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Updated Early Planning Italy (need help Tuscan Village/Naples Beach)

I posted in here a bit ago, but as we are in the very early planning stages, I keep coming up with new ideas! This trip will likely be last 2 weeks of June 2027. At this time the only direct flight is Rome and we prefer flying direct. We do not want to rent a car for a few reasons and a big one being driving after having wine. Open to trains/walking/biking/taxi and even splurge on private transfers (have looked at Day Trip in the past). Travelers are 2 adults and one 14 yo girl.

Looking on advice for places to stay (we like having a pool option!) in the areas noted; recommendation on Tuscan village to visit for a few days; and desperately need a beach hotel idea with beach access or recommendation on beach club (we do enjoy renting chairs etc). Could be open to changing the Naples section of the trip.

Day 1: Land Rome (am) | Florence (train)
Day 2: Florence - city sights
Day 3: Florence - day trip to Bologna
Day 4: Florence - city sights
Day 5: Leave Florence - Arrive Montepulciano (or other??)
Day 6: Montepulciano - Wine Tasting/Walking Around
Day 7: Montepulciano - Hike/Wine Tasking
Day 8: Leave Montepulciano - Arrive Naples (considering splurge for car service - ie Day Trip - with a stop on the way)
Day 9: Naples area - beach day/city night
Day 10: Naples area - beach day/city night
Day 11: Naples area - beach day/city night
Day 12: Leave Naples - Arrive Rome
Day 13: Rome sights
Day 14: Rome sights
Day 15: Fly Home

Posted by
6369 posts

For your Naples time, I would stay close to the port and take ferries to the three islands. Maybe beach time on Ischia? You could go to the Amalfi coast, but you’ll sit in traffic a lot, and there are alternatives.
If the beach part is more important than the city attractions of Naples, I would again consider staying somewhere close to Rome instead, where there are lovely beaches and towns that are vibrant in summer..

Posted by
1683 posts

Hydrofoil trip Naples to Capri. Pompei. Hotels with Pool, best bet for sunning and swimming. Naples is a very Metropolitan Port City. I agree with the 1st answer.

Posted by
62 posts

Where would be suggestions closer to Rome? I feel we would like Naples, but it isn't on a bucket list for us. We have great memories from our beach stays during our sightseeing Europe vacations, so really just looking for beauty/relaxation/good food.

Posted by
6369 posts

I love the coastal area of the Tuscan coast from Cecina south to the border with Lazio, but you might want a car, which you could use dung the day for exploring and keep parked in evenings.

Posted by
1808 posts

Montepulciano is best with a car. It can be done with a 2 hour train from Florence to Chiusi-Chianciano and then coordinate an hour long bus to Montepulciano or two buses from Florence but the travel logistics are not simple. Trenitalia will sell you the train/bus in a single ticket if you choose "Montepulciano centro" so it is doable but allow 3-4 hours and a train bus change to make it happen. In general the tiny Tuscan hilltowns of film and photos are not well served by public transportation. And because you have to reverse this process getting to Naples from Montepulciano will take 5-7 hours.

If you want easily train accessible towns there is Siena (large but very scenic and touristy), Arezzo (modern but ancient, less touristy) but if want the small hilltown experience your best bets are probably Cortona (train but bus up the hill from the station) or Orvieto (train plus cool funicular ride up the hill or short, boring bus). Orvieto is in Umbria not Tuscany but is a great little hilltown with an oversized cathedral and sweeping countryside views.

Happy planning and have a great trip,
=Tod