Sailing adventures

Check Out Our Upcoming Sailing Opportunities!

Check back often for updates: on new opportunities to join our crew and experience the adventure of a lifetime.

Join our Crew List: for last-minute discounts and updates on available spots. Don’t miss out on a spontaneous sailing adventure!

Create your own opportunity: If you can’t find the right passage, Contact us directly to create the perfect opportunity for you.

Cruise Croatia : August 2025

Let us help you create fantastic memories cruising the stunning coastlines of Croatia and Montenegro this July and August. You select the time and location for the perfect sailing adventure. Whether you’re looking for hidden coves, charming coastal towns, or serene anchorages, this journey will be fully tailored to your desires.

Berths Available: 4

Date: Flexible

Magical Mystery Tour – Eastern Mediterranean  Sept – Nov 2026

Catch the Last of the Summer Warmth with Us

From September to November, sail with us as we revisit Montenegro, Discover Albania, Corfu and Greece, or maybe even return to Sicily, which we loved — Help us decide where to explore! Together, we’ll chase the final golden days of summer, discovering hidden coves, quiet anchorages, and welcoming coastal towns. You choose the time and destination that call to you, and we’ll shape the perfect sailing adventure to capture every moment of that lingering Mediterranean sunshine.

Berths Available: 4

Date: Flexible

Sailing Plans 2026 – PART A Greece, Malta, Tunisia

Sailing Plans 2026 – March to Mid July

From March to mid-July next year, we’ll be sailing together through Greece, Malta, and Tunisia. Expect crystal-clear waters, stunning anchorages, great food, and plenty of time to relax and explore. Whether you’re up for some adventure or just want to unwind in the Mediterranean sun, there’ll be something for everyone on this trip.

Berths Available: 4

Date: Flexible

Sailing Plans 2026 – PART B Tunisia, Sardinia. The Balaeric Islands, Tangier, The Canary Islands

Sailing Plans 2026 – September to Mid November 2026

This season, we’ve got three months to explore the vibrant coasts of Tunisia, sail to the beautiful island of Sardinia, make a quick trip to The Balearics Islands as we pass onto Tangier and down to the Canaries. We’ll experience a mix of Mediterranean culture, dramatic Atlantic island landscapes, and the thrill of bluewater sailing along the way. This journey isn’t for the inexperienced—unless you’re just island hopping. It’s the perfect chance to build sea miles, sharpen your skills, and dive into the cruising lifestyle before the big Atlantic crossing. Preference goes to crew who haven’t sailed with us before and are keen to continue on the Atlantic crossing.

Berths Available: 4

Date: Flexible

Sailing Plans 2026 – PART C Atlantic, Caribbean

Sailing Plans 2026 – Nov to December 2026🌊 Sail Across the Atlantic! 🌊🌊
Ready for a true bluewater adventure? We’re looking for enthusiastic, adventurous crew to join us on an epic passage from the Canary Islands — and then onward for a classic Atlantic crossing to St Lucia. In company with the ARC Rally 2026 TBC. Preference is given to those who have sailed with us before. Experienced sailors only. 

This is the stuff of sailors’ dreams: trade-wind sailing, breathtaking sunrises, night watches under a blanket of stars, and the pure satisfaction of making landfall after weeks at sea.

🗺️ The Plan:
➡️ Arrive Canaries 3 days prior to leaving
➡️ Refit & rest in the Canaries
➡️ Set off across the Atlantic — approximately 3 weeks at sea
➡️ On arrival in St Lucia, enjoy 3 nights on board to relax, explore, and celebrate

⏱️ Timing:
– Whole adventure is around 27 days total
– Atlantic crossing leg is about 17 – 21 days at sea, the last one I did was 19 on a smaller boat.
– Plus 3 nights on board in St Lucia once we arrive

🌟 Who’s this for?
– Keen sailors wanting serious sea miles
– Adventurers ready for watch rotations, cooking, and sharing the rhythms of ocean life
– Beginners welcome if you have a solid spirit of teamwork and willingness to learn

This is more than a sailing trip — it’s a commitment to an ocean passage, with a crew you’ll come to trust and rely on. You’ll gain confidence, skills, and unforgettable memories.

Interested? Drop me a message and let’s chat — there are only a couple of berths left!

⛵ See you on deck.

Berths Available: 4

Date: Nov 20 – Dec 20 approx

Get In Touch

If you are ready for adventure, teamwork, and unforgettable experiences on the sea, get in touch! Let us know a bit about your sailing background, interests, and availability — and let’s plan an incredible voyage together. We’d love to welcome you onboard.
Disclaimer: Osprey Sailing Adventures is a private sailing activity operated on a cost-sharing basis only. Participants share actual expenses and are active crew, not passengers. No commercial transport or passenger fares are offered.