Gay Sailing Holidays
Learn about our gay sailing holidays: what it’s like, who’s coming & how to book.
Dates now available for 2023.
Gay Sailing Trips in Croatia, Greece & Italy
We’re gearing up for another fantastic season of gay sailing trips. Join me this coming summer in Croatia, Greece, or Italy! wolfyy has all the essential details to plan your trip below. Space is now available to book for 2023.
Gay sailing holidays are a lovely way to explore new areas of the world with a fun group of guys. The vacations are carefree, adventurous, and inclusive of all types of people.
Pride Sailing Holidays has gay sailing availabilities from June through September in Croatia, Greece and Italy. Standard trips are seven days, include 8 guests (plus captain and host), include breakfast/lunch, and are packed with fun activity options.
You can join one of my personal boats, join another group that has a vacant spot, 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. I partner with Pride Sailing Holidays, the global leader in gay sailing holidays.
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.
Stay Up to Date by
Completing this Form!
Get a Discounted
Now, let’s dive into some details. I 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.
If you have any other questions after reading this page? Send me an email directly. I’d be happy to help you out. Now, check out this epic Pride Sailing montage from one of our 2019 trips!
Joining Gay Sailing Holidays with wolfyy
I partner with Pride Sailing Holidays, one of my favorite gay tour and vacation companies, hosting my own personal boat trips as well as helping interested guys book their own reservations joining pre-scheduled trips or chartering their own private boat.
Pride Sailing primarily operates Croatia gay sailing trips and Greece gay sailing trips. Custom routes are also available, though. I can give you details about special sailing trips in Italy as well as Turkey.
Most guys book single spots, joining a boat with other single guys. Couples or pairs of friends also book cabins of their own. All boats hold 8 guests, plus the captain and a host. There are four guest cabins, each shared by two people.
Most guys book a single spot just for themselves. Some individuals who want extra privacy book two spaces in order to have an entire cabin to themselves. And remember that it’s also possible to privately book a boat with your own group of friends!
Next, I’ll tell you all about what the gay sailing experience is like, so you know exactly what to expect. After, I’ll go over the granular details of boats, meals, and other specifics in the frequently asked questions section.
Everything below is based on my experiences sailing in the Mediterranean with Pride Sailing Holidays. If you’re looking for gay sailing holidays in other parts of the world though, I’d suggest checking out Southeast Asia gay sailing trips with Everything to Sea.
A Typical Week Gay Sailing
Whether you’re gay sailing the Croatian Islands or the Greek Islands, there will be plenty of activities, new sights, fun guys, and delicious food.
Daytime Gay Sailing Activities
Each morning we have breakfast and immediately set will sail for a couple of hours. Everyone enjoys the open sea and luxurious yacht sun deck and lounge area. In the afternoon, we drop anchor and have some time for swimming, lunch, and relaxation on the bow of the boat.
Some days there will be 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. Most of the time, Pride Sailing is operating several trips in tandem, so there may be another group or two of 8 more guys to meet.
Depending on the location/island, there may be nearby bars, clubs, or parties to visit. In Korčula, Croatia there is an epic foam party. Dubrovnik has a huge nightclub with top DJ performances.
Depending on the itinerary (which I’ll explain later in this article), 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 acts in a respectful manner. 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 meet amazing islands. 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 gay sailing! 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.
Gay Sailing Cruises: What Are the Guys Like?
It may seem intimidating to join a gay sailing cruise at first. Sometimes guys are skeptical about booking group gay trips. Rest assured though, I wouldn’t compare gay sailing holidays with anything like an Atlantis Cruise. Things are tamer, more personal, and filled with much more authentic exploration and culture.
In my experience, everyone who books these gay sailing holidays 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 that 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 the gay sailing holidays start on a Saturday. Keep in mind that for some trips, these itineraries will be in reverse depending on which origin-destination you choose. Here are the gay sailing itineraries for Croatia and Greece.
Croatia Gay Sailing Itinerary: Split to Dubrovnik
Sunday: Sail toward Vinogradse Bay, stop for a swim, 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 best sexy gay swimwear!
Thursday: Short sail to another town on the island of Mljet called Okuklje. One of the smallest Croatian towns, 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
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.
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.
Thursday: Visit Epidavros, the largest, and oldest Greek Amphitheatre. Good day for hiking and exploring the ruins.
Friday: Sail 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: Sicily
Pride Sailing’s newest itinerary is their Sicily gay sailing route. In 2023, you can bet I’ll be here, exploring southern Italy on a glorious catamaran! (Reserve your spot below!)
To join this year, or even in future years, add your name to the signup form on this page.
Past Croatia & Greece Gay Sailing Trips
If you’d like to check out some Instagram stories of my 2021 Greece trips or my 2019 Croatia trip, head to my @laffaloui Instagram profile and look for the first Instagram story highlight circle below the bio.
On my page, you’ll get a play-by-play of the entire week of island hopping and jumping off beautiful sailboats. I can’t wait to enjoy it all over again!
Reserve Your Spot for 2023
Don’t miss out on an epic gay sailing adventure. Sign up for more info below, then check available dates, coordinate your work schedule and vacation time.
Make it happen! You’ll have an unforgettable experience.
Booking Croatia, Greece, or Italy Gay Sailing
Sign up for information about Pride Sailing Holidays trips using the form below.
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.
Stay Up to Date by
Completing this Form!
Get a Discounted
Flexible Booking & Transferable Deposits
While the worst of the COVID-19 pandemic is behind us, Pride Sailing still 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 rare case that Pride Sailing needs to cancel your trip, a full refund will be credited to you.
So what are you waiting for? Use the form above to sign up and get started!
Gay Sailing FAQ’s
We’ve covered the basics, so now I’ll answer common questions about smaller details that I get from many guys thinking about joining.
What is The Boat Like?
Croatia gay sailing trips will use the Beneteau Oceanis 48 yacht. The boat sleeps 10 people. There are four double beds for 8 guests and two bunk beds for the Capitan and host.
There are three bathrooms on the boat, all equipped with a shower and space to store toiletries. Many island locations offer free shower facilities on land near the port.
Greece gay sailing holidays are on a Lagoon 42 catamaran. This boat is incredibly luxurious, way more spacious, and always exceeds everyone’s expectations.
The Lagoon 42 has four cabins on board, each with its own bathroom. Two cabins are master suites, with walk-in showers. Crew sleep in separate top-entry cabins at the front of the boat.
All the boats used for the gay sailing holidays 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, space doesn’t feel tight at all! Trust me, I’ve been there. If anything, it’s more fun because its always friends to hang out with.
Should I Buy Travel Insurance?
Travelers are strongly recommended to obtain a CFAR travel insurance policy, which is short for “cancel for any reason” to guarantee that your hard-earned trip is safe from unforeseen situations like flight cancellations, Covid-19 complications, or any other of the long list of potential reasons.
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 gay sailing trips on Lagoon catamarans will have air conditioning (both the Athens and Ionian routes), while Croatia gay sailing adventures 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 on this page.
When/Who Do We Pay?
To reserve your spot on any gay sailing trip, you must pay an initial deposit. The final payment will be due a few weeks before the trip begins. Be sure to read each company’s 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 going on these adventures 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, procure a good group and have fun with you on the holiday!
Ready to Book A Gay Sailing Holiday?
If you’re interested in booking a gay sailing holiday to Greece, Italy, or Croatia, enter your email in this form at the top of this page. I’m looking forward to seeing you on the open seas!
For gay sailing holidays in Southeast Asia, take a look at scheduled trips in Indonesia by Everything to Sea.
Pride Sailing also organizes private charters for gay sailing in Thailand, one of their all-new options.
Get ready for your trip with some sexy swimsuits from these popular gay swimwear brands! Or browse these gay beach essentials.