Greece Sailing Trips

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
$102
Private Morning Tour Lagoon 400-380 Sailing in Santorini,lunch, drink, transfer

Discover the most beautiful locations that Santorini has to offer on our beautiful Lagoon 400. Our crew will welcome you with open arms and provide …More

Santorini, Greece

Discover the most beautiful locations that Santorini has to offer on our beautiful Lagoon 400. Our crew will welcome you with open arms and provide...

5 hours Hotel pickup offered Free Cancellation
5.0 (62)
from
$162
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
Santorini - Volcano and Hot springs Boat Trip with Bus Transfer

This iconic boat tour is the perfect choice if you're looking for an easy way to visit Santorini's famous volcano without spending more time and …More

Santorini, Greece

This iconic boat tour is the perfect choice if you're looking for an easy way to visit Santorini's famous volcano without spending more time and...

3 hours Free Cancellation
4.3 (75)
from
$51
Private sailing cruise-Mykonos Southern Beach Hopping withLunch

Set Sail from Mykonos new port at 09:00 and enjoy the legendary Southern beaches of Mykonos (Ornos - Platys Gialos, Super Paradise, Elia, Agrari). Let …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Set Sail from Mykonos new port at 09:00 and enjoy the legendary Southern beaches of Mykonos (Ornos - Platys Gialos, Super Paradise, Elia, Agrari). Let...

6 hours Hotel pickup offered Free Cancellation
5.0 (3)
from
$1,722
Private Rhenia sailing cruise with Lunch & Transfer

Our team is highly qualified, with years of experience in the Greek waters; they are our home. Over the last decades, our business has included …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Our team is highly qualified, with years of experience in the Greek waters; they are our home. Over the last decades, our business has included...

6 hours Hotel pickup offered Free Cancellation
5.0 (3)
from
$2,227
Athens Riviera Private Sunset Cruise with Drinks & Bites

Step aboard Sofia Star 1, our luxury 52ft sailing yacht, and experience the Athenian Riviera in total privacy. This 4-hour private sunset cruise is designed …More

Likely to Sell Out
Likely to Sell Out
Athens, Greece

Step aboard Sofia Star 1, our luxury 52ft sailing yacht, and experience the Athenian Riviera in total privacy. This 4-hour private sunset cruise is designed...

4 hours Free Cancellation
5.0 (2)
from
$1,814
Morning and Sunset Cruise with Meal and Transport Included

Choose between a morning or sunset cruise when booking. On the day, depart from your hotel via air-conditioned minivan to Mykonos' new port for the …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Choose between a morning or sunset cruise when booking. On the day, depart from your hotel via air-conditioned minivan to Mykonos' new port for the...

5 hours Free Cancellation
5.0 (6)
from
$114
Aegina Island Private Yacht, Guided Tour and Tasting Experience

Embark on the Aegina Experience with SailBliss for a full day of adventure, culture, and relaxation that showcases the best of Greece. Sail across the …More

Likely to Sell Out
Likely to Sell Out
Athens, Greece

Embark on the Aegina Experience with SailBliss for a full day of adventure, culture, and relaxation that showcases the best of Greece. Sail across the...

11 hours Hotel pickup offered
5.0 (2)
from
$4,518
Full Day Private Cruise on Speed Boat in Corfu island

Set off on an unforgettable adventure to the beautiful islands of Paxos and Antipaxos aboard a luxury speedboat. Enjoy a comfortable and exciting journey as …More

Corfu, Greece

Set off on an unforgettable adventure to the beautiful islands of Paxos and Antipaxos aboard a luxury speedboat. Enjoy a comfortable and exciting journey as...

8 hours Free Cancellation
5.0 (51)
from
$1,791
Premium Santorini Private Day Tour Elba 45, BBQ, drinks, transfer

Explore the most attractive sights and beaches in Santorini on board the Luxurious Lagoon 450, exclusively for your party. Captain and crew will make this …More

Santorini, Greece

Explore the most attractive sights and beaches in Santorini on board the Luxurious Lagoon 450, exclusively for your party. Captain and crew will make this...

5 hours Hotel pickup offered Free Cancellation
4.9 (45)
from
$210
Private Sailing Yacht Cruise for up to 10 guests in Corfu

Discover the beauty of Corfu with Balos Yachts on a private sailing cruise along the island’s stunning coastline. Enjoy breathtaking views of the historic Old …More

Corfu, Greece

Discover the beauty of Corfu with Balos Yachts on a private sailing cruise along the island’s stunning coastline. Enjoy breathtaking views of the historic Old...

3 to 8 hours Free Cancellation
5.0 (44)
from
$496
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
2-Day Santorini Bus Tour with Volcanic Cruise

See all of the best of Santorini in this 2-day tour, visiting all must-sees and experience the island's culture before you go back home. Explore …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

See all of the best of Santorini in this 2-day tour, visiting all must-sees and experience the island's culture before you go back home. Explore...

2 days Free Cancellation
5.0 (3)
from
$114
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
$6,405
Temple Of Poseidon, Private Sailboat and Temple Visit Experience

Embark on an unforgettable journey to the iconic Temple of Poseidon, where history and breathtaking beauty converge. Sail along the stunning Athenian Riviera aboard our …More

Likely to Sell Out
Likely to Sell Out
Athens, Greece

Embark on an unforgettable journey to the iconic Temple of Poseidon, where history and breathtaking beauty converge. Sail along the stunning Athenian Riviera aboard our...

11 hours
5.0 (2)
from
$2,922
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
Private full day cruise to Antiparos with Paros Sail

You came to your vacation in Paros, there is one thing you must do! Sail and swim in the Blue Lagoon and all the places …More

Paros, Greece

You came to your vacation in Paros, there is one thing you must do! Sail and swim in the Blue Lagoon and all the places...

7 hours Free Cancellation
5.0 (20)
from
$2,441
Private half day cruise The Blue Lagoon with Paros Sail

You came to your vacation in Paros, there is one thing you must do! Sail and swim in the Blue Lagoon with Paros Sail. You …More

Paros, Greece

You came to your vacation in Paros, there is one thing you must do! Sail and swim in the Blue Lagoon with Paros Sail. You...

3 hours 30 minutes Free Cancellation
5.0 (38)
from
$1,357
Nafplio Sun Sail Cruises | Full Day | Private | With Full Meal

Sail from Nafplio to explore the Argolic Gulf’s hidden beauty. This cruise stops at secluded spots with crystal-clear waters, perfect for swimming, snorkeling, or relaxing …More

Nafplio, Greece

Sail from Nafplio to explore the Argolic Gulf’s hidden beauty. This cruise stops at secluded spots with crystal-clear waters, perfect for swimming, snorkeling, or relaxing...

8 hours Free Cancellation
5.0 (11)
from
$142
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

Frequently Asked Questions

These answers are based on answers previously given to Key West Private Charters customers' questions.

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