Kennebunkport is a charming seaside town that offers more than just pretty views. It’s a place where you can explore by boat, walk through historic neighborhoods, or uncover local legends—making it ideal for a wide variety of tours and activities.
We particularly love the Luxury Catamaran Sailing Charters for their relaxed, wildlife-filled sails, and the Walking Through Time tour for its engaging glimpse into the town’s past.
Whether you’re into scenic boat rides, ghost stories, or culinary walks, Kennebunkport has something to offer every traveler.
If you’re trying to decide what to do, this list covers the best options, including lively boat excursions, historic explorations, culinary adventures, and even scavenger hunts—all with enough variety to fit your schedule and interests.
- 1. Luxury Catamaran Sailing Charters in Maine
- 2. A Walk Through Time in Kennebunkport – Celebrating 200+ Years!
- 3. Sail Away: Explore Maine’s Coastal Beauty on a 2-Hour Excursion
- 4. From Boston: Kennebunkport Day Trip & Optional Trolley Tour
- 5. Golden Hour Escape: Private Sunset Sail in Coastal Maine
- 6. Kennebunkport, Maine: Lunchtime Culinary Walking Tour
- 7. Kennebunkport: Haunted Ghost Walking Tour
- 8. 90 Minutes Ghost Walking Tour in Kennebunkport
- 9. Discover Maine’s Coastal Charms: Half-Day Scenic Sail
- 10. Kennebunkport: A Tasty Lunchtime Walking Tour
- 11. Krazy Kennebunkport Scavenger Hunt
- 12. Private Two Hour Sail on the Saco River
- How to Choose the Right Tour in Kennebunkport
1. Luxury Catamaran Sailing Charters in Maine
At number 1, the Luxury Catamaran Sailing Charters in Maine offers a relaxing two-hour cruise along the beautiful Maine coast. This trip stands out for its small-group setting (with a 5.0/5 rating from 85 reviews) and the opportunity to see lighthouses, beaches, and fishing villages from the water.
Captain Nils takes you from the Saco River past Wood Island Lighthouse into the Gulf of Maine, where you might spot minke whales, seals, bald eagles, and shore birds.
The boat features multiple seating areas, allowing you to unwind while taking in coastal sights. You’re welcome to bring your own food and drinks to make it a truly personalized experience.
Many travelers appreciate the captain’s knowledge and friendly attitude, with reviews highlighting the smooth sailing and wildlife sightings. For a romantic sunset or family outing, upgrading to a private tour adds a special touch.
Bottom line: This cruise is perfect for those seeking a peaceful, wildlife-rich sail with plenty of space to relax and enjoy the scenery.
2. A Walk Through Time in Kennebunkport – Celebrating 200+ Years!
Number 2 on our list is the A Walk Through Time tour, which costs around $50 and lasts about two hours. This guided walk through the Historic District offers a detailed look at Kennebunkport’s early days. Led by a local guide, the small group (with a 5.0/5 rating from 68 reviews) explores historic homes and landmarks, including the notable Knott House.
What makes this tour special is the chance to enter some historic homes, giving you a real feel for life in the 18th and 19th centuries. Your guide shares stories about Maine’s first families and the town’s development over 200+ years. Many travelers find this tour both educational and intimate, with reviews praising the knowledgeable guides and the opportunity to ask questions.
Bottom line: Ideal for history lovers who want a personal, in-depth look at Kennebunkport’s past without the crowds.
3. Sail Away: Explore Maine’s Coastal Beauty on a 2-Hour Excursion
Next up is the Sail Away experience, which also lasts about two hours and comes with a 5.0/5 rating from 39 reviews. This trip offers a chance to glide through Saco Bay and the Saco River on an intimate sailboat. The crew shares stories about the islands of Saco Bay, including Wood Island Lighthouse and the popular Old Orchard Beach.
You’ll appreciate the chance to witness the changing tides and the natural beauty of Maine’s coastline, all while enjoying a relaxing cruise. As the crew points out the various islands and wildlife, you can settle in with a drink and soak up the scenery. Many travelers mention how educational and fun the experience is, with the crew’s storytelling adding a memorable touch.
Bottom line: Perfect for ocean lovers and those wanting a laid-back, informative sail with beautiful coastal views.
4. From Boston: Kennebunkport Day Trip & Optional Trolley Tour
For around $125, the Kennebunkport day trip from Boston makes a full day of Maine’s coast accessible. This 11-hour excursion includes stops to see Nubble Light in York, Marginal Way in Ogunquit, and the Bush Compound (if you add the trolley tour). The tour offers a great mix of sightseeing and leisure, with ample time to explore or relax.
The optional trolley tour in Kennebunkport adds a fun way to see the town’s highlights without walking miles. Many travelers enjoy the convenience of leaving Boston behind for a day to experience Maine’s iconic lighthouses and scenic coastal paths. Reviews note the tour’s well-organized itinerary and friendly guides.
Bottom line: Excellent for travelers short on time who want a comprehensive taste of Maine’s southern coast, especially if you enjoy guided bus tours with options.
5. Golden Hour Escape: Private Sunset Sail in Coastal Maine
Number 5 is the private Sunset Sail, costing around $1,020 for your group—up to 6 people—and lasting two hours. This experience is aimed at couples or small groups wanting a romantic, personalized outing. As you sail along the coast, you’ll see the Wood Island Lighthouse, Saco Bay islands, and the beach of Old Orchard.
The highlight is watching the sun set in a blaze of color—perfect for memorable photos or quiet reflection. The crew serves drinks, desserts, or even dinner, adding a gourmet touch to the voyage. Reviewers praise the serenity and intimacy of the trip, making it ideal for special occasions. Be prepared for a peaceful, scenic cruise with plenty of opportunities for photographs and quiet moments.
Bottom line: Best suited for couples or small groups seeking a private, romantic experience with breathtaking sunset views.
6. Kennebunkport, Maine: Lunchtime Culinary Walking Tour
Number 6 on our list is the Culinary Walking Tour, which is a tasty way to explore Kennebunkport—costing $150 and lasting about two and a half hours. You’ll walk through Dock Square and into the Lower Village, sampling local specialties like Maine lobster sliders, chowder, and craft beer.
The tour offers a relaxed pace and the chance to learn about the town’s maritime and culinary heritage. Many reviewers appreciate the variety of food stops, as well as the opportunity to see waterfront sights along the way. It’s a fun, flavorful introduction to Kennebunkport’s food scene, especially for those interested in local flavors and history.
Bottom line: Perfect for food lovers who want a leisurely, guided tasting tour with plenty of opportunities to ask questions and enjoy local treats.
7. Kennebunkport: Haunted Ghost Walking Tour
Number 7 offers a spooky twist: the Haunted Ghost Walking Tour for $35, which lasts about 1.5 hours. This tour explores the town’s maritime mysteries and haunted landmarks, including the Louis Graves Library and the Nonantum Resort.
The guide shares stories about ghosts, poltergeists, and sea serpents, making it both entertaining and a little eerie. Reviews highlight the guide’s storytelling skills and the chance to learn about Kennebunkport’s haunted past while strolling through its historic streets. It’s especially popular among families or those interested in local legends.
Bottom line: A fun and engaging way to experience Kennebunkport’s spooky side, perfect for an evening outing.
8. 90 Minutes Ghost Walking Tour in Kennebunkport
This shorter, 90-minute ghost tour costs about $35 and covers haunted sites like White Columns and the Nathaniel Lord Mansion. It features stories of spiritualist seances, ghost ships, and local poltergeists. Many reviews mention the lively guide and the interesting stories about celebrity summerers and lighthouse hauntings.
The route includes several historic homes and landmarks, making it a concise but lively exploration of Kennebunkport’s supernatural tales. The tour is suitable for those who want a quick but thrilling glimpse into the town’s haunted reputation.
Bottom line: A compact ghost tour for those with limited time but a curiosity for paranormal tales.
9. Discover Maine’s Coastal Charms: Half-Day Scenic Sail
Number 9 offers a 4-hour sailing adventure for those who want a longer, more immersive experience. This trip includes sightings of Wood Island Lighthouse, Old Orchard Beach, and Biddeford Pool. The tour emphasizes natural wonders and maritime stories, including tales of shipwrecks and rescues.
Reviewers note the quality of the crew and the peaceful atmosphere of this longer excursion. It’s ideal for travelers seeking a more in-depth maritime experience, with ample time to relax and enjoy Maine’s coastline.
Bottom line: Great for those wanting a leisurely half-day adventure with storytelling and scenic views.
10. Kennebunkport: A Tasty Lunchtime Walking Tour
Number 10 is a culinary walking tour that combines local flavor with sightseeing. For about $160, you’ll visit spots like Ocean Avenue, Fiafia Smoothie Café, Federal Jack’s, and The Clam Shack. The tour lasts between 2 and 3 hours and features tastings of lobster sliders, clams chowder, and macaroons.
This tour is highly praised for its combination of food, history, and scenic views. Many reviewers mention the fun of trying different local dishes and the knowledgeable guide who keeps the pace lively.
Bottom line: Perfect for foodies who want to explore Kennebunkport’s culinary delights on foot.
11. Krazy Kennebunkport Scavenger Hunt
Number 11 turns sightseeing into a game. The Krazy Kennebunkport Scavenger Hunt costs $29 per person and lasts about two hours. It’s a fun activity for families, friends, or co-workers, supporting teamwork and exploration.
Participants follow clues, collect objects, and learn about the town’s sights. The reviews mention how much fun it is and how it encourages you to see parts of Kennebunkport you might otherwise miss. It’s a lively way to get active and engaged in a relaxed setting.
Bottom line: Best suited for active groups who want to combine sightseeing with a friendly competition.
12. Private Two Hour Sail on the Saco River
Finally, the Private Two Hour Sail offers an exclusive experience for up to six people at $795. This tailored cruise along the Saco River focuses on natural beauty and local history, including the Wood Island Lighthouse and Biddeford Pool.
You can customize the experience—whether you want to focus on wildlife, the lighthouse, or just relaxing with friends. Many reviewers value the privacy and personalized service, making this ideal for celebrations or quiet getaways. It’s a more expensive but highly exclusive way to enjoy Maine’s coast.
Bottom line: Best for small groups or couples seeking a private, flexible sailing adventure.
How to Choose the Right Tour in Kennebunkport
Choosing between these options depends on your interests, budget, and schedule. For a relaxing wildlife cruise, the Luxury Catamaran Sailing or the Half-Day Scenic Sail are excellent. If you love history, the Walk Through Time tour offers a deep dive into Kennebunkport’s past, while the Haunted Ghost Tours are perfect for a spooky evening.
Food lovers should consider the Culinary Walking Tour, with tastings along the waterfront, or the Tasty Lunchtime Tour. For families or groups, the Krazy Kennebunkport Scavenger Hunt is a lively, active choice. Those seeking intimacy and romance might opt for the Sunset Private Sail, and if you want a completely private experience, the Two-Hour Saco River Sail is your best bet.
Book early, especially in peak season, and consider combining experiences if your schedule allows—like a sailing trip followed by a historic walk or a culinary adventure. Check the Kennebunkport tours for availability and to customize your visit.
Kennebunkport offers a surprising variety of ways to enjoy its scenic coast, historic streets, and local legends. Whether you prefer a peaceful sail, an active scavenger hunt, or a spooky ghost walk, you’ll find something memorable here. We recommend booking your favorites in advance, especially in busy summer months, so you don’t miss out on these authentic Maine experiences.