Top Cyclades Islands Sailing Trips

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Cyclades Islands Adventures

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Morning and Sunset Cruise with Meal and Transport Included
Special Offer
Special Offer
Mykonos, Greece
5.0 (5)

Morning and Sunset Cruise with Meal and Transport Included

Choose between a morning or sunset cruise when booking. On the day, depart from your hotel via air-conditioned minivan to Mykonos' new port for the...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (5)
$116.69
$115.69
Milos Private Full Day Catamaran Cruise with Lunch and Drinks
Special Offer
Special Offer
Milos, Greece
5.0 (8)

Milos Private Full Day Catamaran Cruise with Lunch and Drinks

Set sail on a private full-day cruise aboard a luxurious sailing catamaran from Adamantas Port, Milos, for an unforgettable journey to Kleftiko Bay and Polyegos...

9 hours • Free Cancellation
9 hours • Free Cancellation
9 hours • Free Cancellation
5.0 (8)
$3,374.75
$3,373.75
Milos Full-Day Premium Catamaran Cruise Kleftiko and Polyegos
Special Offer
Special Offer
Milos, Greece
5.0 (5)

Milos Full-Day Premium Catamaran Cruise Kleftiko and Polyegos

Experience the magic of Milos on a luxury catamaran cruise designed for total comfort and adventure. Your journey begins at Adamantas, sailing first to the...

9 hours • Free Cancellation
9 hours • Free Cancellation
9 hours • Free Cancellation
5.0 (5)
$221.10
$220.10
Milos Private Half-Day Catamaran Cruise to Kleftiko with Lunch
Special Offer
Special Offer
Milos, Greece
5.0 (4)

Milos Private Half-Day Catamaran Cruise to Kleftiko with Lunch

Experience a private half-day cruise from Adamantas to Kleftiko aboard a luxurious sailing catamaran. Perfect for family, friends, special celebrations, with activities, dining, & breathtaking...

5 hours 30 minutes • Free Cancellation
5 hours 30 minutes • Free Cancellation
5 hours 30 minutes • Free Cancellation
5.0 (4)
$2,792.90
$2,791.90
EXPLORE - Tour Adventure Koufonisia & Naxos (Private max 10 Pax)
Likely to Sell Out
Likely to Sell Out
Paros, Greece
5.0 (1)

EXPLORE - Tour Adventure Koufonisia & Naxos (Private max 10 Pax)

From Paros Piso Livadi Port - Exclusive Private Sailing Adventure Around the Koufonisia Archipelago and Naxos. Enjoy an exclusive sailing trip through the stunning waters...

9 hours • Free Cancellation
9 hours • Free Cancellation
9 hours • Free Cancellation
5.0 (1)
$1,983.69
$1,982.69
Sail the Aegean with Mykonos Tour
Special Offer
Special Offer
Mykonos, Greece
5.0 (20)

Sail the Aegean with Mykonos Tour

This isn’t just sailing — it’s your private Mykonian chapter, written by the wind, the waves, and the smell of fresh seafood on deck. Step...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (20)
$2,562.22
$2,561.22
Private Rhenia sailing cruise with Lunch & Transfer
Special Offer
Special Offer
Mykonos, Greece
5.0 (2)

Private Rhenia sailing cruise with Lunch & Transfer

Our team is highly qualified, with years of experience in the Greek waters; they are our home. Over the last decades, our business has included...

6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
5.0 (2)
$2,263.74
$2,262.74
Full Day Boat Tour Around Milos and Poliegos
Special Offer
Special Offer
Milos, Greece
4.7 (7)

Full Day Boat Tour Around Milos and Poliegos

Every side of the island has complete different things to offer you! There are caves and stories about pirates . There are huge piles of...

10 hours • Free Cancellation
10 hours • Free Cancellation
10 hours • Free Cancellation
4.7 (7)
$186.70
$185.70
Half Day Catamaran Afternoon Cruise in Kleftiko
Special Offer
Special Offer
Milos, Greece
5.0 (1)

Half Day Catamaran Afternoon Cruise in Kleftiko

The Half day afternoon cruise will remain etched in your mind until you repeat it. Enjoy the natural beauties and the incredible variety of rocks,...

6 hours • Free Cancellation
6 hours • Free Cancellation
6 hours • Free Cancellation
5.0 (1)
$180.37
$179.37
Full Day Santorini Catamaran Private Cruise with meal and transfer
Special Offer
Special Offer
Santorini, Greece
5.0 (16)

Full Day Santorini Catamaran Private Cruise with meal and transfer

Booking a Private Catamaran Tour in Santorini is a dream come true! We offer daily cruises to Santorini’s beautiful sights. The best way to spend...

7 hours • Hotel pickup offered
7 hours • Hotel pickup offered
7 hours • Hotel pickup offered
5.0 (16)
$2,562.22
$2,561.22
Santorini Private Cruise Sightseeing Tour with BBQ and Drinks
Special Offer
Special Offer
Santorini, Greece
5.0 (10)

Santorini Private Cruise Sightseeing Tour with BBQ and Drinks

Enjoy swimming & snorkeling in the clear blue waters of the Aegean Sea. You can go snorkeling near the shore and experience the amazing underwater...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (10)
$465.48
$464.48
Mykonos Catamaran Private Delos Rhenia cruise
Special Offer
Special Offer
Mykonos, Greece
5.0 (5)

Mykonos Catamaran Private Delos Rhenia cruise

Indulge in this daily cruise to Delos and Rhenia islands, which lets you bask in the warm Mykonian sun, enjoying the summer breeze as you...

6 hours • Free Cancellation
6 hours • Free Cancellation
6 hours • Free Cancellation
5.0 (5)
$2,734.71
$2,733.71
Katerina Sailing Sunrise and Sunset Cruises
Special Offer
Special Offer
Milos, Greece
5.0 (9)

Katerina Sailing Sunrise and Sunset Cruises

Katerina Sailing Boat Milos is a family-run sailing experience offering authentic and intimate trips around the island of Milos. With Captain Katerina at the helm,...

6 to 8 hours • Free Cancellation
6 to 8 hours • Free Cancellation
6 to 8 hours • Free Cancellation
5.0 (9)
$1,166.88
$1,165.88
Santorini 3 Islands Trip by Sailing boat
Special Offer
Special Offer
Santorini, Greece
5.0 (2)

Santorini 3 Islands Trip by Sailing boat

Enjoy the classic tour trusted by thousands of visitors to Santorini for decades. Ideal for cruise travelers, as the boat tour begins at the port...

5 hours 30 minutes • Free Cancellation
5 hours 30 minutes • Free Cancellation
5 hours 30 minutes • Free Cancellation
5.0 (2)
$40.73
$39.73
Half day Private Sailing cruise in Santorini island up to 6 pax
Special Offer
Special Offer
Santorini, Greece
5.0 (6)

Half day Private Sailing cruise in Santorini island up to 6 pax

Enjoy the cruise like a real sailor and experience moving with the force of the wind! Maria our captain will stand our, together with our...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (6)
$1,048.18
$1,047.18
Santorini: Private Sailing Yacht Cruise with Meal and Drinks
Special Offer
Special Offer
Santorini, Greece
5.0 (6)

Santorini: Private Sailing Yacht Cruise with Meal and Drinks

The Day and Sunset Private Sailing Yacht Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a sailing...

6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
5.0 (6)
$554.27
$553.27
Santorini Private Tour Half-Day Sailing Platinum Catamaran Cruise
Special Offer
Special Offer
Santorini, Greece
4.9 (9)

Santorini Private Tour Half-Day Sailing Platinum Catamaran Cruise

This tour provides a complete experience of Santorini! You can swim in unique and otherwise impassable locations, enjoying the most wonderful of vistas while sailing...

5 hours • Hotel pickup offered • Free Cancellation
5 hours • Hotel pickup offered • Free Cancellation
5 hours • Hotel pickup offered • Free Cancellation
4.9 (9)
$1,435.87
$1,434.87
South Beaches Cruise From Mykonos
Special Offer
Special Offer
Mykonos, Greece
5.0 (2)

South Beaches Cruise From Mykonos

Full Day Mini Cruise Mykonos "South Beaches" ORNOS, DRAGONISSI, FRANGIAS, PARADISE, TROPICANA BAR & KALAFATIS 9-hour excursion with guaranteed departures from 2 May to 31...

8 hours • Free Cancellation
8 hours • Free Cancellation
8 hours • Free Cancellation
5.0 (2)
$112.02
$111.02
Luxury Private Power Catamaran Tour in Santorini
Special Offer
Special Offer
Santorini, Greece
5.0 (7)

Luxury Private Power Catamaran Tour in Santorini

This is not a cookie-cutter approach to cruise sailing! Make your own schedule with us and choose the places you wish to see! Lucky 8...

3 hours
3 hours
3 hours
5.0 (7)
$1,863.43
$1,862.43
5 HourS Blue Lagoon start 1530 - cliff jumping in TRIPITI
Special Offer
Special Offer
Paros, Greece
5.0 (1)

5 HourS Blue Lagoon start 1530 - cliff jumping in TRIPITI

Staring from Piso Livadi port, located at the South East coast of Paros we offer a HALF DAY sailing cruise, tailored for the traveller who...

4 hours 45 minutes • Free Cancellation
4 hours 45 minutes • Free Cancellation
4 hours 45 minutes • Free Cancellation
5.0 (1)
$128.36
$127.36

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