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?

$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): Honeymaker Mead Hardshore Distilling Blue Lobster Wines 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 circumstancesWe’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!

$72 Cultural & Theme Tours

Portland Food Tasting Tour in Old Port

-Make the most of your time - enjoy six tastings of locally, sustainably and responsibly sourced food at nationally-acclaimed restaurants. -Deepen your understanding of the farmers, fishermen, foragers, and chefs whose efforts fill our plates. -Have an authentic experience by discovering Maine’s advantages, challenges, and innovation in the food sector. -Meet local chefs and enjoy a behind the scenes VIP experience. -Be entertained by our knowledgeable and passionate local guides eager to satisfy your appetite and thirst for all things related to Maine. -Small-group tour limited to 12 people ensures a more personalized experience Our restaurant partners tell the story of the Maine food system through their menus; each is unique and each is rich in local ingredients. UNIONOur name represents the restaurant’s relationship with the community – the local farmers, fishermen, brewers and craftsmen that create the uniquely Portland experience. EVO Kitchen + BarEVO kitchen + bar cooks contemporary Mediterranean and Middle Eastern inspired food using local, seasonal ingredients. Solo ItalianoSolo Italiano represents truly authentic, Italian cuisine. All components are prepared by hand and are fresh from the farm and sea. ScalesScales is a local seafood restaurant focusing on the best quality ingredients sourced locally whenever possible. East EnderEast Ender is a casual, two level restaurant located on Portland’s food famous Middle Street. PiccoloPiccolo is a restaurant where everything is made with the best local produce, fish, meat, and the finest imported Italian ingredients.

$19.99 Cultural & Theme Tours

A Comedy of Haunted History

Meet up with your fellow thrill seekers for comedy and fresh Atlantic Ocean breezes as we begin in a small waterfront park in Portland's Old Port at 8:00pm.  As your expert guide wends you through dark corners, cobblestone streets and alleys, you will be regaled with a fascinating blend of authentic history, stand up comedy and chilling story telling.  With 8 stops, all out of doors but most covered, the half mile of walking is packed with award winning, original material not to be found anywhere else.  Tour ends near some of the best seafood, ice cream, nightlife and craft beer in Maine

$2299 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.