AIRBNB EXPERIENCES

Things to do in Cumberland County

Book unique activities hosted by local experts on Airbnb.

Top-rated activities

View our most highly rated experiences, loved by guests.

5 out of 5 average rating, 92 reviews

Sightseeing Boat Tour - Bird's Eye Maine

Enjoy a private boat tour of Casco Bay, while cruising by lighthouses, wildlife, and more!

4.99 out of 5 average rating, 546 reviews

Hike with Alpine dairy goats at Ten Apple Farms

Take a stroll through the Maine woods on a unique hike with Alpine diary goats

4.97 out of 5 average rating, 29 reviews

Explore Portland's hidden histories on foot

Go beyond lobsters and lighthouses to find the hidden past of the Old Port and waterfront.

5 out of 5 average rating, 281 reviews

Private oyster farm tour & shucking class

Climb aboard for a relaxing private boat cruise over to our oyster farm. Learn how to shuck fresh Maine oysters on our floating oyster dock in a quiet nature preserve.

4.99 out of 5 average rating, 164 reviews

Sail Saco Bay at Sunset

Enjoy coastal Maine's natural beauty and a peaceful ocean sunset. Let the day melt away as

4.97 out of 5 average rating, 264 reviews

Cycle Maine’s coast and uncover lighthouse lore

Pedal a scenic trail, learn local lore, and stop at historic lighthouses.

4.93 out of 5 average rating, 90 reviews

Guided sunset kayak

Embark on a kayak trip oh the serene waterways. Discover natural beauty and wildlife.

4.98 out of 5 average rating, 219 reviews

Sail Saco Bay with Lifelong Sailing Captains

Enjoy coastal Maine's natural beauty and marine wildlife on a 42' sloop. Discover a..

5 out of 5 average rating, 8 reviews

Honor Portland's Black history on a walking tour

Trace 400 years of Black leadership in Maine with a trusted public historian.

5 out of 5 average rating, 71 reviews

Sunset Boat Tour - Bird's Eye Maine

Enjoy the serenity of sunset relaxing on a private boat tour of Portland's coastline.

Latest Activities

Explore new local experiences, activities for everyone.

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Portland Maine: Self-Guided Driving Audio Tour

Explore Portland with my GPS-triggered Audio Tour app. Pick any time slot when booking; it’s only for reservation purposes. Start anytime, any day, travel at your own pace, and enjoy offline access.

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Taste wine through a Maine lens

90-min guided tasting with a certified wine educator. 4 curated wines, explored through tannins, acidity, color, aroma, texture, taste and story behind each pour. Private group? Message me to book.

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Woodturning experience in a working artisan studio

Learn woodturning in a private artisan studio in Kennebunk, Maine. Create your own handcrafted project with one-on-one personalized instruction from a professional woodturner. No experience necessary.

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Seek ghosts with a haunted historian

Discover paranormal events and spectral stories as you walk the historic cobblestone streets with a haunted history expert.

New place to stay

Discover Maine whiskeys with a bourbon steward

Experience four Maine whiskeys expertly paired with unique bites, hosted by a whiskey connoisseur and learn the history of Maine's ice harvesting industry.

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Create French confections with a chocolatier

Dive into the art of chocolate tempering, taste exquisite ingredients, and craft mendiants under the guidance of an award-winning professional at our French Artisan Chocolate Shop in Portland, ME.

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Fly Fish Warmwater Species with a Maine Guide

We'll meet up at the boat launch in Topsham, Maine, load up in my 14-foot boat, and target bass, crappie, and sunfish on the Androscoggin River. This is an approachable adventure for new anglers.

New place to stay

Forage wild Maine blueberries on a hike

Trek on hidden trails in Maine’s wilderness to uncover wild blueberry patches with a guide who’s spent 20 years exploring the area. Dog and kid friendly. All dogs must be leashed and well-behaved.

5 out of 5 average rating, 3 reviews

Savor donuts with a food storyteller

Learn the fascinating tale of Maine’s donut history, taste fresh variations, and discover hidden food gems with a guide spotlighted by The Boston Globe.

5 out of 5 average rating, 1 reviews

Birding on the Eastern Promenade

Guests will learn to identify the migrant and resident birds that frequent Portland's shores. Each guest will observe birds with binoculars and spotting scope to learn tips on identifying birds.