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Top Macedonia Sailing Trips

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Macedonia Tours

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Thessaloniki : Half-Day Sailing Cruise to Shipwreck Bay!

Join us for a private, memorable and breathtaking experience. Enjoy a full day cruise in the crystal clear sea of Thermaikos bay! Embark on our …More

Thessaloniki, Greece
4.9 (62)

Thessaloniki : Half-Day Sailing Cruise to Shipwreck Bay!

Join us for a private, memorable and breathtaking experience. Enjoy a full day cruise in the crystal clear sea of Thermaikos bay! Embark on our...

6 hours • Free Cancellation
4.9 (62)
from
$110
Blue Lagoon-Vourvourou Lunch Cruise from Ouranoupolis

The luxurious family-run Glassbottom vessel provides you with the perfect swimming experience around the most beautiful places of Halkidiki. Catch the boat from Ouranoupolis port …More

Halkidiki, Greece
4.6 (64)

Blue Lagoon-Vourvourou Lunch Cruise from Ouranoupolis

The luxurious family-run Glassbottom vessel provides you with the perfect swimming experience around the most beautiful places of Halkidiki. Catch the boat from Ouranoupolis port...

6 hours • Free Cancellation
4.6 (64)
from
$52
5 hours from Sithonia: Sailing trip secluded coves & Islands

Travellers choose this tour because it is one of the few small group tours in Halkidiki that sails some of the most beautiful areas that …More

Likely to Sell Out
Likely to Sell Out
Halkidiki, Greece
4.9 (23)

5 hours from Sithonia: Sailing trip secluded coves & Islands

Travellers choose this tour because it is one of the few small group tours in Halkidiki that sails some of the most beautiful areas that...

5 hours • Free Cancellation
4.9 (23)
from
$68
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
5 hours from Kassandra: W Sithonia Coves & Islands Yacht Sailing

Discover west Sithonia islets and Porto Carras seclude coves. Swimming the crystal clear lagoon water under the Mediterranean forest and sailing the afternoon sea breeze, …More

Halkidiki, Greece
4.8 (23)

5 hours from Kassandra: W Sithonia Coves & Islands Yacht Sailing

Discover west Sithonia islets and Porto Carras seclude coves. Swimming the crystal clear lagoon water under the Mediterranean forest and sailing the afternoon sea breeze,...

5 hours • Free Cancellation
4.8 (23)
from
$80
3 hours Neos Marmaras: Day or Sunset Sailing Tour Coves & Islands

This is one of the few small group tours in Halkidiki that sails some of the most beautiful areas that you can’t reach by car. …More

Likely to Sell Out
Likely to Sell Out
Halkidiki, Greece
4.7 (18)

3 hours Neos Marmaras: Day or Sunset Sailing Tour Coves & Islands

This is one of the few small group tours in Halkidiki that sails some of the most beautiful areas that you can’t reach by car....

3 hours • Free Cancellation
4.7 (18)
from
$45
Halkidiki Private Yacht Cruise: Kassandra or Sithonia (3–7 Hours)

Experience Halkidiki on a private classic sailing yacht. Choose your departure base—Kassandra or Sithonia—and customize your journey with a 3-hour sunset, 5-hour, or 7-hour cruise. …More

Halkidiki, Greece
4.9 (21)

Halkidiki Private Yacht Cruise: Kassandra or Sithonia (3–7 Hours)

Experience Halkidiki on a private classic sailing yacht. Choose your departure base—Kassandra or Sithonia—and customize your journey with a 3-hour sunset, 5-hour, or 7-hour cruise....

3 to 7 hours • Free Cancellation
4.9 (21)
from
$603
Best of Halkidiki Daily Private Cruise

Explore Halkidiki on a private classic sailing yacht. Choose to depart from Kassandra or Sithonia for a customized 3-hour sunset, 5-hour, or 7-hour cruise. Option …More

Halkidiki, Greece
5.0 (36)

Best of Halkidiki Daily Private Cruise

Explore Halkidiki on a private classic sailing yacht. Choose to depart from Kassandra or Sithonia for a customized 3-hour sunset, 5-hour, or 7-hour cruise. Option...

3 to 7 hours • Free Cancellation
5.0 (36)
from
$626
3 hours Kassandra Sunset or Day sailing yacht tour

This is one of the few small group tours in Halkidiki that sails through some of the most beautiful and areas that you can’t reach …More

Likely to Sell Out
Likely to Sell Out
Halkidiki, Greece
4.7 (17)

3 hours Kassandra Sunset or Day sailing yacht tour

This is one of the few small group tours in Halkidiki that sails through some of the most beautiful and areas that you can’t reach...

3 hours • Free Cancellation
4.7 (17)
from
$57
Private Boat Trip in Halkidiki, Greece

This is the best tour you can book in the area. We want you to feel that you are hanging out with your Greek friend …More

Halkidiki, Greece
5.0 (33)

Private Boat Trip in Halkidiki, Greece

This is the best tour you can book in the area. We want you to feel that you are hanging out with your Greek friend...

7 hours • Free Cancellation
5.0 (33)
from
$870
Thessaloniki : Sunset Cruise

Join us for a semiprivate, memorable and breathtaking experience in the Gulf of Thessaloniki to see the amazing Sunset that you will not forget. With …More

Likely to Sell Out
Likely to Sell Out
Thessaloniki, Greece
4.9 (13)

Thessaloniki : Sunset Cruise

Join us for a semiprivate, memorable and breathtaking experience in the Gulf of Thessaloniki to see the amazing Sunset that you will not forget. With...

3 hours • Free Cancellation
4.9 (13)
from
$104
Full-Day Private Sailing Experience in Nikiti

Live the Ultimate Sailing Experience within a day! Our experienced skippers are more than willing to introduce you to the art of sailing, share their …More

Likely to Sell Out
Likely to Sell Out
Thessaloniki, Greece
5.0 (6)

Full-Day Private Sailing Experience in Nikiti

Live the Ultimate Sailing Experience within a day! Our experienced skippers are more than willing to introduce you to the art of sailing, share their...

6 hours • Free Cancellation
5.0 (6)
from
$1,286
Private Full-Day Cruise on a Catamaran in Nikiti

SCHEDULE | ROUTE Route : Nikiti – Kalogria Beach – Kelifos ( Turtle ) Island – Agios Georgios Beach - Nikiti Duration : 7 hours …More

Likely to Sell Out
Likely to Sell Out
Thessaloniki, Greece
5.0 (5)

Private Full-Day Cruise on a Catamaran in Nikiti

SCHEDULE | ROUTE Route : Nikiti – Kalogria Beach – Kelifos ( Turtle ) Island – Agios Georgios Beach - Nikiti Duration : 7 hours...

6 hours • Free Cancellation
5.0 (5)
from
$1,738
Private Sunset Catamaran Cruise from Nikiti

An unforgettable, romantic sunset cruise is provided every evening at 18:00. During this cruise you have the opportunity to enjoy a breathtaking sunset while you …More

Likely to Sell Out
Likely to Sell Out
Thessaloniki, Greece
5.0 (2)

Private Sunset Catamaran Cruise from Nikiti

An unforgettable, romantic sunset cruise is provided every evening at 18:00. During this cruise you have the opportunity to enjoy a breathtaking sunset while you...

3 hours
5.0 (2)
from
$1,043
Private Day SailBoat Tour Visit to Halkidiki

We extend our invitation to those seeking relaxation and the opportunity to bask in the beauty of Halkidiki. Experience the coastline in the most ecological, …More

Likely to Sell Out
Likely to Sell Out
Halkidiki, Greece
5.0 (1)

Private Day SailBoat Tour Visit to Halkidiki

We extend our invitation to those seeking relaxation and the opportunity to bask in the beauty of Halkidiki. Experience the coastline in the most ecological,...

7 hours • Free Cancellation
5.0 (1)
from
$800
Full Private Day Tour Sailing Experience in Halkidiki

We sail with a 14m sailing yacht to secluded beaches and extraordinary spots that are not accessible by car. During the day we make a …More

Halkidiki, Greece
5.0 (3)

Full Private Day Tour Sailing Experience in Halkidiki

We sail with a 14m sailing yacht to secluded beaches and extraordinary spots that are not accessible by car. During the day we make a...

7 hours • Free Cancellation
5.0 (3)
from
$649
3-Hour Private Sunset Sailing Experience in Halkidiki

Join us on a 3-hour trip sailing Halkidiki, featuring a swim stop just at the point when the sun is about to touch the horizon, …More

Halkidiki, Greece
5.0 (2)

3-Hour Private Sunset Sailing Experience in Halkidiki

Join us on a 3-hour trip sailing Halkidiki, featuring a swim stop just at the point when the sun is about to touch the horizon,...

3 hours • Free Cancellation
5.0 (2)
from
$522
Full Day Private Sailing Cruise Kavala to North or South Thassos

Aegean sea Cruises provide personalized Day and Multi-Day Private Cruises with Luxury Sailing Yachts, Catamarans and Motor Boats in all Greek islands and especially across …More

5.0 (3)

Full Day Private Sailing Cruise Kavala to North or South Thassos

Aegean sea Cruises provide personalized Day and Multi-Day Private Cruises with Luxury Sailing Yachts, Catamarans and Motor Boats in all Greek islands and especially across...

10 hours • Free Cancellation
5.0 (3)
from
$638
Private Catamaran Cruise from Kavala to North or South Thassos

Aegean sea Cruises provide personalized Day and Multi-Day Private Cruises with Luxury Sailing Yachts, Catamarans and Motor Boats in all Greek islands and especially across …More

Private Catamaran Cruise from Kavala to North or South Thassos

Aegean sea Cruises provide personalized Day and Multi-Day Private Cruises with Luxury Sailing Yachts, Catamarans and Motor Boats in all Greek islands and especially across...

10 hours • Free Cancellation
from
$1,101

Frequently Asked Questions

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

Recent tour reviews
One of the best experiences in Greece
New York City
Thessaloniki : Half-Day Sailing Cruise to Shipwreck Bay!
D840XIsandras, Sep 2026
One of the best experiences in Greece
Very nice experience. The guide was good and friendly. The day started a bit windy and a little chilly, but we had enough clothes, so we were okay. We swam in the shipwreck bay, and the water was lovely and warm. We had a nice Greek lunch prepared by the guide with some white wine. I would recommend this trip to families, couples, or friends. It would be suitable for everybody.
Read more
Fantastic half day trip
New York City
Thessaloniki : Half-Day Sailing Cruise to Shipwreck Bay!
Christian_S, Sep 2026
Fantastic half day trip
6 of us just got back from a fantastic afternoon with Mike. As well as a great captain..& chef, Mike is a lovely guy. Two swim stops & a history tour. Lunch was great too.
Read more
Excelent
New York City
Blue Lagoon-Vourvourou Lunch Cruise from Ouranoupolis
941cristianal, Sep 2026
Excelent
Very Nice everything. 🩷🩷🩷 Thank you
Read more
Five Stars
New York City
Blue Lagoon-Vourvourou Lunch Cruise from Ouranoupolis
tastytraveld, Sep 2026
Five Stars
Absolutely fantastic boat trip! The food was beautiful, the crew were so friendly and welcoming, and the Blue Lagoon was absolutely stunning. The whole day was really well organised and such great value for money, especially considering everything that was included.We also did the Mount Athos trip, which was just as amazing. Both trips were highlights of our holiday and I would highly recommend them. Fantastic experiences at such reasonable prices – definitely worth doing!
Read more
Great experience
New York City
5 hours from Sithonia: Sailing trip secluded coves & Islands
847tarikr, Sep 2026
Great experience
Really enjoyed the cruise, the weather the sites and the overall atmosphere were fantastic.Everything was very well organized, and we had a wonderful time. We would definitely be happy to come back and do it again, or to recommend it.
Read more
Half day cruise
New York City
Best of Halkidiki Daily Private Cruise
Trixietrip, Aug 2026
Half day cruise
Sensationally good! Adonis our guide was lovely, and the scenery stunning. A great way to spend five hours, sailing from bay to bay and diving into the clear waters.
Read more
Just a perfect relaxing day
New York City
5 hours from Sithonia: Sailing trip secluded coves & Islands
P9697VLlynnes, Aug 2026
Just a perfect relaxing day
Amazing trip and very well organised from start to finish. Clear instructions to get to the meeting point and Captain George was very kind and helpful. We saw and swam in some beautiful picturesque bays, despite being slightly windy on the day. Overall, a lovely day, finishing off with a glass of wine from Captain George. Thank you very much
Read more
Great experience.
New York City
Private Full-Day Cruise on a Catamaran in Nikiti
_nabeln2025, Aug 2026
Great experience.
We rented a catamaran for 5 hours for a bachelorette party, and the whole experience was absolutely amazing! Everything was perfect, but the best part was definitely the crew. They were so friendly, welcoming, and incredibly chill, which made the experience even more enjoyable. Georgia and the gentleman whose name I’m unfortunately forgetting were both fantastic! We had such a great time and would definitely recommend them!
Read more
Highlight of our holiday
New York City
Private Boat Trip in Halkidiki, Greece
Kerry_J, Aug 2026
Highlight of our holiday
We had THE BEST day with Captain Aris on the Thalassini. It was the highlight of our holiday and a day that our kids will always remember. We visited some stunning beaches and swam in the beautiful Blue Lagoon. There were 8 of us, 4 adults & 4 kids, and plenty of room. We have all said that we want to do it again next year, highly recommend.
Read more
Athens Catamaran For the Day
New York City
Luxury Catamaran Morning Semi-Private and Greek Gastronomy Athens
Ron_D, Jul 2026
Athens Catamaran For the Day
Lots of fun on the water in Athens. Plenty of time to swim, snorkel, or paddleboard. Elena and Antonia were fantastic! They were so helpful and served amazing food for the journey.
Read more
Amazing!
New York City
Private Boat Trip in Halkidiki, Greece
mike_oln, Jul 2026
Amazing!
The sailing trip around Sithonia was top-notch – the views and hidden beaches were absolutely epic. The crew were solid, professional guys who kept it laid-back and made the whole trip smooth sailing.
Read more
Spent an amazing day with...
New York City
Best of Halkidiki Daily Private Cruise
Neda_V, Jul 2026
Spent an amazing day with...
Spent an amazing day with our two kids and skipper George sailing and snorkeling around Sithonia. Beautiful nature and crystal clear waters. Highly recommend!
Read more
Unforgettable trip
New York City
Luxury Catamaran Morning Semi-Private and Greek Gastronomy Athens
liardetlili, Jun 2026
Unforgettable trip
Amazing experience, the boat was super cosy and Anastasia and Adonia were extremely kind with our group. The food was fresh and tasty and service on top ❤️ I highly recommend
Read more
Unmissable experience!
New York City
5 hours from Kassandra: W Sithonia Coves & Islands Yacht Sailing
MariaEugenia_C, Jun 2026
Unmissable experience!
Exactly what it says in the tin: wonderful experience to swim in the clear blue-green waters of the Eagean see in such remote parts.
Read more
Best experience in Greece
New York City
Halkidiki Private Yacht Cruise: Kassandra or Sithonia (3–7 Hours)
Dana_T, Jun 2026
Best experience in Greece
Great experience! we had such a good time! we took the 5 hour tour with Adonis and he was a delight! took care of all of our needs and was super nice and responsive! Would definitely recommend!
Read more
Kostas was very...
New York City
Full Private Day Tour Sailing Experience in Halkidiki
Paula_D, May 2026
Kostas was very...
Kostas was very welcoming, friendly and professional a real superstar. We were taken to an amazing restaurant for lunch, wonderful refreshments onboard. A truly memorable experience and great value for money.
Read more
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