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 filled with LGBTQ+ guests, and all staff members are extensively trained to provide you with a welcoming and gay-friendly experience. It’s a very open environment—one where you can relax both mentally and physically. The atmosphere is friendly, with a great social vibe. And depending on the size of the boat, there might even be onboard entertainment included.

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 different from that of a gay cruise, which typically takes 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.

View the Top 10 Sailing Trips

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 to explore, as well as have the opportunity to relax on great beaches for an afternoon dip. You will generally sail for 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, with daily swim stops, a selection of beaches, a handful of gay bars, and a great variety 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 as 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 this comes 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-sized ships, which tend to offer a wide range of entertainment but are less intimate. Medium-sized 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 accommodates only 6-20 guests, making it much easier to meet and connect with others. With smaller boats, you also experience the sailing itself—the wind, the sea, and the sun—​​much more personally, and you have far greater freedom with your skipper to adjust itineraries or stop for a quick swim. You can literally jump right off the side of the boat due to its small size.

Medium-sized ships, on the other hand, follow a more fixed itinerary and offer less connection with nature and the sea. The trade-off is that they provide more amenities, such as a gym, spa, bar, and onboard entertainment. They also tend to be more expensive but offer a more luxurious experience. While a small sailing boat is not “roughing it” by any means, 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 offering 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 dock in small port towns that you might not otherwise explore on a traditional land trip. Medium-sized ships, however, tend to dock in larger towns or cities, though not always.

While we enjoy both small-ship sailing and large gay cruises, our favorite between the two are the smaller, private yacht experiences. We love being immersed in the sea, enjoying amazing views along the beautiful coastlines, and connecting with the other guests on the boat. On most sailing trips, the group enjoys both breakfast and lunch onboard, typically prepared by a host who also assists the skipper while sailing. These shared meal experiences just aren’t quite the same on 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-sized ship might be the best option for you—especially if you have a larger budget and prefer luxury travel.

Why Take a Gay Sailing Trip?

There are many great benefits to 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 getting to know your travel companions because the experience is so intimate. On the larger sailing ships, there are plenty of activities designed to help connect guests, giving you a better chance to meet others 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 the full price of a two-person room if you’re traveling alone.

Be yourself – Probably one of the most attractive aspects of a gay sailing trip is the comfort zone it provides. The entire boat is filled with LGBTQ+ guests, and all crew members are extensively trained to provide a welcoming and gay-friendly experience. It’s a very open environment—one where you can relax and truly 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 as you sail from port to port. On a smaller boat, you experience sailing firsthand, with the captain steering 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! Plus, you have much more freedom with your skipper to make spontaneous stops in a cove for a quick dip or to explore a nearby beach. Smaller private yachts also allow you to jump right off the edge into the sea, something not typically possible on the medium-sized ships, which feel more like a small gay cruise.

Clothing-optional – Many gay sailing trips are considered clothing-optional, meaning you’re welcome to take it all off or leave it all on during your time sailing at sea. Of course, once you pull into port, you’ll need to cover up a bit—your port neighbors might not want to see your white bum or other parts hanging about! Generally, clothing-optional trips are offered 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’ll 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’re going on a gay sailing trip for the ports of call, the sailing experience itself, or both. Some people might prioritize the destination over the sailing experience, so be sure to check the route and places you’ll visit to help guide your decision.

Budget – The price of the trip is an obvious factor. You’ll also need to add the cost of flights or transportation to your budget, so the location of the departure and arrival ports should be part of your planning process. The entry-level price for 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 a small one. Large groups and full ship takeovers offer great parties and headline 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, as the experience of a small sailboat with just 8 guests onboard is worlds apart from that of a larger ship with 250 people.

What’s included? – Most gay sailing trips come with a crew/staff to sail the boat and serve food. The price usually includes the cabin, some or all meals, and onboard entertainment (for larger ships). However, unless you book an all-inclusive trip these items are typically not included in the price: pre- and post-hotel stays, land tours and excursions, specialty drinks/alcohol, and airport transfers.

One of the advantages of private/small sailboats is that they often allow you to bring your own alcohol onboard. You can simply stop at a shop in port to stock up on wine, beer, or spirits, which helps keep your travel spending down. Medium-sized ships with a full bar, however, usually prohibit bringing alcohol onboard, so you may need to factor this into your total trip cost.

8 Gay Sailing Trips to Checkout for 2025

We recommend and partner with a handful of different sailing operators who offer amazing experiences and have great reviews. In particular, we used to partner directly with a Europe-based gay sailing company, Pride Sailing, to host our own sailing trips in Croatia, Italy, and Greece, listed below. Although we don't directly host those trips anymore we still highly recommend them. They typically have departures weekly from multiple locations all summer long, from June through September.

Our other top recommendations below include Everything to Sea and GaySail. We’ve been collaborating with these companies for years and also hear great reviews from guests who book their trips.

Pride Sail Croatia with Pride Sailing

Dates: there are 7 scheduled departure dates in June, July, August and September 2025
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 →

France: Côte d'Azur with GaySail

Dates: September 13 – 20th, 2025
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 →

Pride Sail Thailand with Pride Sailing

Dates: March 15 – 22nd, March 22 – 29th,  March 29 – April 5,  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 →

GayNudeSail Exclusive St. Martin with GaySail

Dates: May 10, 2025 – May 17, 2025
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 →.

Pride Sail Greece with Pride Sailing

Dates: 21 – 28 June or 5 – 17 June, 2005
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 →

The Spectacular Naked Sail in Southeast Asia with Everything to Sea

Dates: May 16 – 22 or October 14 – 20, 2025
Destination/Route: Southeast Asia,  The Coral Triangle
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 2025, 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 with GaySail

Dates: November 2025 (exact dates to be announced)
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 →

Pride Sail Sicily with Pride Sailing

Dates: Dates on request for 2025
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 →