Whether you are excited by the city’s rich history, panoramic views from the lighthouses, the creative culinary scene, or the architecture of the East End, there is a Portland tour just for you. First, decide how you’d like to see the city — by boat on the water, rolling around on two wheels or four, or walking through the city streets.
By Water
Portland is known for its working waterfront, so it is only fitting that some of the best views the city has to offer can only be seen from the sea. Explore the city from Casco Bay and learn about the rich maritime traditions of Maine from expert guides on historic ships.
The Rocky Bottom Lobster Demonstration Tour offers a chance to experience the life of a Maine lobsterman for a day on their working fishing vessel, the Wild Duck. The hour-and-a-half tour offers views of the city from the water and the chance to haul and set lobster traps.
Not interested in working on vacation? Opt for a sunset cruise instead and leisurely enjoy the working fishing boat by the light of the fading summer day. Complete the experience by adding on a lobster roll from Luke’s Lobster.
If you’re looking for a unique experience out on the water, SeaPortland offers a wide range of tours and cruises including a Sunset Harbor Cruise, Scenic Harbor Lighthouse Tour, and a Fort Tour on a Private Island.
An appealing tour for historians and imbibers, during the Island Rum Cruise, sip, sail, and uncover Portland’s rum heritage! While seated on the pier of House Island, home to Fort Scammel, discover the secrets of renowned distilleries, learn about legendary rum smugglers, and indulge in the flavors of carefully crafted rum samples.
These small group charters each come with a tour guide and ship captain, each dedicated to exceptional service while you are onboard. Their two historic vessels were built in and designed for the Maine coast, scattered with handmade details and personal touches. Every 2-hour charter has the option to order locally-sourced food and beverages. The sunset dinner cruise includes a chef onboard for a freshly prepared meal to enjoy on the water.
Portland Discovery Tours runs cruises from April – October, offering a wide variety of tours, from a 60-minute Lighthouse Lovers Cruise to a more expansive Harbor Lights and Sights Cruise. They also offer trolley tours of the city – and the opportunity to combine the two for a package land-and-sea tour. Additionally, they are dog friendly!
Take in the scenic views of Casco Bay and Portland’s lighthouses with a glass of good wine in hand. On weekends from June-October, Sommelier Erica Archer leads themed educational cruises around the Bay, exploring wine regions, styles, and grape varietals. Each 2-hour Wine sail includes a box of snacks and wine tasting to enjoy while exploring Maine’s waterways.
Looking to get a little closer to the water? Head to East End Beach for a sea kayak or paddle board tour. Take the 2-hour sunset kayak tour for sunset views over the city, to the 3-hour tour to Fort Gorges, which can only be accessed from the water by small vessels. Portland Paddle also offers tours via stand-up paddle board, including a unique once-a-month full moon tour. If you love the idea of seeing Maine from the water, they offer multi-day excursions to nearby islands
By Wheel
Worried about seasickness? Stay dry and see the entire city – and its beautiful surroundings – on wheels. Whether by luxury bus or pedal power, Portland offers a variety of tours focused on all that this city has to offer: history, food and beverage, stunning vistas, and plenty of personality.
Maine is famous for its craft beer scene, so of course there is a tour based on beer. Take the Brews Cruise for a behind-the-scenes look at Maine’s craft breweries, distilleries, and wineries. Their all-inclusive model includes sample flights at each stop, snacks and water on the bus, and a designated driver to make sure you finish the day safe and sound. They offer options to visit just breweries or a mix of breweries and local distilleries, always with at least one stop behind the scenes at a production facility. If the bus isn’t your style, they also offer bike and walking tours.
From May-October, Summer Feet Cycling offers a variety of both guided and self-guided bicycle tours. Their 2.5-hour Around the Peninsula Tour offers a sampling of Portland’s history and architecture, waterfront views, and a few hotspots to check out after the ride. If you’re more comfortable on the bike, try the daylong lighthouse tour for 5 lighthouse stops and a Maine lobster roll.
The Scenic Route focuses on a small group tour style, with passionate local guides excited to interact with each guest. Their City & Lighthouse Tour takes a 2-hour route through Portland’s highlights with a 30-minute stop at Portland Head Light to take in the craggy coastline.
This 60-minute cross-category tour takes you by both land and sea through the city and Casco Bay. It is a great way to orient yourself to the town through history and hot spots, with signature duck tour humor.
This 50-minute city tour on a vintage fire engine is fully narrated by local guides, and outfitted with a flat-screen TV to show historical images of the city’s hotspots. It is intentionally shorter than other trolley tours, designed to get you excited about Portland before setting you free to explore on your own.
Explore the coastline on a 2.5-hour tour of Portland’s scenic lighthouses, with stops to walk around Portland Head Light, Spring Point Ledge Light, and Portland Breakwater. Portland Explorer’s 12-seat Ford transit van includes a flatscreen TV for slideshows during the tour, Owner-guide Eric is a lobsterman during the offseason, so he has plenty of stories about Maine’s coastline to share.
Owner-guide Derek is a college librarian in the winter and a tour guide in the spring, summer and fall. He loves to dig into Portland’s history and find the best stories to share. Born and raised in Portland, Derek takes pride in providing an informative and entertaining tour, using his life as a Maine local to narrate his 1-hour and 45-minute full city historical tour, which also includes stops at three nearby lighthouses.
By Foot
Take things slow and get an on-the-ground look at the city by hitting the cobblestone streets. Portland’s waterfront offers endless history and culture in a compact geographical area, making it perfect for on-foot exploration
Maine Day Adventures used to be known as Maine Foodie Tours. Their flagship tour is a 3 hour walk through the Old Port and beyond sampling Maine classics, local artisanal goods, and the work of up-and-coming creatives from the city’s bustling food scene.
They’ve expanded their offerings to include not only culinary tours, but historical walks, garden tours, doggy walks, oyster adventures, and more. Each tour is a walk through time exploring the history and future of the vibrant city of Portland. All food samples are included in the cost of a ticket, and they offer accommodations for many dietary restrictions.
These walking tours focus on three distinct neighborhoods of the city through three themes; the Western Promenade, Homes of Portland’s Golden Age, and India Street: immigration and innovation. Each 60-75 minute tour is led by a passionate volunteer guide with deep knowledge of the city’s history. This one isn’t for last-minute planners, though. They require booking a week in advance. Missed the booking window? They offer self-guided walking tours on their website.
Have you ever wanted to delve into the dark and haunted history of Portland? Yes? Then a Wicked Walking Tour is the tour for you!
Combining entertainment with education, these tours explore the truly remarkable legends and history of haunted Portland while discovering little known facts that will leave you in awe. With Wicked Walking Tours uncover the secrets that lie beneath the surface as their team guides you through the shadowy corners of the city. Their seasoned performers bring the past to life with rich storytelling, clean stand-up comedy, and even hysterical impersonations. Brace yourself for street theater and more surprises along the way!
Touted as “the sweetest walk there ever was,” this 75-minute walking tour stops at three of Portland’s favorite donut shops: The Holy Donut, Eighty 8 Donuts, and HiFi Donuts. Not only do you get to skip the line at each location for samples, but you also get a dose of the city’s history as you cross through the Old Port between stops, past City Hall, the Old Customs House, and the city’s working waterfront.
Offering two exciting tours for history buffs! During the 2-hour, 2-mile Old Port Historic Walking Tour, explore over 50 historic stops including historical landmarks, architecture, and monuments. This is an exciting historical adventure for all members of the family!
Looking to add in a quick workout during your sight seeing? Check out the Historic Workouts tour. A full body workout, this tour consist of speed walking and/or light jogging past many historic buildings to landmarks learning historical facts and anecdotes of the area’s rich history since 1632.
If you’re looking for an alternative to the mainstream tour stops, this walking tour is a wonderful way to see both the city’s major landmarks and many hidden gems. Through their Black History Tour, Hidden History Tour, and Crime and Injustice Tour, Portland by the Foot focuses on the surprising and often untold stories of marginalized people and histories with a 2-hour, 1.5-mile walk.
This 75-minute walking tour through the Old Port blends comedy, history, and a few spooky legends. Each tour is led by a professional actor and guide, who is sure to not only educate but entertain with authentically researched stories about ghosts, witch trials, and pirates delivered in stand-up style. They offer both daytime and nighttime tours to fit into your busy vacation schedule.
However you choose to see the sights, Portland’s tour guides are eager to show you the history, personality, and hidden gems of this wonderful city by the sea.
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