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Cliffs and Caldera

Santorini, Positano, Capri


Designed by Molly

This example itinerary from


8 days


  • Combine some of Europe’s most famous coastal destinations in Italy and Greece
  • Sunset cruise in Santorini caldera
  • Michelin star restaurant hopping on the island of Capri
  • Watch the world go by from your private terrace in picturesque Positano
  • With a skipper and private charter, head to wonderfully secluded beaches

What’s Included

  • 7 nights Bed & Breakfast
  • 3 boat excursions 
  • A daily choice of experiences 
  • International Economy class flights
  • All ground transfers and European flights

Example Itinerary

Day 1-4


  • Discover the famous red sand beaches of the south coast
  • A day trip to the island of Folegandros

A world-famous island, the product of a volcanic eruption and with arguably the greatest sunsets on Earth.

Begin in Santorini where you’ll spend three nights at Perivolas. The oldest hotel in Oia, rooms are located in caves once used by fishermen, full of bursting colour against plenty of white. Enjoy this family-owned and charmingly authentic property with exceptionally high service. A trip to Santorini isn’t complete without a day’s snorkelling from your own private boat, returning to land as the sun sets on the horizon. A spot of Santorini wine tasting is also highly recommended; wine is produced uniquely here owing to the non-traditional environment.

Day 4-6


  • Enjoy a cooking lesson with the famous Mamma Agata
  • Discover the secrets of southern Italy’s most celebrated liqueur whilst limoncello tasting

Positano is considered the crown jewels of the Amalfi Coast and one of the most photogenic corners of Italy.

Hop on a flight from Santorini to the cliff tops of the Amalfi, Coast where you’ll begin with two nights in Casa Angelina in Positano. Whilst in the celebrated Positano, amble the streets and enjoy a spot of yacht-ogling. Hop on your own private boat for a picnic at sea, the ultimate opportunity to escape the crowds of the coast. We can source guides for limoncello tasting or book you into the world-famous Mamma Agata’s cooking school to learn how to recreate an Italian lasagne at home.

Day 6-8

CAPRI, Italy

  • Enjoy a private picnic spot on the rocks by the sparkling Blue Grotto
  • Explore the iconic island and its history with a local guide

Away from the hustle and bustle of the Amalfi Coast, Capri offers all the beauty and coastal views but with the added luxury of peace and quiet.

Finish your trip on the island of Capri, where you’ll spend two nights at the Capri Tiberio Palace. Learn about Capri’s ancient history with your local guide – keep up to date with the role of this iconic island over time. When the tides are in your favour, enjoy a prepared picnic on the rocks by the Blue Grotto. Alternatively, swim out at low tide after the boats have left, or better, hop on your own private boat to reach the Blue Grotto before whizzing around Capri’s more secluded sea spots.

The Donnellys

We are just leaving the villa now to go to the hotel and I wanted to let you know that we have had the best week ever. I’m nearly crying leaving Angelina and Kimberly. We have never met kinder people who became part of our family for the week. They looked after us so so well and the kids adored them. Can we book again for next year? I can be happier leaving knowing that I will meet them again.

Call +44 (0)203 137 1247

Call +1 (800) 635 8124

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These four to five-star accommodations offer the high level of service that our team look always look for, with a range of facilities on offer.


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These properties won't necessarily offer all of the typical luxurious facilities, but will always provide memorable experiences, from camping out in the bush to climbing up to a treehouse.

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