of days to spend in Tuscany: How many days are ideal to really experience Tuscany without feeling rushed but also without feeling repetitive? I realize this question is based on what we would like to do/see, so here are the must-sees currently on our list: Siena, Chianti, San Gimignano and Val D'Orcia (specifically Montepulciano). If we have time, we'd also like to see: Lucca, Perugia and Cortona. However, I'm wondering if seeing all of these cities would be repetitive? Also note we will have a rental car.

3) Home bases: We are trying to figure out which cities make the most sense as home bases, as well as how many home bases are ideal. We think it makes sense to stay at least three nights in each home base to avoid wasting time traveling, therefore we will probably only have 2-3 home bases. These are the home bases we are considering: Florence, Siena, Chianti and somewhere in Val D'Orcia. Regarding a home base in Val D'Orcia, does anyone have recommendations? We are considering Montepulciano but are worried it might be too small. Which home bases do you recommend based on the towns we are planning to visit?

4) Coast: My fiance would really like to see some water for part of our trip if we don't end up staying in Venice. A friend recommended Cinque Terre, but that seems a bit out of the way from Tuscany (correct me if I'm wrong). Other destinations we're considering are Porto Ercole or somewhere else in Maremma, but we don't know much about the region. Ideas for a coastal home base or day trips are welcome!

5) Wine: We definitely want to do some wine tasting. Do you have any recommendations for where to do this or specific vineyards/wineries? Also, is it possible to hire a driver for a day to take us around to vineyards? Or any recommended small group tours? That way we don't have to worry drinking and driving.

I realize this is a lot of information, so many thanks in advance for any help you're able to provide!


Well-known member

I'm trying to plan our honeymoon in Tuscany, but am having some trouble deciding on an itinerary. We will be there 11 nights in September. Here are my questions for those Tuscany experts out there.

1) Flying into Venice vs. Rome:

3) Home bases:

Buongiorno -

I have always suggested coming into Rome or Venice and leaving from the other to save travel time. Venice can be expensive and my suggestion is though you may do two days, try to stay only one night. You could fly into Venice, stay the night - most of the next day then TRAIN it to Florence, stay the night and then pick up a car for your travels.

As for a home base, I would suggest splitting your time between the San Gimignano area and Montepulciano. Montepulciano is definitely not a small area and is the perfect base for many of your suggested visits.

day 1 arrival Venice sleep here one night
day 2 Enjoy Venice go to Florence in the late afternoon, Twilight walk and dinner
day 3 Hit the museums & markets in Florence
day 4 Go to San Gimignano, Chianti and area. Make your base for two nights
day 5 from the San Gimignano area go to Volterra & Cecina (coast)
day 6 Go to Montepulciano passing through Siena, sleep in Montepulciano
day 7 Montepulciano & Relax You will need a day of soaking up the sun, wine and culture
day 8 Montepulciano Pienza, Bagno Vignoni
Day 9 Montepulciano visit Perugia & Assisi or Cortona & Arezzo
Day 10 go to Rome
Day 11 Rome

Day 8 or 9 could be an optional if you want another day in Rome

Buon Viaggio


The Tuscan Expert ;-)
Staff member
Donna has already provided a great suggested itinerary! Keep in mind that everywhere you go in Tuscany you'll have the chance to taste great local wines - including at local wine shops, many run directly by the producers. If you want to take a tour, you'll find local agencies that offer them in the immediate area - but you can also take a look at the mains ones here:
Also do searches for particular areas - for example, Chianti, Montepulciano, Montalcino, San Gimignano.... to see wider range of results.