Top Cyclades Islands Sailing Trips

Santorini Volcanic Islands Cruise: Volcano, Hot Springs and Thirassia
Likely to Sell Out
Likely to Sell Out
Santorini, Greece

Morning visit to Volcano and its sulfur waters on a Traditional Greek Caique Boat. The first stop of your adventure is the volcano of Santorini,...

6 hoursHotel pickup offeredFree Cancellation
6 hoursHotel pickup offeredFree Cancellation
6 hours • Hotel pickup offered • Free Cancellation
4.1 (193)
$58.29
$57.29

South Coast Premium Sail Cruise–Lunch, Drinks, Swim & Sunset
Special Offer
Special Offer
Mykonos, Greece

Spend an evening sailing along southern Mykonos and taking in the beauty of its beaches during this sunset cruise. Spend the late afternoon discovering idyllic...

4 hoursHotel pickup offeredFree Cancellation
4 hoursHotel pickup offeredFree Cancellation
4 hours • Hotel pickup offered • Free Cancellation
4.9 (69)
$104.37
$103.37

Luxury Catamaran Semi private cruise with meals & drinks and transportation.
Special Offer
Special Offer
Mykonos, Greece

Take a break from the resort crowds and get offshore for a while on this chilled-out sailing excursion around Mykonos. Choose a trip to the...

5 hoursHotel pickup offeredFree Cancellation
5 hoursHotel pickup offeredFree Cancellation
5 hours • Hotel pickup offered • Free Cancellation
4.5 (41)
$186.62
$185.62

Milos & Poliegos Catamaran Cruise Homemade Full menu BBQ & Drinks
Special Offer
Special Offer
Milos, Greece

Experience a luxury full-day cruise aboard the new catamaran Lagoon 46 “Naya II”, where elegance meets comfort and have a special day by exploring the...

9 to 10 hoursFree Cancellation
9 to 10 hoursFree Cancellation
9 to 10 hours • Free Cancellation
5.0 (41)
$244.94
$243.94

Sailboat Full Day Tour in Kleftiko and Blue Lagoon with Lunch
Special Offer
Special Offer
Milos, Greece

Make this day unique, forget about any distraction while onboard. Enjoy a genuine adventure that will remain unforgettable. Take some stunning photos and videos that...

9 hoursFree Cancellation
9 hoursFree Cancellation
9 hours • Free Cancellation
5.0 (36)
$192.45
$191.45

Private Full Day Tour in South Paros Caves Despotiko
Special Offer
Special Offer
Paros, Greece

We sail from Pisso Livadi to the southwest by 09:30, hoisting our sails and adjusting our course according to the prevailing winds we enjoy a...

8 hoursFree Cancellation
8 hoursFree Cancellation
8 hours • Free Cancellation
5.0 (24)
$1,574.61
$1,573.61

Santorini: Caldera Private Sailing Boat Cruise with Beneteau Oceanis 46.1
Likely to Sell Out
Likely to Sell Out
Santorini, Greece

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number...

5 hoursHotel pickup offeredFree Cancellation
5 hoursHotel pickup offeredFree Cancellation
5 hours • Hotel pickup offered • Free Cancellation
5.0 (16)
$641.51
$640.51

Sunset cruise to Rhenia& Little Venice with transfer
Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Although not a day trip, this experience provides the perfect ending to a day in beautiful Mykonos. Set sail towards the horizon, with a glass...

4 hoursHotel pickup offeredFree Cancellation
4 hoursHotel pickup offeredFree Cancellation
4 hours • Hotel pickup offered • Free Cancellation
4.9 (17)
$139.97
$138.97

Santorini Full Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport
Likely to Sell Out
Likely to Sell Out
Santorini, Greece

Enjoy unique views of Santorini from the sea during this 7 hour daycruise, starting from the port of Vlychada. Passing from the Red Beach you...

7 hoursHotel pickup offeredFree Cancellation
7 hoursHotel pickup offeredFree Cancellation
7 hours • Hotel pickup offered • Free Cancellation
4.9 (15)
$781.47
$780.47

A Boat Trip to the Pirate Caves & Blue Lagoon
Special Offer
Special Offer
Paros, Greece

Join this boat trip to the South Pirate Caves, where you will enjoy some local white wine and seasonal fruit and snorkelling in the very...

3 hours 30 minutesFree Cancellation
3 hours 30 minutesFree Cancellation
3 hours 30 minutes • Free Cancellation
4.9 (53)
$75.81
$74.81

Santorini Volcanic Islands Cruise: Volcano,Hot Springs,Thirassia and Oia Sunset
Likely to Sell Out
Likely to Sell Out
Santorini, Greece

Morning visit to Volcano and its sulfur waters on a Traditional Greek Caique Boat. The first stop of your adventure is the volcano of Santorini,...

11 hoursHotel pickup offeredFree Cancellation
11 hoursHotel pickup offeredFree Cancellation
11 hours • Hotel pickup offered • Free Cancellation
4.1 (89)
$66.10
$65.10

Milos Luxury Catamaran Cruise to Kleftiko Bay with Lunch
Special Offer
Special Offer
Milos, Greece

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge,...

5 hours 30 minutesFree Cancellation
5 hours 30 minutesFree Cancellation
5 hours 30 minutes • Free Cancellation
5.0 (15)
$180.79
$179.79

Half day Catamaran Morning Cruise in Kleftiko
Special Offer
Special Offer
Milos, Greece

We welcome you to the island of colors with its natural beauty and incredible rock formations, a unique destination for each of you.

 Polychronis Mavros...

6 hoursFree Cancellation
6 hoursFree Cancellation
6 hours • Free Cancellation
5.0 (38)
$169.12
$168.12

Morning Caldera Sailing Cruise
Special Offer
Special Offer
Santorini, Greece

Step aboard this 5 hour morning cruise for a relaxed sail and enjoy your time swimming, sunbathing, snorkeling, taking photos, tasting delicious BBQ meals, Greek...

5 hoursHotel pickup offeredFree Cancellation
5 hoursHotel pickup offeredFree Cancellation
5 hours • Hotel pickup offered • Free Cancellation
5.0 (35)
$145.80
$144.80

Semi-Private Half Day/Sunset cruise
Special Offer
Special Offer
Paros, Greece

Choose Your Perfect Half-Day Cruise Experience Enjoy a unique escape on the sea with one of our three half-day cruises Morning Cruise – 09:30 to...

3 hoursFree Cancellation
3 hoursFree Cancellation
3 hours • Free Cancellation
4.9 (25)
$104.97
$103.97

Catamaran Half Day Afternoon Cruise With Sunset: Kleftiko
Special Offer
Special Offer
Milos, Greece

Enjoy amazing moments in Milos island! An ideal cruise for you in order to see the most famous spots here in Milos such as Kleftiko...

6 hoursFree Cancellation
6 hoursFree Cancellation
6 hours • Free Cancellation
4.9 (26)
$180.79
$179.79

5 Hours Sailing Trip to Mykonos Famous Beaches with Lunch
Special Offer
Special Offer
Mykonos, Greece

The opportunity to see all South beaches, soak up the sun, snorkel to crystal clear waters, and meet new people. The opportunity to explore the...

5 hoursHotel pickup offeredFree Cancellation
5 hoursHotel pickup offeredFree Cancellation
5 hours • Hotel pickup offered • Free Cancellation
5.0 (26)
$138.80
$137.80

Small group,swim in Rhenia,watch the sunset fm LVenice, freetrans
Special Offer
Special Offer
Mykonos, Greece

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice,...

4 to 5 hoursHotel pickup offeredFree Cancellation
4 to 5 hoursHotel pickup offeredFree Cancellation
4 to 5 hours • Hotel pickup offered • Free Cancellation
4.9 (26)
$157.46
$156.46

Private Daily Sailing Cruise to Discover the Highlights of Milos
Special Offer
Special Offer
Milos, Greece

This cruise is unique and a must when visiting Milos . It gets you to places mostly accessible only by boat and offer the comfort...

8 hoursFree Cancellation
8 hoursFree Cancellation
8 hours • Free Cancellation
5.0 (34)
$1,347.16
$1,346.16

Santorini Private Catamaran Cruise
Special Offer
Special Offer
Santorini, Greece

WOW THIRASIA ISLAND!!! How many of us discovering the map of Santorini Island we wondered what is Thirasia Island. The small traditional Thirassia Island was...

5 hoursHotel pickup offeredFree Cancellation
5 hoursHotel pickup offeredFree Cancellation
5 hours • Hotel pickup offered • Free Cancellation
5.0 (28)
$699.83
$698.83

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