2026 Adventure Sailing Itinerary
2026 Expeditions
Our 2026 adventure sailing schedule kicks off with our Caribbean cruiser voyages, offering an idyllic escape where we can explore a vibrant mix of islands, turquoise waters, and powdery beaches, all while enjoying the sanctuary and adventure of life at sea.
Sailing in St. Lucia is a truly unforgettable experience, offering stunning views of its lush landscapes, crystal-clear waters, and dramatic coastlines. The island is famous for its picturesque Pitons—two volcanic spires that rise dramatically from the sea, making for an awe-inspiring backdrop as you cruise along the coastline. Next up, we’ll be heading north to Antigua, a remarkable journey that takes us through the heart of the Eastern Caribbean, showcasing some of the region’s most picturesque landscapes and vibrant islands. We’ll pass by the beautiful islands of Martinique and Guadeloupe before arriving in Antigua, where we are welcomed by its renowned 365 beaches, charming harbors, and rich maritime history, making the journey not just a sail, but an unforgettable adventure.
We’re in the process of finalizing the rest of our 2026 schedule and will be updating in the near future. But we can tell you it’s going to be a good one. So check your emails for updates!
Our Crew
In the 2025 adventure sailing season, we’ll have an all-star roster of folks we have worked with before, that we trust. We’ll list them on each trip page so you know who you’ll sail with.
Sea Dragon
Sea Dragon is an extremely tough 72ft steel yacht that has circumnavigated the world twice. That’s going upwind – or in sailing terms “the wrong direction”! She is designed to keep amateur crew safe in the roughest of conditions for months at a time, and is a great platform to learn on. While no boat is truly comfortable going upwind, Sea Dragon was built for it. She’s the most comfortable boat going to windward in a gale that we’ve ever been aboard. The adventure sailing era suits her well.
The Experience
Sea Dragon is a working expedition vessel. We aim to enable everyone on board to fully participate in all aspects of our voyages. From helming to sail changes, swimming to socializing, cooking and cleaning. We provide a hands-on and immersive environment for learning, adventure, and connecting with your fellow voyagers. Our cuisine is delicious and hearty vegetarian food, and we’re excited to share recipes with you. When we’re at sea, we eat lunch and dinner as a group. This means we can all connect, sharing our stories and plans for the day. Breakfast is an individual affair, powered by freshly ground coffee or loose-leaf tea.
Each crew member gets their own bunk (they may be simple but are extremely comfortable) and storage cubby in a shared cabin. While adventure sailing, we expect everyone to stand watch for 3 hours out of every 9, then have 6 hours of free time. You can sleep, read, chat, or just watch the ocean. On anchor or in port, things vary depending on where we are, but we can always guarantee some adventure. We provide opportunities to snorkel, hike, or explore ashore around scheduled meals throughout each trip on the 2026 adventure sailing itinerary.
