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Chebeague Island

Chebeague Island, ME, USA

Chebeague Island

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Chebeague Island

Chebeague Island is a sun-kissed gem bursting with charm! Picture quaint cottages, sandy shores, and the salty breeze tickling your nose. Stroll idyllic trails, crack crab legs at local eateries, and hop on a kayak to explore hidden coves. With its friendly vibe and stunning sunsets, this tiny island is the perfect getaway for adventure and relaxation!

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Recommendations

Culture5/5

Chebeague Island Library

Chebeague Island Library offers a charming blend of coastal charm and community spirit, featuring a well-curated collection of books and vibrant events that celebrate island culture, making it a must-visit destination for locals and tourists alike.

Culture4.8/5

Museum of Chebeague History

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Culture5/5

Living History Farm at Second Wind Farm

Experience the charm of Living History Farm at Second Wind Farm, where the rich agricultural heritage of Chebeague Island comes alive through interactive exhibits, farm animals, and seasonal activities that engage visitors in a hands-on journey through history.

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Landmark

Chebegue Island Hall Comm Center

Landmark4.3/5

Chebeague Transportation Co

Chebeague Transportation Co offers a charming ferry experience to Chebeague Island, providing stunning coastal views and a glimpse of island life, making it a must-visit for anyone exploring Maine's beautiful islands.

Landmark4.9/5

Stone Wharf Landing

Shop4.8/5

The Niblic

Shop4.6/5

Island Riches

Landmark4.3/5

Chebeague Recreation Center

Landmark4.6/5

Great Chebeague Golf Club

Landmark4.9/5

Chebeague Island Boat Yard

Transport3.6/5

Littlejohn Island Preserve - Parking Lot

Outdoor4.8/5

Little Chebeague Island

Landmark

Chebeague and Cumberland Land Trust

Culture4.9/5

Chebeague Community Church

Landmark

United States Postal Service

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Landmark

Chebeague Island Fire Department

Eat4.4/5

Slow Bell Cafe

Eat

Chebeague Island Inn Restaurant

Eat4.8/5

Doughty's Island Market

Stays

Stay5/5

Chebeague Island Yurts and North House rental

Nestled on picturesque Chebeague Island, the Yurts and North House rental offer a unique blend of cozy accommodations and stunning coastal views, making it an unforgettable escape into nature’s tranquility.

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Stay

Cozy Cottage, Chebeague Island Maine

Nestled on Chebeague Island, Cozy Cottage offers a charming escape with stunning waterfront views, inviting interiors, and a tranquil atmosphere that captures the essence of Maine's coastal beauty, making it a must-visit destination.

Things To Do
Provided byViator

5/5
2 h 30 mins

Guardians of the Harbor Trolley Tour

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.

$59.00
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5/5
48 h

Boston to Acadia National Park, Maine Coast 2-Day Tour, Transfers

Travel north from Boston for a two-day journey along the Maine coast. Visit Portland Head Lighthouse before exploring Acadia National Park through Cadillac Mountain, Sand Beach, and Thunder Hole, then spend the night near the park. The second day offers an optional nature cruise through Frenchman Bay and free time in Bar Harbor before returning to Boston.

$335.00
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5/5
6 h

Private Portland Lighthouses and Kennebunkport Tour - 12 Pax

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.

$1,508.00
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5/5

Private Yacht Tour in Portland, Maine 2hr, 4hr and 6hr Available

Explore the stunning scenery and rich maritime history of Casco Bay on a private 2hr, 4hr or 6hr powerboat cruise. Ideal for families, friends, or small groups, this exclusive charter offers a personal adventure, allowing you to encounter marine wildlife, view iconic lighthouses, and discover unique islands at your own pace. With flexible scheduling and customizable experiences, this cruise promises an unforgettable day on the water, complete with opportunities for swimming and exploring Maine’s rugged coastline. - Private cruise for up to 6 passengers, ensuring an exclusive experience - Encounter marine wildlife like seals, porpoises, and seabirds - View famous lighthouses including Portland Head Light and Bug Light - Flexible departure times and customizable itineraries available – Alternative pickup available in Portland for added cost, saves 30 min of driving, contact us for availability

$648.00
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5/5
2 h 30 mins

Stand Up Paddleboard Tour with Complimentary Oyster Tasting

Learn the basics of stand-up paddle boarding on land before launching at Mere Point in Brunswick for a leisurely 2.5 hour morning tour of Northwest Casco Bay! We will paddle out to a demonstration oyster farm and then to an island to shuck and enjoy a complimentary tasting of the sweet and briny fresh Maine oysters. Stand-up paddle boarding is a great, fun way to sight see from the water. We are likely to see cormorants, sea gulls, osprey, great blue herons, snowy egrets, ducks, and we might see fish jumping or a seal.  Paddlers at least 12 years old will love exploring Casco Bay in this protected, scenic, historic area! There will be a break on land where we will stretch, taste the oysters and have some snacks that you bring.

$92.00
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5/5
2 h

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.

$675.00
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5/5
2 h

Experience Portland's Waterfront Public Scenic Powerboat Cruise

Experience the stunning beauty of Casco Bay on a personalized intimate (up to 6 guests per trip), public 2-hour powerboat cruise. Whether you're looking for a scenic sightseeing tour, an up-close encounter with Maine’s wildlife or a journey through the region’s rich maritime history, this exclusive charter is designed to provide an unforgettable adventure. Departing from the working waterfront, you’ll glide past busy wharves lined with lobster boats, ferries, and historic brick buildings that reflect Portland’s seafaring heritage. From the start, the mix of city energy and natural beauty sets the tone for an unforgettable journey on Casco Bay. Seals often bask on rocky ledges, ospreys and bald eagles soar overhead, and in the summer months, porpoises sometimes surface alongside the boat. Whether it’s spotting seabirds, breathing in the salty ocean air, or simply enjoying the thrill of the ride, a powerboat cruise from Portland offers both adventure and relaxation in equal measure.

$139.00
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5/5
5 h

Private EBike Tour Portland Maine

Some cities are best seen from a car window. Portland, Maine is not one of them. On this fully private e-bike tour, it's just your group, a local guide, and five hours of spectacular coastal scenery — with a Maine lobster roll along the way. Ride through the Old Port's cobblestone waterfront and fishing piers. Climb to Fort Allen Park for sweeping Casco Bay views. Cruise the Eastern Promenade before crossing to South Portland to walk the breakwater to Bug Light, designed by the architect of the U.S. Capitol dome. Continue to Spring Point Ledge — the only lighthouse of its kind you can reach on foot — then Portland Head Light, commissioned by George Washington in 1791. Finish on the Western Promenade, a hidden hilltop park with views to the White Mountains that most visitors never find. Lunch is a fresh Maine lobster roll at a waterfront spot worthy of the occasion. No strangers, no set pace — just your group and the best of coastal Maine.

$349.00
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5/5

The Maine Experience: Coast, Culture & History

This isn’t just another sightseeing trip—it’s a curated journey through Maine’s most iconic landmarks and hidden gems, woven together into one unforgettable day. From the elegance of Portland Head Light, the nation’s most photographed lighthouse, to the playful charm of Eartha, the world’s largest rotating globe, every stop reveals a different facet of Maine’s character. Guests walk a historic suspension bridge built by the engineers of the Brooklyn Bridge, explore the state’s proud maritime heritage in Bath, and visit the legendary L.L. Bean flagship store in Freeport. What sets this tour apart is the balance of scenery, history, and culture: stunning coastal views, hands-on heritage at museums and memorials, and Maine icons you won’t find grouped together anywhere else. And because it’s a shorter itinerary, it’s the perfect choice for cruise ship passengers or travelers with limited time who still want a rich, memorable Maine experience.

$300.00
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5/5
2 h

Intimate Portland Public Sunset Cruise

Witness the stunning sunset over Casco Bay on this two-hour public powerboat cruise aboard the classic Maine-built vessel, Avelinda. As the sun sets, enjoy picturesque views of iconic lighthouses like Portland Head Light and serene islands such as Peaks Island. With a maximum of six guests per boat, relish an intimate experience while keeping an eye out for local wildlife like seals and seabirds. Captains with extensive local knowledge share tales of the region's rich history, making this cruise a perfect way to unwind and soak in the beauty of Maine's coast. Open to all ages, it’s a memorable outing for families and couples alike. - 2-hour scenic sunset cruise through Casco Bay - Maximum of 6 guests for an intimate experience - Spot local wildlife and iconic Portland lighthouses - Knowledgeable captains share local history and ecology

$149.00
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5/5
4 h

Private Half Day Sailing Charter in Portland Maine

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.

$475.00
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5/5
1 h 45 mins

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

Welcome to my hometown! Hop aboard for an authentic 1 hour and 45 minute historical sightseeing tour of Portland, Maine and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, Maine. Get an insider’s look at the current happenings and rich history of my hometown. We’ll go where other tours go, and then I'll take you places other tours don't - you'll see hidden gems and learn little known facts about Portland and the great state of Maine that only a real local knows! As a college librarian I'm always researching the hidden history of Portland, while at the same time keeping on top of what's new in town and visiting as many local establishments that I can. I take pride in representing this city, and providing an informative and entertaining tour, delivered with a true Mainer's sense of humor. This is The Real Portland Tour! Check my website for a complete listing of tour days, times, and availability.

$74.00
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5/5
2 h

Private Sunset Charter on a Vintage Lobster Boat with Drinks

Leave the crowds behind and step aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter, ending with a breathtaking Maine sunset. We’ll navigate through the islands of Casco Bay, passing by Portland’s most iconic coastal sights, including historic 19th-century forts, lighthouses, and the stunning Maine coastline. This experience is perfect for families and small groups, offering a completely private and personalized tour just for you. First round of alcoholic drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the view!

$407.40
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4.9/5
4 h

Casco Bay Half-Day Sea Kayak Tour

Explore the beautiful islands of Casco Bay in this four-hour sea kayak tour. After a brief lesson on the basics of sea kayaking, you'll set out with a licensed Maine Guide. The small group will island-hop through the bay, looking out for seals and seabirds and enjoying the views of lighthouses, 19th-century forts and other fascinating landmarks. We’ll stop at an island for a break and a snack provided by Portland Paddle. This is a great tour for anyone who wants to get a taste of sea kayaking in the rugged islands of the Maine coast. Our most popular trip!

$85.00
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4.9/5
3 h

Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

Our 3-Hour tour leaves at 11:00 am and follows the scenic South Portland Greenbelt Pathway to three local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will continue to Spring Point Ledge Light, located near historic Fort Preble. Next, the tour will pass by Willard Beach before arriving at the final stop, the famous Portland Head Light located at Fort Williams Park in Cape Elizabeth. It is recommended that patrons bring a lunch or we can assist in purchasing lunch from a local food truck that serves Lobster Rolls.

$115.00
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4.9/5
2 h

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

Skip the city and head straight to the coast on this dedicated lighthouse tour of Maine’s best lighthouses. Explore three iconic beacons that have guided sailors for centuries, each offering a chance to delve into their rich history. While most lighthouses aren’t open for tours, you’ll still get up-close views and plenty of opportunities to admire their stunning architecture and scenic surroundings. As you navigate through Portland’s picturesque coastline, you’ll be surrounded by breathtaking views that are as storied as they are beautiful. This focused, relaxed tour is the perfect way to connect with maritime past while soaking in the charm of Maine’s coastal landscape.

$79.00
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4.9/5
2 h

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter. Leave the crowds behind as we cruise through the islands of Casco Bay, passing four iconic lighthouses, historic 19th-century forts, and the stunning Maine coastline. Charters depart from Portland’s Old Port and are perfect for families and small groups. Each charter is completely private for up to 6 guests, and all ages are welcome! First round of drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the breathtaking views!

$380.10
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4.8/5
2 h

Sunset Sea Kayak Tour on Casco Bay

The hours just before sunset offer the best time for paddling on the waters of Casco Bay. The sky tends to explode with color and the seas often become glassy and calm. This trip involves a leisurely paddle just far enough along the waterfront or into the islands to enjoy a panoramic view of the sun setting over the city as we paddle back to the East End Beach.  This two-hour tour is designed for paddlers of all experience levels -- including first-time kayakers. The exact route you take will depend on the weather conditions and the group's interests and experience, but the Sunset Tour often starts out venturing into the waterfront of Portland harbor, and then into the open waters towards the islands of Casco Bay. We will cancel this tour if there is steady rain, strong winds or other conditions that we believe will prevent guests from having a great paddling experience. However, we will run our tours when there are light showers, overcast skies or cooler than average temperatures.

$60.00
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4.8/5
1 h 30 mins

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!

$69.00
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4.8/5
50 mins

Vintage Fire Truck Sightseeing Tour of Portland Maine

This 50-minute sightseeing tour is a fun and unique way to discover Portland, Maine. Board a Vintage Fire Engine and travel back in time as your knowledgeable guide helps relive Portland’s colorful history from a local’s perspective. See lighthouses, Civil War forts, city parks and buildings, interesting stories and a multimedia experience packed with historic images of Maine. This is one family-friendly tour you should not miss out on!

$45.00
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