Top Maine Cruises, Sailing & Water Tours

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Maine Adventures

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1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain
Special Offer
Special Offer
Bar Harbor, USA
4.3 (598)

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

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

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.3 (598)
$70
$69
Harbor Lights and Sights Cruise
Special Offer
Special Offer
Portland, USA
4.9 (720)

Harbor Lights and Sights Cruise

Explore the bustling inner harbor, Diamond Pass, and the main shipping channel to get close up views of civil war era forts and as many...

1 hour 45 minutes • Free Cancellation
1 hour 45 minutes • Free Cancellation
1 hour 45 minutes • Free Cancellation
4.9 (720)
$57
$56
Portland Tall Ship Cruise on Casco Bay
Special Offer
Special Offer
Portland, USA
4.6 (233)

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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.6 (233)
$99.75
$98.75
Windjammer Classic Day Sail from Camden, Maine
Special Offer
Special Offer
Camden, USA
4.8 (411)

Windjammer Classic Day Sail from Camden, Maine

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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (411)
$59.95
$58.95
Port City Lights Cruise
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.8 (266)

Port City Lights Cruise

A fully narrated 60-minute scenic cruise through busy Casco Bay and its innermost islands to see lighthouses, forts, lobster boats, seals, and seabirds. As many...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.8 (266)
$39
$38
Sunset Lighthouse Cruise Tour from Casco Bay
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.9 (163)

Sunset Lighthouse Cruise Tour from Casco Bay

This 105 minute cruise offers guests a chance to relax and unwind as we make our way around the inner islands and lighthouses of the...

1 hour 45 minutes • Free Cancellation
1 hour 45 minutes • Free Cancellation
1 hour 45 minutes • Free Cancellation
4.9 (163)
$56
$55
Sunset Sea Kayak Tour on Casco Bay
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.9 (110)

Sunset Sea Kayak Tour on Casco Bay

The hours just before sunset offer the best time for paddling on the waters of Casco Bay. The sky tends to explode with color and...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (110)
$60
$59
Guided RIB Boat Adventure of Portland
Likely to Sell Out
Likely to Sell Out
Portland, USA
5.0 (36)

Guided RIB Boat Adventure of Portland

Depart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts,...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (36)
$69
$68
Small Group Sunset Lighthouse Boat Cruise With Local Drinks
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.7 (100)

Small Group Sunset Lighthouse Boat Cruise With Local Drinks

Board the Elizabeth Grace to cruise around Portland Harbor while sipping local craft beer. This 1.5-hour harbor cruise will take you out into Casco Bay....

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.7 (100)
$89
$88
Afternoon Lighthouse Cruise Along the Coast of Portland Maine
Special Offer
Special Offer
Portland, USA
4.6 (78)

Afternoon Lighthouse Cruise Along the Coast of Portland Maine

Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. Pack a meal, bring...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.6 (78)
$64
$63
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Special Offer
Special Offer
Portland, USA
4.7 (197)

Afternoon 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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (197)
$69
$68
Morning Lighthouse Cruise Along the Coast of Portland Maine
Special Offer
Special Offer
Portland, USA
4.8 (61)

Morning Lighthouse Cruise Along the Coast of Portland Maine

Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. Pack a meal, bring...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (61)
$59
$58
Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour
Special Offer
Special Offer
Portland, USA
4.9 (67)

Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

Board the Elizabeth Grace for this exclusive one-of-a-kind experience. Whether you are a local or visiting from away, the stone fortresses built in the early...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (67)
$109
$108
Schooner Applejack Sunset Sail Tour in Boothbay Harbor
Likely to Sell Out
Likely to Sell Out
4.9 (46)

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (46)
$59.95
$58.95
Sunset Windjammer Cruise Along the Coast of Portland Maine
Special Offer
Special Offer
Portland, USA
4.7 (154)

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,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (154)
$77
$76
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
Likely to Sell Out
Likely to Sell Out
4.7 (128)

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (128)
$54.95
$53.95
Schooner Eastwind Sunset Sail to see the Maine Coastline
Likely to Sell Out
Likely to Sell Out
4.8 (62)

Schooner Eastwind Sunset Sail to see the Maine Coastline

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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (62)
$59.95
$58.95
Maine Whale Watching Tour in Portland
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.2 (47)

Maine Whale Watching Tour in Portland

Experience the breathtaking beauty of the Atlantic Ocean on our whale-watching tour departing from Portland, Maine. Set sail from the historic harbor, where you'll board...

3 hours 30 minutes • Free Cancellation
3 hours 30 minutes • Free Cancellation
3 hours 30 minutes • Free Cancellation
4.2 (47)
$129
$128
Portland Explorer: Boat Cruise with Oysters & Prosecco
Likely to Sell Out
Likely to Sell Out
Portland, USA
4.9 (9)

Portland Explorer: Boat Cruise with Oysters & Prosecco

Set off on a refined culinary adventure through the serene waters of Casco Bay. Your journey begins at Portland Beer Hub, where you’ll gather before...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (9)
$137
$136
Windjammer Classic Sunset Sail from Camden, Maine
Likely to Sell Out
Likely to Sell Out
Camden, USA
4.9 (435)

Windjammer Classic Sunset Sail from Camden, Maine

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....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (435)
$64.95
$63.95

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