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Tuscany / Rome Itinerary Feedback

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My partner and I (mid-30s) are planning our first trip to Italy this September and would love a sanity check on our itinerary.

We're both fairly well traveled, but neither of us has ever been to Italy. Our travel style leans much more toward unplugging and soaking in a place than trying to check every attraction off a list. We definitely want to see the essential cultural sights... but this is more of a decompress vacation than a race from landmark to landmark. We live in NYC so it's always a treat to escape the big city and relax in the country.

Current two-week plan is:

  • FLY IN: MILAN / SEPTEMBER 25 (land 26)
  • 3 nights in Pontremoli (context below)
  • 6 nights at an agriturismo in Chianti (easy access to train @ Figline)
    • 2 day trips to Florence
    • 1 day in Siena
    • 1 day in Arezzo (or TBD hill town)
    • 1 winery-focused day / chill day to enjoy the nearby area
  • 4 nights in Rome
  • FLY OUT: ROME / OCTOBER 9

The Pontremoli stop probably looks a little random, but it's actually the entire reason we're going to Italy. We're visiting a close friend who lives there, so those three nights are non-negotiable. It'll mostly be dinners at home, spending time with friends, and relaxing. We're not really treating that as our "Tuscany" portion of the trip... even thought it's technically in the region. We WILL have a rental car through the Chianti portion of the trip (dropping of in Florence before continuing to Rome).

Our biggest question is whether we're over-weighting Chianti and under-selling Rome.

Taking Pontremoli out of the equation, we're debating between:

6 (Chianti) / 4 (Rome) or 5 (Chianti) / 5 (Rome)

Our gut says the slower pace in Chianti will end up being the highlight of the trip, and we can absolutely picture ourselves spending an entire day vegging out there. On the other hand, we'd hate to come home feeling like we shortchanged Rome, especially since it's our first time there.

Thanks in advance for any input!!

Posted by
546 posts

I think your plan is fantastic. We stayed in a rented farmhouse as our base in rural Umbria/Tuscany in 2014.. It’s wonderful to have a base where you can truly live like a local.

We were just in Florence with a side trip to Chianti. By the way you describe your travel philosophy , you will love it.

Are you driving or taking trains? If you are driving to Rome, you may want to stop in Ovierto.

If you are taking a poll, I would choose 6 days Chianti and 4 days.

Posted by
1196 posts

Don’t forget that four nights in Rome equals three full days in Rome…. And you will lose a good half day, if not more moving from Chianti to Rome. Four nights/three days is time to see the major sites in Rome. Most of the ancient sites, the Coliseum, Forum, Pantheon, Circus Maximus, are all close together and it makes a nice day to visit them. If you find the crowds in Rome overwhelming after Chianti, there are a couple of trips outside the city. One is to Ostia Antica, a complete Roman city that was the original port for ancient Rome. It’s only about 30 mins. by train from the Testaccio area of Rome. The other trip is to the Aquaduct Park to see the remains of the hydraulic systems that bought water to Rome. Again just outside the city, accessible by bus. The final day could be devoted to just wandering around the old city. Maybe do a food tour, visit some of the stunning churches. The Ghetto with its mix of time periods. RS guidebook for Rome is most helpful with ideas. When you visit Italy you always leave knowing that you will need to return because there is so much to see everywhere.

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