Itinerary: Positano, Florence & Tuscany

The Itinerary:

The Highlights:

Boston to Rome to Positano

  • Arrive in Rome & hop a train from Rome to Naples via
  • Arrange transport from Naples to Positano (I arranged through my hotel)


  • Stay at La Casa de Peppe, a beautiful renovated villa close to Via Fornillo
  • Eat at Ristorante Mediterraneo and soak up the views at Hotel Ancora; make a reservation at Le Sireneuse for a scenic lunch
  • Visit Fornillo beach – the smaller of the two Positano beaches – and soak up the local scene.
  • Take a ferry to Sorrento, and enjoy the bustling shops and winding streets
  • The weather didn’t cooperate for me, but if you’re more lucky – check out the Path of the Gods, or book a day trip by boat to explore Capri & the coast.


  • Stay in the Santa Croce neighborhood at this epic Airbnb – you might be tempted to just stay in!
  • Eat at Zeb – OMG it was good
  • Hike up to Plaza Michelangelo and enjoy the amazing views of the city
  • Lounge in Piazza Santo Spirito for a lively local vibe
  • Grab drinks at this extremely scenic (but very randomly located) roof deck bar, atop a department store by the Duomo
  • Shop for leather at Noi
  • Check out an Airbnb experience – I went on an excellent street art tour
  • PSA: Make your reservations for the Duomo & museums in advance – if you don’t, you’ll be unable to visit!

For more detail, check out my posts about each step in the journey!

Author: Jess

Always planning my next adventure.

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