Trips + Tours

Whether you want to explore by foot, bike, bus or boat – you can do it all right here in Downtown. Learn about Portland’s unique history, our working waterfront, or simply get out and commune with nature. From urban adventures to island trips – this is your one-stop-shop for trips and tours.

Beaten Path Tours

Lobsterman's Park | 207-749-1105

Take a walk through Portland, and discuss the historical and current events of the city. Visit website.

Casablanca Cruises

18 Custom House Wharf | 774-7220

Harbor cruise vessel specializing in private charters. Ideal for sunset party cruises & company outings. Visit website.

Casco Bay Lines

56 Commercial St | 207-774-7871

Ferry terminal to the Casco Bay Islands. Take the famous “mail boat” trip. Visit website.

First Parish Portland Unitarian Universalist

425 Congress St | 207-773-5747

Welcoming congregation in the heart of our city. Visit website.

Greater Portland Landmarks

93 High St | 207-774-5561

Walking tours around Portland’s authentic historic architecture & Portland Observatory. Visit website.

Henry Wadsworth Longfellow Statue

Longfellow Sq |

Bronze statue of poet by native sculptor Franklin Simmons.

In The Know Shopping Tour

21 Chestnut St | 207-831-4155

The best shopping in Portland. Walking tours designed for your taste and needs. Visit website.

John Ford Monument

4 Pleasant St |

John Ford (1894-1973) memorial listing some of his most famous movies.

Longfellow House

487 Congress St | 207-774-1822

Childhood home of poet Henry Wadsworth Longfellow built 1786. May-Oct, holiday hours in Dec. Visit website.

Lucky Catch Cruises

170 Commercial St | 207-761-0941

1.5 hour lobstering excursions. Pull traps near lighthouses, Civil War forts & seal rocks. May – Oct. Visit website.

Maine Beer Tours

111 Commercial St | 207-233-7485

Maine is a haven for craft beer. Come experience AND taste it with us! Visit website.

Maine Duck Tours

177 Commercial St | 207-774-3825

Climb aboard Portland’s only amphibious touring vessel for a fun, exciting land & sea adventure. Visit website.

Maine Foodie Tours

227 Commercial St | 207-233-7485

Taste your way through town! Our tasty tours introduce you to local culinary artisans to enjoy the bounty of flavors from Maine! On foot or on a boat, join us soon.

Visit website.

Maine Foodie Tours

227 Commercial St | 207-233-7485

Taste why Portland was named the “Foodiest Small Town in America”! Visit website.

Maine Historical Society

489 Congress St | 207-774-1822

Changing exhibits on Maine history. Unique gifts & books. Home of Longfellow House & Garden. Visit website.

Maine Sailing Adventures

Maine State Pier | 207-749-9169

Changing exhibits on Maine history. Unique gifts & books. Home of Longfellow House & Garden. Visit website.

Odyssey Whale Watch

170 Commercial St | 207-775-0727

Cruise up to 20 miles to known whale feeding grounds. Great family fun & entertainment. Visit website.

Old Port Historic Tours

Monument Square | 646-845-9714

Old Port Historic Waking Tours and Old Port Historic Workouts® – Learn the rich history of the Old Port in a casual walking tour or workout! Visit website.

Portland City Hall

389 Congress St | 207-874-8300

City Hall designed in the grand French Hotel de Ville style; houses Merrill Auditorium & 1912 Kotzschmar organ. Visit website.

Portland Discovery Land & Sea Tours

170 Commercial St | 207-252-6358

Narrated tours by land & sea! Trolley tours, lighthouse cruises and sunset cruises. May-October. Visit website.

Portland Fire Engine Co.

180 Commercial St | 207-252-6358

A fully narrated multimedia sightseeing tour of Downtown Portland aboard a vintage Fire Engine. Visit website.

Portland High School

284 Cumberland Ave | 207-874-8250

Built in 1821, it’s the second oldest public school in the U.S. Visit website.

Portland Schooner

Maine State Pier | 207-766-2500

Step aboard our fleet of historic, wooden windjammers for 2-hour sails and private charters. Sailing four times a day from May through October. Visit website.

Portland Soldiers & Sailors Monument

Monument Sq |

Sculpted by Franklin Simmons, dedicated in 1891 to Portland’s Civil War soldiers & sailors.

The Maine Brew Bus

111 Commercial St | 207-200-9111

All-inclusive tours to breweries, distilleries and wineries. Hop aboard the Green Bus for a unique experience. Visit website.

The Real Portland Tour

96 Commercial St | 207-329-7401

An authentic sightseeing tour of Portland and nearby lighthouses given by a REAL local, born and raised in Portland! Visit website

The Scenic Route Maine Tours

177 Commercial St | 207-51803342

Providing scenic and local experiences throughout Southern Maine in 15-passenger vans. Visit website.

United States Custom House

312 Fore St |

Built after the Great Fire of 1866. Visit website.

Whaling Wall

Maine State Pier |

450-foot long waterfront mural by artist Robert Wyland.

Wicked Walking Tours

72 Commercial St | 207-730-0490

Join a group of your fellow thrill-seekers for an entertaining romp through Portland’s past. Visit website.