Boat Charters in Portland, Maine
Embark on exceptional sailing adventures with Sail Portland Maine. Our charters offer stunning views, local culture, and customizable experiences that will stay with you for a lifetime. Join us for a memorable journey where every sail is an opportunity to explore the breathtaking Maine coastline.
Experience Portland, Maine Like Never Before
Treat yourself to the best Portland, Maine boat tours with Sail Portland Maine. Our charters offer a unique blend of breathtaking views, local culture and cuisine, and unique purpose-driven experiences that enhance our community and environment. Join us for a memorable journey as we enjoy the sights and sounds of our lovely Casco Bay and the Portland skyline and waterfront.
Trademark Chartered Trips
DAY AND SUNSET CHARTER CRUISES IN CASCO BAY
Every day we offer two-hour or more custom private charters where we can cruise past lighthouses, historic forts, and seals swimming in the harbor of Casco Bay. Longer trips we can stop for a swim or take you to an island restaurant for a fun unique experience. At Sail Portland Maine we offer intimate, crowd-free, professionally-captained and crewed excursions aboard our beautiful and well-maintained vessel. You can even BYOB!
Take your group out in style on our classic motor yacht, accommodating up to 12 passengers.
Daily Casco Bay Sailing Schedule
Explore Casco Bay sailing with our flexible schedule, designed to fit perfectly into your plans. From May through October, we offer multiple Portland, Maine boat tours daily.
Due to rising costs and labor shortages, we will not be offering sails on the Eleanor Hawkes this season. However, we invite you to experience the beauty of Casco Bay aboard our other vessel, Calista Ann, which is available for private charters. Book your adventure today and enjoy an unforgettable time on the water!
One-of-a-Kind Boat Tours in Maine
Discover unique experiences with Sail Portland Maine, where each tour offers something special. From purpose-driven journeys that positively impact our community to excursions that explore local culture and cuisine with Portland's finest, our unique tours are crafted to enrich and inspire.
Join us for a heartwarming sunset sail around Casco Bay with an adoptable dog and other animal-lovers. Have a great time while supporting a great cause!
20% of ticket sales directly support the Animal Refuge League of Greater Portland.
Crown Jewel Flappy Hour
Cruise with us to Great Diamond Island for brunch or happy hour at the popular Crown Jewel, featuring complimentary onboard rosé and spectacular ocean views.
Local Chef Culinary Events
Join us for a unique four-course gourmet meal aboard a sunset cruse with breathtaking views. Private charter only up to 10 guests.
“We had a blast on our morning sail! The weather was perfect along with the beer and mimosas we brought with us. Ian was an excellent captain and showed us all a great time on his beautiful sailboat. I highly recommend sailing with Sail Portland Maine.”
CODY HENDERSON
Why Sail Portland Maine?
Stories From the Sea
Browse our latest blog posts for insider tips, stories, and ideas for making the most of your time in Portland, Maine.
Book Your Sailing Tour in Portland, Maine
Come enjoy a trip of a lifetime on the most unique Portland, Maine boat tours in town. Book your charter with Sail Portland Maine today!
End-of-Season SALE