Skip to main content
Easy cancellation
16,000 activities in 25 countries
2 million+ happy customers
DestinationsGift vouchersBlog
Take a sailing tour and let the wind take you to unique locations
Compare offersBest pricesEasy booking
GRGreeceCycladesSantorini

Sailing Tours Oía

8 Offers with the Best Prices 2025/2026
Sort by:
Popular Options
Categories
Included services
Ideal for
Languages
Duration
Popular Options
Categories
Included services
Ideal for
Languages
Duration
Boat Trip in Santorini to the Volcano & Thirasia Island from Caldera's Boats Santorini.Caldera's Boats Santorini
Boat Trip in Santorini to the Volcano & Thirasia Island
Caldera's Boats Santorini
4.8(112)
Starting from: Santorini, Fira
6 hours
Free cancellation
Hotel pickup available
4.8(112)
Hotel pickup available
From
18 €
Check availability
Boat Trip to Thirasia Island & Volcano with Sunset in Oia from Caldera's Boats Santorini.Caldera's Boats Santorini
Boat Trip to Thirasia Island & Volcano with Sunset in Oia
Caldera's Boats Santorini
4.7(18)
Starting from: Santorini
9 hours
Free cancellation
Hotel pickup available
4.7(18)
Hotel pickup available
From
29 €
Check availability
Sailing Cruise around Santorini Caldera with Swimming in Thirasia from Angel Sailing Santorini.Angel Sailing Santorini
Sailing Cruise around Santorini Caldera with Swimming in Thirasia
Angel Sailing Santorini
Starting from: Vlychada
5 hours
Free cancellation
Hotel pickup available
Hotel pickup available
From
80 €
Check availability
Sunset Sailing Trip from Santorini to the Volcano from Caldera's Boats Santorini.Caldera's Boats Santorini
Sunset Sailing Trip from Santorini to the Volcano
Caldera's Boats Santorini
4.7(6)
Starting from: Santorini, Fira
6 hours
Free cancellation
Hotel pickup available
4.7(6)
Hotel pickup available
From
40 €
Check availability
Sunset Sailing Cruise with views of the Caldera, Firá & Oia from Angel Sailing Santorini.Angel Sailing Santorini
Sunset Sailing Cruise with views of the Caldera, Firá & Oia
Angel Sailing Santorini
5.0(7)
Starting from: Vlychada
5 hours
Free cancellation
Hotel pickup available
5.0(7)
Hotel pickup available
From
80 €
Check availability
Private Sailing with an exclusive half-day cruise to enjoy the surroundings of Santorini and share this unforgettable adventure.Angel Sailing Santorini
Private Sailing Cruise around Santorini Caldera with Swimming in Thirasia
Angel Sailing Santorini
5.0(1)
Starting from: Vlychada
5 hours
Free cancellation
Hotel pickup available
5.0(1)
Hotel pickup available
From
800 €
Check availability
Private Sunset Sailing Cruise with a View of Caldera and Oia from Angel Sailing Santorini.Angel Sailing Santorini
Private Sunset Sailing Cruise with a View of Caldera and Oia
Angel Sailing Santorini
5.0(3)
Starting from: Vlychada
5 hours
Free cancellation
Hotel pickup available
5.0(3)
Hotel pickup available
From
800 €
Check availability
Full Day Private Sailing Cruise to Discover Santorini from Angel Sailing Santorini.Angel Sailing Santorini
Full Day Private Sailing Cruise to Discover Santorini
Angel Sailing Santorini
Starting from: Vlychada
10 hours
Free cancellation
Hotel pickup available
Hotel pickup available
From
1300 €
Check availability

Offers available nearby

What customers love about boat trips in Oía

4.8
147 reviews
Boat Trip in Santorini to the Volcano & Thirasia Island from Caldera's Boats Santorini.Caldera's Boats SantoriniBoat Trip in Santorini to the Volcano & Thirasia Island
112 Reviews
Rafael · CoupleFRFrance

We had an amazing experience. It was nice visiting the volcano and to have some explanations about how today Santorini was created. Even if it was short the swimming in hot springs was a nice and adventurous experience.

Sunset Sailing Cruise with views of the Caldera, Firá & Oia from Angel Sailing Santorini.Angel Sailing SantoriniSunset Sailing Cruise with views of the Caldera, Firá & Oia
7 Reviews
Paul · CoupleIEIreland

This was an absolute dream of a trip. George was so knowledgeable and also so accommodating, he explained the trip before we sailed so there was so surprises. Sailing the yacht without the motor as the sun was setting was magical. The food was top class, as good as many restaurants. Anyone thinking of doing a yacht cruise should definitely use these. You will have a fabulous experience

Sunset Sailing Trip from Santorini to the Volcano from Caldera's Boats Santorini.Caldera's Boats SantoriniSunset Sailing Trip from Santorini to the Volcano
6 Reviews
Virginie · FamilyPTPortugal

Excellent outing in a traditional sailboat. No complaints. Top. My son and I enjoyed ourselves. Volcano stop / boat jump to access the hot springs / another stop for swimming and the most beautiful sunset in Oia with meals on board. Drinks are offered as a widely accessible supplement. Very friendly staff. Crazy atmosphere at the end of the day....in any case, the people on board that day were super nice.

Popular Boat Tour Providers in Oía

Caldera's Boats SantoriniCaldera's Boats Santorini
188 Reviews
4 Offers
View of the Caldera's boats on the sea from Santorini.
Free cancellation for all offers
Instant booking confirmation for all offers
Davide · Group of friendsITItaly

Wonderful trip, with an Italian-speaking guide who explained all the island's hidden details. The trip was supposed to last 9 hours (as stated in the description), but we ended up leaving at 8:45 and returning at 9:45, so it was worth it. Fantastic experience.

Angel Sailing SantoriniAngel Sailing Santorini
11 Reviews
5 Offers
null-null-hero
Free cancellation for all offers
Joshua · FamilyUSUnited States

Captain George & Elias made it a unforgettable experience! The boat is huge with locks of comfortable decks to sit & admire the views. Would highly recommend booking with them!

Oía: Similar activities

Boat Trip in Santorini to the Volcano & Thirasia Island from Caldera's Boats Santorini.
Boat Trips Oía

35 offers

Private Targa Motor Yacht Cruise around Thirasia Island with BBQ & Transfer.
Private Boat Tours Oía

17 offers

A woman enjoys the Private Sunset Boat Trip with Volcano Hike with Spiridakos Sailing Cruises Santorini.
Sunset Boat Trips Oía

14 offers

Catamaran Trip around Santorini with BBQ, Open Bar & Snorkeling from Volcano Yachting Santorini.
Catamaran Trips Oía

14 offers

A catamaran sailing along the Caldera of Santorini during the Private Full Day Catamaran Trip to the Santorini Islands with BBQ & Open Bar from Volcano Yachting Santorini.
Boat Trips with Snorkeling Oía

11 offers

Discover checkyeti

RIB Boat Rental from Marsala to the Egadi Islands (up to 6 people) from Sea Star Marsala.
Boat Rental with snorkeling Sicily

20 offers

Winter Guided Kayaking and Hiking Tour in the Reinefjord from Hamnøy with Snacks from Saga Adventures Lofoten.
Kayak & Canoe Northern Norway

10 offers

A couple enjoying their time during the Private Boat Trip from Capri to Amalfi and Positano with Giuliani Charter Sorrento.
Boat Trips from Positano to Li Galli Islands

6 offers

The boat used during the Boat Trip from Sliema to Gozo, Comino and Blue Lagoon with Luzzu Cruises Malta.
Lagoon Trips Cittadella

6 offers

View of the Afrodite boat used for the Boat Trip from Marettimo to Favignana and Levanzo with Swimming Stops with Aegates Rent Boat Marettimo.
Boat Trips with Aperitif Marettimo Island

5 offers

Canyoning in the Nefeli Canyon along Voidomatis River from Alpinezone Epirus.
Canyoning with Kids Ioannina (Yannena)

4 offers

Sailboat Trip along Skjálfandi Bay from Kúsavík with Whale Watching from Northsailing Húsavík.
Half-Day Trips Diamond Circle

4 offers

Boat Rental in Torrevieja (up to 8 people) with Licence from Argo Nautic Torrevieja.
Boat Rental Playa de la Mata

3 offers

Sailboat Trip from Portocolom to the East Coast with Tapas & Drinks from Caribia Sailing Alcúdia.
Luxury Boat Trips Cala Ferrera:

3 offers

A boat is floating on the crystal clear water while doing a Private Boat Trip with Dinner & Swimming stops at Sunset organized by Aloha Boat Charters Malta.
Culinary Boat Trips for Foodies Crystal Lagoon Comino

3 offers

More on checkyeti

Private Ski Instructors Kranjska GoraCulinary Boat Trips for Foodies PortugalBoat Trips for Fishing Enthusiasts AlcúdiaBoat Trips with Snorkeling Isola delle FemmineRIB Boat Trips ChietiBoat Trips with Dolphin Watching ElbaScuba Diving for Kids Las Palmas de Gran CanariaBoat Trips with Stops to Swim Piscine di Venere (Orosei)Full Day Boat Rental BolBoat Trips with Snorkeling MarbellaBoat Trips with Snorkeling Son SauraBoat Trips from Ayia Napa to Cape Greco and Blue Lagoon
Customer reviews
checkyeti.com
4.5
2874 Reviews on
4.3 Excellent | 1409 reviews
As seen on:ForbesThe TelegraphemerceFazSport ActivFit for FunBlick CH
Company
About
New look
PressTermsPrivacyAccessibility
Providers
Provider loginWork with us
Support
Help Center
lauraainaravictor
Secure payment
Carte Bleue logoBancontact logo
© checkyeti 2025 · ImprintMade in Austria, Switzerland & France
Official partnerAtomic
Connect with us
instagramfacebooklinkedinyoutube