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.
Daily Public Charters
Experience the best of sailing in Casco Bay with small-group public charters offered every day.
Private Group Charters
Cruise in style with friends and family with private boat charters in Portland, Maine.
Unique Sailing Experiences
Join us for unforgettable sailing tours featuring local Portland culture, cuisine, and community.
Trademark Chartered Trips
DAY AND SUNSET CHARTER CRUISES IN CASCO BAY
Every day we offer two-hour public or private charters where we can cruise past lighthouses, historic forts, and seals swimming in the harbor of Casco Bay. At Sail Portland Maine we offer intimate, crowd-free, professionally-captained and crewed excursions aboard our beautiful and well-maintained vessels. You can even BYOB!
Embark on a 2-hour Day or Sunset Sail in Casco Bay for up to 6 passengers, starting at $80 per person.
Take your group out in style on our classic motor yacht, accommodating up to 12 passengers at $85 per person.
Daily Casco Bay Sailing Schedule
Explore Casco Bay sailing with our flexible schedule, designed to fit perfectly into your plans. From May through August, 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!
The Eleanor Hawkes is a Friendship sloop, a beautiful traditional-style sailboat that glides effortlessly over the water. With space for up to 6 guests, this is the most private sail you can get in Portland shy of owning a boat!
Public and custom private charters available. You’re welcome to bring your own food and beverages aboard.
DAILY CASCO BAY SAILING SCHEDULE:
- 12:00 PM – 2:00 PM (Fall hours vary)
- 3:00 PM – 5:00 PM (Fall hours vary)
- 6:00 PM – 8:00 PM (Fall hours vary)
If you’re looking for a private cruise for a larger party, Calista Ann is the boat for you! This classic motor yacht, also sometimes referred to as a picnic boat or cocktail cruiser, has slightly more seating and space to move about.
The Calista Ann is available for both public and private charters. Guests are welcome to bring their own food and beverages to enjoy onboard.
DAILY CASCO BAY CHARTERS SCHEDULE:
- 12:00 PM – 2:00 PM (Fall hours vary)
- 3:00 PM – 5:00 PM (Fall hours vary)
- 6:00 PM – 8:00 PM (Fall hours vary)
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 limited series of pop-up dinners featuring guest chefs who craft a unique four-course gourmet meal aboard a sunset cruse with breathtaking views.
“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!
