Best results for
Sailing in Brunswick, ME
Showing 1-11 of 11 results
Portland Harbor 2-Hour Sailing Cruise
Sail Portland Harbor with your own snacks and drinks
Schooner Sail Past Burnt Island Light in Boothbay Harbor
Help sail Boothbay Harbor’s oldest windjammer
Portland Sunset Sailing Cruise
Sail Portland Harbor at golden hour with room for your favorite snacks and drinks
Classic Schooner Sail in Boothbay Harbor
Take in Maine’s rugged coastline with open views from every seat
Sunset Schooner Sail in Boothbay Harbor
Take in Maine's rugged coast with 360-degree views from your seat
Wednesday Night Sunset Cruise With Live Music
Sail Casco Bay at sunset with live music and a BYOB vibe
4.9 • 160 reviews
Sail Boothbay Harbor on a 1.5-Hour Guided Cruise
Sail Boothbay Harbor aboard the Friendship Sloop Bay Lady on a 1.5-hour trip
4.7 • 190 reviews
Sailing Charter on Casco Bay Aboard 36' Sailboat
Enjoy a private sail aboard Endurance with views of Casco Bay’s islands and lighthouses
Boothbay Harbor Sunset Schooner Sail Past Burnt Island Light
Take in Maine's rocky coast with 360-degree views from your seat
2-6 Hour Sailing Cruise in South Portland
Celebrate or unwind aboard Endurance on a custom sail
Sunset Sailing Cruise in Casco Bay
Sail Casco Bay at sunset past islands, lighthouses, and local wildlife