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Top Portland Tours, Sightseeing & Cruises

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Vintage Fire Truck Sightseeing Tour of Portland

Vintage Fire Truck Sightseeing Tour of Portland

star-5
Visit Portland’s scenic coast, historic sites and most vibrant neighborhoods with a sightseeing and shopping tour on a classic fire engine. Get great views of picture-perfect lighthouses and architecture from high up on the engine, and listen to live narration as you tour the city. Learn about Portland’s maritime past as you explore cobblestone streets with enjoy plenty of time to browse souvenir shops and sample the area’s most distinctive foods. Finish your tour in the heart of downtown, near historic wharves, restaurants and boutiques.
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  • 50 minutes
  • Free Cancellation
  • Taking safety measures
From
$35.00
From
$35.00
Taking safety measures

Whimsy & History

Loved this tour! Fun & cool. Full of history. So well done. My fave tour ever. They hit all the important spots. My baby loved the fire truck. So different from all the tours of my life!

AnnMarie_C, Aug 2020

19 Portland Tours, Sightseeing & Cruises | All Portland Tours

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The Real Portland Tour: City & 3 Lighthouses Historical Tour with a Real Local

The Real Portland Tour: City & 3 Lighthouses Historical Tour with a Real Local

star-5
Explore the heart of Portland and head out to see some of the area's hidden gems and less-visited spots with this guided sightseeing tour. Your guide, a born-and-raised Portlander who works as a college librarian by day, shows you off-the-beaten-path locations and shares with you all sorts of local lore along the way.
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  • 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$42.00
From
$42.00
Taking safety measures

Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat

Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat

star-5
Charter a vintage lobster boat, dubbed MONHEGAN, and set sail with this two-hour tour into Casco Bay. You'll get great views of the Maine coastline, passing by four lighthouses as you go. This is a great opportunity to take photos of the coastline and waters, while learning about local nautical history from a knowledgeable captain.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$358.98
per group
From
$358.98
per group
Taking safety measures

Private Sunset Charter on a Vintage Lobster Boat

Private Sunset Charter on a Vintage Lobster Boat

star-5
Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses and natural feature, and you're welcome to bring food and beverages, even the adult kind, on board.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$358.98
per group
From
$358.98
per group
Taking safety measures

Portland Tall Ship Cruise on Casco Bay

Portland Tall Ship Cruise on Casco Bay

star-5
What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$68.33
From
$68.33
Taking safety measures

Hovercraft Tours of Portland Maine

Hovercraft Tours of Portland Maine

star-5
It is the only hovercraft tour on the East Coast. We travel into areas to see natural beauty and wildlife that no other can access . The craft travels at speeds in access of any other tour which allows for more to be seen in the same amount of time. We can get a closer look at historical sights do to our shallow draft capability. If you would like a customized tour there is no limit to the possibilities. Find a remote beach for a picnic or go to that secluded Island restaurant. Observe Osprey and Eagles in their environment and watch seals swim and fish off the ledges of the Bay.
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$65.00
From
$65.00
Taking safety measures

5 Lighthouse Bike Tour with XL Lobster Roll

5 Lighthouse Bike Tour with XL Lobster Roll

star-5
Discover Portland Maine and the shores of Casco Bay by bicycle! Join us for the 5 lighthouse bicycle tour of Portland, Maine featuring the Maine coast, lighthouses, and Portland’s history. We have made some modifications to the 5 Lighthouse tour in response to COVID-19. We have modified the tour to allow us not to have guests in our vehicles. As a result of this change, guests will begin biking from the Ocean Gateway and return to the Ocean Gateway by bicycle.  Groups will generally see only 4 lighthouses (Bug Light, Spring Point, Portland Head Light and Ram Island Ledge). Lunch will be provided by we will source all food from vendors.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$132.31
From
$132.31
Taking safety measures

Around The Peninsula Bike Tour

Around The Peninsula Bike Tour

star-5
Explore the Portland Peninsula by bike with this guided tour. Start at the Eastern Promenade, making your way along the waterfront bike path until you reach the Back Cove Trail. Your guide takes you to the Old Port to see some of Portland's prettiest old brick buildings, and you learn the significance of local food, history and culture of this area.
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  • 3 hours
  • Free Cancellation
From
$60.52
From
$60.52

A Walk Through Time in Portland - History Tour

A Walk Through Time in Portland - History Tour

star-5
Curious about Portland's history with railroads, fires, wars, famous poets and Hollywood producers? Join us for a Walk Through Time! This tour begins on Commercial Street and continues for 2 hours through the historic Old Port, downtown and waterfront areas, sharing highlights of Portland's history since 1632. Some of the locations we may feature on your tour include; the lobster statue, the home of Henry Wadsworth-Longfellow and his place of worship, the Eastern Cemetery, the Abyssinian Church, the U.S. Customs House and more. ***Tour duration is two "ish" hours, based on guest engagement and pace of the group. Planning on 2.5 hours for arriving early to check-in and make it back to your vehicle post tour is recommended.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$34.95
From
$34.95
Taking safety measures

Portland: Old Port Culinary Walking Tour

Portland: Old Port Culinary Walking Tour

star-4.5
Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.
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  • 2 to 3 hours
  • Free Cancellation
  • Taking safety measures
From
$109.00
From
$109.00
Taking safety measures

Private Narrated Portland Sightseeing Tour Aboard Vintage Fire Engine

Private Narrated Portland Sightseeing Tour Aboard Vintage Fire Engine

star-4.5
Hop aboard a vintage fire engine for this short sightseeing tour of Portland. You'll drive past some of the city's most beautiful sites, including its old lighthouses and pretty buildings. A knowledgeable guide will be onboard to narrate the tour, while photographs provided by the Maine Historical Society will play on a large flat-screen TV!
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  • 50 minutes
  • Free Cancellation
  • Taking safety measures
From
$190.00
per group
From
$190.00
per group
Taking safety measures

Private Full-Day Trip To Kittery Premium Outlets From Boston

Private Full-Day Trip To Kittery Premium Outlets From Boston

Find great deals on world famous brands on a private full-day shopping tour to Kittery Premium Outlets in Maine. Located only 60 miles north of Boston near the coast, the outdoor shopping center offers popular brands like Cole Haan, Old Navy, and Calvin Klein at low prices. You can stop at the mall's dining venues when needed, and store your purchases in your spacious private vehicle. Relax in your comfortable private vehicle as your own private driver takes you between your Boston hotel and the outlet mall with ease.
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  • 8 hours
  • Free Cancellation
From
$681.31
per group
From
$681.31
per group

Portland, Maine Lighthouse Tour

Portland, Maine Lighthouse Tour

star-5
Explore Portland and Historic Landmarks from a Local Perspective! Experience Portland, Maine in the beautiful summer and fall months with our family owned and operated small group tour. Visit 3 lighthouses for epic photo stops and tour through the working waterfront to see how the lobster industry operates year round. We will be walking through the waterfront streets so please wear comfortable walking shoes. This tour is entirely on land, we will be driving to the 3 lighthouses. This tour may change slightly based on the weather and group or as the State of Maine regulations change with social distancing guidelines and safety requirements for parks and local establishments.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

The Eastern Promenade: Explore the sounds and vistas on an audio walking tour

The Eastern Promenade: Explore the sounds and vistas on an audio walking tour

This self-guided GPS audio walk brings you through one of the most beautiful vistas in Portland, Maine. It starts with a spectacular overlook of Portland Harbor, Casco Bay and the islands, and continues down by the waterfront to East End Beach. Along the way, you’ll hear stories from a local about what it was like growing up on Munjoy Hill and having access to the Eastern Prom. As you cross the railroad tracks, you’ll hear from the engineers that keep the historic steam engines running. Included are tips on what birds to look out for depending on the time of year. Put on a pair of headphones and start the tour by downloading the app. The audio plays automatically at exactly the right place using your smartphone’s GPS. This self-guided tour is narrated by Dianne Ballon - a sound artist, sound designer and an avid bird watcher. She invites you to discover through sight and sound the Eastern Promenade — a place she returns to in all seasons.
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  • 25 to 45 minutes
From
$5.20
From
$5.20

Portland: West End Walk Through Time

Portland: West End Walk Through Time

Wend your way through the West End of Portland, an often overlooked section of town, deep in history.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$34.95
From
$34.95
Taking safety measures

Pedal Peaks Island Day Trip from Portland

Pedal Peaks Island Day Trip from Portland

star-5
Get to know Peaks Island on this cycling day trip from Portland. Traveling via bicycle means you're not trapped behind bus or car windows and you can really experienced the island air. Pedal around the island, stopping for lunch, with a small group; this group size ensures personalized attention from your guide and plenty of chances to ask questions.
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  • 5 hours
  • Free Cancellation
From
$128.21
From
$128.21

Stand Up Paddleboard Tour in Casco Bay

Stand Up Paddleboard Tour in Casco Bay

star-5
Enjoy a relaxing morning paddleboarding along Portland's Casco Bay. After a brief instruction, set out for a stand-up tour of the area—searching out native wildlife such as great blue herons and osprey as you slowly explore the waters. Learn about the area's fascinating history, from ways Native Americans used the land to how lobsters play a big part in the local economy. This leisurely and informative 2-hour tour includes an on-shore snack break before making your way back to Mere Point.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$50.00
From
$50.00
Taking safety measures

Portland Scavenger Hunt: The Maine Event

Portland Scavenger Hunt: The Maine Event

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.
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  • 2 hours
From
$12.31
From
$12.31

Fall Foliage Private Sightseeing Cruise

Fall Foliage Private Sightseeing Cruise

star-5
Take in the famous autumn foliage of New England during a private 2.5-hour sightseeing cruise from Portland. With room for six people, it's an ideal intimate experience for couples, friends, or families. It’s also a great opportunity to photograph the leaves and wildlife from a unique perspective. Learn about the area from your private guide as you cruise at a gentle pace.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$435.90
per group
From
$435.90
per group
Taking safety measures

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Things to do near Portland


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