Guided Tours + Cruises

SAMPLE THE SIGHTS AND SOUNDS OF THE REGION

When you visit the Greater Portland, Maine region you get a hands-on experience. Get up close and personal with our rocky coastline and sandy beaches. The region is your oyster and you can take on everything from kayak trips to lobstering tours to brews cruises.

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Portland Head Light
Situated along the shores of Fort Williams Park in Cape Elizabeth, Portland Head Light sits at the entrance of the shipping channel into Casco Bay.
Top 10 Must-Do’s for First-Time Visitors
Must-do experiences that will leave a lasting impression on your first trip to the region. Find essential activities you can't afford to miss for a successful trip to Vacationland.
What’s New in the Portland, Maine Region
New places to stay. play, and eat in the region await you! Learn more about what's in store for 2023 in Greater Portland.
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Boat Cruising on Casco Bay. Photo Credit: PGM Photography
Boomerang Yacht Charters

Offering specialty food cruises, harbor tours, and private charters. Complimentary beer and wine with all cruises!

Cap'n Fish's Cruises Tour. Photo Credit: Megan Clouse
Cap'n Fish's Cruises

Visiting Maine and want to see whales, puffins, or the sights? Cap’n Fish is the way to experience Boothbay Harbor.

Casco Bay Lines Ferry. Photo Provided by Casco Bay Lines
Casco Bay Lines

Portland's iconic ferry system with year-round ferry services, specialty cruises and private charters to the islands of Casco Bay.

Lighthouse Bikes at Bug Light, Photo Credit: Lighthouse Bikes / Leah Day
Lighthouse Bikes

Join us for a guided tour, pedicab ride, or explore the region at your own pace with a worksman bike rental.

Group Tour, Photo Courtesy of: Maine Day Trip Tours
Maine Day Trips & Tours

Private sightseeing tours are available for couples and all size groups, from minivan to motor coach.

Lobster Roll at Bug Light. Photo Provided by Maine Day Ventures
Maine Day Ventures

Highly interactive tours that will educate and entertain you all along the way. Foodie tours, history tours, and more!

Frances on Casco Bay. Photo Credit: Sam Dow
Maine Sailing Adventures

Come aboard Frances, our 74’ traditional British cutter for a day sail, evening sail, wine sail, or an acoustic sunset series sail. Private charter available.

Boat Tour. Photo Provided by Maine Tour Co.
Maine Tour Co.

Home to the best tours and activities in Maine. Authentic experiences led by locals. Your gateway to an unforgettable Maine.

Tour Boat Passing Lighthouse Photo Provided by New England Eco Adventures
New England Eco Adventures

Skip the crowds and jump into a thrilling Maine adventure! We take you closer, stay longer, and explore places other tours can’t reach. 

Helicopter at Sunset. Photo Credit: Pine Tree Helicopters
Pine Tree Helicopters

Witness the beauty of Maine from above with Pine Tree Helicopters' extraordinary flight services, offering breaking aerial views of Maine's iconic lighthouses and more.

Portland by the Foot Tour. Photo Credit: Hannah Daly
Portland by the Foot

Experience unforgettable storytelling—rich with heart, humor, and humanity—on a walking tour with Maine's top-rated guide!

Boat Tour. Photo Credit: Bill Frappier
Portland Discovery Land & Sea Tours

Don't just see Portland- Discover it! Offer a wide variety of sightseeing and charter options by Land and Sea.

Tour at Portland Head Light. Photo Provided by Portland Fire Engine Co Tours
Portland Fire Engine Co. Tours

Operate a unique multimedia history tour aboard a Vintage Fire Engine. We explore the peninsula of Portland.

Two Sailboats. Photo Provided by Portland Schooner Co
Portland Schooner Co.

Refresh your spirit with a two-hour sail on Casco Bay and witness first-hand the forts, lighthouses, sea life and rugged coastline.

Bob Leading Tour. Photo Provided by Rugosa Lobster Tours
Rugosa Lobster Tours

Known as one of the top-rated boat tours in the region, Rugosa offers an exclusive, hands-on journey aboard our traditional wooden Downeast-style lobster boat.

Group Biking near Lighthouse, Photo Courtesy of Summer Feet Cycling
Summer Feet Cycling Adventures

For 20 years we have been offering cycling, walking, and multi-sport vacations in the most beautiful places in Maine.

Casablanca Cruises

Portland's #1 party boat! Join us on the water for a fully immersive way to experience Casco Bay and the islands, all while live bands set the soundtrack.

Casco Bay Custom Charters

Explore the best of Maine with private sightseeing tours featuring chef prepared local cuisine and drinks. Unforgettable experiences await on our historic boats.

Fogg’s Water Taxi & Charters

Discover the wonder of Casco Bay with Fogg's Water Taxi & Charters, offering a diverse range of services across our seven boats.

Fortland

A unique island experience within Fort Scammel on the private House Island in Casco Bay. Camp and tour the historic island!

Lucky Catch Cruises

A lobstering excursion for all ages while enjoying close-up views of historic lighthouses, civil war forts, and seals.

Maine BayCycle

Maine’s first human-powered party boat. Book individual seats or the whole boat for a private tour of Portland.

Maine Brews Cruise

All-inclusive tours providing guests a behind-the-scenes look at Maine’s breweries, distilleries, wineries, and more.

Maine Narrow Gauge Railroad Company + Museum

Scenic train ride along beautiful Casco Bay. Activities, historic railroad cars & exhibits.

Portland Explorer Tours

Join our family owned and operated tour company for unforgettable explorations. Customized year-round tours.

Portland, Maine Walking Tours

Residents and guides, with enthusiasm and expertise in Portland’s history, food, drinks, art, music, and literature.

Rocky Bottom Tours

A day in the life of a lobsterman from pulling traps and setting traps to examining sea life and selling the catch.

SeaPortland

We offer unique boat-based tours and experiences on the beautiful waters of Casco Bay!

The Real Portland Tour

City & 3 lighthouses Historical Sightseeing Tour with a REAL local, born & raised in Portland!

The Scenic Route Maine Tours

A family-owned and operated tour company sharing what we love about our charming city and the state of Maine.

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