Welcome to Portland


Set on a peninsula jutting into the gray waters of Casco Bay, Portland's always been a city of the sea. Established in 1633 as a fishing village, it grew to become New England's largest port. Today, the Old Port district is the town's historic heart, with handsomely restored brick buildings filled with cafes, shops and bars. The working wharves keep things from getting too precious or museum-like, though, as fishmongers in rubber boots mingle with well-heeled Yankee matrons.


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Portland activities

$24 Tours & Sightseeing

Narrated Sightseeing Tour of Portland, Maine, Aboard a Vintage Fire Engine

Portland Fire Engine Co. operates a unique narrated sightseeing tour of Portland, Maine aboard a Vintage Fire Engine. We explore the peninsula of Portland and its many lighthouses and forts as well as the amazing architectural buildings hidden inside the cobble stoned streets that make up our wonderful city. The tour is a great way of reliving Portland’s past. Viewing the area while high up on the Fire Engine gives amazing views of Casco Bay as well as fantastic opportunities for photographs. The tours are approximately 50 minutes in length and are fully narrated by a very knowledgeable guide while displaying high resolution photographs from the Maine Historical Society via our on-board multimedia system, which includes a large flat LED TV. Tours require a minimum of 4 passengers to run, with a maximum of 13 people per Engine. Larger groups/parties will be split up allowing time for shopping, eating, or just exploring the Old Port.

$350 Cruises, Sailing & Water Tours

Private Sunset Charter on a Vintage Lobster Boat

Each charter includes a captain as well as a deckhand who will serve as your guide.  You will meet your guide at Bell Buoy Park, 72 Commercial Street, Portland ME.  This is adjacent to the Casco Bay Lines Ferry Terminal.  Your guide will escort you down the ramp to the water taxi dock and assist you with boarding MONHEGAN, our vintage lobster boat.We will depart Portland Harbor and pass by Bug Light, Fort Gorges, Spring Point Ledge Light, and Fort Scammel as we make our way toward Portland Head Light. Your guide will point out these and other interesting sights as well as any wildlife we encounter.  If you wish, you can bring aboard food or beverages, and your guide will be happy to assist in serving.  MONHEGAN is stocked with glassware, plates, and utensils.  We provide a cooler with ice and bottled water on all charters.  Alcohol may be responsibly consumed by our guests of legal age. From Portland Head Light, your captain will navigate through some of the islands of Casco Bay.  You will watch Maine's rocky, tree-lined coast slip by as you relax on our deck chairs.  MONHEGAN is a very stable vessel, and she is outfitted with a retractable weather cover so your comfort aboard is assured.  As the sun gets low and bathes Casco Bay in golden light, your captain will round Great Diamond Island and turn into the setting sun for the final leg of your cruise.  You will be treated to views of Portland's skyline silhouetted by the setting sun.  Throughout the cruise, guests will find ample opportunities for photos.  Can you imagine a more perfect finish to your day in Maine?

$75 Walking & Biking Tours

Eastside Distillery Row Bike Tour: Brew, Barrel Age, Grow

Your tour begins at 3 p.m. at our bike shop in inner SE Portland, 833 SE Main: the heart of distillery row. But distilleries aren't all that thrive in the inner Eastside; breweries and cider houses now pepper the inner east side. (Coffee roasters, restaurants, chocolate shops, food carts, and plenty more also thrive nearby; there is truly something for everyone here!) Your guide will meet you at our shop and fit you for a bike and a helmet and get to know you. As the route can vary somewhat based on the group's needs, your guide will take some time to learn why it is YOU came to Portland before you head out. Once you are fitted, you and your group will wind through the pretty nearby neighborhood full of funky homes, hipster parks, and the artsy elementary school that served as Shining Star Preschool in Portlandia. Our first stop will be a ciderhouse famous for its funky style and birth in a Portland basement -- it now sells cider as far away as Japan. Wind through the inner NE neighborhood, past other unique Portland-grown specialties, and down the Willamette River back into the southeast into the heart of distillery row. House Spirits lives only a few blocks away from where Portlandia filmed its apocalypse episode, and what better place to spend the end of the world as we know it than a warehouse towering with whiskey barrels and distillery tanks? The company makes its own rum, aquavit, and coconut-husk-filtered vodka, as well as unique specialities like creme de cacao, and of course the signature whiskey. You will taste a few spirits while you are provided with a tour the facility, learning how modern-day Portlandians riff on Portland's wild bootlegging past. Get back on your bikes and ride to a nearby brewpub, where you will sample some of Portland's amazing IPAs and barrel-aged Belgian beers at Hair of the Dog; or world-famous sour beers at Cascade Brewing Barrel House; or one of the newer local favorites, like the beautifully designed Baerlic. Feel free to  You'll return to the shop by 7, near enough to a wide variety of restaurants, wineries, and more breweries and distilleries to stroll to dinner or a show afterward. Or you can hop on our Portland at Night Bike Tour and do Portland the way we do: by bike! Beer, cider and spirits samples are included, as well as bike and helmet and our professional guide.

$2139 Holiday & Seasonal Tours

10-Day New England Fall Foliage Tour including Cape Cod

Day1Start your adventure Merrimack, New Hampshire. The Merrimack Premium Outlets will be open and we will offer complimentary transportation to the Outlets or to the Anheuser Busch Brewery for a tour and a tasting. This evening, we will welcome you to New England with a welcome drink and dinner.  Dinner includedDay 2Travel to coastal Maine and explore the Light House Trail. The first stop will be at Nubble Light, one of the most photographed points in Maine. This will be followed by a New England Lobster Lunch. In the afternoon, you'll visit Portland and the famous Portland Head Light as well as other lighthouses in the area. Breakfast & Lunch includedDay 3Enjoy a cruise of Squam Lake, used as the setting in the movie "On Golden Pond". Enjoy a gourmet box lunch or lunch at Walter's Basin restaurant before having an interactive experience at the Squam Lake at the Squam Lake Science Center staring New Hampshire Wildlife. Breakfast & Dinner includedDay 4Have a "Taste of Vermont". Your first stop is at the Cabot Creamery Annex for a sampling of some of Vermont's finest Cheeses.We will continue on to Cold Holler where you can enjoy a taste of Apple Cider and lunch on your own at the Apple Core Dinner. We will stop to see how maple syrupp is made and a tasting on the way back. Breakfast includedDay 5Travel to the top of Cannon Mountain by Aerial Tram. In the afternoon, cross the Kancamagus Highway, which offers some of the most dramatic fall colors and scenic covered bridges. Breakfast & Dinner includedDay 6Visit Newport, Rhode Island and enjoy a sail aboard a schooner around Newport Harbor followed by a tour on one of the historic Mansions.  Breakfast & Dinner includedDay 7Enjoy a tour of historic Boston. The first stop is the USS Constitution. Next see the Old North Church and Paul Revere's home. Visit Quincy Market for shopping and lunch. In the afternoon, see the State House, Boston Common, Trinity Church and other Boston Highlights. Breakfast includedDay 8Enjoy a full narrated historic tour of Nantucket, famous as the world's foremost whaling port in the 18th century. The tour covers The Old Mill, "Sconset" Village with its rose-covered cottages, Low Beach, Sankaty Head Lighthouse, Cranberry bogs and Nantucket moors. That evening, you'll enjoy a New England Lobster dinner.Day 9Tour Cape Cod National Sea Shore on the way to Provincetown. In the afternoon, enjoy a whale-watching cruise or a Cape Cod Dune Tour. Breakfast & Dinner includedDay 10On the last day, tour Hyannis with stops at the Kennedy Memorial before continuing onto the JFK Presidential Library.

$70 Food, Wine & Nightlife

Best of Portland Craft Drink Tour

Turns out Portland really does have it all. Find out how our breweries, wineries, and distilleries are turning out amazing craft alcohol products. Enjoy the best of all beverages with this 3-hour tour through some of Portland's best breweries and distilleries! The city may be well known for its beer, but Portland is also home to craft drinks of the wine and spirit variety.  We pick up at Old Port Spirits and Cigars on Commercial Street in Portland, the main thoroughfare running along the working waterfront downtown. Hop aboard the bus and we’ll head out on the Best of Portland Tour. All tastings, transportation, food, bottled water, and a take-home souvenir bag are included in the ticket price. This itinerary varies. We will be choosing 3 stops out of the following options (based on availability): Maine Mead Works Hardshore Distilling Austin Street Brewing Shipyard Brewing Urban Farm Fermentory New England Distilling Geary's Brewing Cellardoor Winery Stroudwater Distillery Rising Tide Brewing  Foulmouthed Brewing  Foundation Brewing Please note that tour venues and details may change without notice due to unforeseen circumstances We’ll drop you back off at Old Port Spirits and Cigars on Commercial Street, where you can continue to explore the downtown area on foot!

$20 Tours & Sightseeing

MetroDemic Scavenger Hunt in Portland

Race to save Portland from a deadly epidemic. This off-beat game is played by teams of 2-4 people. Armed with only your wits and your cell phones, you will try to help a team of completely inept scientists discover the cure to a mysterious disease known as “the playgue”.As you walk to different outbreaks within a 4 block radius (starting Pioneer Courthouse Square), be prepared to solve scavenger hunt questions, pub-style trivia, and brain puzzles at each location to earn points. Points earned are lives saved. Your entire team must work together using their collective knowledge and the ability to find all of the world’s information on their mobile phones.The game permits up to 2 pauses in case the kids create a bio-hazard or your sister-in-law starts complaining about blisters. This self-guided event can be played on any smartphone or tablet device. Your team can start whenever they are ready, as long as it is during daylight hours.