Sailing trips · GREECE SAILING TRIPS
The caldera boats, the Rhodes all-inclusive days and the Ionian coves. These 15 Greek sails are priced per person, with the meltemi season flagged on the crossings it can cancel.
Spend five hours aboard the 74-foot Ocean Voyager or 80-foot Tahiti catamaran, stopping at the hot springs, Red Beach, and White Beach for swimming and snorkeling. A barbecue with meat, vegetarian choices, white wine, and soft drinks is served onboard, with hotel pickup and music included.
“Excellent trip - well organised from start to finish”
Spend about five hours aboard a small catamaran with a crew such as Captain John, George, or Elena. Swim at Mesa Pigadia and a quiet cove, visit the hot springs, view the caldera from sea level, and enjoy a BBQ buffet with Greek wine. Daytime and sunset departures are available.
“Absolutely incredible. The captain and crew on the Evanna could not have been better. Was a wonderful experience from start to finish”
Cruise from Vlychada along Santorini’s volcanic coast, with photo stops at Red and White beaches, swimming at Mesa Pigadia and Palea Kameni, and a Greek BBQ with wine and soft drinks. Choose daytime or sunset sailing, with hotel transfers, towels, and snorkel gear included.
“We took the sunset cruise and it was amazing . It was a lot of fun mainly because of the all women crew we had. They took really great care of us and the food was delicious. Kudos to Elena and team.”
Spend 5 to 6 hours aboard a luxury catamaran with a maximum of 20 people. Swim near Red Beach, White Beach, and the volcanic hot springs, then enjoy a Greek meal, open bar, music, and caldera views. Sunset trips include a cocktail and Oia sunset, with crews such as Evi, Giannis, and Angela helping set the mood.
“Nikos our captain, and our crew members Ilias, Giannis and Rafaela were amazing! This was an unforgettable experience for us on our honeymoon and the whole day was so great. The swim spots were awesome and our Greek feed was 10/10. Such an incredible day ☺️”
You’ll sail from Vlychada Marina with a crew that may include Giannis, Alex, Natalie, Mika, Kostas, or Bill, depending on the boat. Expect Red Beach, the volcano, hot springs, Thirassia, snorkeling, a fresh onboard meal, open wine and beer, and hotel pickup.
“It was social and informative, and a wonderful way to see the landscape. The crew was beyond fantastic!! They made the entire experience genuinely fun and were beyond accommodating.”
Sail from Vlychada Marina with an English-speaking guide and a small group, stopping at Red Beach, the White Beach area, the volcano hot springs, and Mesa Pigadia. You’ll get snorkeling gear, towels, a Greek BBQ, meze, soft drinks, and open white wine. Crews have included Hris, Filipos, Vivi, and Alice.
“The experience was 10/10. This was one of the excursions we did for our honeymoon. The views were beautiful and food was great. Some things I would love to share for the next group: - One of the stops to swim is near the volcano, they don’t suggest you wear light color swimwear because of sulfur in the water. - Bring a light jacket/sweater for the ride back if you are doing sunset. - They provide everything, water,’sodas, beer, wine, a light app, and dinner. - They have a room downstairs to change too. Ammos, and the crew were amazing. So friendly and genuine.”
Sail from Heraklion’s Venetian Harbour to protected Dia Island aboard a comfortable yacht with a maximum of 14 people. Swim, snorkel, paddleboard, and enjoy shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks. Afternoon departures can include a beautiful sunset sail back.
“It was amazing experience. Definitely a highlight of my vacation. Mariana and Manos was fun and helpful. Good food and beautiful views.”
Sail from Ammoudi Bay aboard a spacious catamaran with swimming stops at the hot springs, Mesa Pigadia, White Beach, and Red Beach. Enjoy fresh Greek appetizers, onboard BBQ skewers, wine, soft drinks, and attentive English-speaking crew. Sunset departures may include music and dancing.
“The sightseeing tour, customer service and food was great. We had a wonderful time!”
Spend six hours on a sailing or power catamaran along Rhodes’ east coast, with swim stops at Anthony Quinn Bay, Ladiko, Kallithea Springs, and, on the power boat, Afandou Caves. The crew provides snorkels, floats, lunch, fruit, soft drinks, beer, and wine.
“It was perfect! Ideal length, best swimming spots, delicious lunch, great team.”
Spend about five hours on a shared Santorini catamaran with hotel pickup, volcanic hot springs, Red Beach, swimming stops, a Greek meal, wine, beer, and soft drinks. Choose a morning or sunset sailing, with luxury options adding Oia and Ammoudi Bay views.
“Such an amazing experience with a friendly and knowledgeable crew. We would definitely recommend this sunset cruise to any of our friends who may come to Santorini in the future.”
Spend 10 hours with Sailing Milos circling the island and visiting Polyaigos, Gerakas, and Kleftiko. Guides such as Dora, Niki, and Alexandra share local stories while the crew serves snacks, tuna pasta, salad, drinks, and wine. Expect three swim stops, caves, and a motor-powered boat rather than a quiet sailing trip.
“We can’t say enough wonderful things about Katherine and the rest of the crew. Everything was super well organized and the we learned so much about the history and geography of the island. They kept us well fed and the swimming stops were gorgeous. It is a long day though so just keep that in mind if you plan on bringing any kids/older guests as it is a full 10 hour sailing trip.”
Spend five hours aboard a luxury catamaran with English-speaking crew, three swim stops, volcano views, a BBQ, and drinks. Choose a morning or sunset sailing, with guides such as Maria and Neta praised for friendly service and thoughtful help.
“This is my second time on this tour, with the same company, and I still recommend them. Safe, fun, informative, with a great lunch and plenty of time to swim and relax while listening to music and coasting on the water.”
Spend five hours aboard a Lagoon 450 with up to 14 passengers, sailing from Ammoudi or Vlychada to Santorini’s hot springs, White Beach, Red Beach, and Oia. Your English-speaking crew serves a fresh BBQ, local wine, beer, soft drinks, and water. Sunset departures include views beneath Oia.
“The crew, Adonis, chris and Helen were amazing. Nice swimming sessions, the Aegien sea is beyond belief. Great food and BBQ on the boat. This tour was the best part of my visit to Santorini, i cannot recommend enough!”
Choose a shared half-day sail to Dia Island with lunch, wine, soft drinks, snorkeling gear, paddleboards, and fishing equipment, or book a private trip. A one-hour coastal option stays near Heraklion and includes drinks but no lunch or water activities.
“It takes a conciderable while to get to the island and there isn't a lot to look at in the meantime, I wish the boat was faster. The island looks nice upclose, but it's unfortunatelly not allowed to take a look around from a hill - you can only stay on the beach and visit an old... church? On the other hand, staying in the water is perfectly fine, as it's crystall clear, you can see the sea floor and there's a lot of fish around. While I recommend bringing your own snorkel, the equipment is provided. Good thing they also have flippers. Beware the see urchins - the shore…”
Sail from Alimos Marina with a small group of up to 10, swimming and snorkeling near Voula and Vouliagmeni. Your crew serves Greek salad, vegetables, shrimp saganaki, BBQ, beer, wine, and soft drinks. Choose a morning lunch cruise or sunset dinner, with hotel pickup and return.
“Everything was awesome. Great crew and nice dinner Only problem was sun didn’t cooperate but we made the most of it”
Pick the boat, the hour on the water or the country.
