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Greece

Gay sailing trip | Sailing & Relaxation

6 Sep.- 13 Sep. 2025

6 - 10 gays |  Spots availaible 

Discover the land of gods and heroes as you explore the legendary Peloponnese on an unforgettable gay sailing trip. Sail past ancient temples and amphitheatres aboard a yacht, enjoy countless hours of sunshine and ultimate relaxation on deck or swimming in the crystal-clear waters of secluded bays in the Saronic Gulf – all the while being caressed by the refreshing Mediterranean breeze.

  • ​Discover the magic of sailing on a yacht

  • Experience the natural and architectural wonders of ancient Greece

  • Indulge in delicious Mediterranean cuisine

  • Explore the many facets of Greek island life

Visual inspiration

Never sailed before?

Anyone can sail with us, even if you have no sailing experience at all.

A trained, English-speaking skipper will brief you on how to sail a yacht and will even let you take part in the navigation of the vessel. As a beginner, you’ll begin to enjoy active sailing after just a few short hours – and you might even decide to take the helm from time to time! But don't worry – our gay sailing trips are uncomplicated adventures that are guaranteed to make your gay sailing holiday one you’ll never forget.

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Indeed, everyone is literally “on the same boat” and space is limited on a yacht.

But no one needs to worry about being too cramped. Everyone has their own bunk, and you’ll also find enough space to relax with others or on your own on deck or in the yacht’s cosy lounge. The shared double cabins are allocated during the introduction round. Couples, friends, and guys who have booked a cabin for themselves are allocated a double or single cabin. Keep in mind that this is not a “clothing-optional” gay sailing trip – so please keep your swimsuits on to avoid making your cabin mate or the rest of the crew feel uncomfortable.

 

Everyone is involved in running the yacht.

Daily tasks such as cooking or cleaning are done together and are lots of fun as a group activity. Even though for safety reasons the skipper has the final say on board, everyone is involved in running the yacht – within reason – and actively helps plan the trip.

Details

Day 1, Sat, 06.09.2025: Get ready for your sailing adventure

A gay sailing trip in Greece doesn’t just sound relaxing – it absolutely IS relaxing! Nevertheless, it does require some preparation. You and the other guys will arrive at the marina between 2 and 4 p.m. The first item on the agenda is to go grocery shopping to get everything you and the rest of the crew will need for your gay sailing adventure in the legendary Peloponnese. After all, you’ll be cooking and eating together with the other guys aboard the yacht – the kitchen is well equipped so feel free to let your culinary skills shine. You’ll spend the rest of the afternoon making the final arrangements. Check-in on the yacht is after 5 p.m. Tonight, you’ll have a delicious dinner at Constantinos near the harbour. Yiamas – here’s to an unforgettable gay sailing holiday!

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Why Greece?

  • Sailing in the turquoise waters of the Peloponnese is sure to give you the feeling of ultimate freedom. The region is truly one-of-a-kind and has all the ingredients needed for a dream gay sailing holiday and much more.

  • Enjoy stunning views from the deck of the yacht, jump into the sea to cool off after working on your tan, take excursions on shore through quaint, picturesque fishing villages and to ancient sites, discover secluded bays, and learn the basics of sailing on a yacht.

  • The Greeks are warm-hearted and unbelievably hospitable. The islands are more relaxed than the mainland, but even the mainland Greeks are gradually becoming more liberal.

  • The younger Greeks are typically very open-minded, and the country is becoming increasingly more gay-friendly. In 2015, legislation was passed to legalise same sex unions.

Day 2, Sun, 07.09.2025: Guys ahoy!

After an important sailing yacht briefing, it’s finally time to cast off! You start your gay sailing holiday in Greece heading south. Taking part in the actual sailing is an integral component of a gay sailing adventure. Don’t worry if you’ve never sailed before – your skipper will teach you everything you need to know. Next stop, the harbour of Aegina – it’s time for a refreshing swim.

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Day 3, Mon, 08.09.2025: From Aegina to Spetses

Every day of your gay sailing holiday is different – but one thing remains the same: every day is simply breathtaking! Today, your sailing route continues southeast from Aegina, past Poros to Spetses. In the northwest, a magnificent bay awaits you where the waters are calm and where you can enjoy gazing at the stars while sipping on a cool sundowner.

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Day 4, Tue, 09.09.2025: Ermioni Bay

After an invigorating swim, you set sail with your skipper and the other guys for a short trip to Ermioni Bay on the Peleponnese coast. You drop anchor only a short distance from the island of Spetses. Ermioni is a lovely little town and in the late afternoon, you can relax on the pier and work on your tan. In the evening, you’ll go out to dinner with the other guys in a cosy Greek taverna. This is the stuff gay holiday dreams are made of!

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Day 5, Wed, 10.09.2025: Island of Hydra

Today you’ll only be sailing a short distance. After just under an hour, you reach the spectacular island of Hydra. This harbour (and the whole island!) is truly unique – the only means of transport here are donkeys and horse-drawn carriages! During the day, make sure to stroll through the charming alleyways of the city and treat yourself to a yummy frappé, the typical Greek iced coffee. If you’re feeling adventurous, you can even dive into the crystal-clear waters from the cliffs right in front of the bar!

Yacht

The sailing yacht Sun Loft 47** planned for this gay sailing trip offers space for up to 10 guys plus the skipper. The sleek vessel combines space and comfort with flexibility and efficiency, ideal for sailing with a group.

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** The model of yacht presented in this tour description is planned for this sailing trip; however, if unforeseen circumstances should arise or if there are organisational issues, a different model may be provided on short notice.

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Day 6, Thu, 11.09.2025: From Hydra to Poros

If you’re a party animal, you most certainly celebrated until the early hours of the morning in Hydra. To give you a chance to recover – we want you to be relaxed at all times on your gay sailing holiday –you’ll set sail a little later today. After a 30-minute journey, you reach “Frog Bay”. After a round of swimming, you’ll continue to Poros. Why not go on an excursion on land by scooter? In the evening, Mikelos awaits you and the other guys at his traditional restaurant. Make sure to have some delicious ouzo!

Tour operator

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The sailing trip offered by Guys.travel is organised and operated by sailwithus - the most rated provider of sailing holidays in Germany.

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Day 7, Fri, 12.09.2025: Fun sailing back to Athens

Today, you can relax in the turquoise waters on the north side of the island of Agistri. After you’ve worked on your tan some more, it’s time for some fun sailing. Once you have had a swim, it’s time to return to Alimos Kalamaki. You’ll sail into the harbour of Athens between 3 and 6 p.m. Together with the guys, you’ll reminisce about the fun you’ve had. One thing is certain: it’s been an eventful week of unforgettable gay sailing in Greece!

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Day 8, Sat, 13.09.2025: Next port: Athens!

Your awesome gay sailing holiday in Greece has sadly come to an end. You already packed your things on Friday. At 9 a.m., you and the other guys disembark the yacht together – it’s hard not to feel a little sad… You’ve seen and experienced so much, you’ve relaxed to your heart’s content and have made new friends – it was pure gay sailing fun. Antío and see you next time!

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Detailed travel itinerary (PDF)

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Please note that depending on the weather conditions, changes may be made to the itinerary. Of course, this is done in discussion with the participants.

Prices and services

Greece | Gay sailing trip | Sailing & Relaxation

6 Sep.- 13 Sep. 2025

6 - 10 gays |  Spots available 

Shared double cabin

  € 799,-  

≈ US$ 872*

Have a cabin all to yourself

  € 1598,-  

≈ US$ 1744*

Price per person includes:

  • 7 nights on a sailing yacht

  • English-speaking skipper

  • One towel per person

  • Bedding

  • Dinghy

  • Outboard engine

  • Navigation equipment

  • Final cleaning of the yacht

  • Proof of nautical miles (on request)

Not included:

  • Cash on board for additional on-site expenses – food, diesel, national parks, harbour fees etc. (€200-€300 per person are deposited in the on-board cash box)

  • Meals for the skipper (paid for using funds from the on-board cash box)

  • Flights and transportation to the marina*

  • €100 deductible on the deposit

* The USD prices quoted are approximate conversions of the binding EUR price. The actual USD amount will vary depending on the conversion rate of the payment service provider on the date of payment.

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FEEDBACK

Brian | Ireland

We had a wonderful week sailing in Greece: beautiful bays, coastal towns, exciting sailing experiences, fine food, good drinks, swimming in the open sea, a large, comfortable sailing yacht, beautiful sunsets and starry skies...

Hank | Norway

Thanks to our skipper for a great week. He planned everything perfectly and took us to wonderful places and introduced us to the art of sailing.

Patrick | Austria

It was my first sailing trip and definitely not my last. How wonderful it is to let these magnificent landscapes pass you by from the water and to be able to moor where no one else can. A real dream holiday for me.

Book your trip now

Travel cancellation insurance:

You can purchase travel cancellation insurance from us immediately after booking by clicking on the link provided in the confirmation e-mail.

Next steps

STEP 1:

After submitting the booking form, you will receive an automatic confirmation of receipt from Guys.travel with a comprehensive overview of the next steps.

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STEP 2:

You will receive a booking confirmation by e-mail from the tour operator sailwithus with an invoice and secured payment certificate. You will be asked to make a 25% deposit up front (full payment also possible).

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STEP 3:

Once the minimum number of participants for the tour has been reached, you will be notified by sailwithus and it is safe to book your flights.

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STEP 4:

sailwithus will send you your travel documents by e-mail three weeks before the start of the tour.

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