Cruises, Charters + Tours

TOURS BY LAND OR BY SEA

Sunset cruises, walks and tastings, breweries, trolley tours, and much more! Cruise the bustling harbor of Casco Bay and get a first hand look at Portland’s working waterfront—groups and corporate events are even more memorable out on the water with the ocean breezes and salty, sea air.

Skip to content
Meetings > Activities > Cruises, Charters + Tours
Featured Articles
Business Meets Adventure
Where business meets adventure and natural beauty inspires productivity. More than a meeting place, Maine is an exciting getaway.
Work + Play in Maine: Turning Business Into Vacation
From the mountains to the sea, there’s so much to discover and many opportunities to turn a business trip into a full-on vacation!
Maine Meeting EXCURSIONS Sure to Impress Attendees
If you're hosting a meeting or conference, you have to keep excursions for your attendees in mind. All work and no play, makes meeting mundane.
See All Articles
Business Listings
Ferries. 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

Take your group for a guided tour, pedicab ride, or to explore the region at their own pace with a worksman bike rental.

Foodie Tour. Photo Provided by Maine Day Ventures
Maine Day Ventures

Maine Day Ventures will help make your upcoming event a memorable one. We offer private tours for Maine locals and visitors alike!

Group Shot of Tour. Photo Provided by New England Eco Adventures
New England Eco Adventures

Searching for an unforgettable experience for your team in Southern Maine? Step aboard for an exclusive adventure that redefines the corporate outing! 

Boat at Portland Head Light. Photo Provided by Portland Discovery Land & Sea Tours
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

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.

Boomerang Yacht Charters

Offers a great platform for business meetings, team building, and celebrations. Join us for an unforgettable experience on the water.

Casablanca Cruises

Thinking about hosting an event that'll really make a splash? Come aboard and let us provide you with a true New England coastal experience!

Casco Bay Custom Charters

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

Find Your Way Charters

Casco Bay... Your Way. Whether you're looking to reward your team or impress your clients, let us help you give them an experience like no other.

Fortland

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

Maine Brews Cruise

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

Maine Tour Connection

Full service receptive tour operator offering local sightseeing tours customized for your group.

Pine Tree Helicopters

Elevate your next event with Pine Tree Helicopters' corporate services, providing efficient transportation to and from remote sites, ensuring you arrive promptly and in style.

Portland Explorer Tours

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

SeaPortland

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

Wine Wise

Join Sommelier Erica Archer for an incredible fine-wine experience while sailing in beautiful Casco Bay.

Event Planner's Guide Ad, Designed by Visit Portland