Kennebunkport is a charming seaside town that offers a surprising variety of tours for visitors eager to explore its coastal beauty, history, and local flavor. Whether you’re into sailing past lighthouses, uncovering the town’s past on foot, or enjoying a private sunset cruise, Kennebunkport’s tour scene is rich and diverse. I particularly enjoy the Luxury Catamaran Sailing Charters for its relaxed, wildlife-filled voyage or the A Walk Through Time in Kennebunkport for its engaging glimpse into the town’s early days. Both experiences give you a taste of Kennebunkport’s maritime charm and history, making them perfect choices for different kinds of travelers.
If you’re after a mix of fun and education, the Kennebunkport: Haunted Ghost Walking Tour offers spooky stories and historic homes, ideal for those who like a little thrill with their sightseeing. For a more exclusive experience, the Private Two Hour Sail on the Saco River lets you enjoy the coast in total privacy. Whatever your style, this list has a tour to make your time in Kennebunkport memorable.
1. Luxury Catamaran Sailing Charters in Maine
Cruise along the Atlantic Ocean aboard a spacious catamaran on this small-group tour that fits up to 25 passengers comfortably—though most groups are smaller, offering a more personalized experience. Captain Nils will take you from the Saco River past Wood Island Lighthouse, with chances to see minke whales, seals, and bald eagles. The itinerary includes views of Old Orchard Beach from the water, the mansions of Biddeford Pool, and the fishing village of Cape Porpoise, making this a comprehensive coastal cruise.
What makes this tour stand out is its flexibility and the captain’s friendly, knowledgeable approach. You’re encouraged to bring your own food and drinks, turning the cruise into a relaxing picnic on the water if you like. Reviewers love the attentive crew and beautiful boat—”The boat is very sophisticated and in excellent condition,” one guest notes—plus the chance to see wildlife up close.
Bottom line: If a peaceful, wildlife-rich sailing experience with stunning coastal views appeals, this is a top pick. It’s ideal for those who value comfort, flexibility, and wildlife spotting.
2. A Walk Through Time in Kennebunkport – Celebrating 200+ Years!
For a deeper understanding of Kennebunkport’s roots, this guided walking tour offers a vivid look at its historic district. Led by a knowledgeable local guide, you’ll explore homes from the earliest residents, including the Knott House—one of Maine’s first families—and walk through charming streets away from the crowds of the Lower Village.
This tour is perfect for history lovers or anyone who enjoys a leisurely exploration of architecture and local stories. With only nine people in the group, you get plenty of personal attention. Reviewers praise the tour for its engaging storytelling: “Peter made the tour interesting and enjoyable,” one visitor shares. You’ll see historic homes, learn about the town’s founding, and get to enter some preserved buildings—adding a tactile, immersive element.
Bottom line: This tour is well suited for history enthusiasts or travelers interested in the early days of Kennebunkport. The small group size ensures a personal experience.
3. Sail Away: Explore Maine’s Coastal Beauty on a 2-Hour Excursion
A two-hour sail along Maine’s coast offers a relaxing way to soak up coastal scenery. The crew takes you from the Saco River past Wood Island Lighthouse and the eight islands of Saco Bay, with plenty of opportunities for wildlife viewing—porpoises, seals, and shorebirds are common sights. The itinerary also includes a panoramic view of Old Orchard Beach’s seven miles of sand.
No prior sailing experience is needed; the crew is friendly and knowledgeable, sharing stories about the islands and local landmarks. Reviewers call it “an educational and fun experience,” emphasizing the intimate boat size and scenic stops. The tour is ideal for those wanting a peaceful escape on the water with a focus on natural beauty.
Bottom line: Perfect for families or couples seeking a laid-back coastal adventure with ample wildlife encounters and stunning vistas.
4. From Boston: Kennebunkport Day Trip & Optional Trolley Tour
Travelers who want to explore Maine’s coast without the hassle of planning will appreciate this full-day guided trip from Boston. It covers Nubble Lighthouse, built in 1879, and the scenic Marginal Way cliff walk in Ogunquit. The trip also includes a visit to Kennebunkport, with an optional trolley tour that offers a quick, guided overview of the village.
The tour provides a hassle-free way to see multiple highlights in a single day, making it a good choice for travelers with limited time. Reviews highlight the opportunity to see the Bush Compound at Walker’s Point if the trolley is included. The day ends with free time to explore or enjoy local eateries.
Bottom line: This is an excellent choice for those who want a comprehensive day of sightseeing with minimal planning, especially if you’re visiting Boston and want to see Maine’s coast.
5. Golden Hour Escape: Private Sunset Sail in Coastal Maine
This private sunset sail offers a dreamy, intimate experience for up to six people. Departing in the late afternoon, you’ll glide along the coast as the sun casts a golden glow. The crew serves drinks, desserts, or even dinner, making it feel like a special occasion. The tour includes views of Wood Island Lighthouse, Saco Bay’s islands, and the long sandy beaches of Old Orchard.
Guests rave about the “mesmerizing hues” of sunset and the peaceful, personalized atmosphere. This trip is best suited for couples, families, or small groups celebrating something special. The experience’s exclusivity and flexibility make it stand out.
Bottom line: If you want an unforgettable, romantic sunset with all the personal touches, this private sail is a superb choice. Book early, as availability is limited.
6. Kennebunkport, Maine: Lunchtime Culinary Walking Tour
Taste your way through Kennebunkport’s culinary scene on this 2.5-hour guided walking tour. You’ll sample locally caught lobster, homemade chowder, and craft beer, all while strolling through the waterfront and historic neighborhoods. It’s an excellent way to combine food, history, and local culture.
The tour is ideal for food lovers who want to experience authentic Maine flavors in a relaxed setting. Reviewers mention the “wonderful food” and fun, easy pace of the walk. You’ll visit several stops, including Fiafia Smoothie Café, Federal Jack’s Brewery, and The Clam Shack—where lobster sliders are a highlight.
Bottom line: This tour suits travelers eager to explore Kennebunkport’s culinary traditions and enjoy a tasty, leisurely afternoon.
7. Kennebunkport: Haunted Ghost Walking Tour
Step into Kennebunkport’s spooky side with this ghost tour, where you’ll explore haunted landmarks like the Louis Graves Library and the Nonantum Resort. The guide shares chilling stories about maritime mysteries, ghost ships, and local legends. This 1.5-hour walk is perfect for those who enjoy a good scare combined with local history.
Reviews rave about the entertaining storytelling and the guide’s humor. The tour’s mix of history and ghost tales makes it a fun, atmospheric way to see the town after dark. It’s suitable for most ages, but beware—the stories can be quite spooky.
Bottom line: Great for fans of ghost stories or anyone curious about Kennebunkport’s paranormal tales, especially in the evening.
8. 90 Minutes Ghost Walking Tour in Kennebunkport
For a shorter, punchy experience, this 90-minute ghost walk explores Kennebunkport’s supernatural tales in a compact format. Starting at the historic White Columns, the tour visits sites like the Louis Graves Library and Nathaniel Lord Mansion, sharing stories of poltergeists, spirits, and maritime mysteries.
Rated highly for its informative guide, the tour offers a mix of history, ghost stories, and local lore. It’s perfect for those who want a quick but engaging dose of Kennebunkport’s haunted history without spending too much time.
Bottom line: Ideal for a fun, spooky afternoon or evening, especially if you’re short on time but still want a taste of Kennebunkport’s ghostly stories.
9. Discover Maine’s Coastal Charms: Half-Day Scenic Sail
This half-day sailing trip offers a 4-hour immersion into Maine’s coastline, with stops near Wood Island Lighthouse, Old Orchard Beach, and Biddeford Pool. The crew shares stories about the area’s wrecks, rescues, and hauntings, turning your cruise into a mini adventure.
It’s designed for those who want a more in-depth experience than a quick cruise but still value comfort and scenic views. The tour is highly rated for its natural wonders and informative narration.
Bottom line: Perfect for travelers seeking a longer, relaxing sailing experience combined with engaging stories.
10. Kennebunkport: A Tasty Lunchtime Walking Tour
This tour offers a delicious walk through Kennebunkport, sampling lobster sliders, clam chowder, and local baked goods. Over 2 to 3 hours, you’ll explore Dock Square, the Lower Village, and enjoy tastings at popular spots like Federal Jack’s and The Clam Shack.
Aimed at food lovers who want to experience authentic Maine flavors in a relaxed setting, this tour combines history, food, and scenic views. Reviewers particularly enjoy the fun pace and the variety of tastings.
Bottom line: Great for those who want a culinary adventure with a side of sightseeing, especially if you’re interested in local seafood.
11. Krazy Kennebunkport Scavenger Hunt
Looking for a lively way to explore town? This scavenger hunt turns Kennebunkport into a game, where teams solve clues and collect objects around town supported by a live remote host. It lasts about two hours and encourages teamwork and active exploration.
Perfect for families, friends, or co-workers, it offers a fun, interactive way to see the sights and learn about the town’s features. Reviewers mention how it pushed them out of their comfort zone but in a good way.
Bottom line: If you enjoy puzzles and a bit of friendly competition, this scavenger hunt is a memorable alternative to traditional sightseeing.
12. Private Two Hour Sail on the Saco River
For a completely personalized experience, this private 2-hour sail on the Saco River allows up to six people to enjoy the sights at their own pace. The captain shares stories about Wood Island Lighthouse, Biddeford Pool, and Old Orchard Beach, with plenty of opportunities to relax, take photos, and watch wildlife.
While it has no reviews yet, its exclusivity and flexibility make it appealing for families or small groups celebrating special occasions. The tour’s quiet, intimate atmosphere ensures a memorable, tailored experience.
Bottom line: If privacy and customization matter most, this private sail offers a serene and flexible way to enjoy Maine’s coast.
$795.00 per group (up to 6)
How to Choose the Right Tour
When selecting a tour in Kennebunkport, consider your interests, budget, and how much time you want to spend. For instance, if you love being on the water, the Luxury Catamaran Sailing or the Half-Day Coastal Sail are excellent options. Want a taste of local history? The Walk Through Time is perfect for you.
If you’re after a lively activity, the Krazy Kennebunkport Scavenger Hunt offers fun and activity for all ages. For a spooky evening, the Haunted Ghost Tour is a good pick, while the Tasty Walking Tour combines food and sightseeing beautifully.
Booking early is advised, especially for private experiences like the Sunset Sail, which tend to fill up quickly.
Kennebunkport offers a wide variety of tours to suit every traveler—whether you’re after scenic sails, historic walks, or ghost stories. For a relaxing day on the water, the Luxury Catamaran or the Half-Day Scenic Sail are top choices. For history buffs, the Walk Through Time provides a personal glimpse into the past. And if you’re feeling adventurous or playful, the Scavenger Hunt adds a lively twist.
No matter your interests, booking a tour in advance ensures you won’t miss out on these memorable experiences. Now, all that’s left is to pick your favorite and enjoy all that Kennebunkport has to offer.