Special Events
Island Sail hosts special programs and regattas throughout the season to bring our community together on the water.
Discover Sailing!
Join us for an exciting introduction to the world of sailing. This program is for year-round Vinalhaven kids and is designed for beginners to get comfortable on the water and learn the basics of boat handling in a safe and supportive environment.
Date: Saturday, July 18
Time: 1:00–3:00 pm
Location: Island Sail, Skoog Park
Cost:Â FreeÂ
Give your youngest sailors a fun, gentle introduction to life on the water in our smallest boats, the Optis. With a focus on safety, confidence, and simple skills, kids will get to sit in, steer, and feel what it’s like to sail. A parent or caregiver should plan to stay on shore for the entire clinic to share the experience and help little sailors feel comfortable.
Date: Saturday, July 25Â
Time:Â 11:00 am-1:00 pm
Location:Â Island Sail, Skoog ParkÂ
Cost: $20 per child
Prefer Venmo? Pay @ISLAND-SAIL and note the event name.
Adult Group Sail & Lesson
Whether you’re new to sailing or already comfortable at the helm, join us for a relaxed Adult Group Sail & Lesson. Certified instructors will be on the water to offer coaching and short lessons for anyone who wants to build skills, while experienced sailors are welcome to simply enjoy time on the bay in our boats. Note that our boats are 420 sailboats, which are 13-foot, 9-inch sailing dinghies designed for 2 people. Â
Date: Tuesday, July 28
Time: Â 4:30-6:00 pm
Location:Â Island Sail, Skoog ParkÂ
Cost:Â $40 per person
Prefer Venmo? Pay @ISLAND-SAIL and note the event name.
The Dogtown Cup
Mary Lou and Joe Upton started the Dogtown Cup in 2007. This annual regatta for Island Sail's sailors will be held in Sands Cove this year. Stay tuned for additional details.Â
Date: Thursday, July 30
Time:Â 1:00-4:00 pm
Location:Â Island Sail, Skoog ParkÂ
The Gates Cup
The Gates Cup, named in honor of long-time Island Sail Commodore Karen Gates, is our annual regatta where we host sailors from North Haven's Casino for an afternoon of racing against Island Sail's sailors. Date and time will be added here soon. We look forward to seeing our sailors compete in this traditional event.
Date: Thursday, August 6
Time:Â 1:00-4:00 pm
Location:Â Island Sail, Skoog ParkÂ