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
GRGreece

Private Sailing Trips Cyclades

20 Offers with the Best Prices 2025/2026
Sort by:
Popular Options
Locations
Included services
Ideal for
Languages
Duration
Popular Options
Locations
Included services
Ideal for
Languages
Duration
Private Sailing Boat Trip to the Blue Lagoon & Epitaphios Cave with Greek Lunch from Glaraki Cruises Antiparos.NewGlaraki Cruises Antiparos
Private Sailing Boat Trip to the Blue Lagoon & Epitaphios Cave with Greek Lunch
Glaraki Cruises Antiparos
Starting from: Antiparos, Pounta
7 hours
Free cancellation
Food & Drinks available
Food & Drinks available
From
1500 €
Check availability
Private Sailing Trip from Paros to Koufonisia with Food, Snorkeling & SUP from Voreas Paros Cruises.NewVoreas Paros Cruises
Private Sailing Trip from Paros to Koufonisia with Food, Snorkeling & SUP
Voreas Paros Cruises
Starting from: Piso Livadi
9 hours
Free cancellation
Food & Drinks available
Food & Drinks available
From
2250 €
Check availability
Private Sunset Sailing Trip to the Fira Channel with Swimming & Open Bar from Glaraki Cruises Antiparos.NewGlaraki Cruises Antiparos
Private Sunset Sailing Trip to the Fira Channel with Swimming & Open Bar
Glaraki Cruises Antiparos
Starting from: Antiparos, Pounta
3 hours
Free cancellation
Drinks available
Drinks available
From
900 €
Check availability
Private Sunset Sailing Boat Trip from Naxos with SUP from Sail Naxos.Sail Naxos
Private Sunset Sailing Boat Trip from Naxos
Sail Naxos
5.0(1)
Starting from: Naxos
2 hours
Free cancellation
Drinks available
5.0(1)
Drinks available
From
400 €
Check availability
Private Sailing Trip from Paros to Antiparos with Food, Snorkeling & SUP from Voreas Paros Cruises.NewVoreas Paros Cruises
Private Sailing Trip from Paros to Antiparos with Food, Snorkeling & SUP
Voreas Paros Cruises
Starting from: Piso Livadi
5 - 8 hours
Free cancellation
Food & Drinks available
Food & Drinks available
From
1450 €
Check availability
Private Traditional Wooden Boat Trip to the Blue Lagoon with Greek Lunch from Glaraki Cruises Antiparos.NewGlaraki Cruises Antiparos
Private Traditional Wooden Boat Trip to the Blue Lagoon with Greek Lunch
Glaraki Cruises Antiparos
Starting from: Antiparos, Pounta
7 hours
Free cancellation
Food & Drinks available
Food & Drinks available
From
4000 €
Check availability
Private Sailing Boat Trip from Naxos with Lunch and SUP from Sail Naxos.NewSail Naxos
Private Sailing Boat Trip from Naxos with Lunch and SUP
Sail Naxos
Starting from: Naxos
9 hours
Free cancellation
Food & Drinks available
Food & Drinks available
From
1100 €
Check availability
Half-Day Private Sailing Boat Trip to the Blue Lagoon with Open Bar from Glaraki Cruises Antiparos.NewGlaraki Cruises Antiparos
Half-Day Private Sailing Boat Trip to the Blue Lagoon with Open Bar
Glaraki Cruises Antiparos
Starting from: Antiparos, Pounta
3 hours 30 minutes
Free cancellation
Drinks available
Drinks available
From
950 €
Check availability
Private Sailboat Trip to Iraklia, Schinoussa & Naxos with Lunch from Lady K Sailing Cruises Paros.NewLady K Sailing Cruises Paros
Private Sailboat Trip to Iraklia, Schinoussa & Naxos with Lunch
Lady K Sailing Cruises Paros
Starting from: Piso Livadi
9 hours
Free cancellation
Food & Drinks available
Food & Drinks available
From
1700 €
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
The boat on the water, with people on it and swimming in the water during the Private Boat Trip from Vlychada along Santorini's coastline with BBQ & Swimming from Barca Sailing Santorini.Barca Sailing Santorini
Private Boat Trip from Vlychada along Santorini's coastline with BBQ & Swimming
Barca Sailing Santorini
Starting from: Vlychada
5 hours
Hotel pickup available
Hotel pickup available
From
780 €
Check availability
The sailing boat sailing on the ocean with the beautiful orange sunset in the background during the Private Sunset Boat Trip from Vlychada along Santorini's coastline with BBQ & Swimming from Barca Sailing Santorini.Barca Sailing Santorini
Private Sunset Boat Trip from Vlychada along Santorini's coastline with BBQ & Swimming
Barca Sailing Santorini
5.0(1)
Starting from: Vlychada
5 hours
Hotel pickup available
5.0(1)
Hotel pickup available
From
780 €
Check availability
Private Boat Trip around the Cyclades with BBQ from Jason Daily Cruises.Jason Daily Cruises
Private Boat Trip around the Cyclades with BBQ
Jason Daily Cruises
Starting from: Naxos
8 hours
Food & Drinks available
Food & Drinks available
From
5000 €
Check availability
The catamaran Apollon from Naxos Catamaran is sailing along the rocky coast of the Cyclades during the Private Sailing Cruise on a Luxury Catamaran from Naxos.Naxos Catamaran
Private Sailing Cruise on a Luxury Catamaran from Naxos
Naxos Catamaran
Starting from: Naxos (Town)
6 hours 30 minutes
Free cancellation
Food & Drinks available
Food & Drinks available
From
1800 €
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
Private Sailboat Trip to Koufonisia & Naxos with Lunch from Lady K Sailing Cruises Paros.NewLady K Sailing Cruises Paros
Private Sailboat Trip to Koufonisia & Naxos with Lunch
Lady K Sailing Cruises Paros
Starting from: Piso Livadi
9 hours
Free cancellation
Food & Drinks available
Food & Drinks available
From
1700 €
Check availability
Showing 1 - 16 out of 20 offers

What customers love about boat trips in Cyclades

5.0
3 reviews
Boat Trip to Paxos (Gaios), Antipaxos & Caves from Corfu from Corfu Cruises.Corfu CruisesBoat Trip to Paxos (Gaios), Antipaxos & Caves from Corfu
172 Reviews
Tanja · FamilyDEGermany

It was a great experience with a wonderful crew.

Boat Trip to Paxos (Gaios), Antipaxos & Caves from LefkimmiCorfu CruisesBoat Trip to Paxos (Gaios), Antipaxos & Caves from Lefkimmi
35 Reviews
Nadine · FamilyFRFrance

Very friendly staff, a wonderful day, I recommend it to you absolutely, superb site 🤩 We even danced on board the boat

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
Christophe · FamilyFRFrance

Great outing! Great crew! Awesome guide! Great value for money! I honestly recommend it!!

Popular Boat Tour Providers in Cyclades

Angel Sailing SantoriniAngel Sailing Santorini
11 Reviews
5 Offers
null-null-hero
Free cancellation for all offers
Torsten · CoupleDEGermany

Nice small international group (9 persons + the entertaining Captain George and his female assistant). You also really sail under sails and without engine. Women are allowed to navigate, if they like. Good food (fish, seafood pasta, salad...) with white wine, soft drinks and water. One long stop for swimming, fish observing and dinner in front of the Island of Therasia. Stunning Sunset with the red sun going down into the ocean at the horizon...

Jason Daily CruisesJason Daily Cruises
8 Reviews
3 Offers
null-null-hero
Free cancellation for all group offers
Valentina · CoupleITItaly

A wonderful experience! I recommend everyone to try this wonderful activity. The sea is crystal clear and you can see enchanting landscapes. Rina's cave is beautiful!! The staff is helpful and very kind.

Sail NaxosSail Naxos
3 Reviews
4 Offers
Picture of a luxurious sailing boat navigating aroun the Small Cyclades.
Free cancellation for all offers
Instant booking confirmation for all offers
Laetitia · CoupleGBUnited Kingdom

Lovely experience as a couple.

Voreas Paros CruisesVoreas Paros Cruises
2 Reviews
3 Offers
Some sailing boats of Voreas Paros Cruises in the turquoise waters near Paros during a sailing boat trip.
Free cancellation for all offers
Ragnhild Cathrine · FamilyNONorway

Everything was great. We had the best day on the boat with a very dedicated crew ❤️

Barca Sailing SantoriniBarca Sailing Santorini
1 Review
4 Offers
The sailing boat of Barca Sailing Santorini with people on it, enjoying the sun and the blue water on the coast of Santorini.
Free cancellation for all group offers
Valentin · CoupleATAustria

It was so unbelievably great! There were only two of us + 2 skippers who were really nice and funny. The food was extremely plentiful and delicious! The sunset on the “high seas” was fantastic.

Naxos CatamaranNaxos Catamaran
1 Review
2 Offers
The sailing yacht of Naxos Catamaran, who offers different cruises starting from the Port of Naxos, is tthe perfect place to observe the sunset over the Aegean Sea.
Free cancellation for all offers
Sari · Solo travelerFIFinland

Nice crew, good trip.

Trending boat trips in Cyclades

View of the boat during the boat trip from Santorini to the volcano with Caldera's Boats.Caldera's Boats SantoriniBoat Trip in Santorini to the Volcano & Hot Springs
Bestseller
Free cancellation
From15 €
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
Bestseller
Free cancellation
From18 €
Sailing Trip from Adamas along the Coast to Kleftiko with Lunch & Snorkeling from Excellent Yachting Milos.Excellent Yachting MilosSailing Trip from Adamas along the Coast to Kleftiko with Lunch & Snorkeling
Recently booked
From100 €

Cyclades: All locations

Private Sailing Trip from Paros to Antiparos with Food, Snorkeling & SUP from Voreas Paros Cruises.
Paros

9 offers

Private Sunset Sailing Boat Trip from Naxos with SUP from Sail Naxos.
Naxos

7 offers

Private Sunset Sailing Cruise with a View of Caldera and Oia from Angel Sailing Santorini.
Santorini

6 offers

Private Sailing Trip from Paros to Antiparos with Food, Snorkeling & SUP from Voreas Paros Cruises.
Antiparos

5 offers

Similar activities in Cyclades

Sailing Trip from Paros to Antiparos with Lunch, Snorkeling & SUP from Voreas Paros Cruises.
Beach Boat Trips Cyclades

97 offers

Full Day Pirate Boat Trip around Antiparos and to Blue Lagoon with BBQ Lunch from Captain Morgan Cruises.
Day Trips Cyclades

80 offers

Catamaran on the water, with the sunset in the back.
Boat Trips with Lunch Cyclades

65 offers

The boat and the sunset during the Sunset Boat Trip to Parikia Bay with Swimming and Snorkeling from Eurodivers Paros.
Island Trips Cyclades

50 offers

A woman enjoys the Private Sunset Boat Trip with Volcano Hike with Spiridakos Sailing Cruises Santorini.
Half-Day Trips Cyclades

48 offers

Private Yacht from The Sailor's Ride Paros on the water.
Sunset Boat Trips Cyclades

40 offers

A catamaran on the blue sea of the Aegean Sea during the Private Morning Catamaran Trip along the Caldera with BBQ & Open Bar from Volcano Yachting Santorini.
Catamaran Trips Cyclades

40 offers

Boat Trip to Blue Lagoon & Caves of Antiparos with Lunch from Pyrgaki Cruises Paros.
Caves Boat Trips Cyclades

22 offers

A catamaran with the colorful backdrop of the sunset during the Private Sunset Catamaran Trip along the Caldera with BBQ & Open Bar from Volcano Yachting Santorini.
Boat Trips with Dinner Cyclades

19 offers

Private Traditional Wooden Boat Trip to the Blue Lagoon with Greek Lunch from Glaraki Cruises Antiparos.
Boat Trips with Aperitif Cyclades

18 offers

Private RIB Boat Trip to Blue Lagoon, Despotiko & Fira with Swimming & Snorkeling from Escape From Reality.
Lagoon Trips Cyclades

15 offers

Luxury Catamaran Cruise around Santorini Caldera w/ BBQ & Cocktails from Spiridakos Sailing Cruises Santorini.
Yacht Trips Cyclades

11 offers

Customer reviews
checkyeti.com
4.5
2872 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