Sailing in Kennebunkport, ME

Enjoy a private sail aboard Endurance with views of Casco Bay’s islands and lighthouses

Celebrate or unwind aboard Endurance on a custom sail

Sail Casco Bay at sunset past islands, lighthouses, and local wildlife

Sail Kennebunkport at midday with a local captain, public or private

Sail Casco Bay at sunset with live music and a BYOB vibe

Sail longer and see more of Saco Bay on a half-day trip

Sail Portland Harbor with your own snacks and drinks

Lounge on deck or lend a hand with the sails

Make a private sailboat the setting for your wedding

Tailored one-on-one instruction for first sails, returning sailors, and J/22 certification prep

Sail into the evening with a small-group sunset cruise

Sail Portland Harbor at golden hour with room for your favorite snacks and drinks

Sip wine on a 90-minute Kennebunkport sail with a sommelier-led tasting

Sail Maine's coast with the option to anchor for a swim

Sail to Wood Island and tour inside the lighthouse and keeper’s house

Sail Kennebunkport with options to relax or take the helm

Sail into the evening light along Kennebunkport’s rocky coast

Sail Maine’s coast in a small group of 6 or fewer

Let the wind shape your journey along Maine's coast

Reserve the boat for an intimate Maine coast sail with your own group

Create a personal farewell at sea with a private boat and crew

Share a private sail with your own group

Sail for 4 hours at sunset with room to spread out

Build confidence on the water with a lesson shaped around your goals