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304 North Cardinal St.
Dorchester Center, MA 02124

Discover charming coastal towns with this private tour from Portland, exploring Kennebunkport, York, and Portsmouth at your own pace with expert guidance.
Imagine a day spent wandering along New England’s storied coast, visiting iconic lighthouses, historic neighborhoods, and quaint seaside villages—all with your own personalized guide. That’s exactly what this Kennebunkport, York, and Portsmouth private tour offers. While we haven’t been on this tour ourselves, the detailed itinerary and glowing reviews paint a compelling picture of a memorable day out.
What we love about this experience? First, the flexibility of a private tour means you can set your own pace and focus on what interests you most. Second, the blend of scenic beauty and history provides a well-rounded snapshot of this beautiful region. The potential downside? The price point of $325 per person might seem steep for some, but considering the private nature and included amenities, many will find it good value.
This tour is perfect for travelers who enjoy a mix of scenic views, cultural discovery, and comfort. Whether you’re a history buff, a lighthouse enthusiast, or simply someone who loves exploring charming towns without the hassle of planning each stop, this trip could be ideal.


For a more personal experience, these private Portland tours deliver individual attention
Starting at Stonewall Kitchen offers more than just a quick breakfast. Known for its artisanal foods, this flagship store is a treat for food lovers and a great place to soak in the locally crafted flavors. You can browse the shop’s inviting grounds, pick up some souvenirs, and enjoy a relaxed start to your day. The free admission makes it a low-cost, high-reward first stop, especially for those who appreciate gourmet foods and cozy atmospheres.
Next, the Nubble Lighthouse in York is one of the most photographed lighthouses on the East Coast, and for good reason. Located on a tiny rocky island just off Cape Neddick, it offers charming views and plenty of photo opportunities. The included admission means you’ll get close enough for great photos and some time to appreciate the lighthouse’s classic beauty. It’s a quintessential New England sight and a favorite among visitors.
A visit here deepens your understanding of the area’s colonial past. The exhibits showcase artifacts from early settlers, maritime history, and local lore, all housed within historic buildings. This stop offers about an hour of engaging exploration, and the admission fee is included, so it’s a straightforward way to learn about the area’s roots.
For something a little quirky, the Wiggly Bridge in York is a pedestrian bridge famous for its gentle wobbling. It’s a short stop, but one that invites a bit of fun and a chance to stretch your legs. Walking across this bridge offers a charming perspective of the natural surroundings and a lighthearted break in the day.
Crossing into New Hampshire, this historic hotel epitomizes Gilded Age elegance. A stop here provides a glimpse into the luxurious past of seaside resorts, with plenty of photo opportunities and stories of the hotel’s storied past. An hour at Wentworth offers a relaxed pace to admire architecture and ambiance; no entry fee is necessary since the focus is on the exterior and atmosphere.
Dating back to 1771, the Portsmouth Harbor Lighthouse is a symbol of maritime heritage. Located at Fort Constitution, the short 15-minute visit allows you to appreciate its classic white cast-iron tower and green lantern. It’s an iconic sight and offers a tangible connection to the region’s seafaring history.
This outdoor history museum spans over 300 years of Portsmouth’s past. Walking through restored homes, gardens, and historic buildings provides an immersive experience of how people lived here through the centuries. The 2-hour visit is ideal for history enthusiasts and those wanting a comprehensive look at local life. The admission fee is included, making it a valuable part of your day.
The final stop in Kennebunkport offers a perfect blend of seaside charm and boutique shopping. You’ll enjoy strolling through the downtown area, browsing galleries, and soaking in the relaxed coastal vibe. An hour here allows enough time to explore without feeling rushed, making it a lovely conclusion to your day.
The most praised feature, according to the sole review, is the knowledgeable guide, who shared local insights that brought each stop to life. The fact that the tour is private means you can spend more time at your favorite spots and less time rushing between attractions.
The scenic views, especially at the lighthouse and coastal stops, are consistently highlighted as highlights. The inclusion of snacks, bottled water, and a provided lunch means you won’t be scrambling for sustenance or paying extra along the way, adding to the overall value.
The cost of $325 per person, considering the private nature, transportation, and entrance fees, provides a good balance of convenience and exclusivity. For travelers wanting a personalized, relaxed day with a knowledgeable guide, this tour is a solid choice.

This experience suits travelers who prefer a customized day rather than a crowded bus tour. It’s perfect for those with a curiosity for local history, stunning coastlines, or charming towns. Families, couples, or small groups wanting a flexible itinerary will find this especially appealing. It’s also ideal for visitors who want a hassle-free way to see multiple sights without the stress of planning each detail.

In essence, this private tour offers an excellent balance of scenic beauty, historical insight, and personalized service. The knowledgeable guide makes each stop informative and engaging, while the included amenities make the day comfortable and convenient.
If you’re looking for a way to explore Maine and New Hampshire’s coast without the chaos of large tours, this experience offers genuine value. It’s particularly suitable for those who appreciate authentic local sights, relaxed pacing, and a touch of luxury in their travel adventures.
“AJ was a fabulous guide all day! Booking a private tour made the day even that much betterbeing able to take a little extra when needed to see more…”

What is the duration of the tour?
The tour lasts approximately 7 to 9 hours, giving you plenty of time to explore each stop comfortably.
Is transportation included?
Yes, the tour provides private transportation in an air-conditioned vehicle, making long days of sightseeing more enjoyable.
What’s included in the price?
All entrance fees, snacks, bottled water, and lunch are included, which helps keep the day stress-free and predictable.
Can I customize the itinerary?
Since it’s a private tour, the itinerary is flexible and can be tailored to your interests and pace.
Is this suitable for all ages?
Most travelers can participate, and service animals are allowed. It’s suitable for anyone able to enjoy walking and sightseeing.
How far in advance should I book?
On average, this tour is booked about 29 days ahead, so it’s best to reserve early, especially during peak seasons.
What’s the cancellation policy?
You can cancel up to 24 hours in advance for a full refund, providing peace of mind if your plans change.
This private tour from Portland truly offers a well-rounded, authentic taste of Maine and New Hampshire’s coastal treasures. Whether you’re after scenic views, historic sites, or just a relaxing day exploring charming towns, it’s an experience worth considering.