Top activities
Top landmarks
Trip ideas
Nearby places
Port schedule

Top Greece Sailing Trips

345 Results
Private luxury Escape free drinks & Meals Cruise

Looking for an Escape? Leave your comfort zone and embrace nature to the fullest. The best place to start your eco-quest is the island of …More

Likely to Sell Out
Likely to Sell Out
Heraklion, Greece

Looking for an Escape? Leave your comfort zone and embrace nature to the fullest. The best place to start your eco-quest is the island of...

5 hours Free Cancellation
5.0 (22)
from
$1,010
Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne

Romance in Rhodes – Sea, Spice & Serenity Enjoy an intimate private sunset cruise aboard Sailing Edisa, with swimming and snorkelling at the crystal-clear waters …More

Rhodes, Greece

Romance in Rhodes – Sea, Spice & Serenity Enjoy an intimate private sunset cruise aboard Sailing Edisa, with swimming and snorkelling at the crystal-clear waters...

4 hours Free Cancellation
5.0 (18)
from
$1,016
Private Coast to Coast Sailing Trip from Rhodes City

Our cruise departs from Mandraki Harbor at 09:00 and ends at 16:00 at the same location. The cruise stops at Kallithea Bay which is one …More

Rhodes, Greece

Our cruise departs from Mandraki Harbor at 09:00 and ends at 16:00 at the same location. The cruise stops at Kallithea Bay which is one...

7 hours
5.0 (2)
from
$1,022
Holiday trip Corfu - sailing in the realm of Odysseus

Who doesn't want to jump into the turquoise blue sea again? Let the soul dangle with the sound of the sea. Explore lonely sandy bays …More

Corfu, Greece

Who doesn't want to jump into the turquoise blue sea again? Let the soul dangle with the sound of the sea. Explore lonely sandy bays...

8 days Free Cancellation
4.7 (3)
from
$1,022
Skipper training - yacht

Professional German-speaking skipper 8 days Exclusive yachts Intensive maneuver training Individual course content Small number of participants …More

Corfu, Greece

Professional German-speaking skipper 8 days Exclusive yachts Intensive maneuver training Individual course content Small number of participants...

8 days
from
$1,022
Private Yacht Tour in Santorini (Technohull) - Open Bar&Transfers

• Sail along the iconic caldera, passing volcanic cliffs, the famous Red Beach, and the White Beach. • Swim in crystal-clear waters, explore hidden coves, …More

Santorini, Greece

• Sail along the iconic caldera, passing volcanic cliffs, the famous Red Beach, and the White Beach. • Swim in crystal-clear waters, explore hidden coves,...

5 hours Hotel pickup offered Free Cancellation
from
$1,027
Half day Private Sailing cruise in Santorini island up to 6 pax

Enjoy the cruise like a real sailor and experience moving with the force of the wind! Maria our captain will stand our, together with our …More

Santorini, Greece

Enjoy the cruise like a real sailor and experience moving with the force of the wind! Maria our captain will stand our, together with our...

5 hours Free Cancellation
5.0 (6)
from
$1,033
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
Glaraki Private Sunset Tour

The unique breathtaking sunset in the Greek sea accompanied with traditional local snacks and drinks is the best way to relax on your vacations. …More

Antiparos, Greece

The unique breathtaking sunset in the Greek sea accompanied with traditional local snacks and drinks is the best way to relax on your vacations....

3 hours Free Cancellation
from
$1,033
Daytour Sailboat with Lunch/drinks in Lindos area

Your exclusive sailing experience in complete privacy! A touch of adventure, freedom and direct experience of nature awaits you on our comfortable and sporty sailing …More

Rhodes, Greece

Your exclusive sailing experience in complete privacy! A touch of adventure, freedom and direct experience of nature awaits you on our comfortable and sporty sailing...

6 hours Hotel pickup offered Free Cancellation
5.0 (25)
from
$1,056
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
Exclusive Sailing on a Private Yacht from Athens

Experience the Saronic Gulf like never before with us! Our Exclusive Sailing to Aegina on a Private Yacht from Athens Cruise is all about personalized, …More

Athens, Greece

Experience the Saronic Gulf like never before with us! Our Exclusive Sailing to Aegina on a Private Yacht from Athens Cruise is all about personalized,...

9 hours Free Cancellation
5.0 (7)
from
$1,091
Private Catamaran Cruise from Kavala to 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...

10 hours Free Cancellation
from
$1,091
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
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
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
Santorini Morning or Sunset Romance Private Sailing Volcano Tour

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a …More

Santorini, Greece

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a...

6 hours Free Cancellation
5.0 (4)
from
$1,141
Full-Day Private cruise to Kleftiko, Polyaigos and Kimolos

Our cruises are one-way starting either in Agia Kyriaki beach and ending in Pollonia village or vice versa. We never sail back to our starting …More

Milos, Greece

Our cruises are one-way starting either in Agia Kyriaki beach and ending in Pollonia village or vice versa. We never sail back to our starting...

9 hours Free Cancellation
from
$1,148
Private Sailing Yacht Events in Kalamata for Up to 23 Guests

What makes this experience unique is the combination of exclusivity, flexibility, and capacity. Unlike typical shared boat tours, this is a fully private sailing yacht …More

Pylos, Greece

What makes this experience unique is the combination of exclusivity, flexibility, and capacity. Unlike typical shared boat tours, this is a fully private sailing yacht...

4 to 7 hours Free Cancellation
5.0 (16)
from
$1,164
Private Half Day cruise on Catamaran in Corfu

Enjoy an exclusive escape combining luxury, privacy, and the natural beauty of Corfu. Discover hidden beaches accessible only by boat, swim in crystal-clear turquoise waters, …More

Corfu, Greece

Enjoy an exclusive escape combining luxury, privacy, and the natural beauty of Corfu. Discover hidden beaches accessible only by boat, swim in crystal-clear turquoise waters,...

4 hours Free Cancellation
5.0 (97)
from
$1,240

Frequently Asked Questions

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

Recent tour reviews
Activity name

Discover Greece