Greece Sailing Trips

Catamaran Cruise Heraklion to Dia, Dinner, Drinks & Hotel Pickup

Join us for a semi-private afternoon cruise from Heraklion aboard a sleek, modern catamaran. Set sail to Dia Island and enjoy water activities — swim, …More

Join us for a semi-private afternoon cruise from Heraklion aboard a sleek, modern catamaran. Set sail to Dia Island and enjoy water activities — swim,...

5 hours Free Cancellation
4.9 (70)
from
$144
Mykonos Catamaran Cruise with Meal Drinks and Sup

Go on a half-day cruise in the Aegean Sea. Select your preferred departure time morning or afternoon and sail to the mythical Delos and Rhenia …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Go on a half-day cruise in the Aegean Sea. Select your preferred departure time morning or afternoon and sail to the mythical Delos and Rhenia...

5 hours Free Cancellation
4.9 (14)
from
$1,370
Rhodes Private Luxury Cruise MediterAsian Lunch Champagne coctail

Sail in Style Aboard the Newly Renovated Sailing Edisa ⛵ Enjoy a private luxury yacht experience created for guests who value privacy, comfort and attentive …More

Rhodes, Greece

Sail in Style Aboard the Newly Renovated Sailing Edisa ⛵ Enjoy a private luxury yacht experience created for guests who value privacy, comfort and attentive...

6 hours Free Cancellation
5.0 (73)
from
$993
Sailing Cruise in Nafplio with Meal & Drinks

Embark on an unforgettable half-day sailing adventure with Nafplio4Sail, offering a truly exclusive semi-private experience from the historic port of Nafplio. Escape the crowds and …More

Nafplio, Greece

Embark on an unforgettable half-day sailing adventure with Nafplio4Sail, offering a truly exclusive semi-private experience from the historic port of Nafplio. Escape the crowds and...

4 hours 30 minutes Free Cancellation
5.0 (73)
from
$103
Blue Lagoon-Vourvourou Lunch Cruise from Ouranoupolis

The luxurious family-run Glassbottom vessel provides you with the perfect swimming experience around the most beautiful places of Halkidiki. Catch the boat from Ouranoupolis port …More

Halkidiki, Greece

The luxurious family-run Glassbottom vessel provides you with the perfect swimming experience around the most beautiful places of Halkidiki. Catch the boat from Ouranoupolis port...

6 hours Free Cancellation
4.6 (64)
from
$52
Nafplio Sun Sail Cruises | Small Group | With Full Meal

Sail from Nafplio’s Old Port to Hidden Gems of the Argolic Gulf! Our cruise includes 2–3 stops at remote beaches only accessible by boat, perfect …More

Nafplio, Greece

Sail from Nafplio’s Old Port to Hidden Gems of the Argolic Gulf! Our cruise includes 2–3 stops at remote beaches only accessible by boat, perfect...

4 hours 30 minutes Free Cancellation
5.0 (52)
from
$113
Private sunset cruise in Rhodes with fruits and drinks.

The sunset trip is one of the best evening tour that you can go to,if you want a relaxing time. You can see some historical …More

Rhodes, Greece

The sunset trip is one of the best evening tour that you can go to,if you want a relaxing time. You can see some historical...

3 to 4 hours Free Cancellation
5.0 (59)
from
$441
Daily cruises to Dia Island with All -Inclusive Meal and drinks

Experience a Unique Sailing Adventure and savor our All-inclusive authentic Mediterranean menu, unlimited fragrant white wine, soft drinks and bottled water. The journey to the …More

Heraklion, Greece

Experience a Unique Sailing Adventure and savor our All-inclusive authentic Mediterranean menu, unlimited fragrant white wine, soft drinks and bottled water. The journey to the...

5 hours 30 minutes Hotel pickup offered Free Cancellation
5.0 (38)
from
$68
Naxos All-inclusive Catamaran Cruise with Swim stops & Lunch

The SHARED Full Day Sailing Cruise on-board a catamaran is an experience not to be missed! Sail with us into crystal blue waters, gorgeous sandy …More

Naxos, Greece

The SHARED Full Day Sailing Cruise on-board a catamaran is an experience not to be missed! Sail with us into crystal blue waters, gorgeous sandy...

7 hours
4.9 (402)
from
$207
Santorini Volcanic Islands Cruise: Volcano,Hot Springs,Thirassia and Oia Sunset

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, …More

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 hours Hotel pickup offered Free Cancellation
4.1 (94)
from
$65
Milos & Poliegos Catamaran Cruise Homemade Full menu BBQ & Drinks

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 …More

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 hours Free Cancellation
5.0 (53)
from
$241
From Agia Efimia: All Inclusive Sailing Day Tour to Ithaca

Embarking on a tour of Ithaca from Agia Efimia is a unique experience that offers an array of activities and delights. The tour includes delectable …More

Cephalonia, Greece

Embarking on a tour of Ithaca from Agia Efimia is a unique experience that offers an array of activities and delights. The tour includes delectable...

8 hours Free Cancellation
5.0 (42)
from
$171
Sailboat Full Day Tour in Kleftiko and Blue Lagoon with Lunch

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 …More

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 hours Free Cancellation
5.0 (55)
from
$189
Half day Catamaran Morning Cruise in Kleftiko

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 …More

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 hours Free Cancellation
5.0 (47)
from
$165
Explore Santorini and its volcanic wonders with Alex Private Boat

Join us on this breathtaking trip to Nea and Palea Kammeni,the lava islands in the middle of the crater. First up, we will see the …More

Santorini, Greece

Join us on this breathtaking trip to Nea and Palea Kammeni,the lava islands in the middle of the crater. First up, we will see the...

3 hours Free Cancellation
5.0 (48)
from
$574
South Crete: Small group Full Day/ Sunset Sailing & Lunch

Our crew will meet you at Agia Galini port and welcome you on board, where you will be given a briefing about safety and boat …More

Our crew will meet you at Agia Galini port and welcome you on board, where you will be given a briefing about safety and boat...

5 to 7 hours Hotel pickup offered Free Cancellation
4.9 (48)
from
$103
Santorini Sunset Cruise in Caldera

Experience a calm and romantic trip to the amazing sites of Santorini on a charming wooden sailing boat! The peaceful atmosphere and gentle rocking of …More

Santorini, Greece

Experience a calm and romantic trip to the amazing sites of Santorini on a charming wooden sailing boat! The peaceful atmosphere and gentle rocking of...

5 hours Free Cancellation
4.9 (45)
from
$52
Sailing Trips with Cretan Sailing

From the moment you step onto the vessel, you will experience Greek hospitality at its best. Our mission is to offer our guests an amazing …More

Likely to Sell Out
Likely to Sell Out

From the moment you step onto the vessel, you will experience Greek hospitality at its best. Our mission is to offer our guests an amazing...

4 hours Free Cancellation
4.1 (81)
from
$52
All-inclusice Catamaran Day Cruise from Hersonissos to Dia Island

Our luxury catamaran offers spacious elegance and is designed for your complete comfort. It takes you to the uninhabited Dia Island, where you’ll witness the …More

Our luxury catamaran offers spacious elegance and is designed for your complete comfort. It takes you to the uninhabited Dia Island, where you’ll witness the...

6 hours 30 minutes Free Cancellation
5.0 (46)
from
$166
Santorini Caldera Private Sailing Boat Cruise

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private …More

Santorini, Greece

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private...

5 hours Hotel pickup offered Free Cancellation
4.9 (53)
from
$976
Private Full/Half-Day Boat Trip in Greece with Food and Drinks

Are you looking for a personal experience where you get to steer the boat and trim the sails? Join us and feel the peace of …More

Rhodes, Greece

Are you looking for a personal experience where you get to steer the boat and trim the sails? Join us and feel the peace of...

5 hours 30 minutes Free Cancellation
5.0 (40)
from
$599

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