Santorini · Adventure
Cyclades Sailing & Sunsets
Eight days island-hopping the Cyclades under sail — Santorini, Ios, Naxos and Paros, sleeping aboard.
8 days · 12 Sep
₦3,300,000
per person
Beach
−12% off
★ 4.5 · 2 reviews
Santorini Caldera Escape
Five days on the caldera rim, with a sunset sail, a winery afternoon and enough unstructured time to actually sit still.
- Duration
- 5 days
- Group size
- max 16
- Departures
- 3 dates
- Destination
- Greece
Photographs
About this trip
Santorini rewards a slow pace. This is a short trip built around three fixed points — a catamaran afternoon along the caldera, a tasting at an Assyrtiko winery on the island's windy south side, and a guided early morning in Oia before the cruise ships dock — with the rest of the time left deliberately open. Hotels are cave-style, on the rim, with the view you came for.
Day by day
Private transfer from the airport or port, and an evening to find your footing in Fira. Welcome dinner on a terrace above the caldera.
- Night
- Selected 4★ hotel or similar
- Meals
- Dinner
An early guided walk through Oia while the lanes are still empty, then the rest of the day free. Most people swim.
- Night
- Selected 4★ hotel or similar
- Meals
- Breakfast, dinner
A catamaran afternoon: the hot springs at Palea Kameni, Red Beach, and dinner cooked on board as the sun goes down behind Thirassia.
- Night
- Selected 4★ hotel or similar
- Meals
- Breakfast, dinner
Inland to the volcanic vineyards for a tasting, then the black sand at Perissa. Evening free.
- Night
- Selected 4★ hotel or similar
- Meals
- Breakfast, dinner
Breakfast, then a transfer timed to your flight.
- Meals
- Breakfast, dinner
What’s included
Included
- Accommodation as described
- Daily breakfast
- All transfers and transport in destination
- English-speaking local guide
- All entrance fees listed in the itinerary
- 24/7 emergency contact while travelling
Not included
- International flights
- Travel insurance
- Visa fees where applicable
- Lunches and drinks unless stated
- Tips and personal expenses
Departure dates
What travellers said
The early Oia walk made the trip
We were on the lanes at half six with maybe ten other people. By nine it was shoulder to shoulder and we were already back at the hotel pool. Whoever designed that running order knew exactly what they were doing.
Amara Okonkwo
Santorini Caldera Escape
Beautiful, and busy
No complaints about the hotel or the sailing day. Santorini in June is simply a lot of people, and no itinerary can fix that. The catamaran afternoon was the highlight.
Tom Beckett
Santorini Caldera Escape
Also in Santorini
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