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Top 10 Best Maine Sailing Trips

Found 11 Sailing Trips activities in Maine. Sort by Popularity.
 

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

(4 of 386 reviews)

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical points of interest. View wildlife including eagles, seals and porpoises.... More

Free Cancellation
Start From $70.00
 
2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

  • Maine
  • Very Good386 reviews4

Enjoy a leisurely sail on Frenchman Bay that includes narration about historical and geographical po....

    Free Cancellation
    Start From $70.00
 
 

Windjammer Classic Sunset Sail from Camden, Maine

(4.9 of 331 reviews)

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship is limited to 49 passengers for an intimate sailing experience. She is a modern windjammer with luxurious accommodations and plent... More

Free Cancellation
Start From $64.95
 
Windjammer Classic Sunset Sail from Camden, Maine

Windjammer Classic Sunset Sail from Camden, Maine

  • Maine
  • Superb331 reviews4.9

Maine sunsets are best appreciated from the water aboard the romantic Appledore II! This tall ship ....

    Free Cancellation
    Start From $64.95
 
 

Portland Tall Ship Cruise on Casco Bay

(4.5 of 222 reviews)

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.... More

Free Cancellation
Start From $95.41
 
Portland Tall Ship Cruise on Casco Bay

Portland Tall Ship Cruise on Casco Bay

  • Maine
  • Exellent222 reviews4.5

What better way to see the delights of Portland than from the sea in one of the famous schooner tall....

    Free Cancellation
    Start From $95.41
 
 

Windjammer Classic Day Sail from Camden, Maine

(4.7 of 334 reviews)

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More

Free Cancellation
Start From $59.95
 
Windjammer Classic Day Sail from Camden, Maine

Windjammer Classic Day Sail from Camden, Maine

  • Maine
  • Superb334 reviews4.7

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....

    Free Cancellation
    Start From $59.95
 
 

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

(4.6 of 71 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Start From $54.95
 
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

  • Maine
  • Superb71 reviews4.6

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Start From $54.95
 
 

Schooner Eastwind Sunset Sail to see the Maine Coastline

(4.5 of 33 reviews)

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goa... More

Free Cancellation
Start From $54.95
 
Schooner Eastwind Sunset Sail to see the Maine Coastline

Schooner Eastwind Sunset Sail to see the Maine Coastline

  • Maine
  • Exellent33 reviews4.5

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the....

    Free Cancellation
    Start From $54.95
 
 

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

(4.9 of 19 reviews)

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we... More

Free Cancellation
Start From $54.95
 
Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

  • Maine
  • Superb19 reviews4.9

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Start From $54.95
 
 

Schooner Apple Jack 2-Hour Day Sail from Boothbay Harbor

(4.3 of 20 reviews)

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a c... More

Free Cancellation
Start From $54.95
 
Schooner Apple Jack 2-Hour Day Sail from Boothbay Harbor

Schooner Apple Jack 2-Hour Day Sail from Boothbay Harbor

  • Maine
  • Exellent20 reviews4.3

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Scho....

    Free Cancellation
    Start From $54.95
 
 

Portland Tall Ship Private Charter on Casco Bay

(4.3 of 20 reviews)

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands. ... More

Free Cancellation
Private Tour
Start From $1,005.31
 
Portland Tall Ship Private Charter on Casco Bay

Portland Tall Ship Private Charter on Casco Bay

  • Maine
  • Exellent20 reviews4.3

What better way to see the delights than in the style of a private charter for you and five friends ....

    Free Cancellation
    Private Tour
    Start From $1,005.31
 
 

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

(4.3 of 20 reviews)

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 5... More

Free Cancellation
Private Tour
Start From $650.00
 
2 Hours Sunset Private Charter on Heart's Desire in Casco Bay Likely to Sell Out

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

  • Maine
  • Exellent20 reviews4.3

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - com....

    Free Cancellation
    Private Tour
    Start From $650.00
 
 

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

(4.3 of 20 reviews)

Sail aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in ... More

Free Cancellation
Private Tour
Start From $500.00
 
2-Hour Private Morning Charter on Heart's Desire in Casco Bay Likely to Sell Out

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

  • Maine
  • Exellent20 reviews4.3

Sail aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and fea....

    Free Cancellation
    Private Tour
    Start From $500.00
 
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