Sailing in Arlington, MA


Schooner Sail for Two from Classic Harbor Line (Up to 23% Off). Three Options Available.

Classic Harbor Line

Downtown Boston

Flagship vessel modeled after 1890s schooners can take up to 41 passengers

$80 $62

$95 for a Two-Hour Private Sailing Lesson or Leisurely Cruise from Courageous Sailing ($190 Value)

Courageous Sailing Center

Charlestown

Under instructor supervision, guests sail 19-ft. Rhodes sailboats or enjoy a leisurely cruise on historic Boston Harbor

$190 $95

1.5- or 3-Hour Private Sail for Up to Six with Membership to Cape Cod Maritime Museum (Up to 55% Off)

Cape Cod Maritime Museum

Barnstable Town

Sail off Cape Cod on the Sarah, an 1886 Crosby catboat replica; receive unlimited admission to the maritime museum for one year

$345 $159

Sunset Cruise for Two or Four from Massachusetts Bay Lines (Up to 59% Off). Four Options Available.

Massachusetts Bay Lines, Inc.

Downtown

On sunset cruises, passengers watch the evening overtake Boston’s skyline and get a glimpse of the USS Constitution, a historic Navy frigate

$48.40 $28

$29 for a Whale-Watching Cruise from Cape Ann Whale Watch (Up to $48 Value)

Cape Ann Whale Watch

Gloucester

View humpback and fin whales as they feed and play within close range of the 115 ft. boat, Hurricane II; valid all season long

$48 $29

90-Minute Moonlight Cruise for Two or Four from Massachusetts Bay Lines, Inc. (Up to 36% Off)

Massachusetts Bay Lines, Inc.

Downtown

Cruise passengers observe Boston’s lit-up skyline and spy constellations

$48.40 $32

Two-Hour BYOB/F Public Traditional Sailing Adventure on Boston Harbor from Come Sail Away Now (Up to 61% Off)

Come Sail Away Now

Fan Pier

BYOB/F jaunt across Boston Harbor on the friendship sloop Tupelo Honey offering great skyline views; up to 12 passengers

$150 $65

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

Charles Riverboat Company

Cambridgeside Galleria Mall

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

$18.50 $11

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

Architecture Boat Tour for One or Two from Charles Riverboat Company (35% Off)

Charles Riverboat Company

Cambridgeside Galleria Mall

During a 90-minute cruise, see the architectural sights from throughout Boston Harbor, the Charles River Locks, and the Charles River basin

$27.50 $18

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

Newburyport Whale Watch

South End

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

$48 $29

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

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

Super Duck Tour for an Adult, Child 3–11, or Child Under 3 from Boston Super Tours (Up to 26% Off)

Boston Super Tours

Redeem Online: Departure for Super Duck Tours Only

See the city by land and sea during an amphibious Duck tour

$33.33 $25

Whale-Watching Tour for One or Two from Al Gauron Deep Sea Fishing & Whale Watching (Up to 41% Off)

Al Gauron Deep Sea Fishing & Whale Watching

Hampton Beach

Boats travel up to 40 miles offshore in pursuit of humpback, finback, and minke whales, as well as dolphins and sharks

$33 $20

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

Boston Green Cruises

Boston Green Cruises

Low and zero emission boats carry small groups that glides quietly past famed Boston landmarks during one-hour cruises

$56 $28

$20 for a Tour for Two with Tastings, Glasses, and $10 Toward Wine at Zorvino Vineyards ($30 Value)

Zorvino Vineyards

Zorvino Vineyards

Pairs wander through a pastoral vineyard and savor a variety of reds, whites, blends and fruit wines. Each couple receives $10 wine credit

$30 $20

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

Sea Shuttle

Salem Neck

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

$50 $30

Scenic Cape Cod Tour for Two or Four from Cape Cod Central Railroad (Up to 36% Off). Two Options Available.

Cape Cod Central Railroad

Hyannis Depot

Hop aboard a tourist train to take in views of woodlands, bogs, and the Cape Cod Canal outside the gently rocking cars

$44 $29

Trolley Tour and Harbor Cruise for One, Two, or Four from CityView Trolley Tours (Up to 50% Off)

Cityview Trolley Tours

Boston

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

$40 $22.99

Tours of Harvard and MIT for Two or Four People from Trademark Tours (Up to 44% Off)

Trademark Tours

Multiple Locations

Current Harvard and MIT undergrads share university history, cultural experiences, and facts about famous alumni on walking tours

$24 $15

Kayak Rental for One or Two from Newbury Kayak and Canoe (Up to 41% Off)

Newbury Kayak and Canoe

Newbury

Ply the currents of Parker River with guidance and equipment from watersports enthusiasts

$40 $27

Haunted Walking Tour of Salem for Two or Four from Witch City Walking Tours (Up to 47% 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 $19

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

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

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

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

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 Kayak Tour for Two or Four Including Equipment from EcoTourz (Up to 60% Off)

Eco Tourz

Eco Tourz

Guides lead small groups through the marshlands and estuaries of Upper Cape and point out ospreys, herons, and terns

$150 $69

"Haunted Footsteps Ghost Tour"

Salem Historical Tours

Downtown Salem

$14 $10

Select Local Merchants

  • Yankee Fleet Fishing
    In Focus: Yankee Fleet Specialties: deep-sea fishing and whale watching trips Fleet: includes the 50’ Wojack and the 100’ Yankee Freedom Trip lengths: half-day, full-day, or overnight; occasional specialty trips and charters available Years in operation: more than 70; it has been family-owned since its 1944 founding Chief captain: Thomas Orrell, who has worked for Yankee Fleet since 1979 and bought the company in 2008 Fishing reports: The fleet updates a blog with the latest information on the catches of the day.
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    1 Parker Street
    Gloucester, MA US
  • Community Rowing Boathouse
    Since its inception as a nonprofit organization in 1985, Community Rowing Inc. has guided more than 15,000 students in invigorating rowing sessions held on the Charles River. Their experienced staff of Olympians and coaches helps students to become familiar with industry-standard boats and rowing machines through comprehensive introductory lessons and extended handshakes with the rowing arms. After gleaning the skills necessary to properly use equipment, students gain access to locker rooms, training areas, and any additional courses on the Charles River. The full-body, calorie-burning workouts are available throughout the week, allowing students to learn essential techniques such as sweeping, sculling, and dealing peacefully with the water road rage of aggressive gondoliers. Classes are offered on select Saturday or Sunday afternoons.
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    20 Nonantum Road
    Boston, MA US
  • Riverside Boat Club
    Put your cares aside and sail away at Riverside Boat Club in Cambridge. When you're out and about in the area, you'll love that this center has a restaurant to take care of any last minute hunger. At this center, everyone will find something they love — kids included! Parking is plentiful, so guests can feel free to bring their vehicles.
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    769 Memorial Drive
    Cambridge, MA US
  • Boston's Best Cruises
    As the sun makes its retreat into the horizon, the whales of Stellwagen Bank National Marine Sanctuary come out to play. Their elephantine fins slap the waters with such zeal that the pod seems to be putting on a performance for the catamaran of whale watchers in their midst. This end-of-day nature show experienced by passengers aboard Boston's Best Cruises’ New England Aquarium Whale Watch is hardly a rarity, as the ship’s crews guarantee sightings of these gentle giants with each excursion. Champions of the natural beauty of Boston Harbor and the area’s rich maritime history, Boston's Best Cruises’ expert crew sets sail on cruises to suit all manner of interest. Along with their whale watches, Boston’s Best Cruises whisks passengers away on Harbor Cruises that grant unimpeded views of the Boston skyline and the King Kongs pumping fists within its skyscrapers. The Salem Ferry facilitates leisurely cruises between Boston and the historic city, and aquatic outings to the Boston Harbor Islands National Recreation Area enable activities such as sunset clambakes, hiking, and fishing.
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    1 Central Wharf
    Boston, MA US
  • RIB Adventure Tours
    RIB Adventure Tours conduct informative history tours and scavenger hunts around Baltimore Harbor, even when the horizon becomes a blur; all tours take place aboard 26-foot-long rigid, inflatable speedboats. Built to Navy SEAL specifications by a local Massachusetts boat manufacturer, the boats keep riders secure aboard jockey seats. On guided history tours, passengers snag high-speed glimpses of harbor landmarks including lighthouses and forts, whose history guides can expound upon. During scavenger hunts, guides prompt passengers to look for environmental clues and give individual scores. Captains and tour guides brief passengers on safety before all excursions and supply them with high-grade waterproof cameras to take pictures of passing scenery. More relaxed cruises from partner Hestia Cruises, onboard the 32-foot sailing yacht Hestia, might drift past the USS Constitution or out into the outer harbor. The ship is manned by a captain, a full crew, and friendly cocker spaniel named Ensign. Guests can help with the sailing duties, but padded seats and a BYOB policy for those of age may encourage them to sit back and relax.
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    269 Commercial Street
    Boston, MA US
  • Boston Harbor Cruises
    At the age of 16, Matthew "Matty" Hughes became the youngest-ever licensed captain in the port of Boston. Funneling his passion into a career, he founded Boston Harbor Cruises in 1926 to lead tours up the Charles River. What began as a two-man, one-boat operation has grown tremendously throughout its more than 90-year history, now encompassing a 52-boat fleet and more than 400 employees who transport more than 2.5 million passengers. The Boston Harbor Cruises staff handles all things nautical, from whale watching and Codzilla thrill ride tours to wedding receptions and celebrations for special occasions. Because dolphins are hard to saddle and refuse to obey verbal commands, Boston Harbor Cruises also navigates the waters with ferries and harbor cruises that explore the historic and romantic sights of Boston. Though the leadership has changed, Matty's grandchildren and great grandchildren still perpetuate the traditions of Boston Harbor Cruises, furthering one man's obsession with the harbor and inspiring future generations to create their own memories on its inviting waters.
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    1 Long Wharf
    Boston, MA US

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