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

Two Hour Lighthouse Bicycle Tour from South Portland-Mellow

(52)

from $75

Brewery-hop at brunch time—and visit several of Portland's best-known breweries and beer bars—on this small-group tour. With round-trip coach transit included, you can leave the driving to someone else and focus on enjoyment. Head to breweries that locals love, and enjoy in-depth tours and tastings, plus a light snack to help soak up those suds. By the end of the trip, feel newly immersed in one of the country's top craft beer scenes.

Portland's Best Craft Beverages Bus Tour

Portland's Best Craft Beverages Bus Tour

2 hours 30 minutesFree Cancellation

(38)

from $119

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

MONHEGAN is equipped with a finely finished wooden table in between cushioned "booth style" benches

Price varies by group size

(66)

from $380

Sunset Lighthouse Cruise Along Casco Bay

Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your favorite wine or beer and a delicious meal, and unwind as we cruise through the serene waters of Casco Bay. Journey aboard Ruth—a charming 39-foot classic picnic-style tour boat crafted in 1935 at Handy Boat in Falmouth, Maine. Don't miss out on this unique sunset experience!

Sunset Lighthouse Cruise Along Casco Bay

1 hour 30 minutesFree Cancellation

(37)

from $69

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.

Portland Paddle uses both tandem and solo kayaks

Sunset Sea Kayak Tour on Casco Bay

On this walking tour, we’ll explore the city’s significant role in the Underground Railroad and the individuals who helped shape its fight for freedom. The tour is self guided on our walking tour app. It's hands free, plays as you walk and you can go at your own pace, anytime, it never expires. You’ll walk through historic streets where ordinary citizens took extraordinary risks to assist those escaping slavery. We’ll visit former homes, churches, and workplaces that served as safe havens and meeting places for abolitionists, reformers, and community leaders. Each stop demonstrates how Portland’s waterfront and neighborhoods became centers of courage, compassion, and quiet resistance. Let’s start our journey at the Mariner’s Church Banquet Center, a landmark that saw both Portland’s growth and its dedication to justice.

(107)

from $60

Portland Underground Railroad Self Guided Audio Walking Tour

Portland Underground Railroad Self Guided Audio Walking Tour

1 hour to 1 hour 30 minutesFree Cancellation

3.7

(3)

from $10

Explore one of Maine’s most picturesque boating destinations—and enjoy a more up-close experience of the sights than most other tours offer—on this excursion by rigid inflatable boat. Departing straight from the marina, you’ll set off into the bay with just a small group for company. Spy the region’s many islands and lighthouses; look out for seals, porpoises, and other wildlife; and really immerse yourself in the maritime scenery.

Guided RIB Boat Adventure of Portland

1 hour 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.

(35)

from $69

Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll

5 hoursFree Cancellation

(153)

from $165

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

Price varies by group size

(41)

from $407

As we cruise the waters around Portland Harbor we will make stops at Portland Breakwater Light, Spring Point Light and Ram Island Ledge Light before stopping at Maine’s oldest and most iconic lighthouse, Portland Headlight. This historic beacon, with its striking architecture and stark coastal backdrop, is a sight to behold from the perspective of the Atlantic Ocean as seafarers have done for more than 200 years. After photos and information about this iconic lighthouse, we continue the ride along the rocky shores of Cape Elizabeth to Two Lights State Park, whose twin lighthouses perch atop dramatic cliffs. Our best chance for wildlife comes during the next leg of the ride as we cruise open waters to Halfway Rock Lighthouse, a true maritime relic. Standing proudly on a remote ledge in the open ocean, it has guided mariners through thick fog and turbulent waters for over a century. Seals are often found hanging on the rocks and feeding in the nutrient-rich waters.

Seven Portland Lighthouses Tour

Experience historic architecture, harbor views, and rich seaside culture with this driving tour of Portland, Maine! Cross the cobbled streets of Old Port, chock full of shops, restaurants, and bars, all complemented by the sparkling bay. Dive into the city’s long and embattled history at a church still sporting British cannonballs. See iconic Maine lighthouses and visit pristine beaches. Portland may be a small city, but it packs a big punch! Purchase one tour per car, not per person. Everyone listens together! 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.

4.1

(28)

from $109

Special Offer

Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

1 to 2 hoursFree Cancellation

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, Maine: Black History Guided Walking Tour

Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

(150)

from $54

3 hoursFree Cancellation

On this smartphone-guided adventure, you'll see Portland’s historic streets and discover its stories. Go at your own pace, anytime. The tour never expires. The tour is professionally produced with pro narration and music. It's location-aware walking step by step through the city. You’ll see the cobblestones streets, wharf street, Henry Wadsworth Longfellow’s home, stops on the underground railroad, city hall, exchange street, the lobster square, historic buildings, and the best spots to eat, including the best donut shop ever. Really, it’s that good. You'll hear the stories of Portland, Anna Kendrick’s favorite hangs, Longfellow’s history, stories of lighthouses, adventure, prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, colonial times, and much more.

(118)

from $115

Audio Guided Walking Tour from Old Port of Portland, Maine

1 hour to 1 hour 30 minutesFree Cancellation

4.3

(56)

from $8

Portland Tall Ship Cruise on Casco Bay

The most immersive way to see Historic Portland is on foot. Our 1 hour 15 minute walking tour takes you down the cobblestone pathways of our historic city in search of spirits that linger from times long past. Our knowledgeable guides will enchant you with tales of Portland’s most renown ghosts as well as the area's vast and rich history. You’ll hear fascinating and spooky tales from the first European settlement in 1632 right up to the present day. Discover the many times Portland has fallen and risen anew, and hear about the restless spirits who remain, unable or unwilling to move on. Follow our guides as they lead you by lantern-light sharing the ghost stories, legends, and folklore of this beautiful city.

4.6

(237)

from $100

Jeff shows off the Clapp House where an old sea captain is reported to still patrol the grounds.

Walk With Ghosts in Portland

1 hour 15 minutesFree Cancellation

4.6

(77)

from $33

Portland Explorer: Mobsters and Lobsters True Crime in Old Port

Step into the shadows of Portland’s past on this thrilling true crime tour, where secrets lurk behind historic facades and cobblestone streets whisper tales of corruption, violence, and vice. From ruthless mobsters and bootleggers to power-hungry bosses and shocking scandals, this tour unveils the darker side of Maine’s largest city. Walk the very streets where speakeasies thrived, deals were made in the dead of night, and blood was spilled in the name of power. Led by expert guides, this journey through Portland’s underworld will leave you with spine-tingling stories you won’t soon forget. Dare to explore the city’s past? Book now—if you’re brave enough.

Portland Explorer: Mobsters and Lobsters True Crime in Old Port

1 hour 30 minutesFree Cancellation

Discover the rich history of Fort Williams park, Portland Headlight and Casco Bay on this captivating guided walk. Designed for both history lovers and casual explorers, this tour offers an immersive journey from the majestic Portland Head Light, along the beautiful cliff walk path to the crumbling relics of the Fort's past. You will learn about Maine's past with a knowledgeable local tour guide and have opportunities to stop for photos of the iconic lighthouse on this tour. What to Expect: Start Point: Portland Headlight Parking Lot End Point: Ship Cove Duration: Approximately 1 hour Distance: About 0.8 miles of walking Audience: Perfect for families, new visitors, history buffs, and anyone curious about Maine’s legendary coast.

(4)

from $56

Portland Head Light and Fort Williams Walking Tour

Portland Head Light and Fort Williams Walking Tour

1 hourFree Cancellation

Casco Bay Half-Day Sea Kayak Tour

(9)

from $35

4 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.

(58)

from $85

Special Offer

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

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

Step into the shoes of a newly-minted detective, tasked by Commander Mahoney to solve a gripping case. murder on the streets of Portland. Throughout this crime-solving audio adventure, visit each of the 10 mapped locations. You'll have the option to explore the downtown area using the Walking Map or follow a Driving Map on the city's outskirts. Refer to ‘Meeting Point’ for the starting location. See images for route. Park or stop at each location, listen to the audio story, and put your detective skills to the test by gathering clues and piecing together the evidence. Finally, make your deductions and issue an arrest warrant. Your overall detective skills will be evaluated, culminating in a Case Performance Score to measure your sleuthing prowess. This game is suitable for solo detectives, dynamic duos, or groups of mystery enthusiasts, offering an immersive audio tale filled with intrigue.

(1)

from $10

Murder Mystery Detective Experience in Portland ME

Murder Mystery Detective Experience in Portland ME

2 hours 30 minutesFree Cancellation

3.5

(2)

from $15

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yacht designer, John Alden. Heart's Desire measures 53' feet and features some of John Alden's trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine.

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

Discover the beauty of Northwest Casco Bay on a 3-hour morning kayaking tour. No experience is necessary, as you get a crash course before the tour begins and your guide is on hand at all times. Double kayaks are available, if you prefer to paddle tandem. See Brunswick and its native wildlife from a unique vantage point. Then enjoy complimentary snacks and a brief land excursion, before your return.

(2)

from $675

Per group

Oyster Farm & Complimentary Tasting Sea Kayak Tour in Casco Bay

Oyster Farm & Complimentary Tasting Sea Kayak Tour in Casco Bay

3 hours

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

(36)

from $99

1 2 3 4 5

What are people saying about Portland

Sandy_C, Jun 2026

Absolutely worth taking this tour!!!

Very enjoyable! I love a tour that is run by a person with personality and Derek is that guy. It’s his own business and he’s a long time local that knows soo much. I love his stories about his parents how they are part of his ‘company’ . Thoroughly enjoyed this tour. We were in Bar Harbor when another couple recommended it.

Vintage Fire Truck Sightseeing Tour of Portland Maine

Arlene_I, Jun 2026

Most enjoyable and worthwhile.

It is easy to get onto the seated area. Seats are comfy. Tour leader was excellent, very good voice quality, spoke clearly and paced the information perfectly…also had a sense of humor. Liked the technology as well. Well done. I have been on the Trolley Tour and the fire engine but I liked the fire engine better because it was smaller and you could see and hear the narrator as the engine was roaming the city,,.

Harbor Lights and Sights Cruise

Briand_l, Jun 2026

Great time on Casco Bay

The boat tour around Casco Bay was fantastic! The crew and our guide were all very friendly and helpful as we cruised around the bay and saw several lighthouses and other interesting sites. They also serve beverages on board which, for the adult variety, were reasonably priced.

Sunset Windjammer Cruise Along the Coast of Portland Maine

brenbren713, Jun 2026

Very lovely!

This was a beautiful experience. If you want to enjoy yourself on a windjammer to be at peace, this is the excursion for you. The crew and captain will answer questions, but they'll allow you to enjoy the experience. I would recommend wearing a windbreaker or bringing an extra layer but it was absolutely lovely. We were on the Bagheera and were able to see some sail races as well.

Sunset Lighthouse Cruise Tour from Casco Bay

Michael_B, Jun 2026

Memories made, worth every cent paid!

Our guide and our captain were just tremendous! We did not expect such a wonderful, history-biology-geography-cultural immersion along the way, but it was such a highlight of a fabulous trip to Maine and Quebec. We planned it for our last night so that we could end it (SAD!) on a special note, and it did not disappoint. Our hoodies and long pants were perfect, temperature/weather-wise. Our guide was personable, knowledgeable, humorous, serious--all of the things that make a tour fantastic, and I love the route design which allowed us to see far more than we could have experienced, even having our rental car. I see why these tours are so popular; do not hesitate to book it! Kudos and God's greatest blessings to your wonderful team! P.S. Kudos to our Heavenly Father for the unforgettable sunset...Psalm 19:1!

Afternoon Lighthouse Cruise Along the Coast of Portland Maine

Kathy_M, Jun 2026

Fun cruise to Lighthouses and Forts!

This is a nice cruise that let's you see several lighthouses and forts. We also saw sea birds and a porpoise. Colter, our guide, was an entertaining and fun guy! Our boat captain did a great job navigating choppy waters. It was raining at first but the weather cleared-up and it was dry when we returned. We visited Luke's Lobsters at the end of the pier where we had gotten on the boat. The lobster roll was excellent!

Port City Lights Cruise

Caitlin_M, Jun 2026

Lighthouse lovers rejoice!

Great little cruise around Casco Bay. Saw four (five?) lighthouses and enjoyed the sunny day, the breeze, and the crew commentary. Basically had the whole lower deck to ourselves and did the titanic on the bow. 10/10. Definitely go to the Portland Head Light up close if you have time, but if not this is a good glimpse of the most photographed light house in the US.

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

Jason_B, May 2026

Great Tour - A Must Do!

Derek and Zack greeted us at the meeting location as we got settled in. Both are super friendly and down to earth. Derek was our guide, and he was super informative, funny and laid-back. Great to have someone local to share experiences and history throughout the tour. My wife and daughter loved the tour as well, and we had tons of great pictures. Highly recommend!

Old Port Culinary Walking Tour from Portland

briannebinford, May 2026

Delicious and Worth the Cost!

A great walking tour, we loved all the stops and the food was delicious. Ray knew the city really well, he had great stops for us to go to and we really enjoyed everywhere he mentioned for after the tour. We definitely felt we got our money's worth as the portions were appropriate and honestly we didn't even need dinner!

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

Lindsay_G, May 2026

The donuts are delicious...

The donuts are delicious and fresh. Loved walking around the waterfront - particularly the Portland history and lobster industry information. Our host also provided recommendations for other notable local foods to try. A great way to have a treat and explore!

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Christine_C, Sep 2025

High Point of the Trip to Portland

It’s really sailing! On an amazing antique schooner. It was glorious. We were lucky to have wind and sun. Captain and crew were wonderful. It was a quiet sail but they were very friendly answering any questions regarding place or sea life. We could be sociable or just enjoy the sail quietly.