Gay Sailing Holidays
Learn about gay sailing holidays: what they’re like, who’s coming, how to book & more.
Gay Sailing Trips in Croatia, Greece, Italy & Thailand
I’ve embarked on all kinds of gay sailing trips, and they’re consistently the highlight of my summer. An experience I can’t recommend enough, I’m excited to fill you in on all the essential details about the experience and joining a boat!
Carefree, adventurous, and inclusive of all types of people, gay sailing holidays are a lovely way to explore new areas of the world with a fun group of friends.
The Gay Sailing Basics
Pride Sailing Holidays (a company who I’ve sailed with many times and now partner with) offers gay sailing trips from June through September in Croatia, Greece, and Italy. They also offer a Thailand itinerary for a few weeks in March.
Standard trips are seven days, include a maximum of 8 guests (plus captain and host), include breakfast/lunch, and are packed with fun activities.
You can reserve a single spot on a group trip, join my specific sailing trip, or book an entire boat for yourself or your group of friends.
Before You Scroll Any Further!
If you have even the slightest interest, it’s best to keep updated so you don’t miss out. Pride Sailing Holidays is a global leader in gay sailing holidays that operates dozens of trips each season at an affordable rate.
By signing up using the form below, you’ll be able to join my boat or book your own reservation, while receiving a special referral discount if you decide to make a booking in the future.
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Now, let’s dive into some specifics. I’ll bet you have questions about what type of guys will be joining, how you’ll get there, what’s included, the type of boat, and more. I’ll explain everything you need to know in the sections below.
For any questions you still have after reading this page, send me an email directly. I’d be happy to help you out.
Joining Gay Sailing Holidays with wolfyy
Partnering with Pride Sailing Holidays, I host my own personal boat trips in addition to helping interested guys join pre-scheduled trips or charter their own private boat.
Pride Sailing operates gay sailing trips in Croatia and Greece most frequently, but newer and more custom routes are also available (including in Thailand).
For example, I most recently sailed along the northern coast of Sardinia, Italy. And the summer before that, I sailed Sicily’s Aeolian Islands!
All boats have four guest cabins, each shared by two people. Many guys book typical single spots. But those who want extra privacy book two spaces in order to reserve the entire cabin.
Next, I’ll explain what the gay sailing experience is like so you know exactly what to expect. After that, I’ll go over more granular details about boat types, meals, and other specifics in the frequently asked questions section.
A Typical Week Gay Sailing
No matter the itinerary, there will be plenty of activities, new sights, fun guys, and delicious food to enjoy.
Daytime Activities
Each morning, the boat’s host prepares and serves breakfast on the boat. We then set sail for a couple of hours, enjoying the scenery along the open sea from the boat’s luxurious sun deck and lounge areas.
The first destination of the day is a swim stop, where we drop anchor to enjoy the water, paddleboard, relax on the bow of the boat, and eat a hearty lunch prepared by the host.
Some days include pit stops to local islands or beautiful coves. There is always some sort of exploration going on. Local excursion bookings will be available on certain afternoons, like group cave tours or wine tastings.
Nothing is ever mandatory, though. You are totally free to relax on the boat, go on a solo journey, or just have some alone time if you need it.
Toward mid-afternoon, we will arrive at our destination port for the evening. After reaching this stop, everyone is free to come and go from the boat as they please. It’s super chill and there’s a little downtime before any evening activities.
Some groups will plan to go bike riding, hang on a local beach, or just walk around taking in the gorgeous architecture.
Everything moves at a relaxing pace so you’ll never feel rushed. About half the nights, optional group dinners are organized by the sailing company at the best local restaurants. You’ll certainly get a taste of the local cuisine.
Gay Sailing: Evenings & Nightlife
During the evenings, everyone is quite eager to explore. There are plenty of opportunities to meet other gay travelers on other boats in the port.
Depending on the location/island, there may be nearby bars, clubs, or parties to visit. In Korčula, Croatia, there’s an epic foam party. Dubrovnik has a huge nightclub with top DJ performances.
Depending on the itinerary, there will be different nightlife options roughly half of the nights. Everyone is free to spend the nights as they wish. There is no curfew, but it is expected that everyone is respectful.
The next day, we will do it all over again in a new, beautiful place. Get ready for some clear blue water, a little rosé, and sunshine!
Now you’ve got the idea. It’s a super chill, fun week with good people, delicious food, and an opportunity to get to experience some amazing island destinations.
By the end of every gay sailing trip, you’ve bonded with wonderful new (or old) friends and I guarantee you’ll be hugging everyone goodbye, eager to book another season!
I hope you consider joining me for a gay sailing adventure! Next, I’ll discuss the guys who typically book these trips so you have comfort in knowing how smooth the trip will be. After that, I’ll list the different itineraries available.
What Are the Guys Like on Gay Sailing Trips?
It may seem intimidating to join a gay sailing trip at first. Sometimes guys are skeptical about booking group gay-oriented vacations.
Rest assured though, I wouldn’t compare gay sailing with anything like an Atlantis Cruise. The sailing experience is tamer, more personal, and filled with much more authentic exploration and culture.
In my experience, the travelers who book these trips are fun, energetic, polite, and open individuals. Everyone is interested in making new friends.
Plus, those who want a private experience will typically just book their own boat altogether, meaning you won’t ever have to worry about feeling out of place!
At the end of the trip, I always receive the same feedback from all the guys. They love the intimate, small-group setting.
Everyone ends up mentioning that one of their favorite aspects of the trip was having a smaller group of friends who can connect with one another. I agree 100%.
As opposed to the frenetic large gay cruise line excursions, you can build better relationships on a smaller gay boat trip! At the end of your holiday, you’ll have a bunch of new, quality friendships.
Gay Sailing Itineraries
All trips operated by Pride Sailing set off on a Saturday afternoon, and the trip continues until the following Saturday morning.
While every itinerary is subject to change, here’s what you can generally expect for the sailing routes in Croatia, Greece, and Italy.
Croatia Gay Sailing Itinerary: Split to Dubrovnik
Saturday: Meet & greet in Split, set sail, arrive in Brač for a nude beach adventure.
Sunday: Sail toward Vinogradse Bay, stop for a swim, and cocktails in Vinogradse Bar. Then grab water taxis to the party island of Hvar.
Monday: Sail to Vis, explore the island, take one of my favorite Croatia island tours to the Blue Caves, and enjoy a 5-star local dinner with local wine.
Tuesday: Sail toward the historic small city of Korčula, home of Marco Polo. Enjoy rooftop cocktails with unbeatable views of the Adriatic Sea.
Wednesday: Sailing toward Polače, break out the wigs for a fun-themed sail, plus a pit stop for champagne and swimming in a local bay. Bring your sexy gay swimwear!
Thursday: Short sail to another town on the island of Mljet called Okuklje. A tiny little Croatian town, you’ll get a taste of local life.
Friday: Start the journey toward Dubrovnik. Upon arrival, prep for cocktails in the Old Town, then a night out in Dubrovnik’s mega-club.
Saturday: Breakfast, hugs & goodbyes. From here, you’re free to extend your trip on your own!
Greece Gay Sailing Itinerary #1: Ionian Route
Saturday: Check-in, meet & greet & a quick sail over to Spartochori for a wonderful evening.
Sunday: Vathy, Ithaka: Morning swim at the Blue Caves (Lefkada), then a luxurious afternoon at Tilemachos Beach. The remainder of the evening will be in the port of Vathy.
Monday: Sami, Kefalonia: Morning swim and breakfast before heading to Sami for an afternoon of activities: Visit the Melassani caves & Myrtos Beach for sightseeing or a wine tour.
Tuesday: Fiskardo, Kefalonia: Relax on white-sand beaches, then anchor in a protected bay for the evening. Visit the town of Fiskardo for dinner and evening cocktails.
Wednesday: Sivota, Lefkada: Stop at the famous Porto Katsiki beach for lunch, then sail to the traditional of town Sivota for the evening.
Thursday: After several beach stops, we spend the evening in Kalamos.
Friday: Morning swim, then an afternoon stop at a beautiful beach bar to enjoy our final swim and relaxation in the sun before the port of Lefkada.
Saturday: Breakfast in Lefkada, hugs & goodbyes. From here, you’re free to extend your trip on your own!
Greece Gay Sailing Itinerary #2: Athens / Saronic Islands
Sunday: Sail south to the great island of Hydra. Explore the busy & charming port. Enjoy a spectacular sunset.
Monday: Head toward the charming town of Ermioni, where you can stroll the narrow neighborhood pathways and fill up on authentic Greek dishes at inexpensive restaurants.
Tuesday: Hop over to Spetses, the busiest town in the Saronic Islands.
Wednesday: Sail to Poros and explore the bustling local life and colorful architecture.
Thursday: Visit Epidavros, the largest, and oldest Greek Amphitheatre. Good day for hiking and exploring the ruins.
Friday: Sail back to Athens, explore the city, grab cocktails, and hit the nightlife spots.
Saturday: Breakfast in Athens, hugs & goodbyes. From here, you’re free to extend your trip on your own!
Italy Gay Sailing Itinerary #1: Sardinia
Pride Sailing began offering their all-new Sardinia itinerary in 2024, a breathtaking route around dreamy secluded islands with authentic port towns. There’s also a stop on the French island of Corsica just to the north!
Saturday: Depart from Olbia and set sail for Golfo Aranci, a charming town on the northeastern Sardinian coast with crystal-clear waters and a picturesque harbor.
Sunday: Sail to Caprera, an enchanting island part of the La Maddalena Archipelago.
Monday: Hop over to Santa Teresa, A coastal town on the northern tip of Sardinia with stunning beaches and lively nightlife.
Tuesday: Head to Bonifacio on the wonderful French island of Corsica. Shop at clothing boutiques, climb the historic citadel and enjoy the views.
Wednesday: Sail along the islands between Corsica and Sardinia, making swim stops in beautiful coves with crystal clear waters before heading to the quaint port town of La Maddalena.
Thursday: Enjoy a sail to Cannigione, a picturesque town with plenty of small shops, and the chance to enjoy a large group meal at a local farm-to-table restaurant.
Friday: Gear up for more unforgettable swim stops before heading back to Olbia for the evening.
Saturday: Quick breakfast, checkout, hugs, and goodbyes!
Italy Gay Sailing Itinerary #2: Sicily's Aeolian islands
Pride Sailing’s began offering their Sicily gay sailing itinerary in 2023. I loved this route—there were so many unique experiences.
To join a boat this year (or even in future years), add your name to the signup form on this page.
Photos of Past Gay Sailing Trips
Check out more photos and videos from any of the past six gay sailing trips I’ve taken and get even more of a sense of what the experience is like. View the story highlight on my Instagram: @laffaloui.
There, you’ll get some snapshots of each week, which are always filled with island hopping, jumping off beautiful sailboats, delicious food, and a fun group of adventurous people!
Reserve Your Spot
Don’t miss out on an epic gay sailing adventure. Sign up using the form below, check available dates, and coordinate your vacation time. You’ll be set before you know it.
Make it happen! You’ll have an unforgettable experience.
Stay Up to Date by
Completing this Form!
+
Get a Discounted
Booking Price
Using this form will allow you to join my boat for future trips (or book your own private charter) and entitles you to a special booking discount if you decide to reserve a spot in years to come.
Flexible Booking & Transferable Deposits
Planning travel well in advance or to a distant destination can sometimes be difficult! So, to make things easier, Pride Sailing offers flexible booking options that help take any stress out of planning your sailing trip.
Firstly, there’s a 7-day free cancellation period after initiating your booking. To get started, Pride Sailing requires a 500 Euro deposit, with the remainder of the cost due 12 weeks prior to the trip.
Deposits are also transferable, meaning that if you change your mind, you can get your deposit money back by transferring your trip to someone else. And lastly, in the incredibly rare case that Pride Sailing needs to cancel your trip, a full refund would be credited to you.
So what are you waiting for?! Use the form above to sign up and get started!
Gay Sailing FAQ’s
Here are my answers to some more detailed questions that I commonly get from guys thinking about joining.
What is The Boat Like?
Croatia gay sailing routes largely use the Beneteau Oceanis 48 monohull sailboat. The boat sleeps 10 people, with 4 double beds for 8 guests and 2 bunk beds for the skipper and host.
There are three bathrooms on the boat, all equipped with a shower and space to store toiletries.
Greece and Italy gay sailing trips are hosted on a Lagoon 42 catamaran. This boat is incredibly luxurious, super spacious, and always exceeds everyone’s expectations.
The Lagoon 42 has four cabins, each with its own bathroom. Two cabins are master suites, with walk-in showers. The skipper and host sleep in separate top-entry cabins at the front of the boat.
All the boats used are comfortable, clean, and have loads of room to spread out. You can lounge in the seating area at the rear of the boat or lay out your towels and take in some summer sun on the bow.
Even with 8 guests and 2 crew aboard, the space doesn’t feel tight at all! Trust me, I’ve been there many times. If anything, it’s cozy and fun, and there’s always someone to hang out with.
What Meals Are Included? What about Food Allergies?
Breakfast and lunch are included, personally prepared by the boat staff. Each morning you’ll wake up to a wholesome variety of breakfast foods and mingle with your yacht-mates.
After some daytime activities, fill up on a hearty, well-balanced lunch. We don’t skimp on meals. There is plenty to eat!
The crew can customize all meals to the groups liking. If anyone has allergies, we can surely avoid problem foods. Delicious summer salads, fruit and cheese platters, and hearty chicken bowls will keep you energized and ready to explore the sea.
For dinner, the group will have reservations coordinated at a local restaurant. Everyone is also free to go out on their own for dinner if they choose to. Dinner is not included, so you’ll need some spending money for evening meals.
Is Airfare Included?
You will be responsible for scheduling and purchasing your own flights to and from our destination. The booking price does not include airfare.
Is Alcohol Included?
This depends on the trip. All trips will have at least a few complimentary bottles of champagne, wine, and basic liquors. Beyond that, the price does not include unlimited alcohol.
Remember though, we purchase the alcohol in bulk from a nearby liquor store, so the price is not high.
You’re not paying for individual drinks here. If you wish to pre-order any beverages, we can make it happen. You’ll also have time to shop at a market before we set sail for the week.
Do We Sleep on the Boat? Is there Air Conditioning?
Yes, everyone sleeps on the boat. We dock in a marina each afternoon. Arrival time varies based on whether the day’s itinerary includes swim stops.
In most locations, there will be convenience stores, pharmacies, and other essential establishments, should you need anything.
Depending on the itinerary, some sailboats have air conditioning, and others do not. Greece sailing routes on Lagoon catamarans will have air conditioning (both the Athens and Ionian routes), while those in Croatia will not.
Even in the middle of summer in Croatia, it is not too hot when you’re out at sea. (Greece is a different story, though!) There are dozens of little windows so air off the water is constantly flowing through the rooms of the boat.
Plus, we are sailing and not wearing much clothing anyway! I personally have had no issue with overheating on a sailing trip.
How Much Does It Cost to Book?
Check the respective company for pricing. For Croatia and Greece gay sailing, go to the Pride Sailing Holidays Booking Page for prices.
Note: the referral discount will only apply if you sign up for information from Pride Sailing Holidays via the form near the top of this page.
When/Who Do We Pay?
To reserve your spot, you’ll need to pay an initial deposit. The final payment will be due a few weeks before the actual trip begins. No matter which company you end up choosing, be sure to read the refund and cancellation policy.
wolfyy takes no responsibility for policies enforced by partner gay sailing companies. Rest assured though, everything has always turned out fine! I’ve been booking with Pride Sailing for years.
Payment is made directly to the sailing company associated with the trip you are booking. wolfyy is not affiliated with your payment in any way. I am here to guide you through the booking process, put together a fun group and enjoy the trip!
Ready to Book A Gay Sailing Holiday?
If you’re interested in booking a trip, enter your email in this form at the top of this page. I’m looking forward to seeing you on the open seas!
For even more gay sailing itineraries in Southeast Asia and Europe, take a look at scheduled trips by Everything to Sea.
Get ready for your trip with some sexy swimsuits from these popular gay swimwear brands! Or browse these gay beach essentials.
Want more group trip ideas? Check out the latest offerings by these popular gay tour and vacation companies.