u/Intelligent_Table913

My friend and I (from US) will traveling to Italy for first time from June 28th - July 13th. We are in our 20s and don't mind taking trains every 2-3 days to cover the cities we want to see. We are flying into Milan for cheaper flights.

We are planning 5 nights in Rome, 3 nights in Florence, 2 nights in Venice, 4 nights in Dolomites. Then we head back to Milan by stopping at Verona to spread out travel time across last 2 days.

Yes, it may seem packed, but we each have one checked bag and a backpack. We don't mind lugging it around, and we have time on the train to sleep and chill.

My friend really wants to see Positano, while I'd rather save that day for a closer day trip from Rome or from Florence. On another trip, I want to experience the Amalfi coast fully and visit Capri, Sorrento, Positano, Amalfi, Ravello, and Pompei. But we don't have time for that on this trip.

He suggested a Viator coastal cruise day trip, which will be a 14 hour day for just 2 hours in Positano. I don't think it's worth the amount of travel for 2 hours of experience. But the approach from the water could be cool, and tickets are $83. It seems like a good deal but reviews on the site are mixed due to cancelled cruises for weather conditions.

Has anyone taken this coastal cruise in the summer (July)? Did you actually get 2 hours in Positano? How was trip to and from Positano?

Is it worth it to cram this day trip in our already packed schedule just to tick off Positano?

Hi all, my friend and I are visiting for the first time. We have 16 total days to spend, from June 27 to July 13. We want to visit major cities and a few underrated picturesque spots! We are trying to fit in Amalfi Coast, Pompeii and Dolomites.

I'm worried about the crowds and wait times delaying our schedule. How crowded will train stations be? The train ride from Rome to Milan may be 3 hours, but would the door-to-door be 5+ hours?

We're used to 80-85 humid on east coast of US, and we need to prepare for the heat. That's why we want to go south first, and come back up north to the mountains.

We know it's a packed schedule. We are Americans with not much PTO, so we want to maximize it!
I italicized my questions/doubts below.

Itinerary Rough Draft
----------------------

Sat, 6/27 Evening: Arrive in Milan

• freshen up, dinner, walk near Duomo or city center

Sun, 6/28 - Tue, 6/30: Rome

• Sunday: high speed train to Rome in morning (3 hrs), Spanish Steps, Pantheon, Trevi Fountain at night
  • Is this doable with jetlag?
• Monday: Colosseum, Roman Forum, Palatine Hill
• Tuesday: Vatican City, Trastevere

Wed, 7/1: Sorrento

• high-speed train to Naples, local train to Sorrento (3 hrs total)
• Marina Grande, Piazza Tasso, cliffside

Thu, 7/2: Positano

• take ferry
• hillside viewpoints, explore town, rent a Vespa
• Do we have time for quick trip to another Amalfi town in evening?

Fri, 7/3: Pompeii + Naples or Sorrento?

• Pompeii tour in morning
• Should we go to Naples and quickly visit 1-2 places in evening? Or return to Sorrento and check out more stuff there?

Sat, 7/4 - Sun, 7/5: Florence

• high-speed train from Naples to Florence (3 hrs)
• Still need to plan this out

Mon, 7/6: Pisa

• can we move Pisa up to Sunday? Do we need 2 days for Florence?
• train to Venice

Tue, 7/7 - Wed, 7/8: Venice

• main attractions, gondola rides
• Should we visit Burano for colorful buildings?
• travel to Ortisei on Wed night
  • Train + bus? Or get rental car in Bolzano?

Thu, 7/9 - Sat, 7/11: Dolomites

• Seceda, Lago di Braies
• How to choose between Tre Cime (takes 5 hrs), Val Gardena, Val di Funes, and Alpi di Suisi?
  • What places can we cover for each day?

Sun, 7/12: Verona

• Train from Bolzano to Verona
• major attractions, Old Town
• Romeo and Juliet play in evening

Mon, 7/13: Milan

• train to Milan
• Duomo rooftop, Galleria stroll, city center, relax

Tue, 7/14: Fly out

------------------

I need help planning the Dolomites portion, and deciding to do Pisa on 7/5 or 7/6. What do you think we should remove or change? What are we missing or forgetting?

We did an Eastern Europe trip last year where we moved cities every 1-2 days. So we're kinda used to the fast pace. But travel time on trains and crowds will be tougher in Italy.

Should we remove a day from Rome or Amalfi to have more time for North? What else should we visit in North?

Is it better to visit the hottest places first and then move back to mountains? Or visit each city in a circular path in sequence? Idk if the heat gets progressively worse over our trip.

Any advice would be greatly appreciated!