Top activities
Top landmarks
Trip ideas
Nearby places

Top Greece Sailing Trips

South Paros Antiparos Despotiko Faragas Beach Sailboat SY AGERAS

We sail from Piso Livadi to the southwest by 09:30, hoisting your sails and adjusting your course according to the prevailing winds we enjoy a …More

Paros, Greece

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

8 hours Free Cancellation
4.9 (9)
from
$195
One Full Day of True Sailing to South Naxos & Koufonisi SY AGERAS

We sail from Piso Livadi towards South Naxos by 09:00, hoisting our sails & adjusting our course according to the prevailing winds we enjoy a …More

Paros, Greece

We sail from Piso Livadi towards South Naxos by 09:00, hoisting our sails & adjusting our course according to the prevailing winds we enjoy a...

10 hours Free Cancellation
5.0 (8)
from
$205
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, …More

Milos, Greece

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
5.0 (9)
from
$1,141
Boat and hike tour to the Hidden Beaches of Syros

Our adventure begins at Kini, a charming fishing village on Syros' west coast. We board a boat and leave behind everyday life, cruising toward the …More

Syros, Greece

Our adventure begins at Kini, a charming fishing village on Syros' west coast. We board a boat and leave behind everyday life, cruising toward the...

5 hours Free Cancellation
5.0 (7)
from
$103
Private 2 Hours Sunset Cruise in Milos — Magical Klima Village

Heading to Klima promises not just a glimpse but a full immersion in nature's canvas at sunset. The way hues blend and dance across the …More

Milos, Greece

Heading to Klima promises not just a glimpse but a full immersion in nature's canvas at sunset. The way hues blend and dance across the...

2 hours Free Cancellation
5.0 (3)
from
$534
Private All Inclusive Sailing Day Tour from Agia Efimia to Ithaca

Experience an unforgettable 8-hour private sailing adventure from Agia Efimia, Kefalonia, to Ithaca. Swim in pristine waters at Gidaki Beach and Lygia Islet. Savor crew-crafted …More

Cephalonia, Greece

Experience an unforgettable 8-hour private sailing adventure from Agia Efimia, Kefalonia, to Ithaca. Swim in pristine waters at Gidaki Beach and Lygia Islet. Savor crew-crafted...

8 hours Free Cancellation
5.0 (4)
from
$1,084
5,5 hours Private Sailing Trips from Heraklion to Island of Dia

Escape the crowled 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 crowled 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
5.0 (4)
from
$517
Agios Nikolaos: Private Catamaran Cruise with Meal & Drinks

Experience a private cruise from Agios Nikolaos around Mirabello and Spinalonga aboard a luxurious sailing catamaran. Morning serenity or sunset beauty, tailored for families, friends, …More

Experience a private cruise from Agios Nikolaos around Mirabello and Spinalonga aboard a luxurious sailing catamaran. Morning serenity or sunset beauty, tailored for families, friends,...

5 hours Free Cancellation
5.0 (2)
from
$2,411
Heraklion: Private Catamaran Cruise to Dia with Meal & Drinks

Embark on a private sailing catamaran cruise from Heraklion to the bay of Dia Island—an ideal escape for families, friends, or special celebrations. Aboard our …More

Embark on a private sailing catamaran cruise from Heraklion to the bay of Dia Island—an ideal escape for families, friends, or special celebrations. Aboard our...

5 hours Free Cancellation
5.0 (4)
from
$2,411
Private Sunset Catamaran Cruise from Nikiti

An unforgettable, romantic sunset cruise is provided every evening at 18:00. During this cruise you have the opportunity to enjoy a breathtaking sunset while you …More

Thessaloniki, Greece

An unforgettable, romantic sunset cruise is provided every evening at 18:00. During this cruise you have the opportunity to enjoy a breathtaking sunset while you...

3 hours
5.0 (2)
from
$1,033
Full Private Day Tour Sailing Experience in Halkidiki

We sail with a 14m sailing yacht to secluded beaches and extraordinary spots that are not accessible by car. During the day we make a …More

Halkidiki, Greece

We sail with a 14m sailing yacht to secluded beaches and extraordinary spots that are not accessible by car. During the day we make a...

7 hours Free Cancellation
5.0 (3)
from
$643
Private Cruise West Side of Milo's & Kleftiko

Our "West Side of Milos & Kleftiko" cruise offers a unique blend of natural beauty, historical exploration, and relaxation. Enjoy the privacy of the yacht …More

Milos, Greece

Our "West Side of Milos & Kleftiko" cruise offers a unique blend of natural beauty, historical exploration, and relaxation. Enjoy the privacy of the yacht...

7 hours 30 minutes Free Cancellation
5.0 (2)
from
$2,077
Chania Private Sailing Cruise with Meal and Water Activities

Sail from Kolimvari Port along the gorgeous north coast of Chania on our comfortable sailing yacht and discover the island of Thodorou, home of the …More

Sail from Kolimvari Port along the gorgeous north coast of Chania on our comfortable sailing yacht and discover the island of Thodorou, home of the...

5 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$1,137
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 …More

Santorini, Greece

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
4.5 (8)
from
$40
Athens Full Day Exclusive Sailing to Aegina on a Private Yacht

A premium sailing experience on board our exclusive sailing yacht from Athens, for a full day tour to Aegina's best spots, accessible only by the …More

Athens, Greece

A premium sailing experience on board our exclusive sailing yacht from Athens, for a full day tour to Aegina's best spots, accessible only by the...

10 hours Free Cancellation
5.0 (3)
from
$1,940
Half-day Tour around Zakynthos Island.

From Zakinthos cruising the coast till Navagio - Shipwreck for the first stop for swimming, Second stop at Blue caves for photos opportunity and swim, …More

Zakynthos, Greece

From Zakinthos cruising the coast till Navagio - Shipwreck for the first stop for swimming, Second stop at Blue caves for photos opportunity and swim,...

4 to 5 hours Free Cancellation
3.7 (10)
from
$67
Day trip to Nisyros Island, Volcano and Nikia Village

Board our boat from the port of Kardamena and head to the small island of Nisyros. Enjoy a day on this unique and beautiful island …More

Kos, Greece

Board our boat from the port of Kardamena and head to the small island of Nisyros. Enjoy a day on this unique and beautiful island...

6 to 7 hours Free Cancellation
3.9 (18)
from
$37
Private Boat Tour in Milos with Lunch

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

Milos, Greece

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

6 to 10 hours Free Cancellation
5.0 (4)
from
$1,826
Full Day Private Luxury Escape Sailing

Immerse yourself in the serene ambiance of island life aboard a luxurious yacht, surrounded by breathtaking views and attentive crew. Savor the delightful Mediterranean cuisine, …More

Heraklion, Greece

Immerse yourself in the serene ambiance of island life aboard a luxurious yacht, surrounded by breathtaking views and attentive crew. Savor the delightful Mediterranean cuisine,...

8 hours Hotel pickup offered
5.0 (4)
from
$1,370
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 …More

Milos, Greece

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
5.0 (4)
from
$2,755

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

Recent tour reviews
Activity name

Greece Tours
Attractions
Guides
Calendar