Cyclades Islands Cruises, Sailing & Water Tours

Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer

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 Free Cancellation
5.0 (7,657)
from
$147
Milos Small-Group Full-Day Cruise with Snorkelling and Lunch

The cruise is done at a relaxed pace, trying to avoid crowds with only 12 passengers aboard the sailing boat. Boats are equipped with large …More

Milos, Greece

The cruise is done at a relaxed pace, trying to avoid crowds with only 12 passengers aboard the sailing boat. Boats are equipped with large...

8 hours Free Cancellation
5.0 (1,552)
from
$181
Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

Santorini's notorious Dream Catcher tour lets you experience with a small group, the beauty of Santorini and the magic of sailing in the Caldera with the …More

Santorini, Greece

Santorini's notorious Dream Catcher tour lets you experience with a small group, the beauty of Santorini and the magic of sailing in the Caldera with the...

5 hours Hotel pickup offered Free Cancellation
4.9 (710)
from
$135
Santorini Gold Catamaran Cruise with BBQ, Drinks and Hotel Pickup

Go beyond the typical cruise experience on a spacious and stable catamaran, ensuring a smooth ride for everyone. This exclusive tour is limited to just …More

Santorini, Greece

Go beyond the typical cruise experience on a spacious and stable catamaran, ensuring a smooth ride for everyone. This exclusive tour is limited to just...

5 hours Hotel pickup offered Free Cancellation
4.9 (896)
from
$96
Half Day Premium Catamaran Cruise in Santorini including Oia

A sailing experience to soak up the beautiful scenery of Santorini island surrounded by the clear water of Aegean sea and visit the most popular …More

Santorini, Greece

A sailing experience to soak up the beautiful scenery of Santorini island surrounded by the clear water of Aegean sea and visit the most popular...

5 hours Hotel pickup offered Free Cancellation
5.0 (1,812)
from
$181
Best of Milos and Poliegos Catamaran snorkelling Cruise with BBQ

This cruise is made with a maximum number of 22 people on board a luxury, very spacious 44-foot catamaran with lots of shaded sitting and …More

Milos, Greece

This cruise is made with a maximum number of 22 people on board a luxury, very spacious 44-foot catamaran with lots of shaded sitting and...

9 hours Free Cancellation
5.0 (550)
from
$225
Mykonos: Brand-New Catamaran Cruise with Meal, Drinks & Transport

Cruise with Nostos Mykonos Yachts in sophisticated chic style and discover the gorgeous waters of the nearby Rhenia island or the famous Mykonian southern coast …More

Mykonos, Greece

Cruise with Nostos Mykonos Yachts in sophisticated chic style and discover the gorgeous waters of the nearby Rhenia island or the famous Mykonian southern coast...

5 hours Hotel pickup offered Free Cancellation
4.9 (1,192)
from
$134
Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar

Sail … the dream on a luxurious catamaran and unlock your senses. Cruise around the Caldera of Santorini. Feel the healing waters and mystical surroundings …More

Santorini, Greece

Sail … the dream on a luxurious catamaran and unlock your senses. Cruise around the Caldera of Santorini. Feel the healing waters and mystical surroundings...

5 hours Hotel pickup offered Free Cancellation
4.9 (4,183)
from
$124
Mykonos Sunset Cruise with Drinks

Come onboard and enjoy the breathtaking Mykonian sunset! Set sail and enjoy the magnificent view of Little Venice and Mykonos. Drop anchor to watch the …More

Mykonos, Greece

Come onboard and enjoy the breathtaking Mykonian sunset! Set sail and enjoy the magnificent view of Little Venice and Mykonos. Drop anchor to watch the...

2 hours 15 minutes Free Cancellation
4.2 (64)
from
$56
Semi - Private Fishing Tour (transportation included)

Authentic fishing experience with our traditional boat named 'Giorgaros' 5 hours duration ! Cook the catch of the day. Meet the locals. Avoid crowds! Swim …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

Authentic fishing experience with our traditional boat named 'Giorgaros' 5 hours duration ! Cook the catch of the day. Meet the locals. Avoid crowds! Swim...

5 hours Hotel pickup offered Free Cancellation
5.0 (167)
from
$180
Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

Visit with licensed guide the natural insular archaeological site of Delos and enjoy swimming and snorkeling to a secluded cove off the uninhabited island of …More

Mykonos, Greece

Visit with licensed guide the natural insular archaeological site of Delos and enjoy swimming and snorkeling to a secluded cove off the uninhabited island of...

5 to 6 hours Free Cancellation
4.7 (585)
from
$130
Kayaking Tour to the secrets of Milos

Our kayak tour offers you the unique experience to explore a majestic part of the island of Milos. We will be paddling along the volcanic …More

Likely to Sell Out
Likely to Sell Out
Milos, Greece

Our kayak tour offers you the unique experience to explore a majestic part of the island of Milos. We will be paddling along the volcanic...

3 hours 30 minutes Free Cancellation
5.0 (248)
from
$79
Santorini Semi-private Morning or Sunset Volcano Sailing Tour

Book your Santorini sailing tour to explore the volcano, hot springs, stunning views, and local flavors! …More

Santorini, Greece

Book your Santorini sailing tour to explore the volcano, hot springs, stunning views, and local flavors!...

5 hours Free Cancellation
5.0 (22)
from
$152
Santorini Luxury Catamaran Day Cruise with BBQ,drinks,transfer

A sailing trip is 'a must do' experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most …More

Santorini, Greece

A sailing trip is 'a must do' experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most...

5 hours Hotel pickup offered Free Cancellation
4.9 (213)
from
$147
Santorini Standard Small-Group Catamaran Volcano, BBQ and Drinks

1. Red Beach Relax at Santorini’s Red Beach with dramatic volcanic cliffs and crystal-clear waters—perfect for photos and views. 2. White Beach & Blue-and-White Churches …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

1. Red Beach Relax at Santorini’s Red Beach with dramatic volcanic cliffs and crystal-clear waters—perfect for photos and views. 2. White Beach & Blue-and-White Churches...

4 to 6 hours Hotel pickup offered Free Cancellation
4.8 (124)
from
$96
Half Day Delos Tour of Mykonos from the Cruise Ship Port

Combining 2 in 1, this tour is perfect for those visiting Mykonos as part of their cruise. Once you disembark, the local SeaBus welcomes and …More

Mykonos, Greece

Combining 2 in 1, this tour is perfect for those visiting Mykonos as part of their cruise. Once you disembark, the local SeaBus welcomes and...

5 hours Free Cancellation
4.2 (47)
from
$73
Santorini Luxury Catamaran Sunset Cruise with BBQ, Drink and Transfer

The sunset sailing trip is unique experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most luxurious …More

Santorini, Greece

The sunset sailing trip is unique experience in Santorini. Why you not do it with style? The Brand New Ipanema 58' is the most luxurious...

5 hours Hotel pickup offered Free Cancellation
4.9 (378)
from
$147
Private Caldera Cruise with Power Catamaran ENJOY incl. Meal & Drinks

Create your own itinerary or trust our highly experienced captain to take you to the most wonderful places. Choose either a 3, 4, or 5-hour …More

Likely to Sell Out
Likely to Sell Out
Santorini, Greece

Create your own itinerary or trust our highly experienced captain to take you to the most wonderful places. Choose either a 3, 4, or 5-hour...

3 to 5 hours Hotel pickup offered Free Cancellation
5.0 (82)
from
$121
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
$169
Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks

Discover Santorini by sea on this 5-hour catamaran tour. Admire the island’s volcanic sights, visit its impressive beaches, and soak in its thermal hot springs; …More

Santorini, Greece

Discover Santorini by sea on this 5-hour catamaran tour. Admire the island’s volcanic sights, visit its impressive beaches, and soak in its thermal hot springs;...

5 hours Hotel pickup offered Free Cancellation
4.8 (311)
from
$107
Antiparos & Despotiko: Swim, Explore, and Savor Lunch from Paros

Set off on an unforgettable sea adventure and uncover some of the Cyclades’ most beautiful hidden spots. Departing from Paros and cruising towards Antiparos, this …More

Likely to Sell Out
Likely to Sell Out
Paros, Greece

Set off on an unforgettable sea adventure and uncover some of the Cyclades’ most beautiful hidden spots. Departing from Paros and cruising towards Antiparos, this...

7 hours Free Cancellation
4.7 (161)
from
$107

Frequently Asked Questions

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

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