Under sail · SEMI-PRIVATE SAILING CRUISES

Semi-Private Sailing in Greece: Our Top 15

38 sailings  ·  from $70 a head

Eight or ten guests instead of twenty-five, on the same route, for a middling amount more. These 15 compare the head count, the route and what the smaller boat lets the skipper do about it.

Shared Mykonos Sail Cruise to Delos and Rhenia Islands - Rhenia brings the swimming stop
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Shared Mykonos Sail Cruise to Delos and Rhenia Islands

1.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

★★★★★★★★★★5.0 · 705 reviews · 6 hours (approx.) · from $151Our pick

Review the Mykonos sail to Delos and Rhenia, with ruins, swimming, snorkeling, BBQ lunch, costs, timing, and practical tips.

“Wonderful crew and the food was fantastic. We enjoyed the entire trip and would highly recommend this activity for anyone who wants to spend a day relaxing in the sun while enjoying good food, views and swimming.”

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Shared Catamaran All inclusive-Day Cruise to Naxos or Paros - The first stretch can be a long one
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Shared Catamaran All inclusive-Day Cruise to Naxos or Paros

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

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

Review of Naxos Catamaran Sailing Cruises, with secluded beaches, snorkeling, local lunch, wine, and practical booking tips.

“Wonderful day out in the water with great opportunities to swim in the bright blue waters around Naxos. The Vasili’s were great hosts and the lunch served was delicious. Lots of wine, beer, and other beverages available. Water can get a bit choppy so I’d suggest that you are prepared!”

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Heraklion: Small-Group Sailing Trip to Dia Island with Lunch - The one-hour crossing to Dia Island
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Heraklion: Small-Group Sailing Trip to Dia Island with Lunch

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

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

Review of Heraklion’s small-group sailing trip to Dia Island, with clear-water swimming, snorkeling, local lunch, transfers, and practical tips.

“Overall the experience is very well worth it indeed. The staff are absolutely great and so friendly. Loved having conversations with them. The coast at Dia island is beautiful and snorkelling is highly advised. Food is also reasonably good.”

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Sailing Boat Small Group Kleftiko and Sikia Cave West of Milos - Fourkovouni and the pirate stories
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Sailing Boat Small Group Kleftiko and Sikia Cave West of Milos

Milos caves snorkelling Catamaran Cruise in a small group - Kalogries Beach: the first swim and breakfast
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Milos caves snorkelling Catamaran Cruise in a small group

Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group) - Traganou Beach brings clear water and a different mood
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Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group)

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

Review of Rhodes’ six-hour small-group yacht cruise, with three bays, swimming stops, lunch, drinks, pricing, comfort tips, and booking advice.

“Excellent motor yachting experience… Captain Yannis (aka Poseidon) was an excellent host and cook and being a small group experience shared some excellent company for the day… but people must be prepared for yachting experience with waves and all!”

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Kos: Small Group Full-Day Sailing with Meal, Drinks, & Swim - The First Bay: Clear Water and Time to Swim
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Kos: Small Group Full-Day Sailing with Meal, Drinks, & Swim

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

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

Review of Kos’s small-group sailing day to Pserimos, with Greek lunch, drinks, snorkeling, secluded bays, and practical booking tips.

“It was a great tour. The ship was in good conditions, the crew was very friendly and professional and the food was incredible. My only improvement suggestion would be to add a bit more of information along the way. The 2 stops in these bays or islands are nice but there not much content. Maybe I should have booked another trip with that purpose but I think it would not hurt to provide more input as a crew.”

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Dia island : Small Group Sailing Trip to Dia Island with Lunch - Agios Georgios or Panagia: the main swimming stop
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Dia island : Small Group Sailing Trip to Dia Island with Lunch

8.Small Group Sailing Trip to Dia Island with Lunch

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

Review of Crete’s small-group sailing trip to Dia Island, with snorkeling, SUP, lunch, wildlife, hotel pickup, and practical booking advice.

“- Captain and staff including pick up driver were really nice - water is really clear - boat is clean - captain brought a sea urchin to show to everyone. That was cute. BUT - the Equipment is the worst snorkeling Equipment We ever had on such a trip - at first they just had 8 snorkels for 12 ppl. So the Captain handed me his private one. That one was good. Later he found some more and said i have to change. Then i had to Deal with the rubish everyone had. Water came with EVERY breath. I didnt make it 2 meters of the boat on second attempt.…”

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Athens Semi Private Sunset Catamaran Cruise with meal & drinks - Kavouri Beach and sheltered waters near Hydrousa
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Athens Semi Private Sunset Catamaran Cruise with meal & drinks

Deluxe Santorini Sailing with BBQ and Drinks Shared Tour - Red Beach and White Beach: a short swim stop
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Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

10.Deluxe Santorini Sailing with BBQ and Drinks Shared Tour

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

Review of Santorini’s 5-hour sailing tour with BBQ, drinks, swimming stops, hotel transfers, and volcanic caldera views.

“Beautiful catermeran. Friendly and professional crew who offered excellent service. Fabulous sunset tour with the family sailing around Santorini. It was advertised so we were expecting a bbq. There were 2 on board but unfortunately not. The food was delicious but pre prepared earlier that day. Fortunately we brought our towels as they were not provided as mentioned. With a couple of exceptions overall a fantastic day and would highly recommend.”

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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - Boarding in Heraklion and Sailing Past Rocca a Mare
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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

Athens Semi private Morning Catamaran cruise with meal & drinks - Megalo Kavouri: 90 minutes in clear, shallow water
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Athens Semi private Morning Catamaran cruise with meal & drinks

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

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

Review of Athens’ five-hour catamaran cruise with two swim stops, onboard seafood lunch, drinks, snorkeling gear, and a 10-person limit.

“We had a lovely time enjoying the sea air on a nice comfortable catamaran. The staff was friendly and accommodating making us a lunch for difficult food allergies. Our family of 6 including 4 teenagers had fun swimming even though it’s a bit chilly in November. Relaxing and beautiful scenery.”

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Mykonos Shared Catamaran Tour Experience - Seeing Delos without losing a beach day
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Mykonos Shared Catamaran Tour Experience

13.Mykonos Shared Catamaran Tour Experience

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

Review of Mykonos’ semi-private catamaran cruise to Delos and Rhenia, with swimming, Greek food, beaches, timing, value, and booking tips.

“We had a great experience on the boat trip, with great views, smooth sailing and fantastic food cooked by the crew. We saw the ancient city of Delos and then went to a secluded beach to win, eat and drink. It was a lot of fun, I would recommend this boat tour for anyone wants to experience the authentic Mediterranean sea.”

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Sail Taste Connect a Semi Private Sailing with Seafood and Wine - Two Hours on Rhenia’s Quiet Shore
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Sail Taste Connect a Semi Private Sailing with Seafood and Wine

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

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

Review of Mykonos’ semi-private sailing trip to Delos and Rhenia, with Greek seafood, wine, swimming, snorkeling, and flexible beach stops.

“We had such an incredible day with Captain Dimitri and Parthenia! From the moment we stepped on board, they made us feel welcome, comfortable, and completely at ease. Dimitri was not only a skilled captain but also full of fascinating history and stories that brought the journey to life. Parthenia was so fun and helpful, always making sure everyone was enjoying themselves and had everything they needed.”

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Rhenia island - Small group Sailing adventure (up to 8 guests) - Leaving Mykonos from Agios Ioannis Diakoftis
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Rhenia island – Small group Sailing adventure (up to 8 guests)

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

★★★★★★★★★★5.0 · 98 reviews · from $70Best value

Sail from Mykonos to Rhenia for secluded beaches, snorkeling, Greek food, drinks, and Delos views on a small-group half-day cruise.

“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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