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Sightseeing in Gloucester, MA


Capt. Bill & Sons Whale Watch: Whale-Watching Excursion for One or Two from Capt. Bill and Sons Whale Watch (Up to 44% Off)

Whale-Watching Excursion for One or Two from Capt. Bill and Sons Whale Watch (Up to 44% Off)

Capt. Bill & Sons Whale Watch

Gloucester

A family of experts shares tips on spotting humpback and minke whales—as well as dolphins and seals—during three- to four-hour outings

$48 $28

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7 Seas Whale Watch: Whale-Watching Trip for One or Two from 7 Seas Whale Watch (Up to 43% Off)

Whale-Watching Trip for One or Two from 7 Seas Whale Watch (Up to 43% Off)

7 Seas Whale Watch

Gloucester

Featured on Discovery Channel and in “National Geographic,” boat tours offer the chance to spot whales and also seals and dolphins

$48 $29

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Sweet Baby Vineyard: Wine Tasting with Wine Glasses, Cheese Platter, and 15% off Wine for Two or Four at Sweet Baby Vineyard (Up to 52% Off)

Wine Tasting with Wine Glasses, Cheese Platter, and 15% off Wine for Two or Four at Sweet Baby Vineyard (Up to 52% Off)

Sweet Baby Vineyard

Hampstead

Sip six samples of wine while snacking on cheese plates; take home souvenir wine glasses and wine purchased with a 15% discount

$23 $12

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A&A Balloon Rides, LLC: $299 for a Sunrise Hot Air Balloon Ride for Two with Champagne from A&A Balloon Rides, LLC ($450 Value)

$299 for a Sunrise Hot Air Balloon Ride for Two with Champagne from A&A Balloon Rides, LLC ($450 Value)

A&A Balloon Rides, LLC

Salem

As balloons drift up to 2,000 feet high, passengers get 360-degree views of the landscape; post-flight, they enjoy champagne and cheeses.

$450 $299

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Best Tours (Boston): Drunk History of Boston Tour for One, Two, or Four People from Best Tours (Boston) (Up to 60% Off)

Drunk History of Boston Tour for One, Two, or Four People from Best Tours (Boston) (Up to 60% Off)

Best Tours (Boston)

Boston

Visitors learn about Boston’s history through improv, re-enactments, and trivia and sip welcome shots and drinks at four pubs along the way

$50 $25

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Best Tours: Two-Hour Chocolate Walking tour with Six Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Two-Hour Chocolate Walking tour with Six Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours

Boston

Sample champagne-flavored truffles, chocolatey French pastries, and cupcakes during a two-hour chocolate tour of Back Bay

$50 $25

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Bird's Eye View Helicopters: Mansion Helicopter Tour from Bird's Eye View Helicopters (Up to 40% Off)

Mansion Helicopter Tour from Bird's Eye View Helicopters (Up to 40% Off)

Bird's Eye View Helicopters

Middletown

Pilot navigates a heated helicopter over 18 miles of picturesque mansions, including the Kennedy’s summer home.

$225 $135

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Lighthouse Preservation Society: Meals Atop Newburyport Lighthouse from the Lighthouse Preservation Society (Up to 61% Off). Three Options Available.

Meals Atop Newburyport Lighthouse from the Lighthouse Preservation Society (Up to 61% Off). Three Options Available.

Lighthouse Preservation Society

Newburyport

Breakfast, lunch, or dinner at a private table with harbor views from the top of a historic lighthouse

$900 $349

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Boston Super Tours: Narrated One- or Two-Day Trolley Tours of Boston for Adults or Children from Boston Super Tours (Up to 46% Off)

Narrated One- or Two-Day Trolley Tours of Boston for Adults or Children from Boston Super Tours (Up to 46% Off)

Boston Super Tours

Upper Deck Trolley Tours

Hop on and off a comprehensive trolley tour that stops at Boston’s most iconic landmarks- extra tour day included in winter

$59 $32

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The Mapparium: Admission for One, Two, or Four at the The Mapparium (Up to 50% Off)

Admission for One, Two, or Four at the The Mapparium (Up to 50% Off)

The Mapparium

The Mary Baker Eddy Library

The three-story stained-glass globe hosts a vibrant presentation inside the sphere, complete with LED lights

$6 $5

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Imajine That: One-Month Membership for Two Adults and One, Two, or Three Kids at Imajine That (54% Off)

One-Month Membership for Two Adults and One, Two, or Three Kids at Imajine That (54% Off)

Imajine That

Lawrence

12,000 sq. ft. interactive children’s museum allows kids and their parents to create and explore together with educational activities

$30 $14

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The Butterfly Place: $17 for Admission for Two at The Butterfly Place (Up to $25 Value)

$17 for Admission for Two at The Butterfly Place (Up to $25 Value)

The Butterfly Place

Westford

Get up-close views of colorful butterflies as they flutter and sip nectar from vibrant plants growing in the indoor atrium

$25 $17

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CitySights NY: Admission to Wax Attraction, Harbor Cruise, and Empire State Building from CitySights NY (Up to $61 Off)

Admission to Wax Attraction, Harbor Cruise, and Empire State Building from CitySights NY (Up to $61 Off)

CitySights NY

Visitor Center

Passes for Madame Tussauds wax attraction, Empire State Building, and Midtown harbor cruise

$98 $69

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Smart Destinations: Two-Day All-Inclusive Go Boston Card Including Free Admission to 50+ Popular Boston Attractions

Two-Day All-Inclusive Go Boston Card Including Free Admission to 50+ Popular Boston Attractions

Smart Destinations

 

Card grants free admission to 51 Boston museums, tours & attractions. Save up to 55% off combined gate prices if purchased separately

$55 $49.50

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C-R Helicopters: One or Three Private Flying Lessons with Ground School and Hands-On Flights from C-R Helicopters (Up to 48% Off)

One or Three Private Flying Lessons with Ground School and Hands-On Flights from C-R Helicopters (Up to 48% Off)

C-R Helicopters

Northwest Nashua

Pilots go over instruments and preflight checks before letting students hone flight patterns behind the controls of two-seater helicopters

$207.50 $121

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Charles Riverboat Company: Charles River Sightseeing or Sunset Tour for One or Two from Charles Riverboat Company (Up to 46% Off)

Charles River Sightseeing or Sunset Tour for One or Two from Charles Riverboat Company (Up to 46% Off)

Charles Riverboat Company

Cambridge

Captain and crew lead river sightseeing & sunset tours past Harvard, Fenway Park, and historic sights along Charles River and Boston Harbor

$18.50 $11

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Cityview Trolley Tours: Trolley Tour and Harbor Cruise for One, Two, or Four from CityView Trolley Tours (Up to 55% Off)

Trolley Tour and Harbor Cruise for One, Two, or Four from CityView Trolley Tours (Up to 55% Off)

Cityview Trolley Tours

Boston

Historical sites headline a trolley tour and a 45-minute harbor cruise affords sweeping views of the city

$38 $20

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Bay Spirit Tours: 75-Minute Lighthouse Boat Tour for One, Two, or Four at Bay Spirit Tours (Up to 51% Off)

75-Minute Lighthouse Boat Tour for One, Two, or Four at Bay Spirit Tours (Up to 51% Off)

Bay Spirit Tours

Hyannis

Boat cruises out of Hyannis Harbor on scenic 75-minute tour

$20 $11

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Best Tours (Boston): Italian Food Tour of Boston for One, Two, or Four from Best Tours (Boston) (Up to 60% Off)

Italian Food Tour of Boston for One, Two, or Four from Best Tours (Boston) (Up to 60% Off)

Best Tours (Boston)

Boston

Tour-goers tour Boston’s Little Italy neighborhood and enjoy a four-course lunch while learning all about the Italian immigrant experience

$50 $25

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Jewell Towne Vineyards: Wine Tasting, Cheese, Vineyard Tour, and Glasses for Two or Four at Jewell Towne Vineyards (Up to 53% Off)

Wine Tasting, Cheese, Vineyard Tour, and Glasses for Two or Four at Jewell Towne Vineyards (Up to 53% Off)

Jewell Towne Vineyards

South Hampton

Guests sample red, white & rosé wine with cheese plate in addition to taking a vineyard tour and learning more about the wine-making process

$36 $19

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Boston Helicopters: $199 for an Intro to Helicopter Flying Lesson with Video at Boston Helicopters ($289 Value)

$199 for an Intro to Helicopter Flying Lesson with Video at Boston Helicopters ($289 Value)

Boston Helicopters

North Andover

FAA-approved helicopter flight instructors; aspiring aviators pilot a Robinson helicopter for 30 minutes while an HD video camera records

$289 $199

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Newburyport Whale Watch: Whale-Watching Tour for One, Tour, or Four from Newburyport Whale Watch (Up to 43% Off)

Whale-Watching Tour for One, Tour, or Four from Newburyport Whale Watch (Up to 43% Off)

Newburyport Whale Watch

Newburyport

Passengers head out to sea aboard a custom whale-watching craft to enjoy the majestic mammals, aided by an onboard naturalist

$48 $29

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Boston Tea Party Ships & Museum: $69 for Admission for 2 to Tavern Nights Experience at Boston Tea Party Ships & Museum ($90 value)

$69 for Admission for 2 to Tavern Nights Experience at Boston Tea Party Ships & Museum ($90 value)

Boston Tea Party Ships & Museum

Downtown

Experience the laughter and fun of a colonial-era tavern with dinners of roast pork and chicken and Harpoon beer and live colonial music

$90 $69

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Wacky Walks - Boston: Wacky Walk Adventure for Two, Four, or Six from Wacky Walks - Boston (Up to 50% Off)

Wacky Walk Adventure for Two, Four, or Six from Wacky Walks - Boston (Up to 50% Off)

Wacky Walks - Boston

Boston

Part solo strategizing game and part team quest, this walk around the city leads to clues that need solving—and upheaval in your ranks

$39.95 $20

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Zoo Creatures: Tour of New England Reptile Distributors for Two or Four from Zoo Creatures (Up to 50% Off)

Tour of New England Reptile Distributors for Two or Four from Zoo Creatures (Up to 50% Off)

Zoo Creatures

Plaistow

Get cozy with a pink and purple python or alligator during this reptile tour

$16 $8.50

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Intrepid Sea, Air & Space Museum: Intrepid Sea, Air & Space Museum and Space Shuttle Pavilion Visit with Optional Tour (Up to 35% Off)

Intrepid Sea, Air & Space Museum and Space Shuttle Pavilion Visit with Optional Tour (Up to 35% Off)

Intrepid Sea, Air & Space Museum

Pier 86

Museum features the legendary aircraft carrier Intrepid, the space shuttle Enterprise, the world’s fastest jets, and a missile submarine

$31 $20

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3Quest Challenge: Urban Scavenger Race for Two, Four, or Six from 3Quest Challenge (Half Off)

Urban Scavenger Race for Two, Four, or Six from 3Quest Challenge (Half Off)

3Quest Challenge

3Quest Challenge - Boston

Racing against the clock, players progress through three quests where they find checkpoints, seize clues, and solve the final puzzle

$39.95 $20

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Lighthouse Preservation Society: Breakfast, Lunch, or Dinner in a Lighthouse for Up to 4 from The Lighthouse Preservation Society (Up to 67% Off)

Breakfast, Lunch, or Dinner in a Lighthouse for Up to 4 from The Lighthouse Preservation Society (Up to 67% Off)

Lighthouse Preservation Society

Newburyport

Prix fixe meal at a private table with harbor views from the top of the historic Newburyport Lighthouse

$900 $299

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CityView Trolley Tours: Trolley Tour for One, Two, or Four from CityView Trolley Tours (Up to 55% Off)

Trolley Tour for One, Two, or Four from CityView Trolley Tours (Up to 55% Off)

CityView Trolley Tours

Boston

Historical sites headline a trolley tour that affords sweeping views of the city

$38 $19

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Animal Adventures: Visit to Exotic Animal Rescue Center and Wildlife Show for Two or Four at Animal Adventures (Up to 43% Off)

Visit to Exotic Animal Rescue Center and Wildlife Show for Two or Four at Animal Adventures (Up to 43% Off)

Animal Adventures

Bolton

Exotic animals rescued from neglect or abandonment interact with guests during self-guided tours & live animal shows led by wildlife experts

$28 $17

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Cape Cod Children's Museum: Admission for Two or Four to Cape Cod Children's Museum (34% Off)

Admission for Two or Four to Cape Cod Children's Museum (34% Off)

Cape Cod Children's Museum

Mashpee

More than 20 interactive exhibits include a tree house, music room, and pirate ship

$16 $11

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Best Tours: Two-Hour Cupcake Walking Tour with Five Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Two-Hour Cupcake Walking Tour with Five Tastings for One, Two, or Four from Best Tours (Up to 60% Off)

Best Tours

Boston

Sample 5 designer cupcakes & desserts while walking around historic Back Bay; cupcakeries include Georgetown Cupcake, Sweet, & Robin’s Candy

$50 $25

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JFK Hyannis Museum Foundation: Admission for Two or Four or One-Year Individual or Family Membership to JFK Hyannis Museum (Up to 27% Off)

Admission for Two or Four or One-Year Individual or Family Membership to JFK Hyannis Museum (Up to 27% Off)

JFK Hyannis Museum Foundation

Barnstable Town

Exhibits explore the personal and political lives of John F. Kennedy, America’s 35th President

$20 $15

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Dupont Circle Fountain: Sex, Scandal and Sinners along Embassy Row at Dupont Circle Fountain

Sex, Scandal and Sinners along Embassy Row at Dupont Circle Fountain

Dupont Circle Fountain

Capitol Hill

$40 $25.25

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Boston Tea Party Ships Museum: Visit for One, Two, or Four to Boston Tea Party Ships & Museum (Up to 50% Off)

Visit for One, Two, or Four to Boston Tea Party Ships & Museum (Up to 50% Off)

Boston Tea Party Ships Museum

Downtown

The Boston Tea Party comes to life with immersive exhibits, tea-ship replicas, and one of the original tea chests from December 16, 1773

$25 $13

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Blue Hill Helicopters: Flight-Simulator Experience or 30-Minute Helicopter Tour for Up to Three at Blue Hill Helicopters (Up to 45% Off)

Flight-Simulator Experience or 30-Minute Helicopter Tour for Up to Three at Blue Hill Helicopters (Up to 45% Off)

Blue Hill Helicopters

Norwood

Flight simulator with virtual cityscape and realistic controls; tour takes guests over sights such as Fenway Park and Charles River

$150 $83

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The Histrionic Academy: The Freedom Trail: The Path to Independence for One, Two, or Four from Histrionic Academy (Up to 53% Off)

The Freedom Trail: The Path to Independence for One, Two, or Four from Histrionic Academy (Up to 53% Off)

The Histrionic Academy

Beacon Hill

Costume-clad tour guides lead visitors along the Freedom Trail passing by historic landmarks and imparting facts about revolutionary figures

$14.75 $8

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Best Tours Boston: Pizza Tour for One or Two or Italian Food Tour for Four from Best Tours Boston (Up to 60% Off)

Pizza Tour for One or Two or Italian Food Tour for Four from Best Tours Boston (Up to 60% Off)

Best Tours Boston

Boston

Hungry tour-goers explore the city’s best pizza spots or enjoy a four-course meal in the North End neighborhood

$50 $25

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Cape Cod Museum of Art: Visit for Two or Four or Individual or Family Membership at Cape Cod Museum of Art (Up to 47% Off)

Visit for Two or Four or Individual or Family Membership at Cape Cod Museum of Art (Up to 47% Off)

Cape Cod Museum of Art

Dennis

Galleries highlight art from Cape Cod and the islands, from pastel-colored impressionist landscapes to bold abstract expressionist canvases

$18 $12

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Witch City Walking Tours: Custom Walking Tour of Salem for Two or Four from Witch City Walking Tours (Up to 52% Off)

Custom Walking Tour of Salem for Two or Four from Witch City Walking Tours (Up to 52% Off)

Witch City Walking Tours

Salem

A licensed and certified historian leads groups on foot through historic Salem, the site of witchcraft hysteria in 1692

$30 $17

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Smart Destinations: Two-Day All-Inclusive Go City Card Including Free Admission to Dozens of Popular Attractions

Two-Day All-Inclusive Go City Card Including Free Admission to Dozens of Popular Attractions

Smart Destinations

 

Card grants free admission to museums, tours, and attractions; save up to 55% off combined gate prices if purchased separately

$52.99 $49.50

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CitySights NY: Double Decker Bus Tour and Ferry Boat Cruise Package for One or Two from CitySights NY (Up to 43%Off)

Double Decker Bus Tour and Ferry Boat Cruise Package for One or Two from CitySights NY (Up to 43%Off)

CitySights NY

Visitor Center

On hop-on-hop-off bus tours, visitors explore areas such as Times Square & Top of The Rock at their own pace; boat tours show off the harbor

$78 $45

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Best Tours (Boston): Boston Coffee Tour for One, Two, or Four from Best Tours (Boston) (Up to 60% Off)

Boston Coffee Tour for One, Two, or Four from Best Tours (Boston) (Up to 60% Off)

Best Tours (Boston)

Boston

Two-hour tour includes barista demos, coffee history and trivia, and stops at famous Boston landmarks, plus coffee tastings along the way

$50 $25

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Fuller Craft Museum: Fuller Craft Museum Visit for Two, Guided Tour for Four, or Annual Membership for One (Up to 43% Off)

Fuller Craft Museum Visit for Two, Guided Tour for Four, or Annual Membership for One (Up to 43% Off)

Fuller Craft Museum

Brockton

Rotating, eclectic exhibits of drawing, sculpture, and other art and functional craft forms; membership with workshop discounts

$16 $12

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Plymouth Night Tour: Plymouth Night Tour for One, Two, or Four (Up to 53% Off)

Plymouth Night Tour for One, Two, or Four (Up to 53% Off)

Plymouth Night Tour

Remember Plymouth Gifts

Paranormal investigators lead guests through spooky sites around Plymouth with tales of hauntings

$15 $8

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Boston Haunts: Haunted Boston Tour for Two or Four from Boston Haunts (50% Off)

Haunted Boston Tour for Two or Four from Boston Haunts (50% Off)

Boston Haunts

Irish Famine Memorial

Guides lead 90-minute walking tours by lantern through historic streets of downtown Boston, sharing stories and reported ghost sightings

$34 $17

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Griffin Museum of Photography: Four Full-Day Admissions or Annual Membership for Two at Griffin Photography Museum (Up to 51% Off)

Four Full-Day Admissions or Annual Membership for Two at Griffin Photography Museum (Up to 51% Off)

Griffin Museum of Photography

Winchester Town Center

Three galleries showcase up-and-coming photographers, in addition to well-known contemporary artists and celebrity photographers.

$28 $15

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Stray Boots: Cell-Phone-Guided Scavenger Hunt for Two or Four from Stray Boots (50% Off). Four Options Available.

Cell-Phone-Guided Scavenger Hunt for Two or Four from Stray Boots (50% Off). Four Options Available.

Stray Boots

 

Clues, trivia, and riddles lead explorers through Boston’s colorful, quirky history via the Stray Boots iPhone or Android app

$24 $12

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Candia Vineyards: Wine-Tasting Package with Glasses and Take-Home Gifts for One, Two, or Four at Candia Vineyards (Up to 49% Off)

Wine-Tasting Package with Glasses and Take-Home Gifts for One, Two, or Four at Candia Vineyards (Up to 49% Off)

Candia Vineyards

Candia

Wine lovers receive a tasting, a voucher for dessert wine, chocolates, a wind chime, New England wine book, and a pruning seminar

$58 $35

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Select Local Merchants

  • Hammond Castle Museum
    Five Things to Know About Hammond Castle Museum As far as wedding presents go, this one was a doozy: the medieval-style Hammond Castle was built as a gift from inventor John Hammond (“The Father of the Remote Control”) to his wife, Irene, during the 1920s. For a time, the castle also hosted Hammond’s research corporation—by the end of his life, he had more than 400 patents. Today, it still stands as a marvel of architecture and design, but also serves as a museum to the life of the Hammonds. Before you visit, here are a few helpful things to know: You can drop by anytime. Well, anytime during operating hours (which exclude winter). But you don’t have to wait for a guided tour when you get there; just take a map and explore the museum by yourself. The museum gives you plenty of background to whet your palate. In the castle's AV room, a film tells about the Hammonds and their lives. There's plenty to see indoors and out. Wander through an indoor courtyard, the library, the kitchens, the servants’ quarters, and, of course, a secret passageway indoors; outdoors check out the gardens, which have a stunning view of the Atlantic shoreline. There's also one of the largest residential pipe organs in the world on the premises. Designed by Hammond and located in the Great Hall, the organ comes with more than 8,000 pipes and sits under a large rose window with images of angels playing musical instruments. There are a lot of stairs. This being an old castle, it’s not wheelchair-accessible—you’ll need to step up and down a lot to work your way through the home.
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    80 Hesperus Avenue
    Gloucester, MA US
  • Beauport
    By the Numbers: Beauport Also known as the Sleeper-McCann House, Beauport earned acclaim as the summer home of one of America’s first professional interior designers, Henry Davis Sleeper. Built on the rocks overlooking Gloucester Harbor, the house still contains Sleeper’s collection of crafts, arts. and other curiosities. Here are some numbers behind the house’s prosperity: 14,200— the house’s square footage 1907—the year Davis Sleeper bought the lot and built his initial home, Little Beauport 15—the age Sleeper began receiving $850 per year from his grandfather’s trust, which became the basis for his fortune 40 rooms occupy the house currently, and each is distinguished by a historical or literary figure, theme, color, shape, or object 2003—the year Beauport was named a National Historic Landmark 2 of the house’s restrooms are open to the public, which comes in handy during daily tours and picnics on the property
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    75 Eastern Point Boulevard
    Gloucester, MA US
  • IMAGINE
    Gloucester's IMAGINE is a great place to browse and find your next fashion jewelry piece. When winter comes around, you'll be happy you stopped by IMAGINE for some stylish accessories. What kind of artwork catches your eye? Swing by this store for a look at some of the finest pieces in town. When you are commuting to this store by car, take advantage of the nearby parking options. Great jewelry is just a hop, skip and jump away at IMAGINE in Gloucester so head on over today and go home with a new set.
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    43 Rocky Neck Avenue
    Gloucester, MA US
  • Rockport Art Association
    For those that appreciate the finer things, be sure to explore the artwork at Rockport's Rockport Art Association. Every great place has a restaurant on the side. When you come to this museum, it's no different. This museum is great for families with kids. Public transit and parking are two main forms of transit convenience near Rockport Art Association. Parking is plentiful, so guests can feel free to bring their vehicles.
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    12 Main Street
    Rockport, MA US
  • Shaker Society
    Whether you're solo or with a group, Shaker Museum in New Gloucester is a great place to explore and indulge in works of art. Sure you could eat at home, but you'll want to take advantage of this museum's restaurant for high-class food. Go ahead and bring your rug rats with you — this museum has kid-friendly policy. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    707 Shaker Road
    New Gloucester, ME US
  • Good Dog Gallery
    Looking for some inspiration? Check out the unique and memorable art pieces at Good Dog Gallery in Rockport. Make the trip to this museum even more savory with a visit to their fine restaurant. This museum welcomes kids, too, so you can feel good about bringing the whole family. Parking is plentiful, so patrons can feel free to bring their vehicles.
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    36 Bearskin Neck
    Rockport, MA US

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