All Portland Tours &amp; Excursions in 2026 - page 4

Portland Maine Puzzling Adventure Scavenger Hunt Walking Activity

Go beyond the sights of Portland, Maine and take a day trip to Salem, Massachusetts. The town of Salem is known for its famous witch trials that took place in 1692. Learn about the history of Salem on a guided tour through the town and see several landmarks including the Salem Witch Museum, the memorial, and Phillips House. On your way to Salem, stop in Kennebunkport to explore the historic village.

Private Portland to Cape Ann, MA Castles & Coast

8 to 10 hoursFree Cancellation

As night falls on Portland’s historic waterfront, discover why this is the #1 ghost tour in Portland, ME. Operating nightly, year-round, this one-mile walking tour is led by expert local guides who know the city’s legends, history, and hidden corners firsthand. This outdoor-only experience weaves together documented history, local folklore, and chilling tales that bring Portland’s past to life. Along the route, you'll visit iconic locations including Bell Buoy Park, Andy’s Old Port Pub, the Portland Harbor Hotel, and even a section of the Berlin Wall. Each stop is connected to real events, maritime tragedies, mysterious deaths, or unexplained stories that have become part of Portland’s haunted legacy. Perfect for private groups, bachelorette parties, birthdays, and special events, this unforgettable ghost tour is proudly USMC Disabled Combat-Veteran-owned and women- and minority-led, offering an evening of haunting history, immersive storytelling, and unforgettable mystery.

Phantoms Penance and Poltergeists Portland ME Ghost Tour

1 hourFree Cancellation

USD 26USD 25

Book your private Arrival transfer from Portland International Jetport (PWM) to Portland hotels. Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. Our transfers will provide you with such services: meeting with a name plate, door-to-door delivery, no hidden fees, clean cars and professional drivers, which will make your trip more comfortable and safe. We guarantee the quality of the services provided.

Portland Jetport (PWM) to Portland - Arrival Private Transfer

Portland Jetport (PWM) to Portland - Arrival Private Transfer

15 minutesFree Cancellation

USD 85USD 81

Unlike large group bus tours, this experience is designed to be personal, flexible, and immersive. You’ll walk the streets of Salem with a knowledgeable guide who doesn’t just point out landmarks but brings their stories vividly to life—from the haunting legacy of the Witch Trials to the maritime wealth that built the city, and the literary genius of Nathaniel Hawthorne. What makes this tour unique is the balance of history and atmosphere: you’ll explore centuries-old cemeteries and mansions, admire harbor views and gardens, and even encounter touches of pop culture like the Bewitched statue. With small groups and a customizable pace, you’ll have the freedom to linger where your interests lie most—whether it’s taking photos, diving deeper into Salem’s legends, or enjoying a quiet moment in a hidden garden. This isn’t just sightseeing—it’s a chance to experience Salem’s past and present through stories, scenery, and atmosphere in a way that big tours can’t match.

Private Day Tour of Salem MA, from Portland ME

Private Day Tour of Salem MA, from Portland ME

7 to 9 hoursFree Cancellation

There are a lot of ways to get out on the water in Maine, but we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. A half-day sail is the easiest way to get out on the water and see the Maine coast from a completely different perspective. This small group Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, brush up and your sail trim, or just relax and maybe sneak in a swim on a warm day.

Casco Bay Sailing Escape: Half Day Custom Boat Charter

Casco Bay Sailing Escape: Half Day Custom Boat Charter

4 hoursFree Cancellation

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.

Private Half Day Sailing Charter in Portland Maine

4 hoursFree Cancellation

Book your private transfer from Portland International Jetport (PWM) to Portland hotels and return. Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airport transfer. Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. • Meeting with a Nameplate • We track your Flight • Door-to-door Service • No Hidden Charges • Clean cars & Professional drivers

Portland Jetport (PWM) to Portland - Round-Trip Private Transfer

Portland Jetport (PWM) to Portland - Round-Trip Private Transfer

30 minutesFree Cancellation

USD 170USD 161

Experience the beauty of Maine’s central coast on a fully private, all-day tour designed just for you. Unlike crowded bus tours, our small-group experience offers personalized attention, comfort, and flexibility. Travel in style through autumn-kissed landscapes as your local guide leads you to handpicked highlights—like the iconic Portland Head Light, the charming harbor town of Boothbay, and the historic Fort Edgecomb. Walk the gently swaying Androscoggin Swinging Bridge, shop at the legendary L.L.Bean Flagship Store, and take in riverside views in Bath, “The City of Ships.” This is coastal Maine at its finest—tailored, immersive, and unforgettable.

Boothbay, Freeport and Maine Botanical Gardens Private Day Tour

Boothbay, Freeport and Maine Botanical Gardens Private Day Tour

6 to 8 hoursFree Cancellation

Join us for an exciting Private Coastal Tour from Portland to Camden, exploring the beauty and history of Maine’s coastline! Start with Bath, home to the towering USS Wyoming sculpture and rich shipbuilding heritage. In Wiscasset, stroll through “The Most Beautiful Village in Maine” and visit the world-famous Red’s Eats lobster stand. In Rockland, enjoy a walk to the lighthouse and explore its maritime charm. In Camden, wander the charming streets, enjoy lunch, and see a unique waterfall flowing through town. The highlight of the tour is **Camden Hills State Park**, where you’ll take in the most breathtaking views of Midcoast Maine from the summit of Mount Battie. We'll finish with a brief stop at the Maine State Capitol, designed by the same architect as the U.S. Capitol, offering a fascinating glimpse of Maine’s history. This fun and adventurous tour is perfect for exploring Maine’s hidden gems. Book now to experience the best of the coast!

Camden, Rockland, Pemaquid, and Belfast Private Tour

8 to 12 hoursFree Cancellation

Paint Portland, Maine: Small Group Outdoor Painting Experience

3 hours 30 minutesFree Cancellation

Explore the charming coastal towns of Kennebunkport, York, and Portsmouth on this private day tour. Delve into the rich maritime history, enjoy stunning ocean views, and savor local flavors. With a personalized itinerary, this tour offers the flexibility to explore at your own pace, while an expert guide provides insights into each destination. Enjoy a relaxed atmosphere with included snacks, bottled water, and lunch to keep you energized throughout the day. - Private tour lasting approximately 7 to 8 hours - Customizable itinerary to suit your interests - Included lunch, snacks, and bottled water - Pickup from your location in an air-conditioned vehicle

Kennebunkport, York and Portsmouth NH Private Tour

7 to 9 hoursFree Cancellation

While walking tours are helpful for getting oriented, they rely on guides and discourage independent exploration. With this interactive scavenger hunt, explore Portland at your own pace while completing game-like challenges and hunting for particular items along the way. Submit photos of items found around the city, communicate with a game host via chat during the hunt, and compare scores with other teams across the country when you’re done.

Fun Scavenger Hunt in Portland, ME by Operation City Quest

Castles of Cape Anne, Massachusetts - Private Day Tour

8 to 10 hoursFree Cancellation

The streets of Portland, Maine, are the site of this exciting scavenger hunt. Scour these city streets in search of a variety of objects, landmarks, and works of art. You’ll be given clues about the town’s art, history, and culture to help you find your way from item to item. As you find and photograph each item, your team will earn points. Try to get the most points to rank highest on a leaderboard with other teams across the country completing other scavenger hunts.

Portland, Maine Madness Scavenger Hunt

Use an app to survive a zombie apocalypse in Portland . In Zombie Scavengers, explore the city however you'd like to search for items needed to survive a zombie apocalypse. You'll get points for finding these items. You can also do some zombie themed challenges for points on the app as well. Strategize in order to get the most points and survive the apocalypse. Your remote host will be there for you via chat if you need anything. Can you survive the apocalypse in Portland?

Scavenger Hunt in Portland, Maine by Zombie Scavengers

1 hourFree Cancellation

Sea Kayak to an Island Tour in Casco Bay

3 hoursFree Cancellation

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.

Stand Up Paddleboard Tour with Complimentary Oyster Tasting

2 hours 30 minutesFree Cancellation

Walk around Portland while completing the 3Quest Challenge scavenger hunt! Use our app to find a list of objects (provided in riddle form) around the city and participate in fun challenges for points. Collect points and take a look at your score compared to others on the app's leaderboard. All of the objects and challenges will be divided into 3 quests. Complete the 1st quest, 2nd quest, and 3rd quest, in order, to complete the game! Set a time limit of 2 hours for yourself if you'd like to make the challenge even more intense! During the game, you'll have a remote host who will follow along virtually with you and chat if you need any help! Come explore Portland with us by completing all 3 Quests!

Adventurous Scavenger Hunt in Portland, ME by 3Quest Challenge

USD 10USD 10

During Crazy Dash of Portland, you'll use an app and walk through the city to collect points by finding items around the city and performing challenges. You can find the items in any order you want. Check out the rankings in the app to see your score compared to other teams across the nation. Crazy Dash comes with a remote host to chat with you in case you need anything. Crazy Dash is our most relaxed scavenger hunt. Come explore with us in Portland!

Scavenger Hunt Adventure in Portland by Crazy Dash

Scavenger Hunt Adventure in Portland by Crazy Dash

USD 10USD 10

Uncover the mysteries of Portland’s history with an innovative outdoor escape game that weaves together facts, folklore, and fishy tales. Venture through the city’s historic landmarks as you solve puzzles connected to Portland's stories, from shipwrecks to whispered legends. Guided by a user-friendly app, each clue you discover immerses you deeper into the captivating narrative of Portland, blending reality with fiction. Ideal for families, friends, or team-building, this adventure offers a unique exploration experience where curiosity reigns and puzzle solving is key. With our innovative outdoor escape games your surroundings become the game. Guided by your phone, your team explores real landmarks, uncovering virtual clues and solving puzzles that connect directly to the world around you. It’s part treasure hunt, part walking tour, and part mystery thriller. An immersive experience where history, legend, and imagination collide right in the streets beneath your feet.

Portland Maine Outdoor Escape Room Game

Holly Jolly Hunt is a scavenger hunt that is played using an app on your smartphone, that brings your entire family and friends together for holiday cheer. During the adventure you’ll be seeking out all the traditional, and even the non-traditional holiday items we all see this time of year around the city. You’ll get points for each item you find. The goal is to capture as many items as you can in order to score as many points as possible and get 1st place on the leaderboard. Along the way you’ll be asked to perform silly holiday themed tasks meant to bring laughter and smiles to everyone involved. Come play with us. Young or old, this is a scavenger hunt for everyone that enjoys this time of year. We promise you will create holiday memories that you will not forget! Holly Jolly Hunt can be played in any city!

Holiday Scavenger Hunt in Portland by Holly Jolly Hunt

1 hourFree Cancellation

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Must-Dos in Portland

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What are people saying about Portland

Sunset Windjammer Cruise Along the Coast of Portland Maine

Tara_R, Oct 2026

Such a lovely and...

Such a lovely and relaxing ride. We went out right before sunset and things couldn’t have been more perfect. Luke and his team provided a smooth sailing with lots of great convo and information about the area. It was the perfect end to our trip to Portland.

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

Freda_K, Oct 2026

The three lighthouses were well worth the time and travel

I strongly recommend this excursion. The Maine shoreline is beautiful. The trip to the three lighthouses was interesting all on its own. Seeing the lighthouses, each different from each other made it a wonderful trip. Although the main lighthouse, famous for its many photos was a true sight, I must admit the small one, in the shape of a Greek temple really drew my eye.

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.

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

Philip_W, Sept 2026

Brilliant tour well worth booking.

This was a brilliant tour with Derek the owner/guide keeping everyone amused with his knowledge and anecdotes of the surrounding area. You will not be disappointed and because it is a relatively small group there is plenty of interaction. Make sure you look up the photo of his Minibus so you reckonise it when you are waiting about 3 Blocks down from the cruise terminal it’s not far.

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.

Harbor Lights and Sights Cruise

Pamela_G, Sept 2026

Wonderful Experience!

I would highly recommend this tour! Our boat the Islander was not overcrowded so we were all able to experience the exceptional views. Two clean restrooms were available on the boat, along with drinks and snacks for purchase. The crew was very welcoming and engaging -- Capt, Howard invited those who were interested to join him in the boathouse,while our tour guide Mark entertained us with his knowledge of history in the area and his personal stories. Would go again in a heartbeat.

Sunset Lighthouse Cruise

Hannah_G, Sept 2026

Boat was definitely bare...

Boat was definitely bare bones, but the person giving the tour was interesting to listen to and the scenery was pretty. We got lucky and had a beautiful sunset. I would warn you, there are only a certain amount of spots at the top of the boat, and if you aren't on first, you'll have to sit underneath(they have windows, but it definitely is a subpar view). Lucky we were far enough up in line, but would have been very disappointed had we had to sit underneath the boat by the bar for a boat trip where the goal is site seeing.

Vintage Fire Truck Sightseeing Tour of Portland Maine

Bernice_A, Aug 2026

Nice ride around town

Great one hour ride Tour guide very informative and knew the history of the Portland and downtown area! Riding in the fire truck was a fun way to take a tour! Lots of shops and restaurants along the stripe! And still had time to do other things or see places after your tour ended

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

Michelle_W, Aug 2026

Great tour!

This was a great tour. There was something for both the adults and kids. The donuts were delicious, and Kris was able to accommodate the gluten restrictions for some of our party. Kris was also great about including our daughter and not just focusing on the adults. We highly recommend this tour.