Mediterranean · SAILING TRIPS IN GREECE

Sailing Trips in Greece: Our Top 15

26 tours  ·  from $35 a head

This is the shortlist you would send a friend: 15 sailing trips in Greece worth the money, each with its price, its traveller verdict and the one thing to know before you commit.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Three and a half hours in Dia’s protected waters
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Our pick

Sail from Heraklion’s Old Venetian Harbour to Dia Island aboard a yacht limited to 14 people. Captain Petros and crew members such as Sofia, Giannis, Mariana, and Manos provide English guidance, water equipment, a Mediterranean meal, and unlimited drinks. Choose a morning swim or an afternoon cruise with golden sunset light.

“This was a top notch experience: I strongly recommend this sunset boat trip!”

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Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch - Leaving Adamas and passing Arkoudes
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Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

2.Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

★★★★★★★★★★4.9 · 1,646 reviews · 10 hours · from $147

Spend about 10 hours on a small-group cruise from Adamas, circling Milos and visiting Polyaigos, Gerakas, Kleftiko, Sykia, and Vani. You will swim, snorkel, eat pasta and salad, and hear island stories from guides such as Dora, Niki, and Alexandra. The boats carry up to 25 people, with routes adjusted for weather.

“This was an amazing experience! Milos is gorgeous in and of itself but Dora made the day extra fun! The music and food were both great and shout out to captain George! Dora had a fabulous assistant on board helping to serve us as well! The stops were amazing for swimming and sightseeing and Dora explained many things in a fun and interactive way. Definitely recommend if you want to fill up your day with fun and swims (and some jumps!)”

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Santorini: Sailing Catamaran Cruise with BBQ and Drinks - From Thera to Vlychada Port
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Santorini: Sailing Catamaran Cruise with BBQ and Drinks

3.Sailing Catamaran Cruise with BBQ and Drinks

★★★★★★★★★★4.7 · 1,452 reviews · 5 hours · from $117

Spend five hours aboard a luxury catamaran from Vlychada, with stops at Red Beach, Mesa Pigadia, Palea Kameni, and Santorini’s volcano. You’ll get hotel transport, snorkeling gear, towels, a BBQ, and drinks. Morning and sunset departures are available, with guides speaking English and Greek.

“The most amazing day and experience. The food was amazing Liz. The staff were exceptional would highly recommend.”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island, a swimming stop with a quiet feel
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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

4.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Best value

Sail from Heraklion to Dia Island on a shared yacht trip with lunch, local wine, soft drinks, snorkeling gear, paddleboards, and optional fishing. You get about four to six hours on the water, with crew such as Stavroula, Dennis, or Mido. Private and one-hour coastal options are also available.

“The activity was very well organised (10/10) as well as the pick up and drop off service.”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Red Beach by boat, with time to swim
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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

5.Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

★★★★★★★★★★4.5 · 1,105 reviews · 5 hours (approx.) · from $95

Spend about five hours on a spacious Santorini catamaran, with hotel pickup, swims near the volcano, Red Beach, and White Beach, plus a BBQ, wine, soft drinks, and music. The later departure aims for an Oia sunset. Expect a friendly, social boat with up to 55 passengers, not a quiet private sail.

“We booked this trip to celebrate our aniversary, the reviews were good and it did not disappoint. The boat, crew, food, swimming and views were great.”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Barbati Beach is the first taste of Corfu’s clear water
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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

6.Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

★★★★★★★★★★4.8 · 851 reviews · 5 - 10 hours · from $69

Set out from Gouvia Marina on a small yacht with a skipper such as Ari, Savvas, or Thassos. Swim at Barbati and Gialiskari, snorkel among fish, try a supervised cliff jump, and visit a blue cave. Sandwiches, fruit, and soft drinks are included, while snorkeling gear and alcohol cost extra.

“The itinerary was well-paced and full of variety: we swam in three beautiful swimming holes, snorkeled in a little cave spot, and even got to jump off a small cliff—definitely a thrill! One of the stops included a beach with a charming café, perfect for a quick refreshment and some downtime. Our skipper, Savvas, was a standout. He was chill, informative, and incredibly kind. A fun moment was when he let us feed leftover sandwiches to the fish—watching them swarm was surprisingly entertaining! We also arranged van transportation from the cruise port to the marina, which was smooth and affordable at just €11 per person for a 15-minute ride. Highly…”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Lunch With Tzatziki, Shrimp Spaghetti, and Raki
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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

7.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106

Sail from Heraklion’s Old Venetian Harbor to uninhabited Dia Island with Sailing Grace. You’ll have time for snorkeling, stand-up paddleboarding, fishing, swimming, a short hike, and a Mediterranean lunch with wine, soft drinks, fruit, and raki. Hotel pickup is available, and the afternoon departure may return at sunset.

“Really nice sailing cruise to Dia island. Once you get out of the harbour, the fun really begins. We didn’t get into the water once at Dia, as it was a bit chilly. However, watching the sunset and admiring the rocky island was worth the price. The crew was competent and made us feel safe. The snacks were really tasty. The captain also put some music, made the trip back really enjoyable.”

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Heraklion: Dia Island Sailing Cruise with Snorkeling - The open-water crossing to Dia Island
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Heraklion: Dia Island Sailing Cruise with Snorkeling

8.Dia Island Sailing Cruise with Snorkeling

★★★★★★★★★★4.7 · 742 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island aboard a small yacht with a professional crew, often including Ernesto and George. Swim in clear bays, use the included snorkeling and paddleboard gear, and enjoy drinks plus a meal. Choose a half-day or full-day outing, with hotel transfers available from selected areas.

“A beautiful day, great weather, calm sea. Crew were kind and great to talk with. Really enjoyed snorkelling, the water was magical!”

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Shared Mykonos Sail Cruise to Delos and Rhenia Islands - Leaving Agios Ioannis on a working yacht
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Shared Mykonos Sail Cruise to Delos and Rhenia Islands

9.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

★★★★★★★★★★5.0 · 705 reviews · 6 hours (approx.) · from $151Top rated

Set sail from Agios Ioannis on a shared yacht with an English-speaking host, visiting Delos for ancient ruins and Rhenia for swimming, snorkeling, and a fresh barbecue lunch. You can explore Delos independently or pay extra for a guided visit. Expect about six hours, drinks onboard, and a relaxed, barefoot boat setting.

“Well organized and nice food. Delos very interesting. Sea a bit wavy though so be ready to jump on the boat.”

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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks - Swimming in Rhenia’s clear coves
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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

10.Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

★★★★★★★★★★4.5 · 608 reviews · 6 hours (approx.) · from $145

Join Sunfos Alessia Yachting at 9 a.m. for a six-hour cruise from Mykonos to Rhenia and Delos. Swim from the yacht in a quiet Rhenia cove, enjoy pasta or a Mediterranean buffet with drinks, then tour Delos with an English-speaking guide. Guides and crew vary, with past departures featuring Fanny, Silia, Elisa, Thanos, Marios, and Captain Stellios.

“The experience was incredible and genuinely memorable. The onboard crew were excellent, attentive, and responsive to our needs. Communication before the trip was clear, especially when they let us know our morning cruise was moved to the afternoon due to wind conditions. The food was a bit too carb-heavy for my preference. It included pasta, salad, bread, and cheese, served family style with other passengers. Drinks were complimentary but needed to be requested directly from the crew. The biggest issue was time management, or more accurately, the lack of clarity around how long we had at each stop. We spent a lot of time at Rhenia, which was enjoyable, but…”

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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks - Choosing the morning cruise or afternoon sailing
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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

11.Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 560 reviews · 5 hours (approx.) · from $145

Set sail from Vlichada Marina or Ammoudi Bay on a five-hour catamaran cruise around Santorini. Swim near the Red and White Beaches, visit Palea and Nea Kameni, soak in volcanic hot springs, and enjoy a Greek BBQ with unlimited beer, wine, and soft drinks. Hotel pickup and drop-off are included.

“It was ok cruise.but not the worth 300$ .there is not enough chair under the roof to accomodate all the passengers. The captain priortised the group people for the seating.we ended up sitting in far end of the boat and our belonging get soaked when the cataraman was really rocky during cruising. They only have life jackets for floating device not noodle”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - What You Eat on the Half-Day and Full-Day Trips
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

12.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.7 · 529 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island with a professional crew, stopping for swimming, snorkeling, paddleboarding, and a meal aboard a catamaran. You get roughly an hour at sea each way, time in a sheltered bay, and a sunset return. Full-day trips include Greek salad, tzatziki, seafood pasta, fruit, and raki. Half-day trips include tomato pasta.

“Andreas and Ianos (hope I am spelling it correctly) were great guides, answering a lot of questions about the island. The place is a pretty good place for snorkel activities but you have to venture a bit far out, especially by the old remains of a minoan port underwater. Food was really good, drinks at your discretion. Amazing experience overall!”

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Heraklion: Private Half-Day Sailing Trip to Dia Island - Snorkeling, fishing, and paddleboards
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Heraklion: Private Half-Day Sailing Trip to Dia Island

13.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours

You’ll sail from Heraklion with a two-person English or Greek-speaking crew to Dia Island’s Gulf of Saint George, once explored by Jacques Yves Cousteau. Expect a private boat for up to eight, clear water for swimming and snorkeling, fishing gear, paddleboards, fruit, wine, soft drinks, and about 2.5 hours at anchor. Hotel transfers and full meals cost extra.

“Sailing trip was great, guides gave a lot of explanation concerning the boat, island and history.”

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Kolimvari: Sailing Cruise with Meal & Water Activities - The Agioi Theodoroi stop and the Kri Kri goats
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Kolimvari: Sailing Cruise with Meal & Water Activities

14.Kolimvari: Sailing Cruise with Meal & Water Activities

★★★★★★★★★★4.7 · 390 reviews · 5 hours · from $129

Spend five hours sailing from Kolymvari with a friendly crew such as Loukas and Jason, stopping near Agioi Theodoroi for swimming, snorkeling, and stand-up paddle boarding. A fresh three-course meal, unlimited drinks, music, and small-group service are included. Choose a morning or afternoon departure, with sunset views on later cruises.

“One of our favorite days on Crete. The boat was gorgeous and our guides were very welcoming. The small group made the trip even better. We saw many boats pull up with 30+ people on it and we were grateful for our 10.”

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Skiathos: Full-Day Sailing Cruise with Lunch - Tsougria Island and the First Swim
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Skiathos: Full-Day Sailing Cruise with Lunch

15.Full-Day Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 307 reviews · 7 hours · from $165

Sail from Skiathos at 10:15 aboard Aeolus with captain Lambros, Anastasia, and George. Expect a relaxed small-group day with stops around Tsougria, Skopelos, Kastani, Argos, and Dasia, plus snorkeling, paddleboarding, swimming, and a freshly cooked Greek lunch with drinks.

“It was a lovely day, went in the sea a couple times which was gorgeous and had a delicious dinner. They had a nice level of guidance and leaving us to it which was perfect. Would definitely recommend.”

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Santorini Caldera Sailing Tour with BBQ Lunch and Drinks - Choosing the 10am day cruise or the 3pm sunset sailing
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Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

17★ 5.0Santorini Caldera Sailing Tour with BBQ Lunch and DrinksFrom $229268 reviews

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