Portland On the Water

Discover top on the water tours in Portland, Maine. Enjoy sunset sails, whale watching, lighthouse cruises, and more on Casco Bay with local operators.

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

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 i

From $550.00 USD
2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

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 He

★ 5.0 (2)
From $675.00 USD
Afternoon Windjammer Cruise Along the Coast of Portland Maine

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 coastline, complete with li

★ 4.7 (271)
From $69.00 USD
Casco Bay Half-Day Sea Kayak Tour

Casco Bay Half-Day Sea Kayak Tour

Explore the beautiful islands of Casco Bay in this four-hour sea kayak tour. After a brief lesson on the basics of sea kayaking, you'll set out with a licensed

★ 4.9 (60)
From $85.00 USD
Casco Bay Morning Windjammer Sail

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, c

★ 4.9 (40)
From $61.00 USD
Casco Bay Sailing Escape: Half Day Custom Boat Charter

Casco Bay Sailing Escape: Half Day Custom Boat Charter

There are a lot of ways to get out on the water in Maine, but we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run s

From $199.00 USD
Casco Bay: Private Afternoon Charter on Heart's Desire

Casco Bay: Private Afternoon Charter on Heart's Desire

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten

★ 4.0 (1)
From $650.00 USD
Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

100% Private Charter for Groups up to 16 — Flat Rate Pricing This exclusive 2-hour boat tour is designed for private groups seeking an authentic, intimate expe

★ 4.7 (7)
From $850.00 USD
Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

Experience COLORFUL Maine on this 2-hour sightseeing tour, where you’ll take in the vibrant fall foliage and the best coastal sights in the Portland area. It do

★ 4.6 (11)
From $380.10 USD
Maine Whale Watching Tour in Portland

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

★ 3.7 (67)
From $129.00 USD
Oyster Farm & Complimentary Tasting Sea Kayak Tour in Casco Bay

Oyster Farm & Complimentary Tasting Sea Kayak Tour in Casco Bay

Tasting oysters harvested from the ocean where they were grown is significantly different and better than eating them at an oyster bar, especially when you just

★ 4.8 (36)
From $99.00 USD
Portland ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

Portland ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink on the water. C

★ 5.0 (2)
From $185.00 USD
Portland Tall Ship Cruise on Casco Bay

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 y

★ 4.6 (243)
From $101.66 USD
Portland Tall Ship Private Charter on Casco Bay

Portland Tall Ship Private Charter on Casco Bay

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

From $1,071.13 USD
Private Half Day Sailing Charter in Portland Maine

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 a

★ 5.0 (1)
From $475.00 USD
Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter. Leave the crowds behind as we cruise

★ 4.9 (70)
From $380.10 USD
Private Sunset Charter on a Vintage Lobster Boat with Drinks

Private Sunset Charter on a Vintage Lobster Boat with Drinks

Leave the crowds behind and step aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter, ending with a breathtaking

★ 5.0 (44)
From $407.40 USD
Sea Kayak to an Island Tour in Casco Bay

Sea Kayak to an Island Tour in Casco Bay

Learn the basics of sea kayaking on land before launching at Mere Point in Brunswick for a leisurely 3 hour morning tour of Northwest Casco Bay!  Often we paddl

★ 4.9 (10)
From $89.00 USD
Small Group Sunset Lighthouse Boat Cruise With Local Drinks

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. Keep yo

★ 4.7 (121)
From $89.00 USD
Stand Up Paddleboard Tour with Complimentary Oyster Tasting

Stand Up Paddleboard Tour with Complimentary Oyster Tasting

Learn the basics of stand-up paddle boarding on land before launching at Mere Point in Brunswick for a leisurely 2.5 hour morning tour of Northwest Casco Bay! W

★ 5.0 (2)
From $92.00 USD
Sunset Sea Kayak Tour on Casco Bay

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 the seas often become glassy a

★ 4.8 (129)
From $60.00 USD
Sunset Windjammer Cruise Along the Coast of Portland Maine

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 ligh

★ 4.7 (201)
From $77.00 USD

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