Pride Sailing Holidays

26/10/2026

From sharing morning coffee in the galley to late-night laughter around the saloon table, these quiet spaces are where the real connection happens⚓️

26/10/2026

Nothing beats golden hour on the water! 🍷🌅

As the afternoon breeze cools and our skipper drops anchor in a quiet bay, it is time for one of our absolute favorite traditions at sea: the onboard aperitivo.

Gather in the cockpit of our Lagoon 42 or Oceanis 48, open a chilled bottle, and enjoy delicious local snacks prepped right on board.

Plus, with our no-corkage BYO drink policy, you can bring your favorite wines or spirits on board to enjoy as the sun dips below the horizon.

📖 Read our full blog post.

Experience the magic of golden hour at sea with our guide to the onboard aperitivo. Discover how simple drinks, local snacks, and quiet anchorages in Greece, Croatia, Italy, and Thailand create the ultimate late-afternoon ritual on your yacht charter. Read the full post to start planning your sunset...

23/10/2026

The 4 acts of a perfect day at sea:
Act I: Tropical fruit & pancake feast on deck.
Act II: Plunging into a hidden cove with no name.
Act III: Island lunch overlooking the bay with the crew.
Act IV: Midnight strolls through historic stone alleys.
This isn't a dream itinerary - this is just a regular Tuesday on a Pride Sailing trip⛵️✨

23/10/2026

Ever wondered what it’s really like to work in paradise? ⛵🌊

From morning weather checks in quiet harbors to navigating hidden coves and recommending the best local tavernas, a day in the life of a Pride Sailing Holidays skipper is equal parts expert seamanship, safety, and pure passion for life on the water!

Whether you are curious about what it takes to turn sailing into a career or simply want to kick back while an experienced crew guides your island-hopping adventure, step behind the helm with us!

📖 Read the full behind-the-scenes blog post.

Ever wondered what it is really like to work as a yacht skipper in paradise? Step behind the helm with Med Sailing Holidays to explore a day in the life of a skipper—from morning weather checks and secret swim stops to sunset mooring in historic ports across Greece, Croatia, Italy, and Thailand. D...

21/10/2026

"Did the pride sailing trip from Dubrovnik to Split. Met great people on this trip..." James came as a solo traveler and left with an incredible family. Ready for your turn?

19/10/2026

So… what actually happens on a clothing-optional gay sailing trip in Croatia? 👀⛵️🇭🇷

Yes, the clothes can come off. 😏 But @‌PrideSailingHolidays is about a lot more than tanning in your birthday suit.

Think a week sailing the Croatian coast with other gay travelers, swimming straight off the boat, discovering hidden coves and gorgeous islands, exploring seaside towns, group dinners, nights out and plenty of time to actually get to know everyone onboard. 🌊☀️🍹

Pride Sailing Holidays is back in Croatia for 2027, with individual cabins and private charters available.

Would you try a clothing-optional sailing trip? 👀

19/10/2026

We started the afternoon covered in Adriatic salt, spent the golden hour debating the notes of indigenous Croatian grapes, and ended the night with a white-clad runway🌊🍷✨

19/10/2026

When planning a sailing holiday, unexpected add-ons like port fees, fuel surcharges, and surprise departure taxes can be a stressful surprise. At Med Sailing Holidays, we believe in complete financial transparency so you can focus entirely on unwinding.

📖 Read our complete pricing breakdown on the blog.

Wondering what a yacht charter actually costs? Our latest blog breaks down everything included in your trip price from professional crew and daily meals to marina fees, one-way charges, and unlimited WiFi. Discover how transparent pricing with zero hidden fees makes planning your sailing holiday in....

16/10/2026

Are you currently sitting under fluorescent office lights, or are you ready to ditch the trousers and plunge into the Adriatic? (Be honest in the comments!) ☀️🩳

16/10/2026

Packing for a sailing charter is a bit different than preparing for a standard hotel trip. From teak decks to pebble beaches, getting your footwear right keeps you comfortable and keeps the boat in top shape!

Our latest blog guide breaks down everything you need to know:

👣 Barefoot Etiquette on Deck: Why going barefoot is standard and how non-marking soles protect the boat

👟 Onboard Shoes: How to choose dedicated, light-soled boat shoes if you need arch support

🩴 Shore Sandals: Sturdy footwear for exploring cobblestone harbor towns and ancient viewpoints

🌊 Water Shoes: Lightweight slip-ons for pebble beaches and snorkeling stops in Greece, Croatia, Italy, and Thailand

Leave your street shoes at the dock and step aboard with confidence!

Click the link to read our complete yacht footwear guide.

Wondering what shoes to pack for your yacht vacation? Our ultimate footwear guide breaks down onboard barefoot etiquette, why non-marking boat shoes matter, and what sandals to wear when exploring coastal towns across Greece, Croatia, Italy, and Thailand. Learn how to protect teak decks while keepin...