Sailing in Westbrook, ME

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

Sail Portland Harbor with your own snacks and drinks

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

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

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

Sail the Saco River and Maine coast on your own private boat

Sail the Saco River and Saco Bay in a small group

Sail Saco Bay with island, river, and coastal route options

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

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

Sail into the evening with a small-group sunset cruise

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

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

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

Celebrate or unwind aboard Endurance on a custom sail

Sail for 4 hours at sunset with room to spread out

Sail Kennebunkport with options to relax or take the helm

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

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

Sail into the evening light along Kennebunkport’s rocky coast

Sail Saco Bay and tour Wood Island Lighthouse from tower to Keeper's House

A private evening sail with ocean sunset views

Build sailing confidence with a lesson tailored to your experience and goals

More time to explore the Saco Bay coastline by private sailboat