Sailing

Luxury Sailing in Portland , Maine


Luxury Portland Attractions
Portland

Portland Head Light

12 Captain Strout Circle, Cape Elizabeth

β˜…β˜…β˜…β˜…β˜†4.8 (5,471)
Portland

Casco Bay

Portland

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Portland

Fort Gorges

Hog Island Ledge, Portland

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Luxury Portland Tours
2 Hours Sunset Private Charter on Heart's Desire in Casco Bay Free Cancellation
Portland

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yac…

πŸ• 2 hours β˜…β˜…β˜…β˜…β˜…5.0 (2)
2 Hour Private Morning Charter on Heart's Desire in Casco Bay Free Cancellation
Portland

2 Hour Private Morning Charter on Heart's Desire in Casco Bay

Come sailing aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desir…

πŸ• 2 hours
Private Half Day Sailing Charter in Portland Maine Free Cancellation
Portland

Private Half Day Sailing Charter in Portland Maine

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, wi…

πŸ• 4 hours β˜…β˜…β˜…β˜…β˜…5.0 (1)
Casco Bay Sailing Escape Half day Custom Boat Charter Free Cancellation
Portland

Casco Bay Sailing Escape Half day Custom Boat Charter

Each trip is tailored to your group and the wind conditions that day, but a frequently requested, guest favorite sailing route begins in downtown Portland before heading out into Casco Bay. From there, we'll pass Portlan…

πŸ• 4 hours
Portland Tall Ship Cruise on Casco Bay Free Cancellation
Portland

Portland Tall Ship Cruise on Casco Bay

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.…

πŸ• 2 hours β˜…β˜…β˜…β˜…β˜†4.6 (236)
Sunset Windjammer Cruise Along the Coast of Portland Maine Free Cancellation
Portland

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a narrate…

πŸ• 2 hours β˜…β˜…β˜…β˜…β˜†4.8 (144)
Afternoon Windjammer Cruise Along the Coast of Portland Maine Free Cancellation
Portland

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine β€” the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrat…

πŸ• 2 hours β˜…β˜…β˜…β˜…β˜†4.6 (186)
Casco Bay Morning Windjammer Sail Free Cancellation
Portland

Casco Bay Morning Windjammer Sail

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This…

πŸ• 2 hours β˜…β˜…β˜…β˜…β˜†5.0 (21)