Sightseeing & Tours in Gloucester, MA

Admission for One to RISE of the Jack O'Lanterns (Up to 31% Off). Four Dates Available.

RISE of the Jack O'Lanterns

RISE of the Jack O'Lanterns - Boston

More than 5,000 jack o’lanterns hand-carved with designs such as superheroes and sports figures light up a family-friendly trail

$26 $18

VIP Admission for Two to Fright Kingdom (Up to 43% Off)

Fright Kingdom

Mine Falls Park

Multiple attractions such as Castle of Corpses, Bloodmare Manor and Psycho Circus 3D; VIP pass includes skip-the-line privileges

$68 $39

General Admission for Two or Four at Whydah Pirate Museum (Up to 34% Off)

Whydah Pirate Museum

Whydah Pirate Museum

Explore the glimmering bounty uncovered from a 300-year-old pirate ship, The Whydah, and hear the tale of how she sank

$37 $25

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


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

$23 $12

Walking Tour for Two or Four from Salem Heritage Tours (48% Off)

Salem Heritage Tours

Salem Heritage Tours

Experienced guides lead visitors on a tour of some of Salem’s most historic sites, including the Witch Trial Memorial

$24 $13

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

$30 $22

Naismith Memorial Basketball Hall of Fame Visit for 2, 4, 6, 8, or 10 (Up to 57% Off)

Naismith Memorial Basketball Hall of Fame

South End

40,000-sq.-ft. basketball haven houses shrines to more than 300 Hall of Famers, 70+ interactive exhibits, and a full-size court for practice

$46 $22

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

Animal Adventures


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

$28 $17

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

Cape Cod Children's Museum


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

$32 $21

90-Minute Tour of Salem Sound for Two Adults or Two Adults and Two Kids from Sea Shuttle (Up to 41% Off)

Sea Shuttle

Sea Shuttle

Tourists can choose to debark at Great Misery Island for hiking or stay onboard the catamaran for a 90-minute tour of the Salem Sound

$86 $51

Entry to Midnight Zoo at Franklin Park Zoo (Up to 37% Off). Three Options Available.

Franklin Park Zoo


Stroll through spooky night time scenes with spectacular costumes and imaginative creatures during Midnight Zoo at Franklin Park Zoo

$15 $10

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

CityView Trolley Tours


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

$38 $19

Guided Meadery Tour with Souvenir Glasses for Two, Four, or Six at 1634 Meadery (Up to 50% Off)

1634 Meadery


Tour this family-run operation, producing small batches of mead by fermenting honey from area apiaries and infusing it with local fruit

$54 $27

Boston, MA Costume Crawl for Two or Four on Saturday, October 29 (Up to 50% Off)

Boston, MA Costume Crawl

Howl at the Moon

Donning a Halloween costume, crawlers visit up to eight bars to receive drink and food specials and prizes for best costumes

$20 $12

Up to 54% Off Brewery Tour and Tasting at Beara Irish Brewing Co.

Beara Irish Brewing Co.


From the merchant: Come and sample our brews made with genuine Imported Irish Barley, take a tour and go home with a sleek sampler glass!

$60 $30

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

Zoo Creatures


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

$16 $8.50

Spirit and Wine Tasting & Tour for Two or Four with Souvenir Glasses at Flag Hill Winery (Up to 52% Off)

Flag Hill Winery

Flag Hill Winery & Distillery

Learn how grapes and grains transform into wine and spirits during tastings and private tours

$60 $29

Two-Hour Chocolate Walking Tour of Boston with Six Tastings for 1, 2, or 4 from Best Tours (Up to 60% Off)

Best Tours


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

$50 $25

Admission for Two or Four to the National Museum of American Illustration in Newport (Up to 50% Off)

National Museum of American Illustration


Housed in a French chateau–style mansion, the museum showcases the work of more than 150 American illustrators, including Norman Rockwell

$36 $18

"Haunted Footsteps Ghost Tour"

Salem Historical Tours

Downtown Salem

$10 $7.50

Fuller Craft Museum Visit for Two (25% Off)

Fuller Craft Museum


Rotating, eclectic exhibits of drawing, sculpture, and other art and functional craft forms

$20 $15

Go Boston Card All-Inclusive 2-Day Pass includes admission to 50+ attractions for 2 days. Pay Nothing at The Gate.

Go City Card

Online Deal

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

$55 $49.50

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

Tasting Tour and Take-Home Glasses for One, Two, or Four at Appolo Vineyards (Up to 38% Off)

Appolo Vineyards

Appolo Vineyards

Wines carefully crafted from hybrid wine grapes within a scenic vineyard

$10 $7

Two-Hour Cupcake Walking Tour of Boston with Five Tastings for 1, 2, or 4 from Best Tours (Up to 60% Off)

Best Tours


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

$50 $25

Entertainment Coupon Digital Membership for 3 Months, 6 Months, or One Year from Entertainment (Up to 33% Off)


Online Deal

Access hundreds of half-off and 2-for-1 coupons at local and national retailers to save on groceries, restaurants, travel, and more

$11.94 $8

Distillery Tour for Two or Four of Bully Boy Distillers (Up to 52% Off)

Bully Boy Distillery

Dudley - Brunswick King

Tours travel past mash tanks & copper stills to see how the distillery produces rum, vodka & whiskey

$40 $19

Holiday Jazz Cruise

Northern Lights

Downtown Boston

$46.20 $32.79

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

Best Tours

Best Tours

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

$50 $25

Fall Foliage Cruise

Charles Riverboat Company


$35 $25.25