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Top Crete Sailing Trips

Private Sailing Cruise from Heraklion to Dia Island

Discover the unique destination of Dia island while traveling in style and comfort aboard our luxury sailing boat. Feel the breeze of Cretan sea, swim …More

Discover the unique destination of Dia island while traveling in style and comfort aboard our luxury sailing boat. Feel the breeze of Cretan sea, swim...

6 hours Free Cancellation
5.0 (24)
from
$712
Small Group Sailing Cruise from Agios Nikolaos in Mirabello Bay

Departing from the Marina of Agios Nikolaos, our journey promises a semi-private escape filled with delightful socializing and shared experiences. It begins with relaxation or …More

Departing from the Marina of Agios Nikolaos, our journey promises a semi-private escape filled with delightful socializing and shared experiences. It begins with relaxation or...

6 hours Free Cancellation
4.8 (25)
from
$126
Sailing trip to the Top Coasts of Crete, Daily/Multi-day

We are the only Sailing Yacht in the area,so you will enjoy isolated turquoise coasts with no crowds.Our daily sailing trip take place in the …More

We are the only Sailing Yacht in the area,so you will enjoy isolated turquoise coasts with no crowds.Our daily sailing trip take place in the...

7 hours
5.0 (173)
from
$1,137
SAILING DAY 4.5-5h & SUNSET 3 or 4.5-5h from Hersonissos CRETE

The minibus picks you up outside your hotel and takes you to the port in Gouves, where the boat leaves. DAY & SUNSET of 4.5-5h: …More

Heraklion, Greece

The minibus picks you up outside your hotel and takes you to the port in Gouves, where the boat leaves. DAY & SUNSET of 4.5-5h:...

3 to 5 hours Hotel pickup offered Free Cancellation
4.8 (24)
from
$103
From Heraklion:Small group 5,5h Sunset Sailing trip to Dia Island

Escape the crowded beaches and join us for a lazy day cruise to the island of Dia. You can enjoy a swimming stop in the …More

Escape the crowded beaches and join us for a lazy day cruise to the island of Dia. You can enjoy a swimming stop in the...

5 hours 30 minutes Free Cancellation
4.9 (27)
from
$68
Panormo: Luxury Sunset Catamaran Cruise Sushi & Open Bar

With an afternoon cruise, you avoid the peak heat and enjoy the golden glow of late day, ending with a spectacular sunset over the horizon. …More

With an afternoon cruise, you avoid the peak heat and enjoy the golden glow of late day, ending with a spectacular sunset over the horizon....

3 hours 30 minutes Free Cancellation
5.0 (39)
from
$98
Rethymno: Private Catamaran Cruise with Lunch and Drinks

Set sail from Rethymno on a private cruise aboard one of Crete’s most luxurious catamarans. This exclusive experience combines comfort, relaxation, and adventure, beginning with …More

Set sail from Rethymno on a private cruise aboard one of Crete’s most luxurious catamarans. This exclusive experience combines comfort, relaxation, and adventure, beginning with...

6 hours 30 minutes Free Cancellation
4.8 (16)
from
$2,526
South Crete: Private 5-7hrs Snorkeling & Sailing with Lunch

Explore the Fantastic Unspoiled Beaches in South Crete! Crete is one of the five most prominent islands in the Mediterranean and it’s divided in half …More

Explore the Fantastic Unspoiled Beaches in South Crete! Crete is one of the five most prominent islands in the Mediterranean and it’s divided in half...

7 hours Free Cancellation
4.7 (23)
from
$689
Balos Lagoon Kissamos Shared Sailboat Tour Experience

By our sailing boats "Izabela" and "Poseidon" we organise day cruises to Gramvousa and Balos. Our journey starts from Kissamos Port. After about 90 minutes …More

By our sailing boats "Izabela" and "Poseidon" we organise day cruises to Gramvousa and Balos. Our journey starts from Kissamos Port. After about 90 minutes...

8 hours Free Cancellation
4.7 (23)
from
$149
Chania Sunset Catamaran Cruise from Souda Port

An afternoon cruise allows you to avoid the peak heat of the day and soak in the gentle, golden light of the late afternoon. And …More

An afternoon cruise allows you to avoid the peak heat of the day and soak in the gentle, golden light of the late afternoon. And...

3 hours 30 minutes Free Cancellation
5.0 (14)
from
$86
Agios Nikolaos: Semi-private Sailing trip. Lunch and Water Toys

Set sail on a Lagoon 450F Catamaran from Agios Nikolaos. Enjoy a day of relaxation and fun on the water with friends and family. Onboard, …More

Likely to Sell Out
Likely to Sell Out

Set sail on a Lagoon 450F Catamaran from Agios Nikolaos. Enjoy a day of relaxation and fun on the water with friends and family. Onboard,...

5 hours Free Cancellation
4.8 (12)
from
$160
Black Rose Pirate Boat: 5-Hour Trip from Hersonissos

The black rose will depart every day 11 o clock from the port of Hersonissos. After 20 minutes journey passing by from the bays of …More

Likely to Sell Out
Likely to Sell Out

The black rose will depart every day 11 o clock from the port of Hersonissos. After 20 minutes journey passing by from the bays of...

4 hours Hotel pickup offered Free Cancellation
4.9 (9)
from
$67
Private Sailing Cruise to Dia Island with Meal & Water Activities

Sail with us to the exotic Dia Island on our large and comfortable sailing yachts. Our journey begins at the Heraklion Old venetian port. After …More

Likely to Sell Out
Likely to Sell Out
Heraklion, Greece

Sail with us to the exotic Dia Island on our large and comfortable sailing yachts. Our journey begins at the Heraklion Old venetian port. After...

5 hours 30 minutes Hotel pickup offered Free Cancellation
4.7 (10)
from
$907
Luxury escape Sailing, shared from Hersonissos or Heraklion port

Looking for an Escape? On a yacht, you have the opportunity to appreciate your downtime in an idyllic setting that offers relaxation, freedom, exhilaration, and …More

Likely to Sell Out
Likely to Sell Out
Heraklion, Greece

Looking for an Escape? On a yacht, you have the opportunity to appreciate your downtime in an idyllic setting that offers relaxation, freedom, exhilaration, and...

7 hours Free Cancellation
4.8 (6)
from
$103
Balos Beach and Gramvousa island shared group Sailing Cruise

Set sail on Boat STELLA for an unforgettable journey across the sparkling waters of the Aegean Sea with a shared group program cruise to Balos …More

Likely to Sell Out
Likely to Sell Out

Set sail on Boat STELLA for an unforgettable journey across the sparkling waters of the Aegean Sea with a shared group program cruise to Balos...

8 hours Free Cancellation
4.7 (11)
from
$223
Private Sail in Chania

We sail by Fortezza, with its cannon ports still intact to keep the pirates ships out of the bay. So close you can almost touch …More

We sail by Fortezza, with its cannon ports still intact to keep the pirates ships out of the bay. So close you can almost touch...

8 hours Free Cancellation
5.0 (36)
from
$137
Balos Beach and Gramvousa Island Private-Sailing with Lunch

Set sail on Sailing Boat STELLA or on Sailing Yacht ELECTRA for an unforgettable journey across the sparkling waters of the Aegean Sea with a …More

Likely to Sell Out
Likely to Sell Out

Set sail on Sailing Boat STELLA or on Sailing Yacht ELECTRA for an unforgettable journey across the sparkling waters of the Aegean Sea with a...

8 hours Free Cancellation
5.0 (1)
from
$161
Small Group Sailing Cruise from Heraklion to Dia Island

Embarking from the enchanting Venetian port of Heraklion, our northward journey to Dia Island promises a semi-private escape filled with delightful socializing and shared experiences. …More

Embarking from the enchanting Venetian port of Heraklion, our northward journey to Dia Island promises a semi-private escape filled with delightful socializing and shared experiences....

6 hours Free Cancellation
5.0 (15)
from
$98
Sailing day to Dia island

Join us for an unforgettable sailing trip to the natural island of Dia aboard our comfortable yachts with our experienced crew. After a scenic sail …More

Join us for an unforgettable sailing trip to the natural island of Dia aboard our comfortable yachts with our experienced crew. After a scenic sail...

7 hours Hotel pickup offered Free Cancellation
4.9 (13)
from
$97
Catamaran Sailing Trip - All Inclusive

Join a unique catamaran adventure from Heraklion to the beautiful, unspoiled Dia Island. Sail in comfort and style aboard a spacious catamaran, enjoying a relaxed …More

Heraklion, Greece

Join a unique catamaran adventure from Heraklion to the beautiful, unspoiled Dia Island. Sail in comfort and style aboard a spacious catamaran, enjoying a relaxed...

5 to 6 hours Hotel pickup offered Free Cancellation
4.7 (21)
from
$148

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