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Official Tourism Site of Greater Portland Maine
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Home > Things To Do > Maine's Things To Do >

Sail Portland Maine

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Sail aboard the Eleanor Hawkes!

Our daily two hour public sails will have you cruising past lighthouses, historic forts, and seals swimming in our beautiful playground, Casco Bay. At Sail Portland Maine, we offer intimate, crowd-free, professionally captained sailing excursions aboard our vessel the Eleanor Hawkes.

We are confident you will enjoy your trip whether it be during the cool temps of a morning sail, an afternoon breeze, or the gorgeous sunsets over the city of Portland. We provide multiple trip options for you to enjoy your time on the water here in Portland.

Come sail with us!
Come sail aboard the Eleanor Hawkes a traditional friendship sloop and enjoy a cruise of a lifetime.

Click the Book button to reserve your tickets.

Sail Portland Maine EVENTS

Sunset Cruises and More

May 11–Oct 19
Fore Points Marina, Portland
The weekend of May 11th kicks off our season of sailing. Join us for a fantastic day on the water.

Fore River Brewing Co and Oyster Sails

Jul 4–Oct 3, Sep 26
Fore Points Marina, Portland
Fore River Brewing will be providing beers to go along with local Maine oysters.

Evening with Oysters and Rosé

Jul 6–Oct 12, Sep 21, Sep 28, Oct 5, Oct 12
Fore Points Marina, Portland
Come enjoy fresh oysters from the Shop and delicious rosé from The Cellar Door Winery, while watching the sunset.

Craft Beer and Oysters

Sep 1–30
Fore Points Marina, Portland
Join us and Fore River Brewing Co for freshly shucked oysters and cold beer!

September Day Sails

Sep 1–30
Fore Points Marina, Portland
Grab your favorite coffee and pastry and join us for mornings on the bay. Light winds and cool temps make this a peaceful start to your...

September Sunset Sails

Sep 1–30
Fore Points Marina, Portland
Join us mornings, afternoons, and evenings for a beautiful day on the water aboard our vessel the Eleanor Hawkes. September is the best...

October Foliage Sail

Oct 1–26
Fore Points Marina, Portland
Join us aboard the Eleanor Hawkes to see the changing leaves of the coast line. Fun sailing and beautiful scenery await you.

October Sunset Sails

Oct 1–26
Fore Points Marina, Portland
Join us while the weather is crisp for amazing sunsets on the bay!
Send Inquiry:
58 Fore St
Portland, Maine, 04101
(207) 200.6650
ABOUT US
  • We provide multiple trip options for you to enjoy your time on the water here in Portland, Maine.
  • You can choose from three different sailing times throughout the day: 10:30-12:30PM, 1:30-3:30PM, 6:00-8:00PM.
  • Join Sail Portland Maine every Saturday evening for our unique oyster and rosé sail. Allowing you to sample all that Maine has to offer while sailing and enjoying the magnificent sunsets on Casco Bay.
  • If you have a party of six, a family, or even just a couple who wants the opportunity to have the boat to themselves, a private charter is always an option, if available.
Sail aboard the Eleanor Hawkes!

Our daily two hour public sails will have you cruising past lighthouses, historic forts, and seals swimming in our beautiful playground, Casco Bay. At Sail Portland Maine, we offer intimate, crowd-free, professionally captained sailing excursions aboard our vessel the Eleanor Hawkes.

We are confident you will enjoy your trip whether it be during the cool temps of a morning sail, an afternoon breeze, or the gorgeous sunsets over the city of Portland. We provide multiple trip options for you to enjoy your time on the water here in Portland.

Come sail with us!
Come sail aboard the Eleanor Hawkes a traditional friendship sloop and enjoy a cruise of a lifetime.

Click the Book button to reserve your tickets.


Sail Portland Maine EVENTS

Sunset Cruises and More

May 11–Oct 19
Fore Points Marina, Portland
The weekend of May 11th kicks off our season of sailing. Join us for a fantastic day on the water.

Fore River Brewing Co and Oyster Sails

Jul 4–Oct 3, Sep 26
Fore Points Marina, Portland
Fore River Brewing will be providing beers to go along with local Maine oysters.

Evening with Oysters and Rosé

Jul 6–Oct 12, Sep 21, Sep 28, Oct 5, Oct 12
Fore Points Marina, Portland
Come enjoy fresh oysters from the Shop and delicious rosé from The Cellar Door Winery, while watching the sunset.

Craft Beer and Oysters

Sep 1–30
Fore Points Marina, Portland
Join us and Fore River Brewing Co for freshly shucked oysters and cold beer!

September Day Sails

Sep 1–30
Fore Points Marina, Portland
Grab your favorite coffee and pastry and join us for mornings on the bay. Light winds and cool temps make this a peaceful start to your...

September Sunset Sails

Sep 1–30
Fore Points Marina, Portland
Join us mornings, afternoons, and evenings for a beautiful day on the water aboard our vessel the Eleanor Hawkes. September is the best...

October Foliage Sail

Oct 1–26
Fore Points Marina, Portland
Join us aboard the Eleanor Hawkes to see the changing leaves of the coast line. Fun sailing and beautiful scenery await you.

October Sunset Sails

Oct 1–26
Fore Points Marina, Portland
Join us while the weather is crisp for amazing sunsets on the bay!
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