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Portland, Maine Boats & yachts

Our most recommended Portland, Maine Boats & yachts

Portland: Best of Maine Lighthouse Scenic Cruise

1. Portland: Best of Maine Lighthouse Scenic Cruise

Sit back and relax as you cruise along the serene Casco Bay in Portland, Maine. Immerse yourself in the rich history of Portland and see the four iconic lighthouses, the sights of Portland Harbor, and the picturesque waterway Diamond Pass. During the cruise, explore the bustling inner harbor and main shipping channel to get close-up views of civil war era forts and the lighthouses that guide mariners into Portland Harbor. Along with the historical waterfront, you'll also get the chance to see the Portland Head Light, Bug Light, and the Spring Point Ledge Lighthouse.

Portland: Schooner Tall Ship Cruise on Casco Bay

2. Portland: Schooner Tall Ship Cruise on Casco Bay

Set sail on a two-hour cruise from Portland along the rugged coast of Casco Bay. Pack a meal and your favorite wine or beer, and sit back and relax as you slip through the peaceful waters of Maine. Enjoy views of lighthouses, seals, and other coastal wildlife aboard a famous schooner tall ship. Join the crew to hoist the sails or take a turn at the ship's wheel if you feel inspired. Whether you're nine years old or 99, sailing aboard a Maine schooner is a unique adventure. Learn more about the wooden windjammers which are all listed on the National Register of Historic Places and were built in Maine.

Portland: Sunset Harbor Cruise in Casco Bay with Drinks

3. Portland: Sunset Harbor Cruise in Casco Bay with Drinks

Enjoy a 1.5-hour cruise around the islands of Portland's Casco Bay. Pass historic lighthouses, early-19th century forts, and quaint fishing piers as you explore the area at sunset. Guests over 21 can enjoy 1 craft beer or hard seltzers per person. As you cruise, keep an eye out for seabirds and the occasional seal that call Maine's coast home. When the timing's right, the boat will turn its bow towards Portland so you can enjoy the sunset and the city's skyline from the water.

Portland: Maine Lighthouses Sightseeing Cruise with Drinks

4. Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Uncover the beauty of the Portland Harbor and Casco Bay aboard the Elizabeth Grace on this sightseeing cruise from Portland. Sail past iconic lighthouses, historic forts, and rocky islands while sipping on 1 complimentary alcoholic beverage. Hop aboard a comfortable and spacious ship at the Custom House Wharf. Take in views of the city's charming skyline as you embark on your cruise. Unwind with a delectable craft beverage in hand as you sail. Feel the wind in your hair as you cruise by lighthouses, 200-year-old forts, and rocky and stunning islands. Cruise with confidence knowing that the ship is regularly maintained to the highest safety standards. Keep an eye out for local wildlife like loons, black ducks, and buffleheads as you sail. Return to your starting point at the Custom House Wharf at the end of your cruise.

Portland, Maine: Sunset Kayak Tour with a Guide

5. Portland, Maine: Sunset Kayak Tour with a Guide

The hour just before sunset is the best time to be paddling on the waters of Casco Bay. The sky tends to explode with color and the seas often become glassy and calm. This trip involves a leisurely paddle just far enough along the waterfront or into the islands to enjoy a panoramic view of the sun setting over the city as we paddle back to the East End Beach. This two-hour tour is designed for paddlers of all experience levels -- including first-time kayakers.

Portland, ME: 60 Minute Lighthouse Cruise to Head Light

6. Portland, ME: 60 Minute Lighthouse Cruise to Head Light

Enjoy this fully narrated 60-minute scenic cruise through busy Casco Bay and its iconic islands to see lighthouses, forts, lobster boats, seals, and seabirds. Take in the views of Portland's historical lighthouses, including a close up view of Portland Head Light, Maine’s oldest and most photographed lighthouse. As you cruise along the Casco bay, keep an eye out for Spring Point Ledge Light, Portland Breakwater Light (Bug Light), Ram Island Ledge Light, Portland Head Light, Fort Scammel, Fort Gorges, and Portland Harbor.

Portland: Casco Bay Maine Oyster Cruise with Craft Beverages

7. Portland: Casco Bay Maine Oyster Cruise with Craft Beverages

Enjoy a cruise along the waters of Casco Bay and try some delicious local Maine seafood while relaxing aboard the boat. Enjoy a great introduction to world-class Maine seafood and sip craft drinks of your choice. Begin the tour at 2:30 at the Portland Beer Hub, located at 320 Fore Street, where you will choose from a wide selection of Maine craft beverages, including beers, ciders, and kombucha. Board a former navy launch boat now equipped with comfortable seating and embark on a tour of Casco Bay and its islands. See marine life, lighthouses, military forts, and more as we motor the calm waters. On board, you will learn about and taste oysters from 3 various harvesters in the area. Learn from the experienced guide while they shuck oysters aboard the boat as quickly as possible. Enjoy other seafood and snacks as well while on the tour. Disembark just one block from the starting point at 5:00 pm having enjoyed wonderful sights and culinary delights.

Portland: Private Lighthouse Sightseeing Cruise

8. Portland: Private Lighthouse Sightseeing Cruise

This two hour charter is the perfect way to see lighthouses, historic stone forts, wildlife, & Maine's picturesque coast. Bring your camera and experience authentic Maine aboard our classic wooden lobster boat! This is a private charter, so only you and your group is aboard plus a captain and tour guide. You and your private group will have up close views on Maine's most notable sights. Every private charter includes a licensed captain and an experienced charter host to attend to your every need! Purchase local Portland, ME beers and hard seltzers, important white and red wine, and bubbly aboard!

Portland, Maine: Casco Bay Full-Day Kayaking Tour

9. Portland, Maine: Casco Bay Full-Day Kayaking Tour

Our Full-Day Kayak Tour is a chance to sea kayak to some of the most historically fascinating and scenic landmarks in the Portland region. Unlike our other tours, we limit this trip to 6 or fewer people and we require participants to have at least one previous sea kayaking experience. You'll spend the day island-hopping through the rugged islands of Casco Bay. Along the way you'll visit several 19th century forts, paddle past lighthouses and feel the swell of the open ocean underneath your kayak. On this trip we often visit some of Casco Bay’s lighthouses and forts, including Spring Point Light, Fort Preble, Portland Head Light, Fort Scammel, Ram Island Light, Bug Light and Fort Gorges. You'll also have the chance to hone your paddling skills, learn about the natural history of the area, visit islands on the Maine Island Trail and spot wildlife like seals, osprey and eiders. You'll see many sides of Casco Bay, including the bustling working waterfront of Portland harbor, the cliff-lined outer islands exposed to the open ocean and the more protected coves lined with beaches. This trip is designed for paddlers of a range of skill levels and the group will take many breaks and stops along the way. However, the trip does involve a very full and active day, so we suggest our shorter trips for first-time kayakers or anyone who has difficulty with prolonged physical activity. All participants should have tried sea kayaking at least once before. This trip sometimes starts in a different location than our main site (due to a one-way route), so you may be transported by van to the launching site at the start of the trip. The cost of this trip includes a delicious picnic lunch, with a vegetarian option.

Frequently asked questions about Portland, Maine Boats & yachts

What are other things to do than Boats & yachts that are worth visiting in Portland, Maine?

The other unmissable things to do in Portland, Maine are:

Other Sightseeing Options in Portland, Maine

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What people are saying about Portland, Maine

Definitely not a sailor so when the boat tilts it’s a bit disconcerting until you realize that’s what sailing is supposed to be. We apparently had real good wind on our trip so got to go out past where most end up. Very cool activity, got to see three lighthouses, some very cool houses along the coast and the rugged coast line without the drone of an engine. Captain and the other crew were knowledgeable and very cool, a nice peaceful adventure, definitely worth it in my book

This was the perfect way to end our Maine trip. Staff was friendly and knowledgeable and the boat itself was stunning. Learned A lot of history about the boat. My partner and I Loved every minute of it . Take advantage of the byob.

My husband & I had an awesome time. The weather was beautiful & Christina was very informative. It was a very relaxing ride. I would truly recommend this tour.

This was a great experience and a good way to see the hidden gems in and around Portland! It was a lot of fun!

Great sailboat rode around Casco Bay! Beautiful. Wonderful crew!