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Portland, Maine

Sightseeing Cruises

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Our most recommended Portland, Maine Sightseeing Cruises

Portland: Schooner Tall Ship Cruise on Casco Bay

1. 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: Maine Lighthouses Sightseeing Cruise with Drinks

2. Portland: Maine Lighthouses Sightseeing Cruise with Drinks

Uncover the beauty of the Portland Harbor and Casco Bay aboard the Elizabeth Grace on this sightseeing cruise from Portland. Sail past iconic lighthouses, historic forts, and rocky islands while sipping on 2 complimentary alcoholic drinks. Hop aboard a comfortable and spacious ship at the Custom House Wharf. Take in views of the city's charming skyline as you embark on your cruise. Unwind with a delectable craft beverage in hand as you sail. Feel the wind in your hair as you cruise by lighthouses, 200-year-old forts, and rocky and stunning islands. Cruise with confidence knowing that the ship is regularly maintained to the highest safety standards. Keep an eye out for local wildlife like loons, black ducks, and buffleheads as you sail. Return to your starting point at the Custom House Wharf at the end of your cruise.

Portland: Sunset Harbor Cruise in Casco Bay with Drinks

3. 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

4. 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: Old Port Culinary Walking Tour

5. 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 where you’ll sample a delectable mix of classic Maine, Maine-inspired, up-and-coming, cultural, fancy foods, and beverages. You will have the opportunity to 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 actively 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. While tours vary, 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 honeywine, and dark chocolate truffles made with Aroostook County potatoes.

Portland, Maine: 2-Hour Guided History Tour

6. 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

7. 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.

Portland, Maine: Old Port Tasting Tour of Local Breweries

8. Portland, Maine: Old Port Tasting Tour of Local Breweries

Spend the day walking, talking, and tasting your way through the historic city of Portland, Maine. Led by a local guide, this 2 or 3-hour walking tour takes you through the interesting history of the city's beer culture. From becoming the birthplace of Prohibition in 1851 to establishing the first craft brewery in all of New England in 1983, Portland has a riveting story to tell.  The three locations visited on each tour will vary based on the availability of staff. Stop selections may include Definitive Brewing, Urban Farm Fermentory, Blue Lobster Urban Winery, Bunker Brewing, eighteen twenty wines, Hi-Fidelity Brewing, Hardshore Distilling, Maine Mead Works, and Banded Brewing. Experience the city that saw the first craft brewery to be established in all of New England, Geary Brewing Company in 1983. It welcomed Gritty McDuff’s in 1988 as they opened their doors in the Old Port to become the first brewpub in the state. It witnessed the dramatic rise of Shipyard Brewing Company in 1992 to be one of the county’s largest brewing enterprises that now spans well beyond the U.S. to shores far away.  Pass by one of the world’s only brewery-distillery-restaurants that was formed on Portland’s waterfront once Liquid Riot turned on their open sign in 20111. There are many other breweries in the neighborhood around Portland that are shaping their own history in the present day.

Portland, Maine: Black History Guided Walking Tour

9. Portland, Maine: Black History Guided Walking Tour

Wind through the brick sidewalks and cobblestone streets of Portland's Old Port and working waterfront on this guided walking tour. Immerse yourself in the rich story of the Black community in the East End neighborhood. Meet your local guide at the First Parish Church, Portland's oldest church, and begin your journey back in time. Discover the monuments, places of business, and civic institutions where Black Yankees drove the economy and organized for political power. Head to the East End neighborhood to see the homes of Black sailors and stevedores that served as stations on the underground railroad. Admire the churches where Black families worshipped, celebrated, and learned together from the 19-century up to the present day. Learn how Maine's earliest colonial settlements could not have survived without Black insight, skill, and labor. Uncover the story behind the enslaved Black maid who abolished slavery in Maine during the Revolutionary War. Discover the exceptional figures who shaped Portland and the State of Maine over 400 years of Black history. Printed images of the past together with gifted storytelling will bring the past to life. Hear the stories that usually get left out of history tours. A portion of every ticket sale will help fund the restoration of the Abyssinian Meeting House, Maine's oldest and America's third-oldest Black church. End your tour at the Maine Jewish Museum, less than a half-mile from where it began.

Portland, Maine: Women’s History Guided Walking Tour

10. Portland, Maine: Women’s History Guided Walking Tour

Get to know the historic women of Portland on this guided walking tour through the Arts District and West End. Stop at iconic landmarks and hear about the hidden past from a local guide. Learn about Portland's important women and their contribution to the city. Your tour starts where Maine's first women's suffrage meeting was held. Stroll down Congress Street in Portland's Arts District. Visit the places where working-class women earned economic independence and wealthy female philanthropists saved landmarks and founded the city's most cherished museums. In the West End neighborhood, you'll see 19th-century row houses and churches connected to significant woman-led political and social movements. During your tour visit a woman-run underground railroad station and hear of the most daring escape from slavery it supported. Also, enjoy interactive storytelling about the Chinese laundress who won American mother of the year and the enslaved maid who abolished slavery in Maine. Additionally, see the halls and meet the courageous women involved with Maine's multi-generational fight for women's suffrage. Conclude your tour at the headquarters of the movement's final campaign.

Frequently asked questions about Portland, Maine Sightseeing Cruises

What are other things to do than Sightseeing Cruises that are worth visiting in Portland, Maine?

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Other Sightseeing Options in Portland, Maine

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What people are saying about Portland, Maine

The Harbor Cruise was the highlight of our visit to Portland. The views from the seaside of Casco Bay, the history & points of interest helped us plan the rest of our stay. The great crew and the sunset made the experience memorable! We highly recommend Harbor Sunset Cruise to anyone visiting Portland, Maine!

This was one of the best tours we've taken. Our guide was so knowledgeable about the city and pointed out interesting facts. We saw so many things that we might not have seen on our own.

It was an AWESOME cruise! The Captain and Guide were super friendly and knowledgeable. I really enjoyed myself. Very beautiful area!!!! Will definitely go again when we go back!

100% recomend this tour. Great views of the city with the best tour guide. If you want to see and know the city jump in this tour. ;)

The trip was wonderful but the directions for where to meet were terrible!! Please put a sign up that says, Meet Here for Cruises!!!