Top Cyclades Islands Sailing Trips

Q: What are the best options for Cyclades Islands Sailing Trips?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Cyclades Islands Sailing Trips are: Sailboat Full Day Tour in Kleftiko and Blue Lagoon with Lunch Half day Catamaran Morning Cruise in Kleftiko Explore Santorini and its volcanic wonders with Alex Private Boat Santorini Sunset Cruise in Caldera Santorini Caldera Private Sailing Boat Cruise

Q: What are the best kid-friendly options for Cyclades Islands Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Cyclades Islands Sailing Trips are: Santorini Volcano Hot Springs Santorini - Volcano and Hot springs Santorini Volcano and Hot Springs Cruise Tour from Fira Old Port Santorini 3 Islands Trip by Sailing boat Santorini 3 Islands Trip Sailing Wooden Boat View all kid-friendly Tours →

Q: Which Cyclades Islands Sailing Trips have Instant Confirmation?

Cyclades Islands Sailing Trips with Instant Confirmation include: Santorini Volcano Hot Springs Santorini - Volcano and Hot springs Santorini Volcano and Hot Springs Cruise Tour from Fira Old Port Santorini 3 Islands Trip by Sailing boat Santorini 3 Islands Trip Sailing Wooden Boat View all Tours with Instant Confirmation →

Q: Got any more Cyclades Islands trip ideas?

We sure do. Check out our curated lists of hand-picked Cyclades Islands Tours. Top 10 Cyclades Islands 2026 Senior-friendly tours Cyclades Islands The best tours and activities for culture lovers in Cyclades Islands Top Day Trips from Cyclades Islands Things to do in Cyclades Islands this summer View all Cyclades Islands Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Cyclades Islands?

Based on our sales data over the past year, the most popular styles of tours and activities in Cyclades Islands are: Cyclades Islands Luxury & Special Occasions Cyclades Islands Luxury Tours Cyclades Islands Tours & Sightseeing Cyclades Islands Half-day Tours Cyclades Islands Cruises, Sailing & Water Tours View all tour styles in Cyclades Islands →

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

5.0 (306)

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...

7 hours Free Cancellation

5.0 (306)

from
$154

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

4.6 (28)

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,...

4 to 5 hours Hotel pickup offered Free Cancellation

4.6 (28)

from
$155

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

4.9 (239)

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...

6 hours Hotel pickup offered Free Cancellation

4.9 (239)

from
$157

Mykonos Catamaran Sunset Semi private Cruise with transfer

Although not a day trip, this experience provides the perfect ending to a day in beautiful Mykonos. Set sail towards the horizon, with a glass …More

Mykonos, Greece

5.0 (19)

Mykonos Catamaran Sunset Semi private Cruise with transfer

Although not a day trip, this experience provides the perfect ending to a day in beautiful Mykonos. Set sail towards the horizon, with a glass...

4 hours Free Cancellation

5.0 (19)

from
$159

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

5.0 (441)

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...

7 hours Free Cancellation

5.0 (441)

from
$159

Santorini Half Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport

Enjoy unique views of Santorini from the sea during this 5 hour morning or sunset cruise. Starting from the port of Vlychada, see the Vlychada …More

Santorini, Greece

4.9 (87)

Santorini Half Day Catamaran Private Cruise incl. Meal, Drinks & Free Transport

Enjoy unique views of Santorini from the sea during this 5 hour morning or sunset cruise. Starting from the port of Vlychada, see the Vlychada...

5 hours Hotel pickup offered Free Cancellation

4.9 (87)

from
$159

Kleftiko Full Day Sailing Cruise with Snorkeling & Lunch

Discover the beautiful coast line of Milos and its fantastic and unapproachable beaches with our sailing yachts and find an exciting and alternative way in …More

Milos, Greece

4.9 (133)

Kleftiko Full Day Sailing Cruise with Snorkeling & Lunch

Discover the beautiful coast line of Milos and its fantastic and unapproachable beaches with our sailing yachts and find an exciting and alternative way in...

9 to 10 hours Free Cancellation

4.9 (133)

from
$160

Santorini Sailing for Cruise Guests A Volcano and Beach Tour

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a …More

Santorini, Greece

5.0 (2)

Santorini Sailing for Cruise Guests A Volcano and Beach Tour

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a...

6 hours Free Cancellation

5.0 (2)

from
$160

Private Morning Tour Lagoon 400-380 Sailing in Santorini,lunch, drink, transfer

Discover the most beautiful locations that Santorini has to offer on our beautiful Lagoon 400. Our crew will welcome you with open arms and provide …More

Santorini, Greece

5.0 (62)

Private Morning Tour Lagoon 400-380 Sailing in Santorini,lunch, drink, transfer

Discover the most beautiful locations that Santorini has to offer on our beautiful Lagoon 400. Our crew will welcome you with open arms and provide...

5 hours Hotel pickup offered Free Cancellation

5.0 (62)

from
$162

Santorini Oia: Private Day Cruise with Fresh Fish BBQ & Drinks

The Private Day 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

5.0 (38)

Santorini Oia: Private Day Cruise with Fresh Fish BBQ & Drinks

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

4 hours Hotel pickup offered Free Cancellation

5.0 (38)

from
$164

Santorini Oia:Small Group Sunset Cruise w BBQ Fresh Fish & Drinks

The Sunset Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay in Oia is a great opportunity to enjoy a …More

Santorini, Greece

5.0 (113)

Santorini Oia:Small Group Sunset Cruise w BBQ Fresh Fish & Drinks

The Sunset Luxury Semi- Private Sailing Cruise by Renieris Santorini Sailing Center departing from Ammoudi bay in Oia is a great opportunity to enjoy a...

6 hours Hotel pickup offered Free Cancellation

5.0 (113)

from
$165

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

5.0 (47)

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...

6 hours Free Cancellation

5.0 (47)

from
$165

Catamaran Half Day Afternoon Cruise With Sunset: Kleftiko

Enjoy amazing moments in Milos island! An ideal cruise for you in order to see the most famous spots here in Milos such as Kleftiko …More

Milos, Greece

4.9 (28)

Catamaran Half Day Afternoon Cruise With Sunset: Kleftiko

Enjoy amazing moments in Milos island! An ideal cruise for you in order to see the most famous spots here in Milos such as Kleftiko...

6 hours Free Cancellation

4.9 (28)

from
$166

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

Mykonos, Greece

5.0 (98)

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...

6 hours Hotel pickup offered Free Cancellation

5.0 (98)

from
$170

Santorini Private Cruise Sightseeing Tour with BBQ and Drinks

Enjoy swimming & snorkeling in the clear blue waters of the Aegean Sea. You can go snorkeling near the shore and experience the amazing underwater …More

Santorini, Greece

5.0 (13)

Santorini Private Cruise Sightseeing Tour with BBQ and Drinks

Enjoy swimming & snorkeling in the clear blue waters of the Aegean Sea. You can go snorkeling near the shore and experience the amazing underwater...

5 hours Free Cancellation

5.0 (13)

from
$170

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

5.0 (354)

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...

5 hours Free Cancellation

5.0 (354)

from
$171

Mykonos: Luxury Catamaran Cruise with Meal, Drinks & Transport

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

Mykonos, Greece

4.9 (10)

Mykonos: Luxury Catamaran Cruise with Meal, Drinks & Transport

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

5 hours Hotel pickup offered Free Cancellation

4.9 (10)

from
$171

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

4.8 (196)

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...

8 hours Free Cancellation

4.8 (196)

from
$171

Milos Luxury Catamaran Cruise to Kleftiko Bay with Lunch

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge, …More

Milos, Greece

5.0 (22)

Milos Luxury Catamaran Cruise to Kleftiko Bay with Lunch

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge,...

5 hours 30 minutes Free Cancellation

5.0 (22)

from
$176

Milos Sunset Catamaran Cruise to Kleftiko Bay with Meal & Drinks

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge, …More

Milos, Greece

5.0 (32)

Milos Sunset Catamaran Cruise to Kleftiko Bay with Meal & Drinks

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge,...

5 hours 30 minutes Free Cancellation

5.0 (32)

from
$176

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Cyclades Islands Sailing Trips?

What are the best kid-friendly options for Cyclades Islands Sailing Trips Tours?

Which Cyclades Islands Sailing Trips have Instant Confirmation?

Which Cyclades Islands Sailing Trips have Free Cancellation?

Cyclades Islands Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Cyclades Islands Sailing Trips have Hotel Pickup?

No problem. These Cyclades Islands Sailing Trips include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Cyclades Islands trip ideas?

What are the most popular styles of Tours and Activities in Cyclades Islands?