Private Portland Lighthouses and Kennebunkport Tour – 12 Pax

Exploring Portland and Kennebunkport on a Private Lighthouse and Coastal Tour

Imagine spending a day in Portland, Maine, with its iconic lighthouses, scenic parks, and historic houses, all comfortably arranged in a private van with a knowledgeable guide. For around $1,550 per group, you’ll enjoy approximately six hours of tailored sightseeing, led by local experts who know the ins and outs of this stunning coastline. The tour kicks off in Portland, taking you through its best viewpoints and historical sights, before heading south along the coast to explore Kennebunkport’s charming streets and rocky shores.

Two things we especially appreciate are the customizable nature of this tour—perfect for those who want to focus more on specific sights or spend extra time at a favorite spot—and the inclusion of admission to Portland Head Light, one of America’s most photographed lighthouses. On top of that, the small group size (up to 12 passengers) ensures a more intimate, flexible experience compared to larger bus tours.

One potential consideration is the price point, which might seem high for some travelers, but it reflects the private, personalized attention and the convenience of door-to-door service. This tour is particularly appealing if you value expert local guides who can enhance your understanding of Maine’s coastal history and traditions. It’s ideal for travelers who appreciate a relaxed pace, want to avoid the crowds, and are eager to see both Portland’s highlights and the picturesque charm of Kennebunkport.

Key Points

• Private & Tailored: Fully customizable tour designed to match your interests and pace.
• Comfort & Convenience: Air-conditioned vehicle, local driver-guide, and pickup included.
• Stunning Views & Historic Sights: From Portland’s scenic parks to iconic lighthouses and Kennebunkport’s waterfront.
• Expert Guides: Knowledgeable guides make the experience more engaging and informative.
• Great for Small Groups: With a maximum of 12 guests, everyone gets personalized attention.
• Ideal for Coastal Lovers: Perfect for those seeking authentic Maine coastal scenery and history.

A Closer Look at the Portland and Kennebunkport Private Tour

Starting in Portland: The Best of the City’s Coastal Views

This private tour begins with a visit to Eastern Promenade, a favorite among locals and visitors alike. Here, you’ll stand along the coast, gazing out over Casco Bay, with its boats drifting lazily on the water. It’s a perfect first stop to stretch your legs and get your bearings. The Western Promenade Park offers similar scenic views, with an elevated position that provides a sweeping vista of islands and sailboats. Both parks are free, making them an excellent way to start your day with stunning photo opportunities.

Next, you’ll visit the Portland Observatory on Munjoy Hill. While the observatory itself is free to view from the outside, the real treasure is the panoramic view it offers of the harbor and coastline—especially on a clear day. It’s a classic Portland landmark that connects you visually to the city’s maritime past.

What we love about these early stops is the easy accessibility — all are within a short drive from downtown — and they set the tone for the scenic, relaxed exploration ahead. Plus, the guide’s local knowledge ensures you understand the importance of these spots beyond their beauty.

Portland Head Light: The Coast’s Most Famous Lighthouse

A highlight of any Maine coastal trip is Portland Head Light, perched dramatically on rocky Cape Elizabeth. Included in your tour, this iconic lighthouse is one of the most photographed in the U.S., and for good reason. You’ll have about 30 minutes here, enough time to walk along the rugged shoreline, snap pictures, and soak in the Atlantic’s salty air. The lighthouse itself is part of Fort Williams Park, which offers sweeping views and a peaceful atmosphere.

Our reviewer mentioned that Steve, their guide, was especially knowledgeable about local landmarks, making the visit more meaningful. Expect stories about the lighthouse’s history, construction, and role in maritime navigation—details that bring the scene to life.

South Portland’s Lighthouses and the Wedding Cake House

From Portland, your journey continues to Bug Light Park, a short drive away. This park offers views of another lighthouse, affectionately called “Bug Light,” which adds a quaint touch to your lighthouse collection. It’s a quick stop—around 10 minutes—but a perfect shot of classic Maine coast.

A special highlight is the Wedding Cake House in Portland, often called “the most photographed house in Maine.” Built by a shipbuilder, it boasts a distinctive layered appearance, reminiscent of a wedding cake. This stop is more about capturing a photo-worthy moment and learning a bit about local architecture and history.

The Transition to Kennebunkport: Coastal Charm and Historic Homes

After Portland, the tour heads down the scenic Highway 95 toward Kennebunkport, a village famous for its coastal beauty and Presidential summer home. Along the way, you’ll see Walker’s Point, the seaside estate of George W. Bush, which adds a touch of political history to your journey.

In Kennebunkport, the Dock Square is the hub of activity—full of quaint shops, cafes, and an inviting waterfront. Spending about 30 minutes here, you can wander the streets, watch boats come and go, and get a sense of the town’s lively yet relaxed atmosphere.

The Rocky Coast and Beaches

A short scenic drive along Kennebunk Beach and the rocky coast along Ocean Avenue offers some of Maine’s most rugged, picturesque scenery. It’s a chance to breathe in the ocean air, see rocky outcroppings, and imagine the lives of the shipbuilders and fishermen who once called this area home.

Personalization & Flexibility

What makes this tour stand out is the ability to customize. If you’re more interested in the historic houses, the maritime scenery, or the local neighborhoods, your guide can adapt your itinerary. The reviews highlight how guides like Steve go beyond the script, sharing stories and recommendations that enrich your understanding of Maine’s coastal life.

Why This Tour Offers Real Value

Although the price might seem steep compared to group bus tours, you’re paying for private transportation, a knowledgeable guide, and the flexibility to tailor your experience. It’s perfect for travelers who want to avoid crowded tours and prefer a more relaxed, personal touch. The inclusion of admission to Portland Head Light is a significant bonus, allowing you to enjoy this iconic lighthouse without extra hassle.

You’ll appreciate the comfort of an air-conditioned vehicle especially during warmer months, and the small group size ensures you’re not just another face in a crowd. Plus, the tour is well-timed, with enough stops to enjoy each location without feeling rushed.

The Authentic Experience

From the hands-on stories about local landmarks to the chance to explore seaside parks and historic homes, this tour offers genuine insight into Maine’s maritime heritage. Travelers have raved about guides like Steve, who make the experience engaging and informative, enhancing the scenic beauty with local lore and tips.

Practical Considerations

While there’s no lunch included, the tour’s schedule allows time for you to find a local café or seaside snack spot—something the guide can recommend. The pickup service makes logistics simple, especially if you’re staying downtown or near the coast. Since most travelers book about three weeks in advance, planning ahead ensures you secure your preferred date.

Who Will Love This Tour?

This private tour is ideal for small groups, couples, or families seeking a personalized experience of Maine’s coast. It’s perfect if you’re keen on photography, history, or coastal scenery, and want the flexibility to spend more time at the spots that catch your eye. If you prefer a structured, large-group bus tour, this might not be the best fit, but for those who want a more intimate, engaging exploration, it’s hard to beat.

Frequently Asked Questions

Is the tour suitable for all ages?
Yes, most travelers can participate, and the pace is flexible. It’s family-friendly, though young children should be comfortable with some walking and outdoor exploration.

What is included in the price?
The fee covers private transportation, a local driver-guide, parking fees, and admission to Portland Head Light. Lunch is not included, so plan accordingly.

How long is the tour?
The tour lasts approximately six hours, including travel time and sightseeing stops.

Can the itinerary be customized?
Yes, as a private tour, it can be tailored to your interests—more time at specific landmarks or skipping others depending on your preferences.

Is pickup available?
Yes, pickup is offered, making it easy to start your day without worrying about transportation logistics.

What if the weather is poor?
The experience is weather-dependent. If canceled due to bad weather, you’ll be offered an alternative date or a full refund.

How far in advance should I book?
Most bookings are made about 22 days ahead, so planning early is recommended to secure your preferred date.

What if I need to cancel or change my booking?
This tour is non-refundable and cannot be changed once booked. Make sure your plans are firm before booking.

To sum it up, this private Portland lighthouse and Kennebunkport tour offers a flexible, insightful way to explore Maine’s stunning coastline. With knowledgeable guides, a comfortable vehicle, and the ability to customize your journey, it’s a great choice for those who want to see iconic sights without feeling rushed or lost in a crowd. Perfect for small groups, couples, or families who appreciate a personal touch, this experience promises memorable views, engaging stories, and a true taste of coastal Maine. Whether you’re snapping photos of Portland Head Light or wandering the streets of Kennebunkport, you’ll leave with a deeper appreciation for Maine’s maritime charm and scenic beauty.