Passport To Friday

Passport To Friday

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Passport To Friday
Passport To Friday
Passport To Positano, Italy

Passport To Positano, Italy

Chelsea Martin's avatar
Chelsea Martin
May 09, 2025
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Passport To Friday
Passport To Friday
Passport To Positano, Italy
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This post is a long-time coming, and the first of what I hope to be short, digestible, yet packed with good recommendations, destination guides. To be honest, writing destination guides can be daunting. I am immersed in these destinations daily working on itinerary planning for our travel planning clients, but the thought of putting pen to paper with the knowledge we have built up over the 9 years of my travel business? It’s the thing that gets pushed down on my to-do list each week until eventually it just falls off. Which is why instead of trying to create a full-on guide per destination, I thought if I changed the format it would make me more excited to work on each (I say this now before I start typing, but knowing me I might still blab away at times). So let’s try this out!

First up is Positano which is a fave of so many of our clients! I will caveat that during peak summer it is CROWDED. I personally love May or September or even October. But also summer is a fabulous energy if you are ready to embrace the crowds. Different strokes for different folks!

As a reminder, when booking your trip through us you receive added benefits such as daily breakfast, hotel credit, upgrades and more! Email me at chelsea@passporttofriday.com.


The Logistics

Getting There:

  • 1.5hr drive from Naples Airport

  • or 1hr 15min train from Rome to Naples + 1.5hr transfer

  • or 3-3.5hr drive from Rome


Where To Stay

Le Sirenuse

Perfect For: Those looking to be in the middle of the action & a scene

Highlights: Located in the heart of Positano; Michelin-starred La Sponda with views of Positano; robust calendar of complimentary activities including boat rides & wine tastings & guided hikes

Villa Treville

Perfect For: Those looking for discretion & privacy & an “at-home” feel

Highlights: Ultimate privacy with just 22 rooms/suites; stunning views of Positano with complimentary private boat shuttle to/from the town; private sea access; high-touch personalized service due to the small nature of the property; personally loved every single meal here immensely!

Casa Angelina (technically Praiano)

Perfect For: Those who want a more modern, secluded hotel at a better value

Highlights: Chic white-washed boutique hotel with views out at Positano; located just a few min away from Positano with a complimentary shuttle; beach club & restaurant; often at a slightly lower price point

Il San Pietro di Positano

Perfect For: Those who love sea views & luxury in an old-fashioned, family-run hotel

Highlights: Located 2km from center of Positano (shuttle provided) with views of Positano; private beach club; oceanfront tennis court; Michelin-starred Zass restaurant overlooking the sea; all rooms have sea views

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