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Orr's Island

Orr's Island is a delightful slice of coastal charm! Picture homes hugging the rocky shores, vibrant sunsets painting the sky, and salty sea breezes tickling your senses. Explore scenic trails, feast on fresh lobster rolls at quaint eateries, or simply revel in the peaceful vibe that makes this island a hidden gem of Harpswell. Adventure awaits!

From the Community

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Recommendations

Landmark4.9/5

Bailey Island Bridge

Bailey Island Bridge, aka the Cribstone Bridge, is the cool superstar of Maine! Stretching over 1,500 feet, this picturesque wooden bridge connects Bailey and Orr's Islands. Built in 1928, it boasts a unique cribstone design made of granite blocks. Weathered by salty sea air, it offers stunning panoramic views of Casco Bay. An absolute must-visit for those seeking a delightful coastal adventure!

Outdoor4.6/5

Devil's Back Trail Area

Nestled in Orr's Island, the Devil's Back Trail Area offers stunning coastal views and rugged hiking paths, making it a must-visit for nature lovers and adventure seekers alike. Experience Maine's breathtaking landscape like never before.

Outdoor4.5/5

Houghton Graves Park

Culture5/5

Orr's Island Library

Looking for a bookish adventure? Dive deep into Orr's Island Library, a cozy literary oasis nestled on 1699 Harpswell Islands Rd. With its idyllic location in Orr's Island, ME, this charming hub welcomes travelers with open arms. Immerse yourself in their vast collection, get lost in captivating stories, and let your imagination sail away on the waves of literature. Ahoy, bookworms!

Landmark4.7/5

Old Orr's Island Schoolhouse

Landmark4.6/5

Orr's Bailey Yacht Club

Outdoor

Prince Point

Outdoor5/5

Lowell's Cove

Outdoor

Gun Point Cove

Outdoor4/5

Orrs Cove

Landmark4.9/5

Orr's Island Bridge

Landmark4.9/5

H2Outfitters

Cafe$$4.4/5

Salt Cod Cafe

Eat4.7/5

Bailey Island General Store

Stays

Stay4.5/5

The Harpswell Inn

<h2>Elegant Accommodations</h2> The Harpswell Inn in Harpswell Center offers comfortable bedrooms with private bathrooms, wardrobes, and sea views. Each room includes air-conditioning, balconies, and modern amenities. <h2>Relaxing Facilities</h2> Guests can enjoy a beautiful garden, terrace, and bar. Free WiFi is available throughout the property, ensuring connectivity. <h2>Delicious Breakfast</h2> A continental buffet breakfast is served daily, featuring juice and fresh fruits. The dining area provides a pleasant setting for a leisurely start to the day. <h2>Convenient Location</h2> Located 1.9 km from Widgeon Cove Studios, the inn is 14 km from Bowdoin College and the Peary-Macmillan Arctic Museum. Portland International Jetport is 60 km away.

Stay4.9/5

Sea Escape Cottages & Charters

Nestled on Bailey Island, Sea Escape Cottages & Charters offers stunning ocean views and intimate coastal experiences, making it an iconic getaway for relaxation and adventure in the heart of Maine's breathtaking landscape.

Stay4.8/5

Log Cabin Island Inn

Stay4.7/5

Head Beach Campground

Stay4.4/5

The Driftwood Inn

Nestled on scenic Bailey Island, The Driftwood Inn offers breathtaking ocean views, charming coastal decor, and a welcoming atmosphere, making it a quintessential Maine getaway for those seeking relaxation and natural beauty.

Stay

Waterledge Cottage - Orrs Island, Maine

Stay

Old Farm Cottage - Harpswell, Maine

Stay

Classic Maine cottage set on its own peninsula with stunning views

Things To Do
Provided by

5/5

Private White Mountains Tour with Mount Washington Cog Railway

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.

$395.00

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

5/5

Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse

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.

$300.00

5/5

Private Portland to Cape Ann, MA Castles & Coast

Discover coastal New England on this private day tour from Portland, Maine to Massachusetts’ North Shore and Cape Ann. This thoughtfully curated experience blends grand seaside estates, medieval-style architecture, colonial history, and authentic harbor towns into one unforgettable journey. Admission is included to the breathtaking Crane Estate at Castle Hill in Ipswich, where sweeping lawns lead to panoramic Atlantic views. A favorite filming location for major Hollywood productions, its dramatic setting feels timeless and cinematic. You’ll also enjoy a guided tour inside Hammond Castle, a stunning 1920s seaside castle overlooking the ocean. Explore historic Ipswich, one of America’s oldest towns, and visit Gloucester’s iconic Fisherman’s Memorial while strolling its working harbor. With private transportation and relaxed pacing, this tour offers an elegant and memorable way to experience the beauty, history, and charm of coastal Massachusetts in a single day.

$350.00

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

5/5

Private Portland to Camden & Midcoast Lighthouse Experience

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 Mt Battie. This fun and adventurous tour is perfect for exploring Maine’s hidden gems. Book now to experience the best of the coast!

$350.00

5/5

10 h

Private Full Day Tour to Coastal Maine from Boston with Hotel pick-up

Enjoy this private full day tour with your own private driver and official tour guide and explore the vibrant coast of Maine. Get ready to explore the most beautiful beaches and the nicest spots in this wonderful area. We will pick you up from your hotel or place of choice (hotel or apartment) in Boston and take you on this private tour, with your own chauffeur and guide to the Coastal Maine. During your full day private tour you will discover the best spots of the Coastal Maine with your local expert guide. Get ready to explore the Drowned Coast. This is an example of the itinerary. It will depend on traffic conditions as well as how much time spent in each location.

$1,692.53

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

5/5

1 h 30 mins

Downtown Bath, Maine and The City of Ships Walking Tour

History Awaits! This fun and fascinating tour focuses on the past 400+ years of the historic and quaint downtown of Bath, Maine, the fifth largest port in America during its 19th century heyday. Learn Bath's story by walking among the charming period buildings, hearing unique stories, and uncovering hidden gems. Led by an educator, this perfectly paced, small group tour is designed for those who love history and offers something for everyone, including lots of laughs. You will leave with a new appreciation for Bath, local and American history, plus tips and recommendations for other local attractions in Midcoast Maine!

$30.00

4.9/5

3 h

Sea Kayak to an Island Tour in Casco Bay

Learn the basics of sea kayaking on land before launching at Mere Point in Brunswick for a leisurely 3 hour morning tour of Northwest Casco Bay! Often we paddle south to the end of Mere Point for a photo op and then on to visiting an island for a stretch break, snacks, and shoreline exploring. Then we paddle back on a different route close to an island to our launching point. Your Master Maine Guide will share history of the area while adapting the tour to paddling conditions and participants abilities. Sea kayaking is an easy, fun way to sightsee from the water. We often see different kinds of sea gulls, cormorants, ducks, great blue herons, snowy egrets, osprey and sometimes bald eagles. If we are lucky, we will see a seal. Paddlers of all ages will love exploring Casco Bay in this protected, scenic, historic area! No experience is needed. This a family-oriented experience. Single and double kayaks are used on this guided tour by a Master Maine Guide.

$89.00

4.9/5

Private Portland to Acadia & Bar Harbor Experience

Experience the beauty, history, and charm of coastal Maine on this full-day adventure from Portland. Plan for 10–12 hours, with about three hours of travel each way. Scenic and photo stops break up the drive, but the main focus is exploring the Acadia area and Bar Harbor. We’ll begin with a journey into one of Maine’s most scenic regions, known for rugged shorelines, crashing waves, sweeping overlooks, panoramic summits, and crystal-clear lakes. Next, enjoy two hours in Bar Harbor—savor fresh seafood or a lobster roll, browse shops and galleries, grab ice cream, or stroll the waterfront and take in the views. We’ll also visit the Fort Knox–Narrows Bridge Overlook for striking views of its soaring towers and the Penobscot River, then make a final stop in Bangor for a photo of Stephen King’s home—famous for its deep red Victorian style and eerie wrought-iron gates. By day’s end, you’ll have experienced a rich mix of coastal beauty, history, and pop-culture highlights.

$512.87

4.8/5

3 h

Oyster Farm & Complimentary Tasting Sea Kayak Tour in Casco Bay

Tasting oysters harvested from the ocean where they were grown is significantly different and better than eating them at an oyster bar, especially when you just shucked them! Freshness counts! This sea kayaking tour that teaches you the basics of sea kayaking on land before launching at Mere Point in Brunswick to visit a working oyster farm in NW Casco Bay! After visiting the oyster farm, we'll stop on an island for your lesson on shucking, tasting, and snacks. Learn about aquaculture in Maine and how it improves the health of the bays. Sea kayaking is an easy, fun way to sight see from the water. We often see different kinds of sea gulls, cormorants, black and mallard ducks, eider ducks, great blue herons, snowy egrets, osprey and bald eagles. If we are lucky, we will see a seal. Paddlers of all ages will love exploring Casco Bay in this protected, scenic, historic area! No experience is needed. Single and double kayaks are used on this eco-guided tour by a Master Maine Guide.

$99.00

4.5/5

Private Portland Head Light & Midcoast Explorer

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. Your journey begins at Portland Head Light, one of the most photographed lighthouses in the United States, where dramatic rocky cliffs and sweeping Atlantic views create unforgettable photo opportunities. From there, travel along Maine’s scenic coastline to the picturesque harbor village of Boothbay Harbor. Walk across the historic Footbridge, built in 1901, and enjoy views of working lobster boats, quiet marinas, and classic New England waterfront scenery. Guests also have the option to enjoy lunch along the harbor at a unique restaurant built from a historic tugboat. With a knowledgeable local guide sharing stories and insights throughout the journey, this private coastal Maine tour offers the perfect blend of history, scenery, and authentic coastal charm.

$350.00

Boothbay, Freeport and Maine Botanical Gardens Private Day Tour

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.

$325.00

Private Day Tour of Salem MA, from Portland ME

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.

$325.00

Camden, Rockland, Pemaquid, and Belfast Private Tour

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!

$325.00

Desert of Maine - Wander in Wonder and Mini Golf Combo

Discover the fascinating Desert of Maine, a unique ecological wonder nestled in the lush pine forests of Freeport. This general admission and mini golf combo ticket grants you access to acres of rolling sand dunes, rich history, engaging exhibits, and mini golf. Explore the Tuttle Farmhouse interactive museum, embark on a self-guided ecology tour, and enjoy activities like a scavenger hunt. The Desert of Maine not only offers a glimpse into geological processes but also provides a fun-filled day of adventure for families and curious travelers alike. Come uncover the stories of this century-old attraction today.