All Portland Tours &amp; Excursions in 2026 - page 2

Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

3 hoursFree Cancellation

Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

3 hoursFree Cancellation

Portland Tall Ship Cruise on Casco Bay

Small Group Sunset Lighthouse Boat Cruise With Local Drinks

1 hour 30 minutesFree Cancellation

A Walk Through Time Tour in Portland

Lighthouses are an iconic image associated with coastal Maine and Portland showcases some from the 1800s. Join this bicycling tour in Portland and see two of the city’s lighthouses from the 19th century. Follow quiet roads along South Portland’s coast to reach a small lighthouse called Bug Light, still in use today. Ride farther to Spring Point where a larger lighthouse awaits at the end of a long granite breakwater.

Two Hour Lighthouse Bicycle Tour from South Portland-Mellow

Small Group Afternoon Lighthouse Boat Cruise With Local Drinks

1 hour 30 minutesFree Cancellation

Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

Explore the charm, history, and vibrant culture of Portland, Maine with this self-guided walking tour! Immerse yourself in the sights and sounds of this picturesque coastal city as you traverse the cobblestone streets of Old Port and downtown. Learn about the city’s long, embattled history as you pass the myriad of shops, bars, and eateries which have put it on the map. And discover secrets only locals know! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Portland Maine Self-Guided Walking Audio Tour

Portland Maine Self-Guided Walking Audio Tour

1 to 2 hoursFree Cancellation

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

Hop on the “Guardians of the Harbor” trolley tour, a narrated journey with three lighthouse stops. Explore Portland’s maritime history and scenic beauty, disembarking at each location. First, visit Bug Light Park and the Liberty Ship Memorial, reflecting wartime shipbuilding. Next, discover Fort Preble and Spring Point Ledge Light, learning its unique construction and the remaining WWII gun batteries. Finally, witness the iconic Portland Head Light at Fort Williams Park, Maine’s most vital and the nation’s third oldest lighthouse, also revealing remnants of coastal defenses. The nation’s third oldest lighthouse and one of Maine’s most important beacons. This area also features great examples of remnants of coastal defenses.

Guardians of the Harbor Trolley Tour

2 hours 30 minutesFree Cancellation

Discover the lighthouses and coastal landmarks of Portland on a small-group biking tour. Hop on a provided bicycle and follow your guide to the Bug Light, Spring Point Ledge, and Portland Head lighthouses. Along the way, learn about their storied histories. Other highlights include the Liberty Ship Memorial, Cape Elizabeth, and Willard Beach. Set at a leisurely pace, the adventure also includes a complimentary lobster roll lunch at an award-winning food truck.

Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll

5 hoursFree Cancellation

Introducing Portland’s World of Flavors Walk highlighting hidden gems and great flavors that give Portland its cosmopolitan flair. Enjoy this walkable city with a big palate on our international journey, tasting locally sourced foods prepared with the recipes, customs and spices from other lands. On this 2.5-3 hour tasty romp through Portland’s historic Old Port and waterfront, you will enjoy the flavors while learning their food pathways and the owners journeys to Maine. Portland’s World of Flavor serves up a diversity of tastes and ethnicities in a compact area, packing a punch of flavors you will love. All tour experiences are highly educational and entertaining with trained, local guides.

Portland's World of Flavors Tour

3 hoursFree Cancellation

Explore the beauty and history of Portland with this combo of a walking and driving tour. Dig deep into the city’s history as you stroll down cobblestone streets and admire old brick architecture by the waterfront. Visit bustling neighborhoods like Old Port and the Art District, stop at shops and restaurants whenever you please, and breathe in the coastal air. Then take a drive out to the east and west promenades, before swinging down to the famous Portland Head Light lighthouse. It’s the most comprehensive way to experience this unique, quirky city! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

3 to 5 hoursFree Cancellation

Discover the vibrant history of Portland’s Old Port on this engaging walking tour. Wander through cobblestone alleys and merchant blocks rich with stories of sailors, reformers, and immigrants. Learn about the Portland Freedom Trail, which honors the city’s fight for freedom and civil rights. The tour showcases the Old Port’s architectural charm and its transformation from a bustling shipping hub to a cultural center. Experience the tales of resilience embedded in its streets, from the Great Fire of 1866 to the revitalization efforts of the 1970s. Join fellow history enthusiasts for a memorable journey through Portland’s past and present. — Explore the historic Old Port district, a cultural and commercial hub — Walk along the Portland Freedom Trail, learning about civil rights — Discover stories of resilience, fire, and maritime life — Ideal for history lovers and those curious about Portland's heritage

Self-Guided Audio Tour of Portland’s Historic Old Port District

2 hours to 2 hours 30 minutesFree Cancellation

Experience the breathtaking beauty of New England’s White Mountains on this private guided tour from Portland, Maine. This full-day adventure combines spectacular mountain scenery, historic rail travel, charming villages, and iconic landmarks that showcase New Hampshire’s famous mountain region. The highlight of the tour is the Mount Washington Cog Railway, where guests board the historic train and travel to the summit of Mount Washington, the highest peak in the northeastern United States. At the summit, guests can enjoy panoramic views, explore the observation area, and visit the small museum. The tour also includes scenic drives along portions of the famous Kancamagus Highway, widely considered one of the most beautiful mountain drives in the country. Along the way we visit picturesque villages such as Jackson and North Conway, see the historic Mount Washington Hotel, and stop at scenic overlooks and waterfalls that make the White Mountains unforgettable.

Private White Mountains Tour with Mount Washington Cog Railway

6 to 8 hoursFree Cancellation

All our tours take place in a comfortable vehicle with a local driver-guide and can be tailored to your pace. This private tour is done in our larger passenger van that can take up to 12 passengers. We’re happy to customize the experience to match your interests. This particular tour covers all the major sights in Portland, followed by a visit to the South Portland lighthouses, including admission to Fort Williams Park to see the Portland Headlight. After exploring Portland, you'll journey down the highway to Kennebunkport, a charming coastal village that served as the summer retreat for former President George W. Bush and his family. While we have a standard route, as a private tour, we can personalize the itinerary to suit your preferences.

Private Portland Lighthouses and Kennebunkport Tour - 12 Pax

Maine's Black community is small, but its history here goes back more than 400 years. On this guided tour, you’ll dive deep into Portland’s Black history, discovering how this community—national leaders, laborers, skilled workers, activists, and more—fought for freedom and equality and defined the state's path. From Frederick Douglass to lesser-known Black Yankees, there’s far more here than meets the eye, and with this tour, you’ll learn all about it.

Portland, Maine: Black History Guided Walking Tour

Portland Pedicab Taxi Reserve

5 to 20 minutesFree Cancellation

Few things are more beautiful than a majestic sunset. However to see it from the waters of Portland's magnificent Casco Bay is a truly remarkable experience. Whether a first-time kayaker or experienced hand, this 2-hour tour offers phenomenal vistas of Portland harbor and cityscsape. Your only neighbors are your guide, your small group and the wildlife as you leisurely paddle back to shore.

Sunset Sea Kayak Tour on Casco Bay

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, historic forts, and natural features. A round of drinks is included to toast the sunset with, but more beverages are available to purchase onboard.

Private Sunset Charter on a Vintage Lobster Boat with Drinks

Our White Mountains Day Tour offers more than just scenic views—it’s a thoughtfully curated journey through New Hampshire’s most charming towns, historic covered bridges, and hidden natural wonders. Unlike larger, rushed tours, we keep our groups small for a more personal experience, allowing time to explore, photograph, and connect with each stop. From the iconic Kancamagus Highway to the massive Madison Boulder, every stop has a story—and our guides bring it to life. Guests also have the option to add a ride on the historic Mount Washington Cog Railway for an unforgettable summit experience.

New Hampshire White Mountains Day Tour

6 to 8 hoursFree Cancellation

Amazing Scavenger Hunt: The Maine Event

1 hour 30 minutesFree Cancellation

This is a fully private Southern Maine coastal experience designed exclusively for your party (2–5 guests). No bus groups. No shared travelers — just your group, your pace, and a relaxed day along Maine’s scenic shoreline. Visit historic York’s colonial landmarks, walk through the Old Burying Ground, and enjoy views from John Hancock Wharf before stopping at Cape Neddick Light, one of New England’s most photographed lighthouses. Continue to Ogunquit for time at Perkins Cove, with the option for a short scenic stroll along the Marginal Way overlooking the Atlantic. In Kennebunkport, enjoy unhurried time in Dock Square to browse shops, walk the harbor, and dine at a local restaurant of your choice. A scenic stop at The Colony Hotel adds classic New England charm and sweeping coastal views. Because this tour is private, the experience remains flexible and comfortable, allowing you to explore at your own pace and focus on the scenery and stories that interest you most.

Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse

6 to 8 hoursFree Cancellation

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Must-Dos in Portland

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What are people saying about Portland

Vintage Fire Truck Sightseeing Tour of Portland Maine

abishop, Oct 2026

Fun Day of Learning

It was a well run tour from taking pictures before to having blankets to keep warm on board and pictures on a screen in case you couldn’t see what we were passing well. Our tour guide, Miles, was passionate about his city’s history and stuck in funny parts throughout. Our 7 year old enjoyed the ride too. Good tip is that the check in is at kiosk not a building so no bathroom.

Sunset Lighthouse Cruise

William_B, Oct 2026

Made our day in Portland

The sunset cruise was just what we hoped for. John shared so much interesting information about the lighthouses and islands we passed, lobstering, and local history; and Howard skillfully navigated usamong the islands and then positioned us to see a beautiful sunset. He also found some rocks where seals and cormorants were resting. Sit on the right side for the best views. Arrive early to get an outside seat on the top deck and dress very warmly.

Sunset Windjammer Cruise Along the Coast of Portland Maine

Jessica_D, Oct 2026

Book this sunset cruise!

This was the best sunset cruise! The crew was so friendly. They offered an opportunity to help hoist the sails for those that wanted a full sailing experience. We had ample space. There’s a bathroom on board and you could bring your own beverage and snacks. Views were amazing in October.

Harbor Lights and Sights Cruise

Brian_S, Oct 2026

Awesome tour, wonderful crew

Excellent tour. I arrived on a cruise ship and the tour dock was very easy to find. It’s about a 10-15 minute walk from the terminal. The tour started right on time and we were back in exactly 1 hour and 45 mins. The crew were friendly and welcoming when we boarded. The captain did the introductions and safety stuff and we were in our way. Amazing views of the lighthouses and diamond islands, casco bridge etc the narration was excellent. Really intelligent guy that definitely knew his stuff. I’ve been to Portland a few times via car but never went out on the water. I learned more about Portland in this under 2 hour journey than every prior trip combined. Highly recommend this tour. Captain Kelton was the captain and Islander was the vessel.

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

Kim_S, Oct 2026

Highly recommend!

This is THE tour to take to truly learn about Portland. Derek gives you the native's perspective of this interesting, vibrant town. He is so engaging and informative! His van is very comfortable and the amplification is strong so his narration could easily be heard. He gave us sufficient time at the various lighthouses to explore, take pictures, etc. We thoroughly enjoyed Derek and this excursion.

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

jim_s, Oct 2026

A Fantastic, Personal Lighthouse Tour!

Great experience! The tour was very personal, with a small group of only about 10 people, (van capacity) which made it even more enjoyable. ⭐⭐⭐⭐⭐ Great experience! The tour was very personal, We had a group of around 10, tour capacity, which made the experience feel intimate and enjoyable. Christian was our tour guide and did a fantastic job. The tour lasted a little over two hours, as we were able to get an early start. We had a wonderful time and would highly recommend this tour to anyone visiting Portland!

Portland Walking Food Tour – Warm Donuts, History & Hidden Gems

Paula_S, Oct 2026

History and donuts

We love to take some kind of historical tour any time we arrive in a city - it helps us to get our bearings to the city and gives context to the stay. So when I found one that added donuts - pure bonus! The donuts were great - especially the part where we got to skip the massive line at Holy Donuts. But even better than the donuts were the fun facts we learned about Portland. Our guide was knowledgable and fun. He didn't let facts get in the way of having fun - he definitely had some embellished stories but gave us full warning they were embellished ;) We also loved that he gave a card with personal recommendations at the end of the tour - it was super useful for our trip. We'd recommend to everyone as a first stop when you arrive in Portland.

Port City Lights Cruise

Joan_C, Sept 2026

Great Tour from a Boat

This was a tour from one of the boats. It was rather windy this day in addition to a lot of boats on the water, so the boat had a lot of movement of rocking and rolling. The guide was very informative and told us about all the light houses we encountered and the Civil War maritime history. He also told about the various people that lived along the shore line where some areas they were only there during the warmer weather and some actually stayed year around. I was amazed to hear that the water temperature never went higher than 50 degrees.

Portland City and Lighthouse Tour

Mary_S, Sept 2026

Informative and Easygoing

My family and I had a great experience! Our guide was informative and even recommended some places to dine at as we toured Portland. We also had a short 20-minute excursion at the park where we saw the lighthouse and watched the waves crash on the bluffs. If you're touring in the fall, I recommend wearing layers in case it gets chilly. This is a nice and easygoing experience for tourists and travelers.

Afternoon Lighthouse Cruise Along the Coast of Portland Maine

Judy_B, Sept 2026

Sisters outing

My two sisters and I scheduled a 3:30 cruise on a Thursday. There were only two other couples, Megan our captain, and Coulter the first mate/guide. The day was pretty overcast but it was fine because it eliminated any glare off the water. We had a blast! Coulter was very knowledgeable about the history of the lighthouses and forts that we saw, and answered some of our questions with hilarious stories. We were lucky enough to spot a couple seals, and Megan also had her super sweet Frenchie Noni with her (seriously adorable and very well behaved.) Although the temps were mid to high 70’s, we had brought windbreakers and hoodies, which kept us very comfortable. The hour and a half cruise was the perfect amount of time for us, and we returned with plenty of time to check out more shops before our dinner reservation.

Afternoon Windjammer Cruise Along the Coast of Portland Maine

MaryLou_G, Sept 2026

Sailing the harbor

We had a beautiful and relaxing ride on the water. Everything was great and the crew were knowledgeable and friendly. The only problem was my own fault as I thought this was a lighthouse tour and it was not. I’m not sure how I messed that up. Even without seeing lighthouses up close, it was an amazing experience.