15 Semi-Private Sailing Cruises With Room to Move

1.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

★★★★★★★★★★5.0 · 705 reviews · 6 hours (approx.) · from $151Number one

Spend about six hours sailing from Agios Ioannis to Delos and Rhenia aboard a spacious gulet. Explore Delos with a self-guided walk or paid guide, then swim, snorkel, and enjoy a fresh barbecue buffet with drinks. Hotel transfers and Delos admission are optional extras.

“Loved our trip and snorkeling in these beautiful areas! Food was good, the staff was great - a fun way to spend the day in Mykonos! And they were able to arrange transportation for us from our cruise ship! Highly recommend!”

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2.Shared Catamaran All inclusive-Day Cruise to Naxos or Paros

★★★★★★★★★★5.0 · 297 reviews · 7 hours (approx.) · from $157

Join Captain Izzy, Cornelius, and the Naxos Catamaran Sailing Cruises crew at 10:00 am for a seven-hour shared cruise from Naxos. Expect secluded coves, three possible swim stops, snorkeling masks, a traditional lunch cooked aboard, and wine, beer, coffee, water, and snacks. Routes change with weather and sea conditions.

“The meeting location was perfect and easy to find. The captain and co-captain were fantastic to deal with. Easy going, friendly, professional and always ensuring high safety standards. They made everyone feel at ease, even my fiance is is not fond of the open water, was made to feel at ease.The food was absolutely delicious and they took dietary restrictions into account. The whole day was so enjoyable and a great fun vibe! Recommend this tour! The Apollo, we will never forget!”

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3.Small-Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★4.7 · 277 reviews · 4.5 - 7 hours · from $94

Join a crewed sailing yacht from Heraklion’s Old Venetian port and sail about an hour to Dia Island. With up to 10 people aboard, you’ll swim, snorkel, use a SUP, and enjoy a fresh local lunch with drinks and wine. The crew, including guides such as Stratos, Stefanos, and Aphrodite, also shares island myths and marine-life facts.

“We stayed in malia which was more than 10km away from Heraklion. Cost for transportation is 20e. We took the bus which was cheaper. The crew was very friendly they explained everything we wanted to know. We arrived to the island in 1 hour stayed there for 2.5 hours and left. The food was absolutley amazing. Souflaki very good and thr salad very fresh. Wine was very good. We did snorkeling and saw tons of fish. Very nice experience overall. Absolutely worth the money.”

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4.Sailing Boat Small Group Kleftiko and Sikia Cave West of Milos

★★★★★★★★★★5.0 · 200 reviews · 9 hours (approx.) · from $169

Spend about nine hours aboard a small-group boat from Adamas, exploring Milos’ western coast with stops for swimming and snorkeling. You’ll see syrmatas, Cape Vani, Kalogries Beach, Kleftiko, and Agios Dimitrios. Meals, snacks, drinks, and snorkel gear are included. Crew names vary, with Fay, Facundo, Christos, Alex, and others featured on recent trips.

“This tour is a MUST! The captain was amazing! She got so close to all the major sites and was very informative. This was a very laid back and relaxing experience!”

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5.Milos caves snorkelling Catamaran Cruise in a small group

★★★★★★★★★★5.0 · 199 reviews · 8 to 9 hours (approx.) · from $241

Spend 8 to 9 hours sailing around Milos aboard a shaded catamaran limited to 12 people. Swim at Kalogries, Sykia, Kleftiko, and Agios Dimitrios, enter caves by dinghy, and enjoy homemade Greek food, drinks, snorkel gear, Wi-Fi, and GoPro photos.

“Great trip, Georgina and Marcus were the best. Food, swimming and cave venturing was was the highlight . Highly recommend”

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6.Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group)

★★★★★★★★★★5.0 · 197 reviews · 6 hours (approx.) · from $120

Spend about six hours sailing from Rhodes Town to Anthony Quinn Bay, Traganou Beach, and Ladiko Beach. Swim, snorkel, sunbathe, and enjoy Greek food, fruit, wine, beer, coffee, and soft drinks. The crew may include captains such as George or Dimitri, and the boat carries up to 15 people, though comfort depends on the vessel and group size.

“Great experience. The guides on the boat were very hospitable and nice. Respect was there and there was no sabotage. They were cool too and made it as adventurous as I hoped/prayed it would be. Would highly recommend this tour to outdoor folks and swimmers/snorkeling. Good sights. Cool boat when you get back on.”

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7.Small Group Full-Day Sailing with Meal, Drinks, & Swim

★★★★★★★★★★4.8 · 162 reviews · 7 hours · from $170

Sail from Kos Harbor on a comfortable 20-meter Greek sailing boat with an English-speaking crew, including Nikki and the captain. You’ll stop at two quiet swim and snorkel spots, visit Pserimos, and eat a fresh Greek-style lunch on board. Recent departures have often carried only 10 to 12 people, though the boat may vary by date.

“We had the most amazing time on the boat, we were so well looked after, the food was amazing, the views incredible, the sea was crystal clear and everything about the trip was five star”

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8.Dia island : Small Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★5.0 · 162 reviews · 4 hours 30 minutes (approx.) · from $72

Set sail from Heraklion’s Old Venetian port with a certified crew, such as Costas, Mario, George, or Harry, for Dia Island’s quiet coves. You’ll have about 90 minutes for swimming, SUP, snorkeling, and sunbathing, followed by an organic lunch, fruit, soft drinks, and wine. Pickup is included within 10 kilometers.

“Friendly skipper and crew, great first time sailing experience for my friend and excellent anchorage choice as well. Would return to them again!”

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9.Athens Semi Private Sunset Catamaran Cruise with meal & drinks

★★★★★★★★★★5.0 · 142 reviews · 4 to 5 hours (approx.) · from $169

Sail from Alimos along the Athenian coast on a catamaran limited to 10 people. Swim and snorkel near Vouliagmeni and Kavouri, eat seafood pasta with salads and Greek appetizers, and watch the sun set over the Saronic Gulf. Crews have included Captain Yannis, Steph, Nikki, and Nikkos.

“Great crew great food and fun trip swimming and diving gear included very attentive crew The seafood pasta was delicious”

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10.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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11.Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

★★★★★★★★★★5.0 · 126 reviews · 6 hours 30 minutes (approx.) · from $181

From Heraklion, sail with an English-speaking crew to Dia Island aboard a catamaran limited to 14 people. Expect a light brunch, fresh Mediterranean lunch, local beer and wine, swimming, snorkeling, paddleboarding, fishing, Wi-Fi, and time to relax in a sheltered bay.

“This is the company to use for a snorkel sailing adventure. Thomas, Anise, and Alexander took great care of us. Water was crystal clear. Plenty of time at Dia in a secluded cove. A wonderful day, high recommend! Dolphins were an added bonus.”

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12.Athens Semi private Morning Catamaran cruise with meal & drinks

★★★★★★★★★★5.0 · 123 reviews · 5 hours (approx.) · from $169

You’ll spend about five hours aboard a catamaran from Alimos Marina, stopping near Megalo Kavouri and Vouliagmeni for swimming and snorkeling. A crew of up to 10 serves seafood pasta, salads, appetizers, wine, beer, and water. Hosts such as Nikki, Johanna, and Nikos have been praised for warm service and flexible meals.

“Boat was very nice and roomie. Loved that the cruise is semi-private and limited to 10 guests! Food was amazing, so good! The crew was absolutely wonderful! It was the perfect day on the water to wrap up our trip to Athens! Highly, highly recommend!”

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13.Mykonos Shared Catamaran Tour Experience

★★★★★★★★★★5.0 · 105 reviews · 5 hours (approx.) · from $240

Join a small shared yacht cruise from Ornos for about five hours. You’ll pass Delos, stop at quiet Rhenia for swimming and snorkeling, and cruise Mykonos’ south coast past Psarou, Paraga, Paradise, and Super Paradise. Food, drinks, and water activities are highlighted by past guests, though exact inclusions should be confirmed before booking.

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14.Sail Taste Connect a Semi Private Sailing with Seafood and Wine

★★★★★★★★★★5.0 · 99 reviews · 5 hours (approx.) · from $192

Set out from Ornos on a semi-private yacht cruise for up to 12 people. Captain Dimitris and hosts including Parthenia and Costandina guide you past Delos, stop at Rhenia for swimming and snorkeling, and serve fresh Greek seafood with wine and beer. The route may also include Mykonos’ south-coast beaches.

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15.Rhenia island – Small group Sailing adventure (up to 8 guests)

★★★★★★★★★★5.0 · 98 reviews · from $70Cheapest deck

Set sail from Agios Ioannis with a small crew and up to eight people, stopping at two quiet Rhenia beaches for swimming and snorkeling. Orestes, Agnes, or another crew member shares local history, serves a fresh Greek meal, and offers beer, wine, and water. Optional hotel pickup makes this a simple half-day escape.

“Our wonderful friendly tour guides were very devoted to our experience being a thorough and enjoyable one. Excellent food prepared fresh on the boat and served with the sweetest and friendliest presentation. Wish we could have done the sunset cruise but had to pick day cruise with our travel plans. Great experience!”

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