Greece Sailing Trips

349 Results
Private Sailing Cruise to Blue Lagoon-Holed Cave-Piso livadi

We set sail from Naxos and the surrounding islands and islets with Naxian Captain George Fragiskos on the luxury yacht “Annabella” to meet new friends, …More

Naxos, Greece

We set sail from Naxos and the surrounding islands and islets with Naxian Captain George Fragiskos on the luxury yacht “Annabella” to meet new friends,...

8 hours Free Cancellation
5.0 (6)
from
$2,526
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
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
2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos

This cruise is unique and a must when visiting Milos. It gives visitors the opportunity to experience a night on-board a 13m sailing boat and …More

Milos, Greece

This cruise is unique and a must when visiting Milos. It gives visitors the opportunity to experience a night on-board a 13m sailing boat and...

2 days Free Cancellation
5.0 (10)
from
$2,775
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
Milos Private Full Day Catamaran Cruise with Lunch and Drinks

Set sail on a private full-day cruise aboard a luxurious sailing catamaran from Adamantas Port, Milos, for an unforgettable journey to Kleftiko Bay and Polyegos …More

Milos, Greece

Set sail on a private full-day cruise aboard a luxurious sailing catamaran from Adamantas Port, Milos, for an unforgettable journey to Kleftiko Bay and Polyegos...

9 hours Free Cancellation
5.0 (10)
from
$3,292
Scuba Diving Private Experience Sailing Greek Cuisine and Diving

Our Scuba Diving Experience offers a unique blend of adventure, natural beauty, and luxurious comfort. Dive into the mesmerizing underwater world of the Athenian Riviera …More

Athens, Greece

Our Scuba Diving Experience offers a unique blend of adventure, natural beauty, and luxurious comfort. Dive into the mesmerizing underwater world of the Athenian Riviera...

5 hours
from
$3,317
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
$4,459
Athens Experience Combo Sailing Guided Tour and Food Tasting

Uncover the best of Athens with our exclusive Athens Experience, blending history, culture, and luxury. Begin with a guided tour of the Acropolis, exploring iconic …More

Athens, Greece

Uncover the best of Athens with our exclusive Athens Experience, blending history, culture, and luxury. Begin with a guided tour of the Acropolis, exploring iconic...

11 hours
5.0 (2)
from
$4,825
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
Sailing Vacation in the Aegean, Greece (8 days)

Island hopping in the Aegean together with Sailing School? What more to ask for your holidays in the Aegean? Experience the Greek island hopping while …More

Rhodes, Greece

Island hopping in the Aegean together with Sailing School? What more to ask for your holidays in the Aegean? Experience the Greek island hopping while...

7 days Hotel pickup offered Free Cancellation
from
$7,989
Island Hopping: Santorini Catamaran Charter Cruise with a skipper

Design your own trip and explore the Aegean! Feel free to craft your own personalized sailing route. We are ready to make it happen. Set …More

Paros, Greece

Design your own trip and explore the Aegean! Feel free to craft your own personalized sailing route. We are ready to make it happen. Set...

7 days
4.9 (123)
from
$8,450
Private sailing cruise Athens 1 week 1 to 6 people

Unique stay, tailor-made trip: private sailing cruise with French-speaking crew in the Greek Islands from Athens. All included. Experience a holiday differently. …More

Athens, Greece

Unique stay, tailor-made trip: private sailing cruise with French-speaking crew in the Greek Islands from Athens. All included. Experience a holiday differently....

7 days
5.0 (2)
from
$11,083

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