Cyclades Islands Cruises, Sailing & Water Tours

Milos Full-Day Premium Catamaran Cruise Kleftiko and Polyegos

Experience the magic of Milos on a luxury catamaran cruise designed for total comfort and adventure. Your journey begins at Adamantas, sailing first to the …More

Milos, Greece

Experience the magic of Milos on a luxury catamaran cruise designed for total comfort and adventure. Your journey begins at Adamantas, sailing first to the...

9 hours Free Cancellation
5.0 (20)
from
$214
Mykonos Catamaran Delos Rhenia Cruise with Lunch and Transfer

Indulge in this daily cruise to Delos and Rhenia islands, which lets you bask in the warm Mykonian sun, enjoying the summer breeze as you …More

Mykonos, Greece

Indulge in this daily cruise to Delos and Rhenia islands, which lets you bask in the warm Mykonian sun, enjoying the summer breeze as you...

6 hours Hotel pickup offered Free Cancellation
5.0 (33)
from
$203
Morning Caldera Sailing Cruise

Step aboard this 5 hour morning cruise for a relaxed sail and enjoy your time swimming, sunbathing, snorkeling, taking photos, tasting delicious BBQ meals, Greek …More

Santorini, Greece

Step aboard this 5 hour morning cruise for a relaxed sail and enjoy your time swimming, sunbathing, snorkeling, taking photos, tasting delicious BBQ meals, Greek...

5 hours Hotel pickup offered Free Cancellation
5.0 (36)
from
$141
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
$8,308
Semi-Private Half Day/Sunset cruise

Choose Your Perfect Half-Day Cruise Experience Enjoy a unique escape on the sea with one of our three half-day cruises Morning Cruise – 09:30 to …More

Paros, Greece

Choose Your Perfect Half-Day Cruise Experience Enjoy a unique escape on the sea with one of our three half-day cruises Morning Cruise – 09:30 to...

3 hours Free Cancellation
4.9 (26)
from
$102
Private Boat Tour to Antiparos and Blue Lagoon

Embark on an unforgettable adventure exploring the hidden gems of the Cyclades with our exclusive boat tour departing from Naxos or Paros. Our first stop …More

Naxos, Greece

Embark on an unforgettable adventure exploring the hidden gems of the Cyclades with our exclusive boat tour departing from Naxos or Paros. Our first stop...

6 to 8 hours Free Cancellation
4.9 (33)
from
$1,295
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
$141
Antiparos Odyssey: Caves, Blue Lagoon & Coastal Charms|Boat Tour

Explore the charming streets of Antiparos, a serene destination favoured by celebrities. Marvel at the stunning Cave of Trypiti, a natural wonder, take photos and …More

Antiparos, Greece

Explore the charming streets of Antiparos, a serene destination favoured by celebrities. Marvel at the stunning Cave of Trypiti, a natural wonder, take photos and...

4 hours Free Cancellation
5.0 (24)
from
$1,126
Private sailing cruise to Delos & Rhenia with Lunch & Transfer

Our first stop is an hour away, the renowned Big Delos island. While there, you will have the opportunity to visit one of the most …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Our first stop is an hour away, the renowned Big Delos island. While there, you will have the opportunity to visit one of the most...

6 hours Hotel pickup offered Free Cancellation
5.0 (12)
from
$2,179
Santorini: Private Catamaran Cruise with Fresh Fish BBQ & Drinks

The Private Sailing Cruise by Renieris Santorini Sailing Center starting from Vlychada marina is a great opportunity to customize your own cruise and enjoy the …More

Santorini, Greece

The Private Sailing Cruise by Renieris Santorini Sailing Center starting from Vlychada marina is a great opportunity to customize your own cruise and enjoy the...

5 hours Hotel pickup offered Free Cancellation
5.0 (19)
from
$158
Santorini Caldera Morning Cruise With King Thiras Boat

What makes this tour unique is the opportunity to visit the main landmarks of Santorini in one day, enjoying amazing views and sceneries. …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

What makes this tour unique is the opportunity to visit the main landmarks of Santorini in one day, enjoying amazing views and sceneries....

7 hours Free Cancellation
4.3 (36)
from
$57
Milos Island Full day Private Tour

We know the whole island like the palm of our hand. We can take you to dramatic sea caves and beaches so secluded even the …More

Milos, Greece

We know the whole island like the palm of our hand. We can take you to dramatic sea caves and beaches so secluded even the...

8 to 9 hours Free Cancellation
5.0 (15)
from
$2,565
Santorini Caldera: Private Cruise with Speed Boat & Open Bar

Starting the tour from the marina of Vlychada, our first stop will be the volcanic Red Beach where for half an hour you will enjoy …More

Santorini, Greece

Starting the tour from the marina of Vlychada, our first stop will be the volcanic Red Beach where for half an hour you will enjoy...

4 hours Hotel pickup offered Free Cancellation
5.0 (11)
from
$158
Motor Yacht (2026)Luxury Private Cruise Around Santorini

Enjoy a fully private experience on the luxury motor yacht Diamond, offering speed, comfort and flexibility to explore more of Santorini in less time. Unlike …More

Santorini, Greece

Enjoy a fully private experience on the luxury motor yacht Diamond, offering speed, comfort and flexibility to explore more of Santorini in less time. Unlike...

5 hours Hotel pickup offered Free Cancellation
5.0 (12)
from
$152
Small group,swim in Rhenia,watch the sunset fm LVenice, freetrans

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice, …More

Mykonos, Greece

Join us for an unforgettable day of relaxation and fun as we set sail to Rhenia Island and enjoy a magical sunset at Little Venice,...

4 to 5 hours Hotel pickup offered Free Cancellation
4.6 (28)
from
$152
Private Sunset Cruise to Klima with snacks and drinks

With the stunning backdrop of Milos Island, the tour offers the opportunity to witness a breathtaking sunset from the comfort of the luxurious Saxdor 32GTO. …More

Milos, Greece

With the stunning backdrop of Milos Island, the tour offers the opportunity to witness a breathtaking sunset from the comfort of the luxurious Saxdor 32GTO....

2 hours Free Cancellation
5.0 (16)
from
$68
Santorini: Caldera Private Sailing Boat Cruise with Beneteau Oceanis 46.1

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number …More

Santorini, Greece

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number...

5 hours Hotel pickup offered Free Cancellation
5.0 (17)
from
$148
Santorini Full Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport

Enjoy unique views of Santorini from the sea during this 7 hour daycruise, starting from the port of Vlychada. Passing from the Red Beach you …More

Santorini, Greece

Enjoy unique views of Santorini from the sea during this 7 hour daycruise, starting from the port of Vlychada. Passing from the Red Beach you...

7 hours Hotel pickup offered Free Cancellation
4.9 (16)
from
$259
Sailsational Luxury Santorini Catamaran Sunset Cruise with Dinner

The limited number of participants makes this catamaran sailing experience unique and different. At most, 12-20 guests take place on this catamaran sailing tour. It …More

Santorini, Greece

The limited number of participants makes this catamaran sailing experience unique and different. At most, 12-20 guests take place on this catamaran sailing tour. It...

5 to 6 hours Hotel pickup offered Free Cancellation
4.8 (19)
from
$214
Maria Paros Sea Caves Tour Blue Lagoon Antiparos Despotico

The sea tour combines: A 3-4 stops for swimming and snorkeling , sunbathing on the deck listening music while finger food is served at the …More

Paros, Greece

The sea tour combines: A 3-4 stops for swimming and snorkeling , sunbathing on the deck listening music while finger food is served at the...

7 hours Free Cancellation
5.0 (15)
from
$99
Mykonos Delos Rhenia Cruise with Champagne Welcome

Your sailing adventure begins at the embarkation point in Mykonos, where our crew welcomes you on board with a safety briefing and a glass of …More

Mykonos, Greece

Your sailing adventure begins at the embarkation point in Mykonos, where our crew welcomes you on board with a safety briefing and a glass of...

5 hours Free Cancellation
5.0 (16)
from
$147

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

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