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Portland, Maine

Activities

Our most recommended Portland, Maine Activities

Portland: Sunset Harbor Cruise in Casco Bay with Drinks

1. Portland: Sunset Harbor Cruise in Casco Bay with Drinks

Enjoy a 1.5-hour cruise around the islands of Portland's Casco Bay. Pass historic lighthouses, early-19th century forts, and quaint fishing piers as you explore the area at sunset. Guests over 21 can enjoy 2 craft beers or hard seltzers per person. As you cruise, keep an eye out for seabirds and the occasional seal that call Maine's coast home. When the timing's right, the boat will turn its bow towards Portland so you can enjoy the sunset and the city's skyline from the water.

Portland Maine: Tour in Vintage Fire Engine

2. Portland Maine: Tour in Vintage Fire Engine

Enjoy seeing Portland in an unforgettable way. Hop on board a vintage fire truck with onboard multimedia system, including a large, flat-screen LED TV. Experience Portland in a unique and fun way with this local-led tour aboard a classic fire engine. Explore the city’s peninsula as you drive along the cobble-stoned streets. Enjoy great views of lighthouses, civil war forts, and the historic architecture that make up the wonderful Maine city. Enjoy a 50-minute tour narrated by local guides who love sharing their knowledge of Portland Maine. Get to know the vibrant neighborhoods of this city by the sea from high up on your truck.

Portland: Schooner Tall Ship Cruise on Casco Bay

3. Portland: Schooner Tall Ship Cruise on Casco Bay

Set sail on a two-hour cruise from Portland along the rugged coast of Casco Bay. Pack a meal and your favorite wine or beer, and sit back and relax as you slip through the peaceful waters of Maine. Enjoy views of lighthouses, seals, and other coastal wildlife aboard a famous schooner tall ship. Join the crew to hoist the sails or take a turn at the ship's wheel if you feel inspired. Whether you're nine years old or 99, sailing aboard a Maine schooner is a unique adventure. Learn more about the wooden windjammers which are all listed on the National Register of Historic Places and were built in Maine.

Portland: Old Port Culinary Walking Tour

4. Portland: Old Port Culinary Walking Tour

Enjoy this experience that showcases the culinary culture of Portland, Maine comprised of talented food and beverage artisans, from bakers and brewers to confectioners, chefs, and more. Visit the spots the locals enjoy visiting on a daily basis. Join a friendly and engaging tour guide as they take you to several Old Port and neighboring artisanal shops, restaurants, and pubs. You’ll sample a delectable mix of classic Maine, Maine-inspired, up-and-coming, cultural, fancy foods, and beverages.  Meet and greet culinary artisans along the way, learn what inspires them and how they got their start with a lively narration from your guide. Along the way, your guide will dish about the colorful, social, and culinary history unique to the “Port City” with lots of additional recommendations on how to dine and imbibe. You are sure to leave full of delicious food and local history. This experience works with gluten (not celiac), seafood, nut, and vegetarian dietary preferences and sensitivities to the best of our ability. Guests may pick and choose their participation for any further food issues. Your foodie experience may include: fresh-picked lobster, from-scratch confections, locally-sourced temaki (raw fish) roll, Maine seafood “chowdah”, iconic Maine craft beer, Maine honey wine, and dark chocolate truffles made with Aroostook County potatoes.

Portland, Maine: 2-Hour Guided History Tour

5. Portland, Maine: 2-Hour Guided History Tour

Meet your local guide, a history lover who will bring the stories and facts from Portland’s past alive throughout the tour. Starting on Commercial Street, walk through the cobble stone streets of the historic Old Port, downtown, and waterfront areas.  Some of the locations that may be featured as part of the tour include the lobster statue, the home of Henry Wadsworth-Longfellow, the Eastern cemetery, the Abyssinian Church, and more. Your tour will finish on a sweet note with a local treat.

Portland: Casco Bay Maine Oyster Cruise with Craft Beverages

6. Portland: Casco Bay Maine Oyster Cruise with Craft Beverages

Enjoy a cruise along the waters of Casco Bay and try some delicious local Maine seafood while relaxing aboard the boat. Enjoy a great introduction to world-class Maine seafood and sip craft drinks of your choice. Begin the tour at 2:30 at the Portland Beer Hub, located at 320 Fore Street, where you will choose from a wide selection of Maine craft beverages, including beers, ciders, and kombucha. Board a former navy launch boat now equipped with comfortable seating and embark on a tour of Casco Bay and its islands. See marine life, lighthouses, military forts, and more as we motor the calm waters. On board, you will learn about and taste oysters from 3 various harvesters in the area. Learn from the experienced guide while they shuck oysters aboard the boat as quickly as possible. Enjoy other seafood and snacks as well while on the tour. Disembark just one block from the starting point at 5:00 pm having enjoyed wonderful sights and culinary delights.

  • Guided tours
  • Water activities
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What people are saying about Portland, Maine

Timothy our guide was very informative, the food choices were great. It was an enjoyable experience. Walking was difficult on the cobble stones.

It was a beautiful day on a beautiful vessel. The crew was accommodating, very pleasant and did an excellent job! Highly recommend!

It was fun, just the right amount of time and the price was very affordable. Good value. The driver and tour guide were good guys.

Great activity for the entire family. The tour guys are very knowledgeable and will answer all your questions.

Driver and host were very respectful and explained everything well. Drinks were good and ambience too.