Tours in Orient Heights

Sunset Harbor Cruise for Two from Boston Green Cruises (Up to 50% Off). Morning and Afternoon Also Available.

Boston Green Cruises

Boston

A low-emission covered boat glides quietly past famed Boston landmarks during one-hour cruises

$56 $28

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One- or Two-Hour Historic Harbor Boat Tour for Up to Six from Captain Mike's Boston Coastal (Up to 55% Off)

Captain Mike's Boston Coastal Yacht Charters

Boston Harbor Hotel

Captain Mike takes sightseers on a one- or two-hour ride along Boston's scenic skyline on a comfortable, fully-equipped 30-foot sailboat

$250 $125

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Super Duck or Upper Deck Trolley Tours for Adults or Children from Boston Super Tours (Up to 27% Off)

Boston Super Tours

Redeem Online: Departure for Super Duck Tours Only

Hop on and off a trolley tour that stops at Boston's most iconic landmarks, or see the city by land and sea during amphibious Duck tours

$33.33 $25

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Halloween Pub Crawl for Two or Four on October 25 and October 30–November 1 from Boston Pub Crawl (Up to 80% Off)

Boston Pub Crawl

Multiple Locations

Four-day pub crawl celebrates Halloween with amazing costumes and specials on domestic beers and well cocktails

$50 $10

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$15 for a Haunted Ghost Ship Cruise on Friday, October 31, from HalloweenCruises.com ($30 Value)

HalloweenCruises.com

Downtown

Guests dance to DJ’d music on Halloween party cruise that searches out phantoms in Boston Harbor

$30 $15

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Haunted-History Walking Tour for Two or Four with Ghost-Hunting Equipment from Spirit Expeditions (50% Off)

Spirit Expeditions

Downtown

A two-hour walking tour covers most haunted areas and allows guests to conduct their own paranormal investigation

$50 $25

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Boston Haunts Historical Walking Ghost Tour for Two or Four (Up to 58% 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

$30 $15

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Grave Undertakings Walking Tour for Two or Four from Boston By Foot (50% Off)

Boston By Foot

King's Chapel Cemetery

Narrated tours trek through three of the city's burying grounds to explain the death customs and symbolism of Puritan New England

$30 $15

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Two or Four Tickets to Tour of The Freedom Trail: The Path to Independence from Histrionic Academy (Up to 58% Off)

Histrionic Academy

Downtown

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

$29.90 $14.95

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Boston TV- and Movie-Site Tour for One, Two, Three, or Four from On Location Tours (49% Off)

On Location Tours

Boston Common

Explore Boston's neighborhoods on tours that point out filming locations of famous films and TV shows such as Ted and American Hustle

$41 $21

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Boston-to–New York Tour for One, Two, or Four from Go Go U.S. Tour ($70 Value)

Go Go U.S. Tour

Boston

All-day tour takes groups around some of NYC's most famous sites including Times Square and Rockefeller Center

$70 $29

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Boston Ghost Walk for One, Two, or Four from The Celebrity Planet (Up to 64% Off)

Boston Ghost Walk

Edge of Boston Common

Spooky tour visits Omni Parker House, the site of the Boston Massacre, and two cemeteries in search of eerie apparitions

$35 $17

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Personalized Pedicab Tour for up to Three Adults or Two Adults and Two Kids from Boston Pedicab (Up to 38% Off)

Boston Pedicab

South End

Riders pick a route that matches their interests and passes historic sites, local art, and other notable destinations

$95 $59

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Distillery Tour for Two or Four of Bully Boy Distillers (Up to 56% Off)

Bully Boy Distillery

Boston

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

$40 $20

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Harvard Walking Tour for Two, Four, or Six from Trademark Tours (Up to 53% Off)

Trademark Tours

Harvard Square

Current Harvard undergraduates divulge university history, stories from current students, and facts about famous alumni on 70-minute tours

$40 $19

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Harvard Walking Tour for Two or Four with Option for Harvard Museum Tour from The Hahvahd Tour (Up to 43% Off)

The Hahvahd Tour

Cambridge

Harvard students steer groups to notable landmarks such as the John Harvard statue and Harvard Yard while imparting college factoids

$21.90 $13

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Harvard, Old Cambridge, or Innovations of Cambridge Tour for Two from Cambridge Historical Tours (60% Off)

Cambridge Historical Tours

Cambridge

Guides dressed in period clothing lead guests around famous locations, sharing more than 400 years of history

$30 $12

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Scary Stories Walking Tour for Two or Four at Bewitched After Dark Walking Tours (Up to 50% Off)

Bewitched After Dark Walking Tours

Downtown Salem

The PG-13 Scary Stories of Salem walking tour terrifies participants with ghostly tales of evil spirits and otherworldly creatures

$60 $36

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17th Century Salem Experience for 2 or Up To 5 at The Jonathan Corwin House / The Witch House (Up to 51% Off)

The Jonathan Corwin House / The Witch House

Salem

Home that housed the Corwin family, who were heavily involved in the Salem Witch Trials; Pioneer Village recreates colonial life

$28.50 $15

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In-Depth Tour for Two or Four at Blue Hill Observatory & Science Center (50% Off)

Blue Hill Observatory & Science Center

Milton

Tour the weather observatory, the home of the oldest climate record in the country, and see historical weather instruments still used today

$16 $8

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$225 for a One-Hour Scenic Tour for Up to Three People from Eagle East Aviation Tours ($420 Value)

Eagle East Aviation Tours

North Andover

Enjoy a scenic tour from the air as a pilot flies you and up to three guests around; includes a flash drive and first flight certificate

$420 $225

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Ghost or Sleepy Hollow Cemetery Walking Tour for Two or Four from Gatepost Tours (50% Off)

Gatepost Tours

Concord

Licensed Concord tour guide show the darker untold side of Concord, with visits to Sleepy Hollow and other haunted locales

$50 $25

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Whale-Watching Excursion for One or Two from Capt. Bill and Sons Whale Watch (Up to 49% Off)

Capt. Bill and 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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$299 for a Three-Course Lunch for Four at the Top of the Newburyport Lighthouse (Up to $900 Value)

The Lighthouse Preservation Society

Newburyport, MA

Prix fixe lunch at a private table with harbor views from the top of a historic lighthouse

$900 $299

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Haunted Hayride and Halloween Scream Park for Two or Four at Witch’s Woods (Up to 41% Off)

Witch’s Woods

Westford

Halloween carnival with a spooky hayride, three haunted houses, rides, games, and galleries of jack-o’-lanterns and horror-movie characters

$66 $39

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Semiprivate Hot Air Balloon Ride with Champagne Picnic from Infinity & Beyond (Up to 40% Off)

Infinity & Beyond

Salem

In the care of an FAA-certified pilot, couples take to the skies for sunrise or sunset hot air balloon rides followed by a champagne picnic

$400 $240

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Wine Tasting with Cheese, Wineglasses, and 25% off Wine for Two, Four, or Six at Sweet Baby Vineyard (Up to 56% Off)

Sweet Baby Vineyard

Sweet Baby Vineyard

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

$34 $12

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Paranormal Investigation Tour for Two or Four from The Plymouth Night Tour (Up to 54% Off)

The Plymouth Night Tour

Plymouth

Tour haunted and historical sites across Plymouth while outfitted with professional paranormal investigation equipment

$24 $12

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Select Local Merchants

There are tours that take you to historical destinations, and then there are tours that take place on them. Consider tours aboard the Joseph S. Kennedy UB85 a little of both. This 50-foot Navy utility boat was built in 1985 and was assigned to the Aircraft Carrier U.S.S. Roosevelt. Today, it charters passengers to historical sites such as the Charlestown Navy Yard, site of the U.S.S. Constitution and the World War II destroyer U.S.S. Cassin Young. The boat also ferries guests to one of the National Park Harbor Islands, where history and modern day converge in the form of festivals and events. On George Island, for example, passengers will find beer tastings and weekly recreations of Civil War-era baseball games, complete with original uniforms, original rules, and instant replays performed by actors.

205 Orient Avenue
Boston,
MA
US

Originally built to sail around the world, the New Horizons motorsailer now spends its days providing Maine hospitality to its guests while gliding along the scenic Northeastern coast of the United States. After boarding the sailboat, groups can take in the sweeping views of the New York Harbor, the Hudson River, and past the Statue of Liberty, while sipping drinks and savoring treats such as the classic Maine lobster roll, which can be purchased on board. Seafarers may also embark on special voyages, such as Lobster Day Sail picnics. With its spacious design, semi-private upper deck, and modern sound system, the New Horizons can handle events that range from large family gatherings to old-fashioned ocean-drinking contests.

256 Marginal St.
East Boston,
MA
US

Boston’s Finest Tours unveils the City on a Hill’s hidden charms to residents and visitors with five unique seasonal tours. Native Bostonians John Feeley and Cheryl McDonald lead tours dressed as their midcentury counterparts, Jonathan Wendell Holmes and Frances Appleton, while sharing tales of the city’s history and culture. The ghost tour of Beacon Hill thrusts patrons into close encounters with specters, and on the Irish Heritage tour, trolleys roll through Eire-influenced sites including the Boston Public Garden and Fenway Park. The Beacon Hill tour begins with a sighting of the State House’s brilliant gold dome before groups stroll down the brick sidewalks of Mount Vernon Street, the cobblestone corridor of Acorn Street, and the legendary Boston Strangler’s daily jogging route.

140 Northern Avenue
Boston,
MA
US

City Wine Tours' experienced wine ambassadors take groups on enlightening viticultural explorations in New York City and Boston. Each two-hour walking tour stops by upscale restaurants, neighborhood boutiques, and hidden grape-springs known for their unique wine offerings. Guests sip and sample along the way, trying up to six different varietals, while guides expound on wine tasting, pairing, and history. That focus on entertaining education has proved a winning formula?City Wine Tours' walking excursions have been praised by media outlets including Zagat and the Boston Globe.

3 Battery Wharf,Boston,Boston
Boston,
MA
US

Launched in 1948 by Chicago shipwright Henry C. Grebe, the Full Moon is an antique, 65-foot motor yacht that ravels constantly. In the winters, it cruises the waters of southern Florida, but it returns to New England once it gets warmer, taking passengers on voyages throughout Boston Harbor. Onboard the Full Moon, passengers can take in skyline views and sunset vistas from the sea.

The refitted vessel features wooden decks and varnished rails, as well as intimate gathering areas and seating scattered across the boat. A sun-soaked bow presents passengers with unblocked views of the surroundings. The covered aft deck and indoor salon areas let passengers relax away from the elements.

87 Commercial Wharf
Boston,
MA
US

The Bay State Cruise Company is probably best known for its fast ferry service between Boston and Provincetown, which zips passengers between the two cities in 90 minutes. The company also has a traditional ferry, which takes three hours each way, but costs much less and is available only on Saturdays. All ferries are seasonal, running from mid-May through mid-October. The boats are comfortable, with plenty of seating inside and out, and drinks and snacks are available. In the summer, the company also offers music cruises on the weekends that sail around Boston Harbor, with live acts, DJs and dancing. You can also set sail on the Fourth of July, when the USS Constitution makes its annual turnaround. As the ship slowly floats along, passengers can enjoy the view and a buffet lunch. The ferries can also be chartered for private events.

200 Seaport Blvd, Ste 50
Boston,
MA
US