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Rate my 14 day itinerary

Posted by on

This is my 2nd time in Italy - last time I went to Rome, Florence, and Venice, following the Rick Steve's guide. This time, I want to spend some time in Rome, visit Bologna because I'm a huge foodie, do a roadtrip around Tuscany or Umbria because I would love to see those rolling hills in-person, and then check out south Italy.

May 7 (Rome): We arrive in Rome

May 8 (Rome): Stay in Rome that night

May 9 (Rome): Stay in Rome at night.

May 10 (Sorrento): Take high speed train from Rome to Naples, spend the day exploring Naples and doing a walking tour. By night, go to Sorrento and check into hotel.

May 11 (Sorrento): Do guided tour of Amalfi coast. Stay in Sorrento.

May 12 (Sorrento): Spend day exploring Sorrento, take ferry to Capri. Potentially visit Pompeii. Stay in Sorrento.

May 13 (Tuscany): Take high speed train all the way to Florence, pick up a car in Florence, and drive out to the Tuscan location (either Pienza, Siena, or a hill town).

May 14 (Tuscany): Explore Tuscany region more by car and Umbria, same home base.

May 15 (Tuscany): Explore Tuscany. Can go to Florence, Siena, Umbria, Perugia. Same home base.

May 16 (Tuscany): Last day in Tuscany.

May 17 (Bologna): Drop car off in Florence, take train to Bologna. Go on food tours.

May 18 (Bologna): Explore Bologna more.

May 19 (Rome): Head back to Rome for our last night in Rome.

May 20: Leave early from Rome.

Evidently, I don't have much of the Tuscany/Umbria portion planned out (May 13-15). I was thinking of exploring some subset of Montepulciano, Val d'Orcia, Siena, Orvieto, Monti Sibillini/Castellucio, or Perugia. I don't know exactly where yet, would love suggestions.

Any suggestions or tips are highly appreciated!!

Posted by
5109 posts

2024, or 2025?
Accommodations may be tight in Sorrento area. Is this booked already?
I personally would not combine Tuscany/Umbria and the south, but I do acknowledge that we all enjoy a different pace.

Posted by
333 posts

Sounds like a decent plan to me overall. For the Tuscany section, we are planning a similar trip and we're staying 3 nights in a farmhouse outside of siena. 1.5 days touring Siena, 1 day driving to Montepulciano, 1 day seeing Val d'orcia, Pienza and Monteciano. Spending 1 night in San Gigmanano and visiting Volterra. (you have 3 nights total so maybe skip the night in SG)

For the Amalfi coast, your two travel days getting there and back will take longer than you think and limit your sightseeing on those days. Add another night here and plan a full day for Pompei and Naples. Take a night away from Rome since you've been there before. Better yet, take 2 nights away from Rome and give yourself an extra night in Tuscany.

Posted by
14 posts

Hey, I updated the itinerary with your suggestions to add an extra day in Tuscany and removed a day in Rome (edited the post). Thanks for your suggestion! Feel free to let me know how this updated itinerary looks.

Posted by
539 posts

Maybe check flying open jaws out of Milan, bologna or Florence? Add that day to Florence. Otherwise it seems well-paced

Posted by
23642 posts

I would support Chris's suggestion. It would be easier, quicker, and probably cheaper to continue on to Milan for return flight.

Posted by
23 posts

This sounds like a great itinerary. I did something very similar recently, except we went to Lake Como at the end instead of Bologna. Would love to see Bologna someday.

Do you have a place in Naples to store your luggage while you explore and do a walking tour?

For May 12, I would either do Capri (my choice) OR Pompeii. We did a day trip to Capri, it took nearly the whole day and we only saw the town of Capri and didn't even make it to Anacapri. You might be faster at walking and sightseeing than me though!

For Tuscany, you can group Pienza, Montepulciano and Montalcino together for a great day in Val d'Orcia. For the Chianti region, I did not like Siena (too busy and touristy) but know that others really enjoy it and its history. I did enjoy nearby San Gimignano but it takes less than two hours to see. I agree that Umbria too would be a lot.

Have a wonderful trip!

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