Top activities
Top landmarks
Trip ideas
Nearby places

Top Greece Sailing Trips

344 Results
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
$160
Sailing to Epidavros and Mycenae, Guided Tour and Wine Tasting

Embark on the Peloponnese Experience, a unique journey blending ancient history, breathtaking landscapes, and luxurious sailing. Begin your adventure aboard our premium yacht, cruising to …More

Likely to Sell Out
Likely to Sell Out
Athens, Greece

Embark on the Peloponnese Experience, a unique journey blending ancient history, breathtaking landscapes, and luxurious sailing. Begin your adventure aboard our premium yacht, cruising to...

2 days
5.0 (1)
from
$6,391
Daily Sailing Cruise Thassos

Discover the beauty of Thassos on a relaxing full-day sailing cruise along the island’s stunning coastline. Enjoy swimming stops at beautiful beaches and secluded bays, …More

Discover the beauty of Thassos on a relaxing full-day sailing cruise along the island’s stunning coastline. Enjoy swimming stops at beautiful beaches and secluded bays,...

7 hours Free Cancellation
5.0 (1)
from
$131
Hersonissos: Private Catamaran Cruise, Dia Island with Lunch

Indulge in the private sailing escape with a luxurious catamaran cruise from Hersonissos to the Dia Island. Perfect for celebrating special occasions or enjoying a …More

Indulge in the private sailing escape with a luxurious catamaran cruise from Hersonissos to the Dia Island. Perfect for celebrating special occasions or enjoying a...

6 hours 30 minutes Free Cancellation
5.0 (1)
from
$2,526
Hersonissos: Private Sunset Catamaran Cruise, Snack & Drinks

Experience the ultimate escape on a private sunset cruise aboard a luxurious sailing catamaran, perfect for couples, families, or friends celebrating special moments. Designed for …More

Experience the ultimate escape on a private sunset cruise aboard a luxurious sailing catamaran, perfect for couples, families, or friends celebrating special moments. Designed for...

3 hours 30 minutes Free Cancellation
5.0 (1)
from
$1,541
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, …More

Milos, Greece

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
5.0 (1)
from
$177
Sunset Sail & Gourmet dinning

Escape the ordinary and expand your horizon! A Breath of Fresh Air! Enjoy moments of tranquility, soak up the sun, float in sparkling azure waters …More

Heraklion, Greece

Escape the ordinary and expand your horizon! A Breath of Fresh Air! Enjoy moments of tranquility, soak up the sun, float in sparkling azure waters...

4 hours 30 minutes Free Cancellation
5.0 (1)
from
$792
Shared Day Cruise to Little Venice & Agios Stefanos

Enjoy a most memorable cruise of the most popular highlights of Mykonos, Little Venice and Agios Stefanos. …More

Mykonos, Greece

Enjoy a most memorable cruise of the most popular highlights of Mykonos, Little Venice and Agios Stefanos....

5 hours 30 minutes Free Cancellation
5.0 (1)
from
$80
Private Day SailBoat Tour Visit to Halkidiki

We extend our invitation to those seeking relaxation and the opportunity to bask in the beauty of Halkidiki. Experience the coastline in the most ecological, …More

Halkidiki, Greece

We extend our invitation to those seeking relaxation and the opportunity to bask in the beauty of Halkidiki. Experience the coastline in the most ecological,...

7 hours Free Cancellation
5.0 (1)
from
$787
Private sailing trip to Anthony Quinn Bay and Kallithea Thermes.

Discover the wonders of Rhodes’ stunning coastline on this private sailing trip to Anthony Quinn Bay and Kallithea Thermes. Soak up breathtaking views from start …More

Rhodes, Greece

Discover the wonders of Rhodes’ stunning coastline on this private sailing trip to Anthony Quinn Bay and Kallithea Thermes. Soak up breathtaking views from start...

5 hours 30 minutes
5.0 (1)
from
$769
Full Day Private Luxury Sailing Cruise in North or South Thassos

Aegean Sea Cruises provide personalized Day and Multi-Day Private Cruises with Luxury Sailing Yachts, Catamarans and Motor Boats in all Greek islands and especially across …More

Aegean Sea Cruises provide personalized Day and Multi-Day Private Cruises with Luxury Sailing Yachts, Catamarans and Motor Boats in all Greek islands and especially across...

7 hours Free Cancellation
5.0 (1)
from
$631
Private Cruise with swimming in Athenian Riviera

This private cruise stands out for its seamless combination of luxury, exclusivity, and personalized service, offering private transfers, handpicked swimming stops in hidden coves, and …More

Athens, Greece

This private cruise stands out for its seamless combination of luxury, exclusivity, and personalized service, offering private transfers, handpicked swimming stops in hidden coves, and...

5 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$1,940
Luxury cruise in Greece to the CYCLADES by sailboat with CHEF

The most beautiful Greek islands, an elegant and fast sailing boat, delicious food and wonderful sea... And you? What do you dream about for your …More

Ios, Greece

The most beautiful Greek islands, an elegant and fast sailing boat, delicious food and wonderful sea... And you? What do you dream about for your...

8 days
5.0 (1)
from
$1,492
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 …More

Paros, Greece

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
5.0 (1)
from
$1,952
Private Caldera Cruise Santorini

Our captain’s professionalism, the presence of co-captain Dior - the cutest mini Maltese that steals the show- combined with our rib boat’s amenities offers the …More

Santorini, Greece

Our captain’s professionalism, the presence of co-captain Dior - the cutest mini Maltese that steals the show- combined with our rib boat’s amenities offers the...

5 hours Hotel pickup offered Free Cancellation
5.0 (1)
from
$1,263
CYCLADES, SPORADES AND DODECANESIAN SAILING HOLIDAY, with chef and skipper

FROM 2 TO 30 AUGUST EVERY SATURDAY FROM KOS : Dodecanese means 12!islands, which are actually about 200 islands and islets! Some are so far …More

Kos, Greece

FROM 2 TO 30 AUGUST EVERY SATURDAY FROM KOS : Dodecanese means 12!islands, which are actually about 200 islands and islets! Some are so far...

8 days
5.0 (1)
from
$2,296
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 …More

Paros, Greece

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
5.0 (1)
from
$126
Athens Day Cruise: Agistri, Metopi & Aegina with Lunch on Board

Leave the crowded ferries behind. Your day is spent on a traditional wooden boat with a small group, a warm crew and your own host, …More

Athens, Greece

Leave the crowded ferries behind. Your day is spent on a traditional wooden boat with a small group, a warm crew and your own host,...

10 hours Hotel pickup offered Free Cancellation
4.7 (1,165)
from
$146
Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Enjoy a perfect sailing Sunset tour in the magnificent island of Santorini on board our catamaran. The catamaran sails to the most amazing sights of …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

Enjoy a perfect sailing Sunset tour in the magnificent island of Santorini on board our catamaran. The catamaran sails to the most amazing sights of...

5 hours Hotel pickup offered Free Cancellation
4.6 (1,021)
from
$90
Santorini Volcano and Hot Springs Cruise Tour from Fira Old Port

Your adventure begins at the old port of Fira, where you'll board a traditional boat to explore Santorini's volcanic wonders. The first stop is the …More

Santorini, Greece

Your adventure begins at the old port of Fira, where you'll board a traditional boat to explore Santorini's volcanic wonders. The first stop is the...

3 hours Free Cancellation
4.3 (940)
from
$34

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