Cyclades Islands Cruises, Sailing & Water Tours

Private Speedboat Cruise from Delos to Rhenia and Mykonos

Mykonos along with Delos, Rhenia and some other rocky islets form a single island complex. Visiting these islets is a "must" for someone discovering Mykonos. …More

Mykonos, Greece

Mykonos along with Delos, Rhenia and some other rocky islets form a single island complex. Visiting these islets is a "must" for someone discovering Mykonos....

8 hours Free Cancellation
5.0 (50)
from
$1,860
Milos & Poliegos Catamaran Cruise Homemade Full menu BBQ & Drinks

Experience a luxury full-day cruise aboard the new catamaran Lagoon 46 “Naya II”, where elegance meets comfort and have a special day by exploring the …More

Milos, Greece

Experience a luxury full-day cruise aboard the new catamaran Lagoon 46 “Naya II”, where elegance meets comfort and have a special day by exploring the...

9 to 10 hours Free Cancellation
5.0 (53)
from
$237
Private Full Day Boat Tour: Discover Hidden Gems around Paros

Embark on an unforgettable adventure exploring the hidden gems of Paros and Antiparos with our private boat tour departing from Paros. Our first stop takes …More

Antiparos, Greece

Embark on an unforgettable adventure exploring the hidden gems of Paros and Antiparos with our private boat tour departing from Paros. Our first stop takes...

6 to 8 hours Free Cancellation
4.9 (53)
from
$1,295
Half-Day Private Cruise with Kaiki around Mykonos

You will sail around Mykonos with one of the certified antique boats of Greece! A boat with big history, but recently restored in order to …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

You will sail around Mykonos with one of the certified antique boats of Greece! A boat with big history, but recently restored in order to...

4 hours Free Cancellation
5.0 (51)
from
$135
Sailboat Full Day Tour in Kleftiko and Blue Lagoon with Lunch

Make this day unique, forget about any distraction while onboard. Enjoy a genuine adventure that will remain unforgettable. Take some stunning photos and videos that …More

Milos, Greece

Make this day unique, forget about any distraction while onboard. Enjoy a genuine adventure that will remain unforgettable. Take some stunning photos and videos that...

9 hours Free Cancellation
5.0 (55)
from
$186
Santorini Oia: Private Sunset Cruise with Fresh Fish BBQ & Drinks

The Sunset Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay is a great opportunity to enjoy a sailing cruise at the …More

Santorini, Greece

The Sunset Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay is a great opportunity to enjoy a sailing cruise at the...

6 hours Hotel pickup offered Free Cancellation
5.0 (46)
from
$208
Half day Catamaran Morning Cruise in Kleftiko

We welcome you to the island of colors with its natural beauty and incredible rock formations, a unique destination for each of you.

 Polychronis Mavros …More

Milos, Greece

We welcome you to the island of colors with its natural beauty and incredible rock formations, a unique destination for each of you.

 Polychronis Mavros...

6 hours Free Cancellation
5.0 (47)
from
$163
Morning or Afternoon 3hour Private boat cruise tour in Santorini

Our team of experienced professionals have carefully selected and optimized each of our trips to ensure that you get the best out of this once …More

Santorini, Greece

Our team of experienced professionals have carefully selected and optimized each of our trips to ensure that you get the best out of this once...

3 hours Hotel pickup offered Free Cancellation
5.0 (47)
from
$666
Majestic Catamaran Caldera Cruise with Snacks, Meal & Drinks

The Majestic Day or Sunset Cruise is operated by our newest catamarans which offering luxury setup with plenty of space. You'll set off from Ammoudi …More

Santorini, Greece

The Majestic Day or Sunset Cruise is operated by our newest catamarans which offering luxury setup with plenty of space. You'll set off from Ammoudi...

4 hours 30 minutes Hotel pickup offered Free Cancellation
4.8 (23)
from
$152
Mykonos boat tour-unlimited drinks-small group(new product)

Experience the sea, sun, and tradition aboard a traditional Mykonian wooden boat — a classic vessel rooted in the island’s maritime heritage, offering an authentic …More

Likely to Sell Out
Likely to Sell Out
Mykonos, Greece

Experience the sea, sun, and tradition aboard a traditional Mykonian wooden boat — a classic vessel rooted in the island’s maritime heritage, offering an authentic...

2 hours 30 minutes
5.0 (42)
from
$85
Explore Santorini and its volcanic wonders with Alex Private Boat

Join us on this breathtaking trip to Nea and Palea Kammeni,the lava islands in the middle of the crater. First up, we will see the …More

Santorini, Greece

Join us on this breathtaking trip to Nea and Palea Kammeni,the lava islands in the middle of the crater. First up, we will see the...

3 hours Free Cancellation
5.0 (48)
from
$564
Mykonos Catamaran Private Sunset Cruise, Full Meal & Open-Bar

Mykonos Catamaran is the original and most renowned catamaran company in Mykonos! Sail on a safe and seaworthy catamaran carefully chosen by Captain Michael to …More

Mykonos, Greece

Mykonos Catamaran is the original and most renowned catamaran company in Mykonos! Sail on a safe and seaworthy catamaran carefully chosen by Captain Michael to...

5 hours Free Cancellation
5.0 (42)
from
$190
Santorini Sunset Cruise in Caldera

Experience a calm and romantic trip to the amazing sites of Santorini on a charming wooden sailing boat! The peaceful atmosphere and gentle rocking of …More

Santorini, Greece

Experience a calm and romantic trip to the amazing sites of Santorini on a charming wooden sailing boat! The peaceful atmosphere and gentle rocking of...

5 hours Free Cancellation
4.9 (45)
from
$51
Private Sunset Cruise with Full Greek Dinner

• We will set sail from the Marina of Vlihada, to red beach of the island which is situated in the historic village of Akrotiri …More

Santorini, Greece

• We will set sail from the Marina of Vlihada, to red beach of the island which is situated in the historic village of Akrotiri...

5 hours Hotel pickup offered Free Cancellation
5.0 (49)
from
$183
Private Full Day Catamaran Cruise from Paros with Lunch

Enjoy an unforgettable day aboard our luxury Catamaran. Our professional crew offers a fully personalised service that caters to your every need. Rest your head …More

Paros, Greece

Enjoy an unforgettable day aboard our luxury Catamaran. Our professional crew offers a fully personalised service that caters to your every need. Rest your head...

9 hours Hotel pickup offered Free Cancellation
5.0 (54)
from
$292
Diamond 36 Private Motor Yacht Caldera Cruise

The Diamond 36 Motor Yacht is a mix of comfort, safety and fine design with high tech innovation and a passion for the sea. Create …More

Santorini, Greece

The Diamond 36 Motor Yacht is a mix of comfort, safety and fine design with high tech innovation and a passion for the sea. Create...

3 to 5 hours Hotel pickup offered Free Cancellation
5.0 (47)
from
$121
Santorini Caldera Private Sailing Boat Cruise

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private …More

Santorini, Greece

Dare to be different! Get ready for the ultimate sailing experience in the most beautiful place on Earth! Get on board and your Caldera private...

5 hours Hotel pickup offered Free Cancellation
4.9 (53)
from
$790
Santorini Private Catamaran Cruise

A Lagoon catamaran for your group only: up to 20 guests, 5 hours by day or at sunset from Vlychada Marina. Sail past Red Beach …More

Santorini, Greece

A Lagoon catamaran for your group only: up to 20 guests, 5 hours by day or at sunset from Vlychada Marina. Sail past Red Beach...

5 hours Hotel pickup offered Free Cancellation
5.0 (40)
from
$180
Mykonos: Private Catamaran Cruise—Lunch & Unlimited Drinks

Set sail on a private catamaran cruise from Mykonos with hotel pickup and drop-off included, so your day starts and ends effortlessly. Visit Delos and …More

Mykonos, Greece

Set sail on a private catamaran cruise from Mykonos with hotel pickup and drop-off included, so your day starts and ends effortlessly. Visit Delos and...

5 to 8 hours Hotel pickup offered Free Cancellation
5.0 (54)
from
$1,348
3 Hour Private Cruise – South Coastline Of Mykonos

The beaches of Mykonos are totally intertwined with the island's global reputation, as both quality and number are something you do not encounter on any …More

Mykonos, Greece

The beaches of Mykonos are totally intertwined with the island's global reputation, as both quality and number are something you do not encounter on any...

3 hours Free Cancellation
5.0 (59)
from
$843
Caldera Cruise with Swim Stops, BBQ on board and drinks!

Set out on a unique sailing adventure. The cruise takes you to the emblematic Caldera coastline, by the Black Rock of the Indian and the …More

Santorini, Greece

Set out on a unique sailing adventure. The cruise takes you to the emblematic Caldera coastline, by the Black Rock of the Indian and the...

5 hours Hotel pickup offered Free Cancellation
5.0 (27)
from
$147

Frequently Asked Questions

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

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