• Castle Hill on the Crane Estate - Located in Ipswich, Castle Hill on the Crane Estate offers visitors a magnificent 59-room mansion perched on a hill with panoramic views of the Atlantic Ocean. The estate boasts beautifully manicured gardens, intricate architecture inspired by Italian Renaissance villas, and the impressive “Grande Allée,” a nearly half-mile-long lawn stretching down to the sea. Inside, the mansion features luxurious interiors with period furnishings, fine art, and elegant details that reflect the grandeur of the early 20th century. The estate’s rich history and stunning surroundings make it a must-see on any tour.
• Ipswich - Ipswich, Massachusetts, is a charming coastal town rich in colonial history and natural beauty. Renowned for having one of the highest concentrations of First Period homes (built before 1725) in the nation, Ipswich offers a glimpse into early American life with its well-preserved architecture and picturesque streets. Its tranquil beaches, vibrant marshlands, and the scenic Ipswich River further enhance the town’s charm, making it a delightful destination for history enthusiasts and nature lovers alike.
• Gloucester - A brief visit to Gloucester, Massachusetts, provides the opportunity to see the iconic Gloucester Fisherman’s Memorial, a tribute to the countless fishermen who have perished 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 serves as a poignant reminder of the risks faced by generations of Gloucester fishermen, dating back over 400 years.

From the shoreline, visitors can also enjoy stunning views of Gloucester’s lighthouses, including Ten Pound Island Light and Eastern Point Light, both visible from various vantage points. 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 to any tour when in operation. This is our lunch stop on the historic Cape Ann Marina.

• Hammond Castle Museum - This stop is available seasonally as hours vary. Admission is not included, but it’s definitely worth the visit.
• Russell Orchards - Russell Orchards in Ipswich, Massachusetts, is a delightful farm stop where guests can experience the best of New England’s agricultural heritage. Spanning over 120 acres, it offers apple picking, a farm store with fresh produce, cider donuts, and even local wines and hard ciders made 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 charming addition to any tour of the area.

• Private transportation
• Bottled water and snacks
• In-vehicle air conditioning
• All fees and taxes included
• Hotel or AirBnB drop-off and pick-up

• Gratuities
• Lunch

Experience the allure of New England’s coastline with a private tour from Portland, Maine, to Cape Ann and the North Shore of Massachusetts. This adventure leads you to the breathtaking Castle on Crane Hill in Ipswich, where you can enjoy views over vast salt marshes and soak in historic splendor. Then, visit Hammond Castle in Gloucester, a medieval-inspired estate brimming with art, inventions, and fascinating architecture.

Stroll through the historic streets of Ipswich, where colonial homes and coastal vistas reflect America’s early history. Enjoy a delightful visit to Russell Orchards, where you can wander the orchards, indulge in fresh cider donuts, and taste wines crafted from their own fruit.

This exclusive tour combines magnificent castles, charming towns, and New England’s seasonal abundance—offering an unforgettable experience for those seeking a unique perspective on the North Shore. Join this journey that weaves together history, beauty, and local flavor into one perfect day.

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