Gay Sailing Holidays
Learn about our gay sailing holidays: what it’s like, who’s coming & how to book.
Summer 2021 dates are now available!
Gay Sailing Trips: Croatia, Greece & Italy
We’re gearing up for another fantastic gay sailing season. Join me this coming summer in Croatia, Greece or Italy! wolfyy has all the essential details to plan your trip below. Space is available for summer 2021!
Gay sailing trips 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 and Greece. Trips are seven days, 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 many 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!
Gay Sailing Holidays: Croatia, Greece & Italy
wolfyy will be hosting various gay sailing holidays this coming summer 2021. You can join me for Croatia gay sailing trips and Greece gay sailing trips. I can also give you details to book a spot for Italy gay sailing trips.
I partner with two gay sailing companies. For Croatia and Greece, I work with Pride Sailing Holidays, hosting my own personal boat trips as well as helping interested guys book their own reservation if they are looking for a private group trip. I also work with Italy Gay Sailing to put together a fun group of guys to sail the wonderful island of Sardinia, Italy.
Most guys book single spots, joining a boat with other single guys. Many couples or pairs of friends also book, sharing a cabin. If you like, you can join one of my boats, and I’ll meet you when we start our trip! All boats hold 8 people, plus the captain and host. All boats have four cabins, each shared by two people.
As I mentioned earlier, most guys book a single spot just for themselves. And again, if you want to privately book a boat with your own group of friends, that option is certainly available. Some individuals pay for an entire cabin for themselves for extra privacy, so keep in mind this is another possibility.
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.
Gay Sailing: A Typical Week
Whether you’re gay sailing the Croatian Islands, the Greek Islands or the majestic island of Sardinia, there will always be plenty of activities, new sights, fun guys and delicious food.
Gay Sailing Daytime Activities
Each morning we have breakfast and immediately set will sail for a couple hours while enjoying 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, however nothing is ever mandatory and you are totally free to remain relaxing on the boat or head off for some alone time if you need it. Some afternoons, local excursion bookings will be available like group cave tours or wine tastings.
Toward mid afternoon, we will arrive to 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 down time before any evening activities. Some groups will plan to go bike riding, hang on a local beach or just walk around taking in pretty 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’s plenty of opportunity 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. The island of Sardinia, has relaxed, beachfront gay bars! 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 holiday, 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 2021 gay sailing! Next I’ll discuss the guys who typically book these trips so you have comfortability 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, 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 Itinerary: Split to Dubrovnik
Sunday: Sail toward to Vinogradse Bay, stop for a swim, cocktails in Vinogradse Bar, then grab water taxi’s to the party island of Hvar.
Monday: Sail to Vis, free time to explore the island, enjoy a 5-star local dinner with local wine. Walk the beautiful promenade taking in the local architecture.
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.
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 Itinerary #1: Ionian Route
Saturday: Check in, meet & greet & a wonderful evening on Spartochori, Meganissi
Sunday: Vathy, Ithaka: Morning swim at the Blue Caves (Lefkada), then a luxurious afternoon at Tilemachos Beach. Remainder of evening spent 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: Fishkardo, Kefalonia: Relax on white-sand beaches, then anchor in a protected bay for the evening. Visit the town of Fishkardo for dinner and evening cocktails.
Wednesday: Sivota, Lefkada: Stop at famous Porto Katsiki beach for lunch, the sailing to the traditional town Sivota for the evening.
Thursday: Kalamos: After several beach stops, we spend the evening in Kalamos.
Friday: Lefkada: 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 Itinerary #2: Athens / Sarnoic 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
Last Summer’s Croatia Gay Sailing Trip
If you’d like to check out some Instagram stories of last year’s 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 from Dubrovnik to Split. It was a blast and I’m so excited to get more guys booked so we can enjoy it all over again!
Reserve Your Spot for 2021 (Flexible Booking Now Available)
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.
As of later November 2021, Pride Sailing offers a bunch of new perks that make booking gay sailing holidays during COVID much easier. See more details below.
Booking Croatia & Greece 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 the future.
Stay Up to Date by
Completing this Form!
Get a Discounted
Flexible Booking & Risk-Free Deposits
Considering the uncertainty surrounding COVID-19 and international travel, Pride Sailing now allows you to change your cabin charter date up to 60 days before your departure date, and up to 7 days before the trip if there are COVID restrictions like border closures or travel bans.
With any travel bans you can get a credit for the following season or transfer your trip to another person.
Pride Sailing also only requires a small deposit of 500 Euro and allows cancellation for any reason 7 days after booking. Deposits are now risk-free, meaning if you cancel your trip due to COVID, you can apply your deposit toward a trip next year. So, use the form above to sign up and get started!
Booking Sardinia Gay Sailing
If you’re interested in sailing around wonderful Sardinia, check out the Italy Gay Sailing Website and inquire there for more information. They are a smaller operator, but have lots of local knowledge about the best coves and beaches in Sardinia, the Mediterranean island famous for crystal clear waters. Note any COVID-19 provisions or cancellations.
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 holidays will use the Benteau 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.
The Greece gay sailing holidays will use a Lagoon 42 french-built catamaran. This is a luxurious and even more spacious boat. The Lagoon 42 also sleeps 10 people in the same fashion. It has four bathrooms on board, so every cabin has their own. All the relaxing space is on the upper level 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 10 people aboard, space doesn’t feel tight. Trust me, I’ve been there! If anything, it’s more fun because its always friends 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 tailor 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. Remember that depending on the trip, you may need to book two separate flight legs. For instance, a sailing trip may begin in Dubrovnik and finish in Split.
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. Each night, we dock in a marina with a bunch of other sailors. We usually arrive in the destination port between early afternoon and early evening, depending on the route.
In most locations, there will be convenience stores, pharmacies and other essential establishments, should you need anything.
Some sailboats have air conditioning and others do not, depending on the trip. Greece gay sailing trips will have air conditioning, while Croatia and Italy gay sailing will not.
Even in the middle of summer, it is not too hot when you’re out at sea. 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 holiday companies. Rest assured though, everything has always turned out fine!
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 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!