Ipswich and Cape Ann Private Tour Experience

Experience the beauty and history of Ipswich and Cape Ann on this private tour. Wander Castle Hill’s grand estate, explore Ipswich’s heritage, and enjoy Gloucester’s seaside character. When available, Hammond Castle offers an unforgettable glimpse into medieval architecture on the New England coast. End your journey at Russell Orchards for fresh, local charm

Meeting Point

Downtown

Downtown, Portland, ME 04101, USA

This is a generic meeting location. Your guide will advise on the best meeting location based on where you are coming from or staying.

What to expect:

Duration: between 8 hours and 10 hours

Castle Hill on the Crane Estate

290 Argilla Rd, , Ipswich, 01938-2647, Massachusetts

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.

1 hour • Admission Ticket Included

Ipswich

Ipswich, Massachusetts

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.

45 minutes

Gloucester

Gloucester, Massachusetts

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.

1 hour

Hammond Castle Museum

80 Hesperus Avenue, Gloucester, 01930-5273, Massachusetts

Set against the backdrop of the Atlantic, Hammond Castle is especially stunning in the fall. You’ll explore both the castle’s scenic grounds and its unique interior, filled with medieval-style architecture, artifacts, and the legacy of inventor John Hays Hammond Jr. Admission tickets for the full museum experience are included with your tour.

1 hour • Admission Ticket Included

Russell Orchards

143 Argilla Rd, , Ipswich, 01938-2644, Massachusetts

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.

30 minutes