Going on a gay sailing trip is one of the most enjoyable and relaxing vacations you can take. The destination options range from the Mediterranean and Caribbean to the Panama Canal or even Tahiti. On a gay sailing trip, the entire boat is full of LGBTQ+ guests and all staff has been extensively trained to provide you with a welcoming and gay-friendly experience. It’s a very open environment and one where you can relax both mentally and physically. The environment is friendly with a great social atmosphere. And depending on the size of the boat, there might even be entertainment included onboard.

There are a number of companies that offer gay sailing trips in different destinations around the world. It’s important to note that the experience on a small sailing boat of around 10-20 people is quite a different experience than a gay cruise which would normally take place on a larger ship with hundreds or thousands of people. A sailing trip is more intimate, relaxing and casual than a gay cruise. However, larger sailing ships holding between 50 to 250 guests might feel a bit more like a small gay cruise. 

What Can You Expect on a Gay Sailing Trip?

By joining a gay sailing trip you can enjoy a port hopping vacation around beautiful coastlines with gay guests from around the world. You’ll stop at the best gay-friendly locations in the area for you to explore, as well as have the opportunity to relax on great beaches for an afternoon dip. You will generally sail several hours each morning or early afternoon and then arrive in port with enough time to explore the port town or city, relax on your private yacht or sailing ship or find a nice cocktail sunset bar. ​Sailing trips typically last about a week in length and you will have daily swim stops, a selection of beaches, a handful of gay bars and a great selection of restaurants to choose from.

Gay sailing trips generally fall into two categories: small sailing boats (e.g. a private yacht) and medium sized ships. Small boat sailing trips are nothing like gay cruises. In fact, besides being gay and taking place on a boat, they couldn’t be more different. You can think of a small boat sailing trip a bit like glamping. All the great elements of being outdoors, enjoying the sun, nature and the sea. But instead of your luxury tent being stuck on the ground, your private yacht takes you to a new destination each day with meals and swim stops along the way. All with the comfort of cozy cabins, onboard bathrooms and showers, plus a professional crew to sail your boat and prepare your meals. 

You can opt for a small boat with a more intimate feel or take one of the medium size ships, which tend to have a wide range of entertainment but are less intimate. Medium size sailing trips feel a bit more like a gay cruise and you might expect 50 to 250 guests onboard. A small gay sailing boat on the other hand typically only has 6-20 guests onboard so it’s much easier to meet and connect with other guests. With the smaller boats you also feel the sailing experiencethe wind, the sea and the sun​​much more personally and you have a lot more freedom with your skipper to adjust itineraries or stop for a quick swim. You can literally just jump right off the side of the boat due to its small size. Medium sized ships on the other hand have a more fixed itinerary and you feel less with nature and the sea. The trade off is that the medium size ships have many more amenities like a gym, spa, bar and onboard entertainment. They also tend to be more expensive but offer a more luxurious experience. The experience on a small sailing boat is not ‘roughing it’ by any means, but the space and shared quarters are smaller and more casual. 

The other determining factor in selecting a gay sailing trip is typically the destination and sailing itinerary. While you can technically sail just about anywhere along the coast or open sea, the sailing experience is most enjoyable in locations which offer warm weather and smooth seas. This tends to limit the destinations to popular sailing routes in places like Greece, Italy, Croatia or the Caribbean. Small ship sailing is a fun experience because you will dock in small port towns that you might not otherwise explore on a traditional land trip. Medium sized ships tend to dock in larger towns or cities but not always. 

While we enjoy small ship sailing and large gay cruises alike, our favorite between the two are the smaller, private yacht experiences. We love being immersed in the sea, enjoying amazing views among the beautiful coastlines and also getting the opportunity to connect with the other guests in the boat. On most sailing trips, the group will enjoy both breakfast and lunch onboard together typically prepared by a host who also assists the skipper while sailing. These meal opportunities just aren’t quite the same on the larger ships. However, if you’re looking for a bigger ship with great amenities and want a more romantic and private experience with your partner, then a medium size ship might be the best option for you. This is particularly true if you have a larger budget and prefer luxury travel. 

Why Take a Gay Sailing Trip?

There are a lot of great benefits of choosing a sailing trip as a holiday or vacation compared to other types of land trips or travel experiences. Here are a few things to consider when deciding. 

Easy to meet new people – one great aspect of taking a gay sailing trip is that most of the guests are friendly and open to meeting new people. On the small boats you simply can’t avoid meeting your travel companions as the experience is so intimate. On the larger sailing ships, there are many activities that help connect guests to give you a better chance at meeting people as well. 

Travel alone – most gay sailing companies offer a cabin match program where they will assign you a roommate, so you don’t have to pay for the full price of a two-person room if you’re traveling alone.

Be yourself – probably one of the most attractive parts about a gay sailing trip is the comfort zone. The entire boat is full of LGBT+ guests and all crew has been extensively trained to provide you with a welcoming and gay-friendly experience. It’s a very open environment and one where you can relax and be yourself without fear of harassment. 

Enjoy nature up close – We love being immersed in the sea, enjoying amazing views along the beautiful coastlines and feeling the wind glide across your body sailing from port to port. This is the feeling you get on a smaller boat and you also experience the sailing first hand as the captain steers the boat right next to you while adjusting ropes and sails to adapt to the wind. On a small boat you can even learn to sail yourself if you want. You also have a lot more freedom with your skipper to make random stops in a cove for a quick drip or to explore a nearby beach. The smaller private yachts literally allow you to jump right off the edge into the sea, an option not typically possible in the medium sized ships which feel more like a small gay cruise. 

Clothing-Optional – many gay sailing trips are considered clothing optional which means that you’re welcome to take it all off or leave it all on during your times sailing at sea. Of course, once you pull into port, you’ll need to cover up a bit since your port neighbors won’t want to see your white bum or man parts hanging about. Generally the clothing optional trips happen only on the smaller sailing boats. 

How to Choose the Best Gay Sailing Trip?

Determining which gay sailing trip to take is completely subjective. People have different preferences, budgets or destinations in mind when it comes to booking a trip. All the companies listed here are highly recommended and have great reviews, but you want to make sure you pick the right trip for your travel style and preferences. Below are a few tips to consider before booking your trip.

Destination – decide if you are going on a gay sailing trip for the ports of call, for the sailing experience in general, or both. Some people might prioritize the destination over the sailing so be sure to check out the route and places you’ll visit to help you decide.

Budget – the price of the trip is an obvious factor. You’ll need to add the price of flights or transportation into your budget so the location of the departing and arrival port should be part of your planning process. The entry-level price to a gay sailing trip typically starts around $1,500 per person for a week-long trip.

Size – it’s important to decide if you prefer a large group or small. Large groups and full ship takeovers offer great parties and header liner entertainment, but some people may want to avoid the crowds and opt for a more intimate experience on a smaller sailing boat. The difference between the two can’t be emphasized enough because the experience of a small sailboat with just 8 guests on board is worlds apart from a larger ship with 250 people. 

What’s included? – most gay sailing trips come with a crew/staff to sail and serve food and the price usually includes the cabin, some or all meals and onboard entertainment (for larger ships) in the price. However, unless you book an all-inclusive trip with Brand g, these items are typically not included in the price: pre and post hotel stay, land tours and excursions, specialty drinks/alcohol and airport transfers. One of the nice parts about private/small sailboats is they allow you to bring your own alcohol onboard. Simply stop at a shop in port to stock up on wine, beer or spirits which keeps your travel spending down. Medium sized ships with a full bar usually ban bringing alcohol onboard so you may need to factor this into your total trip cost.

10 Gay Sailing Trips to Checkout for 2024

We recommend and partner with a handful of different sailing operators who offer amazing experiences and have great reviews. In particular, we partner directly with a Europe-based gay sailing company to host our own sailing trip of Croatia, Italy and Greece listed below. We’ve been hosting these trips since 2018 and they have become so popular that we’ve added boats to our fleet and added destinations. They typically have departures weekly from multiple destinations all summer long from June through September. Our other top recommendations below include Pride Sailing and Source Journeys. We’ve been collaborating with these companies for years and also hear great reviews from guests who book their trips. 

Pride Sail Croatia (Pride Sailing)

Dates: there are 7 scheduled departure dates in June, July, August and September 2024
Destination/Route: Split to Dubrovnik, Croatia
Type: Small Boat (8 guests per boat)
Dress code: Clothing-optional 

All aboard for this awesome gay sailing trip – we know it's awesome from first hand experience, having been ourselves three times! You can enjoy an island-hopping vacation around the beautiful Croatian coastline with gay guests from around the world with a certified skipper to pilot the boat.. You ́ll stop at the best gay-friendly locations in the area for you to explore, as well as great beaches for an afternoon dip and arrive in port with enough time to explore the island, relax on a private yacht or find a nice cocktail sunset bar. The amazing destinations include Dubrovnik, the famous island of Vis, Hvar with its buzzing nightlife and fine dining, plus you’ll get the opportunity to party in Split’s bars and clubs. Back in 2018-2022, we partnered with this Europe-based gay sailing company and have sailed this exact route several times – so we can guarantee you'll have a great time. Croatia is the ideal place for sailing with smooth seas, beautiful coastline and fun ports with lots of activities and well-equipped facilities. View Sailing Trip →

Image credit: Source Journeys

Treasures of Venice Dalmatian Coast Cruise (Source Journeys)

Dates: August 17th – 24th, 2024
Destination/Route: Venice to Kotor then back up the Croatian coast to Venice
Type: Large Boat (227 guests per boat)
Dress code: Clothing required

Source Journeys are an LGBTQ+ cruise operator whose cruises effortlessly blend luxury with old school style adventures. Their vessel, The Royal Clipper, is the largest five masted full-rigged sailing ship in the world. August 2024 it sets sail from Venice along the Dalmatian Coast – porting at Kotor, Dubrovnik, Zadar, Hvar, the Pakleni Islands and Rovinj before looping back to Venice. Throughout the all-inclusive cruise you’ll enjoy on shore excursions into ancient old towns, see cascading waterfalls and hidden coves, relax on picture perfect beaches and dine on fine regional food while lubricating your adventure with unlimited free drinks. On board there’s two swimming pools, a spa, a crow’s nest to climb, LGBTQ+ focused entertainment and fun themed parties to keep you entertained when out on the high seas. View Sailing Trip →

The Caribbean (Sailing Samsara)

Dates: Anytime between October 2023 – April 2024
Destination/Route: You choose (in the Caribbean)
Type: Intimate Yacht (4 guests)
Dress code: Clothing-optional

Looking for a more intimate bespoke adventure? Then join chef to the stars Charly – christened the “The King of Bolognese” by Cher herself – and experienced captain Micha, as they explore the Caribbean. The gay couple, having a lot of stories to share, are opening up their clothing optional home for a happy and fun LGBTQ+ sailing trip that goes where the wind takes them. Join them for however long you wish, be that a day or up to weeks. Their 51 feet long leopard catamaran is more luxurious than most hotels, equipped with all the creature comforts you might need for any adventure on the high seas. You’ll venture out into the unspoiled parts of the Caribbean islands, where no Cruise ships can go, and choose the exact whereabouts of where you anchor – adapting to your whims and desires. Whether you’re looking for lively beach bars or quiet coves, Sailing Samsara believes in giving you true autonomy in crafting your own adventures. View Sailing Trip →

France: Côte d'Azur (GaySail)

Dates: September 14 – 21st, 2024
Destination/Route: Round trip from Port Pin Rolland along the French Riviera
Type: Medium-Sized Catamaran (10-14 guests per boat)
Dress code: Nude (GayNudeSail), Clothing-optional (GaySail)

If you're looking for a little je ne sais quoi in your sailing trip, then try GaySail's exclusive France voyage. You'll board a luxury Catamaran and partake in sophisticated sailing down the French Riviera – visiting exclusive beaches, sipping champagne, tasting quality French cuisine and rubbing shoulders with the rich and famous. The cruise is a round trip to and from Port Pin Rolland, found next to Toulon and its international airport. Ports include the gorgeous village of Potquerolles – where cars are forbidden- and the beautiful favored retreat of celebrities, St. Tropez. You can make your trip into a real chef-d'oeuvre by pairing it with a stay at GaySail¡s very own French Gay Boutique resort “La Connexion”.  View Sailing Trip →

Thailand (Pride Sailing)

Dates: April 6th, 2024
Destination/Route: Round trip from Phuket around the Thai islands
Type: Small Boat (8 guests per boat)
Dress code: Clothing-optional

Thailand is Earth’s answer to Heaven and Pride Sailing is launching a new 7-day LGBTQ+ cruise to visit the best of its coastsl region and islands. Setting sail from gorgeous Phuket, you’ll soar across emerald green waters to see the limestone cliffs of Ao Phang Nga, sail to “James Bond Island ”, visit the huge hong of Koh Ro – that’s a lagoon for the dirty minded -, swim with the sharks off Bamboo Island and arrive at the iconically beautiful filming location of The Beach at Phi Phi Islands. There are many hidden coves and rare beauties to be found under the guidance of Pride Sailing from the decks of a private yacht. All this and more await on a Pride Sailing trip to Thailand. View Sailing Trip →

GaySail Exclusive St. Martin (GaySail)

Dates: May 11th – 18th, 2024
Destination/Route: Round trip from St.Martin
Type: Type: Big Catamaran (20 guests per boat)
Dress code: Dress code: Nude (GayNudeSail), Clothing-optional (GaySail)

Another quality-assured sailing trip from GaySail, this time in the Caribbean. How does tanning your bits with a cocktail in hand while on palm treed white sandy beaches sound? If your answer is great – and honestly why wouldn0t it be – then this cruise might be a good place to start. Board one of GaySail's two luxury catamarans – with 19 other lucky gays -as they glide between the tropical islands of St.Martin, Anguilla and St. Barth. You'll have your own gay skipper guide whio`ll take you to all the world class restaurants, liveliest beach bars, best diving/snorkelling spots, legendary beaches – all while telling you all about the islands' fascinating colonial history. On your luxury boat, you'll have your own gay cook providing you with breakfast and lunch everyday. View Sailing Trip →.

Gay Sailing of the Ionian Sea in Greece (Pride Sailing)

Dates: 15th June, 2024
Destination/Route: Round trip from Lefkas, Greece.
Type: Small Boat (8 guests per boat)
Dress code: Clothing-optional

Greece may well be the cradle of modern civilization, the birthplace of democracy and a realm of myth and legend, but it is also a land of mind-blowing beauty with thousands of pristine perfect islands scattered within sailing distance from its shores. Pride Sailing offers an exciting choice of cruises sailing to the cream of the crop of Greek islands to see the most unforgettable beaches, experience the richest Greek culture and dine in the most authentically local tavernas. If relaxation splashed with adevnture is your focus, then this is the cruise for you. Their Ionian Sea Cruise is a 7-day island hopping adventure starts in Lefkas, which is several hours away from Athens by road. With hidden sea caves, lush coastlines and turquoise waters, the Ionian Islands make for the perfect escapism. Sailing the Ionian is what people dream of when they ‘Sail the Greek Islands'. Wine and dine, meet locals and engage in fun activities. There is so much adventure that awaits you on this 7-day trip on a relaxing luxury sailing yacht. Drink, eat, and swim with your friends or other like-minded travelers on this awesome Greek sailing trip. View Sailing Trip →

Gay (Clothing Optional) Sailing in Southeast Asia (Everything to Sea)

Dates: Multiple Departure Dates
Destination/Route: Southeast Asia
Type: Small Boat (16 guests per boat)
Dress code: Clothing-optional

Social, sensual, clothing-optional sailing. Has a nice ring to it, doesn’t it? We love sailing trips because the experience is both vast and unforgettable, yet intimate and tantalizing. Everything to Sea is a sailing company offering relaxing trips across Southeast Asia, visiting exotic islands while enjoying a care-free and naked experience, if you desire. That’s right, a clothing-optional cruise through uninhabited islands. Our friends at Everything to Sea have announced their 2024, all male clothing-optional sailing trips in Paradise. The 7-day trips are on a large wooden sailing ship called a “Pinisi” boat which fits up to 16 men including the crew. So what more is there to see exactly? Expect komodo dragons, stunning beaches, turquoise bays and much more. View Sailing Trips →

GaySail Exclusive Tahiti (GaySail)

Dates: November 16th – 23rd, 2024 (GaySail) or November 23rd – 30th,(GayNude Sail)
Destination/Route: Round trip from Tahiti through the French Polynesia
Type: Medium-Sized Catamaran (14 guests per boat)
Dress code: Dress code: Nude (GayNudeSail), Clothing-optional (GaySail)

Sometimes you just need to get away from it all and there's nowhere in the world more away from it all than Tahiti – I mean, it's literally in the middle of the ocean. Join GaySail for 7 days in the South Pacific utopia as you cruise though five groups of islands, each surrounded by tropical blue waters abundant with exotic marine life – from turtles and dolphins to stingrays and sharks – and containing Tahiti's famed emerald volcanic peaks and thatched huts upon pristine beaches. All five islands boast their own personalities and you'll see the famously romantic Bora Bora, as well as Raiatea, Tupai, Maupiti and Moorea. You'll taste the best French Polynesisan cuisine – both on and off board your luxury catamaran – and snorkel above teeming reefs, hike through  forests, climb volcanic rock faces and visit ancient temples. Choose between either a fully nude cruise – for the bold – or a clothing-optional one, either way you're assured a unique experience in one of the most beautiful – and remote- places in the world.   View Sailing Trip →

Gay Sailing the Aeolian Islands and Sicily (Pride Sailing)

Dates: June 22nd or 7th September, 2024
Destination/Route: Round trip from Portarosa, Italy
Type: Small Boat (8 guests per boat)
Dress code: Clothing-optional

Sicily is hot! From the weather to the men to the nightlife, there’s no denying Sicily has all the ingredients necessary for a perfect sailing trip. Discover the amazing Aeolian islands, off Sicily, and its crystalline waters. The trip starts and ends in Portarosa, reachable easily from Catania airport. Another option is also flying into Palermo airport and getting a private transfer. They have selected only the best crew to keep you afloat as you cross the sea and head to the beautiful Aeolian islands. During the trip you will explore the amazing volcanic islands of Alicudi, snorkel in the transparent waters of Lisca Bianca, bathe in the muds of Vulcano, taste the fine wines of Salina, hike through the parks of Lipari…and more. This exclusive gay sailing experience is a 7-night adventure stopping at islands and ports where you can explore, sunbathe, swim, meet the locals, eat out and plenty more. The gay sailing yachts are modern with space to relax. The cabins are comfortable and there is a fully equipped galley and 2 bathrooms. This gay sailing trip is a great opportunity to relax, enjoy, taste local cuisine, meet new friends and explore beautiful Italian islands. View Sailing Trip →