What we’re about
Building A Community of Sailors!
Boston Sailing Meetup/spiritSAIL is a community-driven sailing adventure group designed for those who don’t want to wait for their friends to finally say "yes" to travel. Whether you're a solo traveler, couple, or group of friends, all are welcome—our trips are typically made up of 90% solo travelers.
What sets spiritSAIL apart is its focus on fun, collaboration, and learning. Each sail/trip is a shared experience where everyone gets involved, whether it’s steering the boat, trimming the sails, or cooking meals together. There's no hired chef or crew—instead, we work as a team, helping each other develop practical sailing skills and enjoying the camaraderie of like-minded travelers.
Our past adventures have taken us to stunning destinations like the British Virgin Islands, Barcelona, Grenada, and through exciting offshore voyages in the Caribbean. spiritSAIL isn’t just about reaching a destination—it’s about the journey, the friendships formed along the way, and the shared sense of accomplishment.
Join us for social events and daysails on Boston Harbor in the spring, summer, and fall - and the Caribbean in winter when it gets cold up here in Boston!
Led by Greg Allen, a certified American Sailing Instructor and volunteer group leader, each voyage combines the thrill of sailing with a flexible, community-centered approach. Greg is not your captain for hire; instead, he is a volunteer who shares his knowledge and experience while guiding the crew in a hands-on, supportive environment. Everyone participates in decisions about the itinerary, land excursions, meals, and boat duties, ensuring every traveler has a voice in shaping the adventure.
So, whether you’re new to sailing or a seasoned sailor, spiritSAIL offers a unique, collaborative travel experience where adventure and learning go hand in hand. Come aboard, meet fellow solo travelers, and sail into your next great adventure together!
For more information contact Greg Allen, Organizer, at gregallen.sail14@gmail.com.