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 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 with Apéritif
Sail Naxos
5.0(1)
Starting from: Naxos
2 hours
Free cancellation
Aperitif available
5.0(1)
Aperitif available
From
380 €
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
8 hours
Free cancellation
Food & Drinks available
Food & Drinks available
From
1000 €
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
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 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 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
During the Private Sunset Sailing Cruise in Naxos with Naxos Catamaran, you can enjoy a wonderful view of the Naxos Port during the night.Naxos Catamaran
Private Sunset Sailing Cruise in Naxos
Naxos Catamaran
Starting from: Naxos (Town)
2 hours 30 minutes
Free cancellation
Food & Drinks available
Food & Drinks available
From
800 €
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
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
Private Sailboat Trip to Iraklia, Schinoussa & Naxos with Lunch from Lady K Sailing Cruises Paros.Lady 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
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
Showing 1 - 16 out of 20 offers

What customers love about boat trips in Cyclades

5.0
2 reviews
The coast of Milos on the sailing trip around Milos to Kleftiko with lunch & snorkeling with Odysseus A Cruises Milos.Odysseus A Cruises MilosSailing Trip around Milos to Kleftiko with Lunch & Snorkeling
8 Reviews
Steffen · Solo travelerDEGermany

Relaxed tour with great guides, great swimming spots and information, and good food! The music wasn't too loud, but pleasant. Guides George and Minoas didn't try to create a party-boat atmosphere, which I found very pleasant.

Odysseus A Cruises Milos cruising in the Aegan Sea on a sailing boat trip to West Milos, Kleftiko & Sikia Cave with lunch & snorkeling.Odysseus A Cruises MilosSailing Trip to West Milos, Kleftiko & Sikia Cave with Lunch & Snorkeling
4 Reviews
IOANNIS · CoupleGRGreece

Unforgettable cruise experience in Milos! We started from Paleochori and ended in Adamas, with the highlight being our stop at the breathtaking Kleftiko – truly one of the most beautiful places we've ever seen. Special thanks to our amazing crew, Facundo and Fay! They were incredibly friendly, professional, and full of positive energy. They took great care of everyone on board, shared fascinating stories about the island, and made sure we had a fantastic time. The boat was spacious and spotless, the food was delicious, and everything was perfectly organized. Highly recommended for anyone visiting Milos – don’t miss it!

The sunset during the Sunset Boat Trip in Santorini from Kamari Tours Santorini.Kamari Tours SantoriniSunset Boat Trip around Santorini
6 Reviews
Monika · Group of friendsPLPoland

A fantastic sunset trip with welcome drink and a nice meal onboard. We were picked up from Kamari and dropped off, which was very convenient. The music and atmosphere on the boat was great, I loved every minute.

Popular Boat Tour Providers in Cyclades

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

It was the best experience in a long time. The snorkeling was breathtaking. The colorful fish madness. The food was absolutely delicious. Getting to know the island in this way is a dream. The captain and his staff are super friendly. Always my pleasure!

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

Great experience to be on the sea and to view the coastline. Loved diving into the ocean, the water is so clear. Good food. Great staff. Well worthed.

Sail NaxosSail Naxos
3 Reviews
4 Offers
Picture of a luxurious sailing boat navigating aroun the Small Cyclades.
Free cancellation for all offers
Sarah · FamilyAUAustralia

We wanted to go swimming and the Sail Naxos crew were more than happy to include this in the sunset tour. The food and beverages were lovely and included local produce. The private tour was very reasonably priced for a group of 5.

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
Ian · FamilyGRGreece

Fabulous crew, friendly, approachable and informative. Took us to some beautiful places to swim, snorkel and relax at. Lunch was delicious and they were generous with everything from the food to drinks. Felt more like being on a friends boat than a professional charter tbh. Thank you.

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.

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.

Trending boat trips in Cyclades

Boat Trip to Kato and Ano Koufonisi & Rina Cave from Naxos with BBQ.Jason Daily CruisesBoat Trip to Kato and Ano Koufonisi & Rina Cave from Naxos with BBQ
Bestseller
Free cancellation
From40 € 36 €
Boat Rental without Licence from Aliki (up to 6 people) from The Sailor's Ride Paros.The Sailor's Ride ParosBoat Rental without Licence from Aliki (up to 6 people)
Bestseller
Free cancellation
From220 €
Odysseus A Cruises Milos Catamaran navigating through the Aegan Sea during the catamaran trip from Adamantas to Kleftiko & Polyaigos with lunch & snorkeling.Odysseus A Cruises MilosCatamaran Trip from Adamantas to Kleftiko & Polyaigos with Lunch & Snorkeling
Bestseller
Free cancellation
From110 €

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

Private Luxury Yacht Trip around Milos, Kimolos and Polyaigos from Indigo Yacht Milos.
Beach Boat Trips Cyclades

100 offers

The luxurious INDIGO yacht in the private luxury yacht trip to Folegandros, Sikinos, Polyaigos & Kimolos with Indigo Yacht Milos.
Day Trips Cyclades

80 offers

Sailing Trip from Adamas along the Coast to Kleftiko with Lunch & Snorkeling from Excellent Yachting Milos.
Boat Trips with Lunch Cyclades

68 offers

Private Sunset Sailing Trip to the Fira Channel with Swimming & Open Bar from Glaraki Cruises Antiparos.
Half-Day Trips Cyclades

51 offers

Sailing Trip to Kleftiko & Sykia Cave with Lunch & Snorkeling from Excellent Yachting Milos.
Island Trips Cyclades

49 offers

One of the landscapes that you will be able to see during the Private Sunset Boat trip to Therasia Island with Swimming and Snorkeling Stops with Sirigos Yachting Fira.
Catamaran Trips Cyclades

43 offers

Two people on the boat of Mykonos Cruises enjoying the Sunset Boat Trip around Mykonos.
Sunset Boat Trips Cyclades

42 offers

The boat that is used during the Catamaran Trip to Antiparos with Snorkeling and BBQ from Captain Yannis Cruises Catamaran Paros.
Caves Boat Trips Cyclades

22 offers

Sunset Sailboat Trip to the Fira Channel with Apéritif & Swimming Stops from Paros Boat Trips.
Boat Trips with Aperitif Cyclades

22 offers

Private Sunset Sailing Cruise with a View of Caldera and Oia from Angel Sailing Santorini.
Boat Trips with Dinner Cyclades

19 offers

Traditional Wooden Boat Trip to the Blue Lagoon & Epitaphios Cave with Greek Lunch from Glaraki Cruises Antiparos.
Lagoon Trips Cyclades

15 offers

Friends are jumping into the crystal clear water during their Luxury Catamaran Cruise from Naxos with Snorkeling Breaks with Naxos Yachting.
Yacht Trips Cyclades

13 offers

You want to book one of our activities? We are here to help you!
Laura_checkyeti_Contact
PauliTalk to our Boat Tour Expert
We'll only use the provided contact information to follow up, in line with our privacy policy.

Discover checkyeti

A group of people is having fun during the ski lessons "all in one" for teens of all levels with ski school Neustift Olympia at Stubai glacier.
Ski Schools Stubaier Gletscher

27 offers

View of the Rib Boat Sea Water 550 that you can rent with our Boat Rental in Arbatax (up to 4 people) with Flamar Vacanze Arbatax.
Full Day Boat Rental Gulf of Orosei

21 offers

People having fun during the Sunset Private Sailing Boat Trip around Alghero with Apéritif with Cruise Sail Charter Alghero.
Romantic Boat Trips for Couples Sardinia

10 offers

Snowboarding Lessons (from 10 y.) - Arc 1800 from Arc Aventures by Evolution 2 1800 .
Snowboard Lessons for Beginners Les Arcs

6 offers

The boat that is used during the Private Boat Trip to the Kamenjak National Park with Snorkeling from Luxe Marine Medulin.
Boat Trips with Snorkeling Kamenjak National Park

6 offers

Odysseus A Cruises Milos Catamaran navigating through the Aegan Sea during the catamaran trip from Adamantas to Kleftiko & Polyaigos with lunch & snorkeling.
Boat Trips with Dogs and other Pets Klima

6 offers

Boat Trip to Cape Greco & Blue Lagoon from Protaras & Pernera with Aphrodite I Cruises Cyprus.
Lagoon Trips Konnos Beach

5 offers

A participant enjoying a paragliding experience over Bjelopolje during a tandem paragliding activity with Sky Riders Paragliding Croatia.
Thermic Tandem Paragliding Flights Croatia

5 offers

Woman on deck during the Private Full Day Sailing Yacht Trip in the Zadar Archipelago The Day Sail.
Sailing Tours Ugljan

4 offers

Private Sailing Trip to Cabo de Gata, Playa de los Muertos & Cala San Pedro from NaveGata Cabo de Gata.
Boat Trips with Stops to Swim Carboneras

4 offers

More on checkyeti

Boat Trips PortocolomDay Trips Porto VenereSSI courses & Scuba Diving Réserve CousteauIsar, Munich - Bad Tölz, Bavaria, GermanyBoat Trips with Aperitif Petite TerreBoat Trips with Snorkeling Blue Cave (Lubenice)Boat Trips from Crete to Balos BeachInstagrammable Boat Trips TuscanyPrivate Full Day Trips Cala LunaBoat Trips from Mellieha to GozoPrivate Boat Tours Macherida BeachBoat Trips with Stops to Swim Trapani
Customer reviews
checkyeti.com
4.5
3086 Reviews on
4.3 Excellent | 1551 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 2026 · ImprintMade in Austria, Switzerland & France
Official partnerAtomic
Connect with us
instagramfacebooklinkedinyoutube