Cyclades Islands Sailing Trips

Semi-private Day Cruise

Experience a premium boat trip with up to 25 guests aboard our spacious 66ft traditional wooden boat, complete with sunbeds and plenty of room to …More

Likely to Sell Out
Likely to Sell Out
Antiparos, Greece

Experience a premium boat trip with up to 25 guests aboard our spacious 66ft traditional wooden boat, complete with sunbeds and plenty of room to...

6 hours 45 minutes Free Cancellation
4.9 (159)
from
$218
Mykonos 6hrs sailing cruise: Delos Rhenia with lunch & transfer

We setsail at 09:00am from Tourlos Marina. Our first stop is an hour away, the renowned Big Delos island. While there, you will have the …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

We setsail at 09:00am from Tourlos Marina. Our first stop is an hour away, the renowned Big Delos island. While there, you will have the...

6 hours Hotel pickup offered Free Cancellation
5.0 (98)
from
$172
A Boat Trip to the Pirate Caves & Blue Lagoon

Join this boat trip to the South Pirate Caves, where you will enjoy some local white wine and seasonal fruit and snorkelling in the very …More

Likely to Sell Out
Likely to Sell Out
Paros, Greece

Join this boat trip to the South Pirate Caves, where you will enjoy some local white wine and seasonal fruit and snorkelling in the very...

3 hours 30 minutes Free Cancellation
4.9 (86)
from
$74
Santorini Fishing Private Cruise boat tour - BBQ, Snorkeling

The local captain “Makis” from “The Pirate fishing tours” in Santorini, loves to share his passion for the sea, with the visitors to Santorini island …More

Santorini, Greece

The local captain “Makis” from “The Pirate fishing tours” in Santorini, loves to share his passion for the sea, with the visitors to Santorini island...

5 hours Free Cancellation
5.0 (354)
from
$170
Sunset Caldera Sailing Cruise

Captain Yiannis and his crew -all experienced sailors- can assure you that all claims about greek hospitality are true and that this cruise will be …More

Santorini, Greece

Captain Yiannis and his crew -all experienced sailors- can assure you that all claims about greek hospitality are true and that this cruise will be...

5 hours Hotel pickup offered Free Cancellation
4.9 (87)
from
$144
Luxury Santorini Sunset Cruise: Dinner, BBQ, Open Bar, Transfers

Get ready for an incredible Santorini Sunset Catamaran Cruise! Our adventure kicks off from the charming port of Vlychada , where we'll sail through the …More

Santorini, Greece

Get ready for an incredible Santorini Sunset Catamaran Cruise! Our adventure kicks off from the charming port of Vlychada , where we'll sail through the...

5 hours Hotel pickup offered Free Cancellation
4.9 (380)
from
$126
Santorini: Small Group Catamaran Cruise with BBQ Fish & Drinks

The Day and Sunset Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

The Day and Sunset Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Vlychada marina is a great opportunity to enjoy a...

5 hours Hotel pickup offered Free Cancellation
4.9 (71)
from
$131
Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

Explore Santorini's volcanic landscape by sea on this 5-hour sailing trip aboard a new luxury catamaran. With its sleek, diamond-like design and comfortable seating areas …More

Santorini, Greece

Explore Santorini's volcanic landscape by sea on this 5-hour sailing trip aboard a new luxury catamaran. With its sleek, diamond-like design and comfortable seating areas...

5 hours Hotel pickup offered Free Cancellation
4.8 (412)
from
$126
Santorini Small-Group Catamaran Sailing Trip(BBQ,drinks, transfer)

Choose this half-day sailing cruise. Your tour begins with convenient transportation from your accommodation or the closest accessible point. At the embarkation dock, you meet …More

Santorini, Greece

Choose this half-day sailing cruise. Your tour begins with convenient transportation from your accommodation or the closest accessible point. At the embarkation dock, you meet...

5 hours Hotel pickup offered Free Cancellation
4.9 (222)
from
$148
Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

Santorini's original and most popular sailing tour. Experience the beauty of Santorini and the magic of sailing in the Caldera on this small-group sailing tour. …More

Santorini, Greece

Santorini's original and most popular sailing tour. Experience the beauty of Santorini and the magic of sailing in the Caldera on this small-group sailing tour....

5 hours Hotel pickup offered Free Cancellation
4.9 (298)
from
$218
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
Santorini Catamaran Cruise: with Lunch, BBQ, Open Bar, Transfers

Step aboard our catamaran with Santorini Yachting Cruises, and join us for an incredible sailing adventure! Our day cruise sets sail from the port of …More

Santorini, Greece

Step aboard our catamaran with Santorini Yachting Cruises, and join us for an incredible sailing adventure! Our day cruise sets sail from the port of...

5 hours Hotel pickup offered Free Cancellation
5.0 (308)
from
$98
All inclusive Delos & Rhenia Islands tour (free transportation)

What makes our product unique is the contact with sea & sun. Sailing away with Nadia K, you will have the opportunity to experience new …More

Mykonos, Greece

What makes our product unique is the contact with sea & sun. Sailing away with Nadia K, you will have the opportunity to experience new...

6 hours Hotel pickup offered Free Cancellation
4.9 (239)
from
$157
Santorini Private Catamaran Cruise with BBQ, Open Bar & Transfers

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Vlychada Marina. Sail past the island's highlights, such as the Red & White …More

Santorini, Greece

Sail around Santorini on a Catamaran during this 5-hour Cruise, departing from Vlychada Marina. Sail past the island's highlights, such as the Red & White...

5 hours Hotel pickup offered Free Cancellation
5.0 (452)
from
$146
Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

Experience the beauty of Santorini and its volcanic caldera on this small-group sailing tour. Cruise by some of the island’s best-known landmarks before venturing into …More

Santorini, Greece

Experience the beauty of Santorini and its volcanic caldera on this small-group sailing tour. Cruise by some of the island’s best-known landmarks before venturing into...

5 hours Hotel pickup offered Free Cancellation
4.9 (286)
from
$184
The Authentic Rhenia-Delos Cruise

Sparkling seas and secluded beaches? Join our Rhenia – Delos cruise and live a day like no other! The Cycladic Sisters, Mykonos, Delos and Rhenia, …More

Mykonos, Greece

Sparkling seas and secluded beaches? Join our Rhenia – Delos cruise and live a day like no other! The Cycladic Sisters, Mykonos, Delos and Rhenia,...

6 hours 30 minutes Free Cancellation
4.8 (432)
from
$102
Catamaran Half Day Shared Kleftiko Trip

Choose Morning 9:00-14:00 or Afternoon 14:30-19:30 Boarding time is 30' minutes before departure. Be on time. Itinerary of the cruise Welcome on board! We sail …More

Milos, Greece

Choose Morning 9:00-14:00 or Afternoon 14:30-19:30 Boarding time is 30' minutes before departure. Be on time. Itinerary of the cruise Welcome on board! We sail...

5 hours Free Cancellation
5.0 (243)
from
$207
Mykonos Catamaran Sunset Cruise with Meal, Drinks & Transfer

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches …More

Mykonos, Greece

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches...

4 hours Hotel pickup offered Free Cancellation
4.9 (127)
from
$114
Half Day Sailing to Kleftiko with Lunch, Open Bar & Snorkeling

Kleftiko Boat Tour an unforgettable journey to Milos’ hidden gems, where adventure meets tranquility on the crystal clear waters of the Aegean. Embark on an …More

Milos, Greece

Kleftiko Boat Tour an unforgettable journey to Milos’ hidden gems, where adventure meets tranquility on the crystal clear waters of the Aegean. Embark on an...

7 hours Free Cancellation
5.0 (306)
from
$154
Milos oneiro-kleftiko sailing experience with local guide

Tour with a sailing boat like a semi private trip with a small group of people. Our local skipper offers a slow close-up approach of …More

Milos, Greece

Tour with a sailing boat like a semi private trip with a small group of people. Our local skipper offers a slow close-up approach of...

7 hours Free Cancellation
5.0 (441)
from
$161
Milos Sailing Tour with snorkeling and lunch

We start from Pollonia or Adamas and we explore beautiful Milos and magnificent Kleftiko • Comfort and luxury: Our boat features 4 double cabins and …More

Milos, Greece

We start from Pollonia or Adamas and we explore beautiful Milos and magnificent Kleftiko • Comfort and luxury: Our boat features 4 double cabins and...

8 hours Free Cancellation
4.8 (196)
from
$171

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Cyclades Islands Tours
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