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Salem, Kennebunkport, Kittery, and Portsmouth Private Day Tour

Salem, Kennebunkport, Kittery, and Portsmouth Private Day Tour

Overview

Discover the charm of New England’s coast with a private tour from Portland, Maine, to Cape Ann and the North Shore of Massachusetts. This journey takes you to the stunning Castle on Crane Hill in Ipswich, offering views across expansive salt marshes and an immersion in historic grandeur. Next, explore Hammond Castle in Gloucester, a medieval-inspired estate filled with art, inventions, and captivating architecture.

Wander through the historic streets of Ipswich, where colonial homes and coastal views capture America’s early history. Then, enjoy a delightful stop at Russell Orchards, where you can stroll the orchards, savor fresh cider donuts, and sample wines made from their own fruit.

This exclusive tour combines majestic castles, authentic towns, and New England’s seasonal bounty—creating an unforgettable experience for those seeking a unique perspective on the North Shore. Join us for a journey that blends history, beauty, and local flavor into one perfect day.

City: Portland

Sat 07 Jun

Other dates

You can choose the date already on the booking website

Starting at $330.00

Make a reservation

Sat 07 Jun

Starting at $330.00

Make a reservation

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What's Included

Private transportation

Bottled water

Snacks

Air-conditioned vehicle

All Fees and Taxes

Hotel or AirBnB Drop off and Pick Up included.

Additional Info

Public transportation options are available nearby
Suitable for all physical fitness levels

What To Expect

Castle Hill on the Crane Estate

At the Castle Hill on the Crane Estate in Ipswich, visitors will experience a stunning 59-room mansion set atop a hill with sweeping views of the Atlantic Ocean. The estate features beautifully landscaped gardens, intricate architecture inspired by Italian Renaissance villas, and the grand "Grande Allée," a nearly half-mile-long lawn leading down to the sea. Inside, the mansion showcases opulent interiors with period furnishings, fine art, and elegant details reflecting the grandeur of the early 20th century. The estate's history and breathtaking surroundings make it a highlight of any tour.

Ipswich

Ipswich, Massachusetts, is a charming coastal town steeped in colonial history and natural beauty. Known for having one of the highest concentrations of First Period homes (built before 1725) in the country, Ipswich offers a glimpse into early American life with its well-preserved architecture and picturesque streets. Its serene beaches, vibrant marshlands, and the scenic Ipswich River further enhance the town’s appeal, making it a delightful destination for history buffs and nature lovers alike.

Gloucester

A quick stop in Gloucester, Massachusetts, offers the chance to see the iconic Gloucester Fisherman’s Memorial, which stands as a tribute to the countless fishermen who have lost their lives at sea. Known as “The Man at the Wheel,” this statue, located on Stacy Boulevard, overlooks Gloucester Harbor and symbolizes the town’s deep connection to the maritime industry. It’s a poignant reminder of the risks faced by generations of Gloucester fishermen, dating back over 400 years. From the shoreline, you can also enjoy stunning views of Gloucester’s lighthouses, including Ten Pound Island Light and Eastern Point Light. Both are visible from various spots. The combination of the historic memorial and the picturesque lighthouses makes Gloucester’s harborfront a must-see, offering both a moment of reflection and breathtaking ocean views. Hammond Castle can be added on to any tour when in operation. This is our lunch stop on the historic Cape Ann Marina.

Hammond Castle Museum

This stop is only available seasonally as hours vary. Admission is not included but it’s definitely worth the add on.

Russell Orchards

Russell Orchards in Ipswich, Massachusetts, is a charming farm stop where guests can experience the best of New England’s agricultural heritage. Set on over 120 acres, it offers apple picking, a farm store with fresh produce, cider donuts, and even local wines and hard ciders crafted from their own fruit. Visitors can explore the scenic grounds, meet farm animals, and enjoy a taste of rural Massachusetts. This stop provides a relaxing and authentic farm experience with a variety of seasonal treats, making it a delightful addition to any tour of the area.

Show 2 more stops

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (3)

813claya

Oct 2023

This was an awesome way to experience Salem and Kennebunk port without all the hassle! AJ arrived in a spacious SUV loaded with snacks drinks and every other road trip essential to make us comfortable! His knowledge of import land marks to visit best, time efficiency of seeing everything we wanted to and friendliness made the trip that much more enjoyable! He even offered to take any and all pictures for us that we wanted! He also had a great knowledge of the history of Salem and the surrounding areas as we walked or drove past different landmarks we got fun information at each site! I would definitely recommend AJ to and his company to anyone looking for a great day trip to Salem!

SANDRA W

Jun 2023

AJ took us to the Portland Lighthouse and Kennebunkport on the way to Salem. He knows the area so well and we had the best viewing spots! He also took pictures for us so that we had nothing do but enjoy the day. Salem was such a fun place and having a guide that knows the city well is a great way to see it all! I would definitely tour with them again!

Response from Host

Jun 2023

You both were wonderful! Even in the rain! Can’t wait to visit y’all in Houston this winter!

belannb

Sep 2021

Our driver Mimi was great! She was very knowledgeable about Yellowstone and the surrounding area. She was very nice and accommodating. Very prepared. Would highly recommend.

Response from Host

Sep 2021

Thank You so much for your review. We are very happy you enjoyed your adventure.