Sailing in South Boston, MA


$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

Boston Harbor Cruise for Two from Classic Harbor Line (Up to 22% Off). Four Options Available.

Classic Harbor Line

Downtown Boston

New England commuter yacht takes passengers on cruises around Boston Harbor to see sunsets, city lights, and harbor islands

$76 $59

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

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

$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

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

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 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

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

$50 $30

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

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

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

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

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

$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

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

Scenic Gondola Ride for Two or Four at Killington Resort (Up to 45% Off)

Killington Resort

Killington Vermont

Relax during a gondala ride to the top of 4,241-foot Killington Peak, where passengers take in breathtaking views

$50 $29

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

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

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

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

90-Minute Haunted Walking Tour for Two or Four from Haunted Boston Ghost Tours (Up to 56% Off)

Haunted Boston Ghost Tours

Downtown

90-minute walking tours explore Central Burial Ground, Boston Commons & Boston Athenaeum & include info about ghosts & Boston history

$36 $19

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

"Haunted Footsteps Ghost Tour"

Salem Historical Tours

Downtown Salem

$14 $10

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

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.
    Read More
    1 Parker Street
    Gloucester, 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.
    Read More
    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.
    Read More
    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.
    Read More
    1 Long Wharf
    Boston, MA US
  • Liberty Fleet of Tall Ships
    Docked adjacent to the New England Aquarium, the Liberty Star and the Liberty Clipper look distinguished. The Liberty Star measures 67 feet long and can hold up to 39 passengers, and the Liberty Clipper measures 125 feet long with a capacity for up to 100 passengers. The massive schooner is an authentic replica of an 18th-century Baltimore clipper ship, thoroughly modernized to transport passengers on Boston Harbor sails and longer private charters. They sail daily throughout the harbor for public and group outings, along with private charters for special events, such as weddings or corporate proms. For a longer respite, they hoist the sails and steer southwards where the Liberty Clipper sails the Bahamas and the Liberty Star sails the Virgin Islands on adventure sailing vacations.
    Read More
    67 Long Wharf
    Boston, MA US
  • Classic Harbor Line
    Classic Harbor Line offers glimpses of modern-day Boston, Manhattan, Newport, and Key West with their fleet of sailboats and classic yachts. Passengers can engage in day trips, private charters, and special events on the water set against a backdrop of sunsets or shimmering displays of city lights at night. Modeled after 1890s schooners, the company's Boston flagship, Adirondack III, uses its long, lean shape to easily cut through any waves or giant blocks of Jell-O floating in the harbor. At 80-feet, the vessel carries up to 41 passengers and provides plenty of room to move around, allowing crew members to serve beverages or guests find the perfect vantage point to snap a picture of the sunset. Classic Harbor Line also offers a 1920s styled climate-controlled and open-air Motor Yacht, the Northern Lights, which has an open sun deck, a top deck with canopy covered bench seating, and a temperature controlled salon with a table and lounge seating. While cruise-goers enjoy the boat’s narration and music, they can also take advantage of the beer, wine, soda, & water available for purchase.
    Read More
    60 Rowes Wharf
    Boston, MA US

Groupon Guide

Grouber