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Top Dodecanese Sailing Trips

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3-Hours Sunset Catamaran Cruise with Dinner all Inclusive

The Sunset Cruise will exploit your senses. Start your relaxing sunset cruise from Mandraki Harbor. Set sail to Kalithea Springs for a swim and relaxing. …More

Likely to Sell Out
Likely to Sell Out
Rhodes, Greece
4.9 (46)

3-Hours Sunset Catamaran Cruise with Dinner all Inclusive

The Sunset Cruise will exploit your senses. Start your relaxing sunset cruise from Mandraki Harbor. Set sail to Kalithea Springs for a swim and relaxing....

3 hours • Free Cancellation
4.9 (46)
from
$81
Sunset Cruise with Greek BBQ & Unlimited Aperol Spritz, Beer Wine

Start your relaxing 3 hour sunset cruise from Mandraki Harbour, where you will head to Kalithea Springs for a swim and to relax. You'll also …More

Rhodes, Greece
4.7 (153)

Sunset Cruise with Greek BBQ & Unlimited Aperol Spritz, Beer Wine

Start your relaxing 3 hour sunset cruise from Mandraki Harbour, where you will head to Kalithea Springs for a swim and to relax. You'll also...

3 hours • Free Cancellation
4.7 (153)
from
$46
Sun & Sea 6 Hour All Inclusive Swimming Cruise with Greek BBQ & Unlimited Drinks

Our Sun & Sea Cruise is designed for those holiday makers looking for a chilled cruise and a true taste of first class Greek Hospitality. …More

Rhodes, Greece
4.8 (616)

Sun & Sea 6 Hour All Inclusive Swimming Cruise with Greek BBQ & Unlimited Drinks

Our Sun & Sea Cruise is designed for those holiday makers looking for a chilled cruise and a true taste of first class Greek Hospitality....

6 hours • Free Cancellation
4.8 (616)
from
$75
Athens: All Day Cruise to Agistri Moni Aegina with Lunch & Drinks

If you are you looking for a relaxing and memorable day trip from Athens, look no further than a full-day cruise on a traditional wooden …More

Rhodes, Greece
4.8 (626)

Athens: All Day Cruise to Agistri Moni Aegina with Lunch & Drinks

If you are you looking for a relaxing and memorable day trip from Athens, look no further than a full-day cruise on a traditional wooden...

10 hours • Hotel pickup offered • Free Cancellation
4.8 (626)
from
$157
Private Full-Day Cruise in Rhodes with Lunch and Drinks

We organise daily cruises,along the eastern coast of Rhodes Island.Our trip is one of the most relaxing and adventurous tours on the island.We have three …More

Rhodes, Greece
5.0 (218)

Private Full-Day Cruise in Rhodes with Lunch and Drinks

We organise daily cruises,along the eastern coast of Rhodes Island.Our trip is one of the most relaxing and adventurous tours on the island.We have three...

6 hours 30 minutes • Free Cancellation
5.0 (218)
from
$848
Catamaran Cruises Rhodes - 6 Hours Day Cruise ALL INCLUSIVE

**Live the Catamaran experience in Rhodes** We offer our clients the comfort and pleasure of luxury cruises around the beautiful island of Rhodes, creating an …More

Rhodes, Greece
4.7 (224)

Catamaran Cruises Rhodes - 6 Hours Day Cruise ALL INCLUSIVE

**Live the Catamaran experience in Rhodes** We offer our clients the comfort and pleasure of luxury cruises around the beautiful island of Rhodes, creating an...

6 hours • Free Cancellation
4.7 (224)
from
$87
Rhodes Day Cruise (with lunch & unlimited drinks) 5,5 Hours

We sail from Marina Mandraki (port) at 10:00am. Enjoy travelling with our traditional wooden boat to one of the most impressive beaches of Rhodes, the …More

Rhodes, Greece
4.8 (475)

Rhodes Day Cruise (with lunch & unlimited drinks) 5,5 Hours

We sail from Marina Mandraki (port) at 10:00am. Enjoy travelling with our traditional wooden boat to one of the most impressive beaches of Rhodes, the...

5 hours 30 minutes • Free Cancellation
4.8 (475)
from
$62
All-Inclusive Swimming Cruise: Anthony Quinn, Traganou & Kalithea

Experience the ultimate day of sun, sea, and Greek hospitality. This is our most popular tour for a reason: it combines the three most iconic …More

Rhodes, Greece
4.8 (240)

All-Inclusive Swimming Cruise: Anthony Quinn, Traganou & Kalithea

Experience the ultimate day of sun, sea, and Greek hospitality. This is our most popular tour for a reason: it combines the three most iconic...

6 hours • Hotel pickup offered • Free Cancellation
4.8 (240)
from
$89
Full/Half Day Small Group Boat Trip with Food and Drinks

Experience sailing with the wind on this semi-private trip limited to 13 people but aiming for no more than 10 each time. After leaving Lindos …More

Rhodes, Greece
4.9 (87)

Full/Half Day Small Group Boat Trip with Food and Drinks

Experience sailing with the wind on this semi-private trip limited to 13 people but aiming for no more than 10 each time. After leaving Lindos...

5 hours 30 minutes • Free Cancellation
4.9 (87)
from
$69
Kos: Small-Group Full-Day Catamaran Boat Trip, Meal, Drinks &Swim

Discover the Magic of the Aegean on a Catamaran Day Cruise from Kos! Set sail on a spacious catamaran as we journey from Kos to …More

Kos, Greece
4.9 (98)

Kos: Small-Group Full-Day Catamaran Boat Trip, Meal, Drinks &Swim

Discover the Magic of the Aegean on a Catamaran Day Cruise from Kos! Set sail on a spacious catamaran as we journey from Kos to...

7 hours • Free Cancellation
4.9 (98)
from
$203
Lindos Full Day Boat Tour with Swimming

Our personnel is annually trained for the sole purpose of providing our customers maximum safety and comfortability that their money can buy. Our unique destinations …More

Rhodes, Greece
4.6 (137)

Lindos Full Day Boat Tour with Swimming

Our personnel is annually trained for the sole purpose of providing our customers maximum safety and comfortability that their money can buy. Our unique destinations...

8 hours • Free Cancellation
4.6 (137)
from
$46
Kos: Small Group Full-Day Sailing Boat Trip, Meals, Drinks & Swim

Take in the beautiful Mediterranean ocean and views from a boat with swim and snorkeling stops along the way. Taste locally-made Greek dishes at lunchtime, …More

Kos, Greece
4.9 (100)

Kos: Small Group Full-Day Sailing Boat Trip, Meals, Drinks & Swim

Take in the beautiful Mediterranean ocean and views from a boat with swim and snorkeling stops along the way. Taste locally-made Greek dishes at lunchtime,...

7 hours • Free Cancellation
4.9 (100)
from
$168
Private sunset cruise in Rhodes with fruits and drinks.

The sunset trip is one of the best evening tour that you can go to,if you want a relaxing time. You can see some historical …More

Likely to Sell Out
Likely to Sell Out
Rhodes, Greece
5.0 (58)

Private sunset cruise in Rhodes with fruits and drinks.

The sunset trip is one of the best evening tour that you can go to,if you want a relaxing time. You can see some historical...

3 to 4 hours • Free Cancellation
5.0 (58)
from
$446
Semi-Private Sailing Cruise to Iconic Bays (Shore-Ex Top Choice)

Escape the large tour boats and experience the Rhodes coastline in total serenity. Join us on a boutique sailing yacht for a semi-private journey limited …More

Rhodes, Greece
4.8 (174)

Semi-Private Sailing Cruise to Iconic Bays (Shore-Ex Top Choice)

Escape the large tour boats and experience the Rhodes coastline in total serenity. Join us on a boutique sailing yacht for a semi-private journey limited...

6 hours • Hotel pickup offered • Free Cancellation
4.8 (174)
from
$116
Luxury Catamaran Morning Semi-Private and Greek Gastronomy Athens

More Than Just a Cruise, It's an Experience. Our Athenian Riviera cruise is more than just a day at sea. It's a unique and unforgettable …More

Halkidiki, Greece
5.0 (61)

Luxury Catamaran Morning Semi-Private and Greek Gastronomy Athens

More Than Just a Cruise, It's an Experience. Our Athenian Riviera cruise is more than just a day at sea. It's a unique and unforgettable...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (61)
from
$191
Private Full/Half-Day Boat Trip in Greece with Food and Drinks

Are you looking for a personal experience where you get to steer the boat and trim the sails? Join us and feel the peace of …More

Rhodes, Greece
5.0 (39)

Private Full/Half-Day Boat Trip in Greece with Food and Drinks

Are you looking for a personal experience where you get to steer the boat and trim the sails? Join us and feel the peace of...

5 hours 30 minutes • Free Cancellation
5.0 (39)
from
$609
Rhodes Private Luxury Cruise MediterAsian Lunch Champagne coctail

Sail in Style Aboard the Newly Renovated Sailing Edisa ⛵ Sailing Edisa offers a private luxury yacht experience designed for guests who value privacy, comfort, …More

Rhodes, Greece
5.0 (73)

Rhodes Private Luxury Cruise MediterAsian Lunch Champagne coctail

Sail in Style Aboard the Newly Renovated Sailing Edisa ⛵ Sailing Edisa offers a private luxury yacht experience designed for guests who value privacy, comfort,...

6 hours • Free Cancellation
5.0 (73)
from
$1,068
Rhodes sea cruises (6 hours pleasure cruise with lunch)

''ALKMINI'' boat is a traditional greek wooden motor and sail boat.Its 20 meter long with 3 main engines.Has two decks,one with shadow and the other …More

Rhodes, Greece
4.7 (36)

Rhodes sea cruises (6 hours pleasure cruise with lunch)

''ALKMINI'' boat is a traditional greek wooden motor and sail boat.Its 20 meter long with 3 main engines.Has two decks,one with shadow and the other...

6 hours • Free Cancellation
4.7 (36)
from
$52
Rhodes Private Luxury Sunset Cruise,Cocktails & Champagne, wine

Sunset Cruise to Kallithea Springs – Aboard Our Luxury Sailing Yacht Embark on Sailing Edisa for an unforgettable sunset cruise as golden light reflects across …More

Rhodes, Greece
5.0 (13)

Rhodes Private Luxury Sunset Cruise,Cocktails & Champagne, wine

Sunset Cruise to Kallithea Springs – Aboard Our Luxury Sailing Yacht Embark on Sailing Edisa for an unforgettable sunset cruise as golden light reflects across...

3 hours 30 minutes • Free Cancellation
5.0 (13)
from
$917
Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne

Romance in Rhodes – Sea, Spice & Serenity Aboard Sailing Edisa, elegant comfort meets the beauty of Kallithea Springs, where crystal waters invite swimming and …More

Rhodes, Greece
5.0 (18)

Rhodes Private Luxury Deluxe Sunset Dinner Coctails Champagne

Romance in Rhodes – Sea, Spice & Serenity Aboard Sailing Edisa, elegant comfort meets the beauty of Kallithea Springs, where crystal waters invite swimming and...

4 hours • Free Cancellation
5.0 (18)
from
$1,092

Frequently Asked Questions

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

Recent tour reviews
Good stuff
New York City
Athens: All Day Cruise to Agistri Moni Aegina with Lunch & Drinks
Donald_W_73659, Sep 2026
Good stuff
An amazing adventure, the crew on board great people, the food, the guidance, the boat is so cool. Highly recommend
Read more
The O’Connor’s
New York City
Sun & Sea 6 Hour All Inclusive Swimming Cruise with Greek BBQ & Unlimited Drinks
Brian_O, Sep 2026
The O’Connor’s
Everything was great and the staff were amazing. Highly recommend this trip. Food and drinks were so good. Thank you.
Read more
Memorable Odyssey
New York City
Athens: All Day Cruise to Agistri Moni Aegina with Lunch & Drinks
Jose_C, Sep 2026
Memorable Odyssey
The tour took us to beautiful islands with a variety of fun activities to do. The whole ship crew and tour guide were fun and helpful. All the food was delicious and plentiful. I went on this experience with a group of friends, and we all agreed it was so good that we would repeat it in the future, possibly even every time we visit Athens.
Read more
We are sailing ... again!
New York City
Kos: Small Group Full-Day Sailing Boat Trip, Meals, Drinks & Swim
tinakQ3772HR, Sep 2026
We are sailing ... again!
What an honour it was to be on-board this beautiful sailing boat which was clearly lovingly taken care of. The captain personally introduced himself to us and it wasn’t too long before we met the lovely lady crew member. We were made to feel so welcome and knew that the trip was going to be the relaxing excursion that we wanted. There was plenty of space on deck for everyone to grab a spot, hanker down towels and enjoy the beautiful views. I believe there were only 5 other couples with us so it really was a very intimate experience. The vibe was so chilled with no ‘banging’ music and once the sails were hoisted, at certain parts of our journey, no engine noise could even be heard. We had the opportunity to leave the boat at our two stops and it was fantastic to swim in the beautifully, clear sea. Bread was thrown in by the captain and other guests and there were fish aplenty to be seen swimming to the surface to grab a bite – absolutely fabulous! At the first stop, my husband and I swam to the little island and enjoyed sitting on the rocks there and watching the fish in the rock pools. Throughout the sailing, the lady crew member would give us plenty of information about the different islands we passed and highlighted the island which housed the Greek army. She was full of knowledge and was so willing to share this with us and other guests on-board. Now lunch … superb! We all sat around a table and shared lunch together – it was really utterly mouth-watering. The moussaka was so tasty, the bread so fresh, tzatziki delicious as were the other side dishes which accompanied our meal – all washed down with a choice of beer, wine or soft drinks. The coconut Greek-Turkish delight was very good too. Thank you for all the effort you put in to fill our tummies! 😊 Your hospitality was very much appreciated – thank you. Would we do this trip again – absolutely YES! Would we recommend this trip to our friends and family who frequent Kos often – absolutely YES! It was totally worth the money we spent – we would not change anything about it. Again, thank you very much for a fantastic day out at sea.
Read more
Wonderful, relaxing and fun day 😊
New York City
Kos: Small-Group Full-Day Catamaran Boat Trip, Meal, Drinks &Swim
Roving48332263084, Sep 2026
Wonderful, relaxing and fun day 😊
We thoroughly enjoyed the Swimming and snorkelling in the crystal clear turquoise waters by the islands and seeing the fish. The catamaran was spacious and comfortable and there were only about another 7 couples on the trip, everyone got on well and had there own space aswell during the sailing. We were also lucky enough to see a dolphin jump out of the sea! The crew were very friendly, informative and entertaining and the food was delicious, drinks were plentiful and nothing was too much trouble. We had a wonderful time, the day flew by from 09:00- 16:15 and we would absolutely recommend this experience, well worth the cost!
Read more
Sail Boat Trip
New York City
All-Inclusive Swimming Cruise: Anthony Quinn, Traganou & Kalithea
simonnW8691LO, Sep 2026
Sail Boat Trip
Friendly staff, great food, cool trip.
Read more
Great day out
New York City
Semi-Private Sailing Cruise to Iconic Bays (Shore-Ex Top Choice)
janicen541, Sep 2026
Great day out
Pick up was smooth. Boat trips was lovely. 3 beautiful swimming stops. Delicious lunch. Really enjoyed being in a small group with no loud music or drinking games! Dropped back at our hotel.
Read more
Five stars - a definite must do
New York City
Kos: Small-Group Full-Day Catamaran Boat Trip, Meal, Drinks &Swim
Scott_P, Sep 2026
Five stars - a definite must do
We had a fabulous day on the catamaran trip. The crossing to Pserimos was a little bumpy which added to the excitement ( we got pretty wet from spray ! )We had two stops on the island for swimming with the second stop being a longer one for swimming then a fantastic Greek lunch followed by more swimming and sunbathing before the return trip to Kos.The crew were fantastic, friendly, welcoming and fun.
Read more
Swimming boat trip
New York City
All-Inclusive Swimming Cruise: Anthony Quinn, Traganou & Kalithea
Joanne_H, Sep 2026
Swimming boat trip
Swimming boat trip, lovely boat and very friendly staff, the food was lovely and the Kyack stop was a real bonus
Read more
Blue ocean, music and vibes
New York City
Rhodes Day Cruise (with lunch & unlimited drinks) 5,5 Hours
V8460EOrebeccal, Sep 2026
Blue ocean, music and vibes
A fantastic experience where we had a relaxing time, helpfull and kind staff and a really fun time. Would really recommend to everybody visiting Rhodes.
Read more
Great experience
New York City
Rhodes Private Luxury Cruise MediterAsian Lunch Champagne coctail
Coastal49241664945, Sep 2026
Great experience
We had an excellent experience. Isabella was the perfect host taking us to some amazing spots across Rhodes. The chicken and vegetarian dishes were particularly tasty.
Read more
Very enjoyable experience
New York City
Rhodes Private Luxury Cruise MediterAsian Lunch Champagne coctail
D7021LGjoec, Sep 2026
Very enjoyable experience
Fantastic trip with great hospitality. Food was amazing. Would definitely recommend.
Read more
Amazing time!
New York City
Rhodes Day Cruise (with lunch & unlimited drinks) 5,5 Hours
isabellewI7698ZM, Sep 2026
Amazing time!
Was a relaxing but fun experience. I loved getting off at all of the swim spots and getting a good amount of time in each one. Each place was beautiful and the goggles and floating noodles were a great bonus in the water. If you go to the cave be warned the rocks are very spiky (only if you try to climb through like we did lol).
Read more
Fresh Fish
New York City
Sun & Sea 6 Hour All Inclusive Swimming Cruise with Greek BBQ & Unlimited Drinks
J6618UFrichards, Sep 2026
Fresh Fish
This was a great trip on the boat and the food was really good . To let everyone know that if you have the fish for lunch on the trip , that this company has an Other boat that take people fishing in the morning that goes fishing and we meet up with then at lunch and cook the fish they catch for lunch.
Read more
Fantastic Sunset Cruise on Gin Tonic – Highly Recommended! ⭐⭐⭐⭐⭐
New York City
Private Full/Half-Day Boat Trip in Greece with Food and Drinks
U9369BNianc, Sep 2026
Fantastic Sunset Cruise on Gin Tonic – Highly Recommended! ⭐⭐⭐⭐⭐
This was our fourth time using Georgios, and once again he didn’t disappoint! We booked a 4-hour sunset cruise on the beautiful Gin Tonic yacht in Lindos for four of us, including drinks and food on board. One of the things we really appreciate about dealing directly with Georgios is his flexibility and understanding. On this occasion, four other friends who were originally planning to join us unfortunately couldn’t make it. Georgios was incredibly accommodating and made changing the arrangements completely stress-free. Nothing was too much trouble. The cruise itself was excellent. We had a fantastic sail around the beautiful local bays, with plenty of time to relax and enjoy the scenery. The swimming stop was perfect, giving us the chance to jump into the crystal-clear water and cool off After four trips with Georgios, we can honestly say that the consistently high level of service, his friendly approach and his willingness to accommodate changes are what keep bringing us back. If you’re staying in Lindos and looking for a relaxing, enjoyable and personal sailing experience, we would highly recommend Georgios and Gin Tonic. We’ll definitely be back for our fifth trip! 🌅⛵️🍾
Read more
Fantastic day out.
New York City
Kos: Small Group Full-Day Sailing Boat Trip, Meals, Drinks & Swim
958iaina, Sep 2026
Fantastic day out.
A fantastic day. We visited 2 small coves and sailed for around 90 minutes each way. Then spent the rest of the time relaxing at anchor. The 2 places we went to were beautifal, blue seas and plenty of fish to snorkel through. The 2 members of staff were brilliant, funny and knowledgeable, both knew a lot and answered questions about thr area and the trip. Lunch was a lovely homemade greek style food, more than enough for us all. There was 13 people on the yacht, varied nationalities and a mix of groups and couples.Would highly recommend, a good day out and would do it again.
Read more
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