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
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.

Boat on water. Photo Provided by Casco Bay Custom Charters
Casco Bay Custom Charters

Private cruises individually tailored to exceed expectations. Include an experienced captain and deckhand.

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.

Boat by Fort Gorges. Photo Provided by Fogg’s Water Taxi & Charters
Fogg’s Water Taxi & Charters

Offer boat rentals and water taxi service & the perfect way to see and explore Casco Bay on a private charter.

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.

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!

Sailing tour. Photo Provided by Maine Sailing Adventures
Maine Sailing Adventures

Aboard the 74-foot traditional sailing vessel Frances for public day sailing or charter. Weekly special events.

Family in a canoe, Photo Credits: Mahoosuc Guide Service
NaviTour

NaviTour connects travelers to local tour guides, who offer an exciting range of unique trips!

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

Jump aboard New England Eco Adventure’s small, intimate excursions that blend adventure and education into one amazing trip.

Portland by the Foot Tour Group in Monument Square Maine. Photo Credit: Dela Murphy
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.

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

Step Aboard The Extraordinary. Sail on an sailing vessel steeped in history and have the experience of a lifetime.

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

Hosted on a traditional lobster boat, Rugosa’s lobster tour offers the most exclusive, personal, and educational cruise in Kennebunkport.

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.

Van Tour, Photo Courtesy The Scenic Route Maine Tours
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.

Casablanca Cruises

Cruise on a 85-ft, two-deck harbor cruiser, outfitted with a full galley and well-stocked bar.

Fore River Sportfishing

We offer a variety of fishing charters and tours for all skill levels, from beginners to seasoned anglers. Join us for a fishing or harbor tour!

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 Duck Tours

Land & sea adventures aboard a modern amphibious vehicle. A quacktastic historical tour of the Old Port and Harbor.

Maine Narrow Gauge Railroad Company + Museum

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

Old Port Historic Tours

Experience the Old Port's rich history since 1632. Over 50 historic stops! Memorable tour experiences not to miss!

Portland Explorer Tours

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

Portland Fire Engine Co.

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

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.

Seacoast Tours of Freeport

Take a scenic trip aboard the vessel, Pamela B., with Seacoast Tours of Freeport in South Freeport.

Seadog Travels

Nautical travel company for people who love exploring, connecting, and protecting oceans through an array of offerings!

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!

Photo Provided by Casco Bay Custom Charters