Greece · SAILING DAY TRIPS

Greek Day Trips on the Water: the 15 Best

35 sailing trips  ·  from $57 a seat

Anything with a hull and a departure time, in one list. The 15 below are the days worth clearing the diary for, priced by the seat and clear about how much of the time is spent sailing rather than swimming.

Santorini: Catamaran Tour with BBQ Dinner, Drinks, and Music - Red Beach brings the first proper swim
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Santorini: Catamaran Tour with BBQ Dinner, Drinks, and Music

1.Catamaran Tour with BBQ Dinner, Drinks, and Music

★★★★★★★★★★4.6 · 5,886 reviews · 5 hours · from $93Number one

Spend five hours aboard the 74-foot Ocean Voyager or 80-foot Tahiti catamaran, with hotel pickup, hot-spring swimming, Red and White Beach stops, a fresh barbecue, unlimited white wine and soft drinks, and music. Choose morning light or a sunset sail through Santorini’s caldera.

“This was so fun. It is more of a boat trip rather than a boat party which I mistaked it for. We made it a party boat though and was so fun with no restrictions. The music was playing either, think ABBA! The drink selection was great and the food was amazing. You stop at a couple of places you get to jump in the sea. The food comes out about 3 hours into the trip so eat before you go but there is plenty food when served. So delicious proper Greek selection.”

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Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch - Leaving Adamas and heading toward Sarakiniko
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Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

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

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

Spend 10 hours circling Milos aboard a small motor-powered sailboat, with swim stops at Polyaigos, Gerakas, and Kleftiko. Guides such as Dora, Niki, and Alexandra share island stories, while the crew serves snacks, tuna pasta, salad, drinks, and wine. Bring sun protection, a towel, and a jacket.

“Amazing day, Dora was an excellent host who worked very hard”

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Santorini: Catamaran Tour with BBQ Meal and Unlimited Drinks - Pickup, ports, and the first minutes aboard
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Santorini: Catamaran Tour with BBQ Meal and Unlimited Drinks

3.Catamaran Tour with BBQ Meal and Unlimited Drinks

★★★★★★★★★★4.8 · 1,449 reviews · 5 hours · from $153

Spend five hours aboard a Lagoon 450 with up to 14 other passengers, sailing from Ammoudi or Vlychada to the Hot Springs, White Beach, and Red Beach. Swim, snorkel, eat a fresh Greek BBQ, and enjoy unlimited water, wine, beer, and soft drinks. Choose the sunset departure for views below Oia.

“We had an amazing time on out Catamaran cruise!! The tour operator is on top of their game!! They were easy to work with when we needed to reschedule. The boat is super clean. The staff was friendly and fun!! The good was fresh and delicious!! Highly recommended!!”

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Mykonos: Yacht Cruise to Rhenia and Guided Tour of Delos - Setting sail from Mykonos
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Mykonos: Yacht Cruise to Rhenia and Guided Tour of Delos

4.Yacht Cruise to Rhenia and Guided Tour of Delos

★★★★★★★★★★4.8 · 802 reviews · 1 day · from $141

Spend a full day sailing from Mykonos to Delos and Rhenia with Sunfos Alessia Yachting. A licensed guide, including guides such as Helen or Alexis on some departures, leads the Delos visit, while the crew serves pasta, Greek salad, fruit, wine, and soft drinks. Expect swimming, snorkeling, sun, and a potentially windy ride.

“We had such a great day! The boat was so nice and a very small group so we all got our own space to sunbathe or relax. The guide for Delos was very informative however it was very hot so make sure you bring something to cover up as it’s around 1 hr 30. Make sure to bring treats for the cats too, there are plenty there! :) Food was delicious which we had after our swim spot, keep your swimwear on as the journey back you can get a little wet. Highly recommend!”

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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks - Lunch onboard with wine and a view
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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

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

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

Spend six hours sailing from Mykonos to Rhenia and Delos with Sunfos Alessia Yachting. Swim from the yacht, use free snorkeling gear, eat lunch onboard, then tour Delos with an English-speaking guide such as Fanny. Expect open-sea views, changing weather, and a group of up to 35 people.

“The Delos architecture tour with a qualified guide and early arrival was worth the whole trip. Food was a little bit depressing and the pick-up fees a bit high. Still loved the day, would recommend, make sure to align your expectations on space and other passengers.”

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Mykonos Catamaran Premium Day-Sunset Tours 8-flavor Meal & Drinks - Leaving Ornos Bay under sail
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Mykonos Catamaran Premium Day-Sunset Tours 8-flavor Meal & Drinks

6.Mykonos Catamaran Premium Day-Sunset Tours 8-flavor Meal & Drinks

★★★★★★★★★★5.0 · 500 reviews · 5 hours (approx.) · from $181Highest rated

Spend about five hours on a catamaran from Ornos Bay, sailing toward Rineia and, when seas are calm, Delos. You get an onboard eight-flavor Greek meal, unlimited beer, wine, sodas, snorkeling gear, a paddleboard, and supervised sea scooters. Choose a daytime or sunset departure, with a south-coast Mykonos route available in windy weather.

“Crew and food was amazing!!! Great day on the water. 10/10 recommend!!! I can’t say enough about the delicious food. The cabin was very comfortable and plenty of places to relax and the sea scooters were so fun.”

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Athens: Riviera Catamaran Tour with Fresh Meal and Drinks - The first 75 minutes along the Athens Riviera
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Athens: Riviera Catamaran Tour with Fresh Meal and Drinks

7.Riviera Catamaran Tour with Fresh Meal and Drinks

★★★★★★★★★★5.0 · 462 reviews · 5 hours · from $144

Spend five hours sailing from Alimos Marina with Captain Roberto and a friendly multilingual crew. Swim and snorkel near Vouliagmeni, visit uninhabited Hydrousa, use the paddleboard and snorkeling gear, and enjoy a freshly prepared seven-dish meal with wine, beer, soft drinks, and water aboard the catamaran.

“Just the best thing we did all holiday, and we proceeded onto a 9 day cruise after this! Do not hesitate to book this trip. I could go on and on about different elements of the trip but the key was the three hosts on the catamaran, who were fantastic. Just book it, you won’t regret it”

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Rhodes: Symi Yacht Tour with Unlimited Drinks and Transfer - Two hours among Symi’s painted houses
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Rhodes: Symi Yacht Tour with Unlimited Drinks and Transfer

8.Symi Yacht Tour with Unlimited Drinks and Transfer

★★★★★★★★★★4.8 · 380 reviews · 8 hours · from $141

Spend eight hours sailing from Rhodes to Symi on a yacht limited to 25 passengers. You get coffee or tea at check-in, about two hours in Symi Town, lunch with unlimited drinks at St. George Bay, and a second swim at Seskli Island. The friendly crew, including hosts such as Anna, Antonio, and Emily, help make this a relaxed day at sea.

“This was a really good excursion and the crew were great. There weren’t many of us on the boat so we got to experience all areas and were not cramped at all. The swimming stops were the best but Symi was also nice (although there was not much to do on the island so maybe bring some card games). Would also recommend bringing a speaker as there was no music provided.”

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Milos Sailing Tour with snorkeling and lunch - The route around Milos, from Adamas or Pollonia
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Milos Sailing Tour with snorkeling and lunch

9.Milos Sailing Tour with snorkeling and lunch

★★★★★★★★★★5.0 · 270 reviews · 8 hours (approx.) · from $181

Spend about eight hours sailing around Milos from Pollonia or Adamas, with stops at Kleftiko, Sykia, Fyrligos, or Gerakas. You’ll snorkel with crew guidance, explore caves by small boat, eat Greek food, and enjoy drinks throughout the day. The crew may include Juliano, Vitaly, RJ, Effi, Christo, or Vasili.

“Vitaly, and the rest of the crew were amazing to ride with! The scenery was spectacular. The accommodations (food, drink, additional small boat explorations) were great. Would HIGHLY recommend joining this excursion. Thanks all!”

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Santorini Caldera Sailing Tour with BBQ Lunch and Drinks - Red Beach and White Beach from the water
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Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

10.Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 268 reviews · 5 hours (approx.) · from $229

Spend about five hours on a catamaran from Vlychada Marina, visiting Red and White Beach, the caldera, Palea Kameni, and Nea Kameni. Choose a 10am day cruise or a 3pm sunset sailing. Expect swimming, snorkeling, barbecue seafood and steak, unlimited drinks, and crew members such as Maria, Joe, Dimitris, or Nancy depending on the sailing.

“This was the 4th time we have been to Santorini and wanted to do something different. This was by far our best excursion in any port for the trip, and the crew and food were phenomenal. We are well seasoned travelers over 40 cruises and have done many catamaran trips but all those others paled in comparison. Great trip, and well worth the cost.”

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Athens Riviera Catamaran tour with fresh Meal Drinks and Swimming - The ride to Prasoniso Island
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Athens Riviera Catamaran tour with fresh Meal Drinks and Swimming

11.Athens Riviera Catamaran tour with fresh Meal Drinks and Swimming

★★★★★★★★★★5.0 · 210 reviews · 5 hours (approx.) · from $157

Spend about five hours aboard a catamaran from Alimos Marina, with stops at Vouliagmeni Bay and Prasoniso Island. Swim, snorkel, and enjoy a Greek meal prepared on board, with Captain Roberto and the crew guiding the trip in several languages. Choose a morning cruise or a sunset sailing.

“This was one of our favorite days on our trip to Athens. It was so relaxing and scenic. Ada and the rest of the crew showed us a great time. We especially enjoyed the swim/snorkeling at the second spot. The homemade lunch was absolutely delicious!”

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Skiathos: Day-Sailing Tour with Lunch on Board - The route between Skiathos, Skopelos, and nearby islands
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Skiathos: Day-Sailing Tour with Lunch on Board

12.Day-Sailing Tour with Lunch on Board

★★★★★★★★★★5.0 · 191 reviews · 7 hours · from $165

Join Yannis and Angela aboard their 55-foot yacht, Rainbow, for a seven-hour small-group cruise around Skiathos, Skopelos, and nearby islands. With no more than 12 people on board, you can swim at boat-access beaches, snorkel, paddle board, enjoy a fresh Greek lunch, and relax with drinks. Naya, the family dog, often joins the crew.

“Opportunity to sail in relaxed atmosphere and see areas only accessible by a yacht of this size. Enjoying the snorkeling and clear waters.”

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All inclusive day sailing tour from Naxos to the small cyclades - Swimming stops are the heart of the experience
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All inclusive day sailing tour from Naxos to the small cyclades

13.All inclusive day sailing tour from Naxos to the small cyclades

★★★★★★★★★★4.5 · 155 reviews · from $209

Meet Xanemo Sailing at Naxos Port at 8:30 am for a small-group day on the Aegean. Expect breakfast, drinks, snorkeling gear, swimming stops, a barbecue lunch, and downloadable photos. Captains and crew may include Alex, Kostas, Tomi, or Anastasia. The route can change with wind and weather.

“This is must go tour. The staff is super friendly. The facilities on the boat is kept quite clean. I enjoyed the swimming experience, the water is so clear. Although it was a very hot day but the water is little bit cold.”

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Deluxe Santorini Sailing with BBQ and Drinks Shared Tour - Pickup, timing, and what to bring
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Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

14.Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

★★★★★★★★★★5.0 · 137 reviews · 5 hours (approx.) · from $193

Spend about five hours aboard a shared Santorini sailing boat with Captain Chris and Theo, stopping near Red Beach, White Beach, the lighthouse, and the volcanic islands. Swim, use the supplied snorkels, and enjoy barbecue food, wine, beer, and soft drinks. Pickup is arranged near your accommodation.

“Lovely cruise - wonderful staff. Lots of chances to swim and explored nooks and crannies around the coast would never have seen otherwise Some comments - I am a pescatarian and gluten free, and booked this cruise particularly as it said there would be fish available. This was not the case. The booking also said that towels would be included, however we were told on the boat that they didn't have enough towels for everyone so my boyfriend and I shared a towel. We would have bought our own if we'd known!”

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Paros: Iraklia, Schinoussa, & Naxos Sailing Tour with Lunch - Alimia on Iraklia and the sunken plane
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Paros: Iraklia, Schinoussa, & Naxos Sailing Tour with Lunch

15.Iraklia, Schinoussa, & Naxos Sailing Tour with Lunch

★★★★★★★★★★4.6 · 131 reviews · 9 hours · from $200

Spend nine hours sailing from Piso Livadi with Lady K Sailing Cruises, stopping at Iraklia, Schinoussa, and south Naxos. You can snorkel above a sunken WWII hydroplane, swim in quiet coves, and eat fresh lunch with wine or beer onboard. Crews may include Kostas, Lido, Harry, Manos, or other English-speaking guides.

“We were a group of 8 people and had an amazing day on the boat together with our two guides Nick & Harry who greatly took care of us! Thanks so much for this amazing day and we can 100% recommend the experience and our two skippers!”

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Just added in Tours

★ 5.0Catamaran’s Private Tour / MykonosFrom $2,062 per boat4 reviews
★ 5.06 Hours Tour to Delos and Rhenia Islands with Sailing YachtFrom $1583 reviews
★ 4.0Full Day Yacht Tour in RhodesFrom $1046 reviews
★ 5.0Dreamy Sails – Sunset Tour With Dinner And WineFrom $655 reviews
★ 4.7Catamaran Cruise, Winery, & Oia Sunset Combo TourFrom $21228 reviews
★ 4.7Full Day Naxos Exploration Yacht TourFrom $11728 reviews
★ 4.9Golden Hour Sailboat Tour with Wine & SnacksFrom $11235 reviews
★ 5.0Private all included yacht Tour in SantoriniFrom $59938 reviews
★ 5.0Private Sailing Tour in Rhodes39 reviews
★ 5.0Shipwreck and Blue Caves Yacht TourFrom $1,322 per boat41 reviews
★ 5.0From Agia Efimia: All Inclusive Sailing Day Tour to IthacaFrom $17939 reviews
★ 5.0Private Catamaran Tour with BBQ Meal and DrinksFrom $1,826 per boat43 reviews
★ 4.7Neos Marmaras: Sunset West Sithonia Islets Sailboat TourFrom $5750 reviews
★ 4.5Kassandra: West Sithonia Coves and Islets Sailboat TourFrom $6951 reviews

Other kinds of day

Catamaran Cruises172Sailing Trips with Lunch & BBQ189Private Sailing Charters83Sunset Sailing Cruises54Island Hopping Sailing Trips73Santorini Sailing Trips65
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Pick a coast, then pick a boat

Every island we sail from, and every kind of day that leaves it.

The Cyclades

SantoriniMilosMykonosNaxosParos

Crete

CreteHeraklionChaniaAgios NikolaosRethymno

Mainland and Ionian

AthensCorfuNafplioHalkidikiThessaloniki

Kinds of day

Catamaran DaysSunset SailsPrivate ChartersIsland HoppingCrewed Yachts