Castles of Cape Ann, Massachusetts Private Day Tour
Active
8h - 10h
For a full refund, cancel at least 24 hours before the scheduled departure time.
Instant confirmation
Mobile or paper ticket accepted
About this experience
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.
Available options
Glouster, and Ipswich
Pickup included
What's included
Private transportation
Bottled water
Snacks
All Fees and Taxes
Air-conditioned vehicle
Hotel or AirBnB Drop off and Pick Up included.
Detailed itinerary
1
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.
2
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.
3
Stop 3
The Gloucester Fisherman’s Memorial, also known as “Man at the Wheel,” is a bronze statue dedicated in 1925 to honor the thousands of fishermen lost at sea from this historic New England port. Standing watch over Gloucester Harbor, the figure embodies the courage, sacrifice, and resilience of the city’s fishing community. Gloucester itself is America’s oldest seaport, founded in 1623, and remains a vibrant fishing town rich in maritime history and coastal charm.
4
Stop 4
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.
What's not included
Gratuities
Lunch
Available languages
Audio guide
EN
Guide guide
EN
Written guide
EN
Reviews breakdown
Tripadvisor
5.0
3 reviews
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Important information
Public transportation options are available nearby
Suitable for all physical fitness levels
About Portland
Portland, Maine, is a vibrant coastal city known for its stunning waterfront, rich maritime history, and thriving arts and food scenes. With its picturesque lighthouses, charming cobblestone streets, and bustling Old Port district, Portland offers a perfect blend of history, culture, and natural beauty.
Top Attractions
Old Port
The Old Port is the historic heart of Portland, featuring cobblestone streets, 19th-century brick buildings, and a vibrant waterfront with shops, restaurants, and galleries.
Historical
Half day to full day
Free to explore, costs vary for dining and shopping
Portland Head Light
One of the most iconic lighthouses in the US, Portland Head Light offers stunning views of the rocky coastline and Casco Bay.
Historical/Nature
1-2 hours
Free (donations welcome)
Portland Museum of Art
The largest and oldest art museum in Maine, featuring a diverse collection of American, European, and contemporary art.
Museum
1-2 hours
$15 for adults, discounts for seniors and students, free for children under 17
Must-Try Local Dishes
Lobster Roll
A classic New England dish featuring fresh lobster meat served in a buttered, toasted roll.
Lunch
Contains shellfish, gluten (from the roll)
Maine Clam Chowder
A creamy, comforting soup made with fresh clams, potatoes, and cream.
Lunch/Dinner
Contains dairy, can be made gluten-free
Blueberry Pie
A sweet and tangy pie made with wild Maine blueberries.
Dessert
Contains gluten (from the crust), can be made gluten-free
Popular Activities
Hiking
Kayaking
Whale Watching
Sailing
Spa Day
Beachcombing
Wine Tasting
Yoga
Best Time to Visit
June to August
Summer is the peak tourist season with warm weather, outdoor festivals, and all attractions fully operational.
15-25°C
60-77°F
Practical Information
Language
- Official: English
- Widely spoken: English
- English: Widely spoken
Currency
US Dollar (USD)
Time Zone
GMT-5 (EST) / GMT-4 (EDT during daylight saving time)
Electricity
120VV, 60HzHz
Safety Information
Overall Safety Rating: Generally safe
Portland is generally safe with low crime rates. However, as with any city, it's important to stay aware of your surroundings and take precautions to ensure a safe visit.
Important Precautions:
- • Keep valuables secure and out of sight
- • Use reputable taxi services or ride-sharing apps
- • Be cautious of strangers offering unsolicited help or services
Getting there
By air
- Portland International Jetport • 4.8 km (3 miles) from city center
By train
Portland Transportation Center
By bus
Portland Transportation Center
Getting around
Public transport
Affordable and efficient, with frequent schedules.
Taxis
Available • Apps: Uber, Lyft
Rentals
Car, Bike, Scooter
Neighborhoods
Old Port
West End
Arts District
Day trips
Casco Bay Islands
Varies by island, typically 1-3 hours round trip • Half day to full day
Explore the scenic Casco Bay Islands, each offering unique landscapes, hiking trails, and charming villages. Perfect for a day trip from Portland.
Freeport
30 km (18 miles) • Half day to full day
Home to the famous L.L.Bean flagship store and outlet shopping, Freeport offers a mix of retail therapy and historic sites.
Boothbay Harbor
90 km (56 miles) • Full day
A picturesque coastal town known for its scenic beauty, lighthouses, and marine life. Boothbay Harbor is a great destination for nature lovers and those seeking a relaxing day trip.
Festivals
Portland International Film Festival • February
Portland Pride • June
Portland Highland Festival • September
Pro tips
- Visit the Old Port early in the morning to avoid crowds and enjoy the scenic views
- Try the local craft beer scene by visiting one of the many breweries in the city
- Explore the Casco Bay Islands for a unique and scenic day trip experience
- Attend a local festival or event to immerse yourself in the city's vibrant culture
- Take a lobster boat tour to learn about the local fishing industry and enjoy fresh seafood
Get Price
per person
Price varies by option
Secure booking
Free cancellation available
Instant confirmation
