Sailing in Gloucester, MA

Entry to the Fenway Park Sprint on November 12 or 13 from Reebok Spartan Races

Reebok Spartan Races

Fenway Park

Reebok-sponsored races pit competitors against natural and manmade obstacles, such as mud, fire, climbing walls, and barbed wire

$35 $15

One-Hour Archery Session with Equipment and Lane Rental for Two or Four at Ace Archers (Up to 45% Off)

Ace Archers


Instructors teach archery skills and safety to you, while students practice with rental equipment on range with 14 lanes

$28 $16

Skating, Laser Tag, and Slushies Four at Roller Kingdom (Up to 66% Off)

Roller Kingdom

Multiple Locations

Top-40 hits play at the roller-skating rink; 10-minute laser-tag games amid obstacles and hideouts; slushie refuel

$65 $22

All-Day Paintball Package for Two, Four, or Six at OSG Paintball (Up to 63% Off)

OSG Paintball


Ten playing fields simulate other-worldly battlegrounds, including a pirate ship, Medieval castle, and replica of a HALO level

$90 $35

One- or Two-Hour Trail Ride on Horseback for One or Two at Cornerstone Ranch (Up to 48% Off)

Cornerstone Ranch

Cornerstone Ranch

Riders aged 10 or older take in breathtaking scenic terrain during one- or two-hour trail rides

$45 $27

$79 for an 18-Hole Round of Golf with Cart Rental and Range Balls at Pinehills Golf Club ($120 Value)

Pinehills Golf Club

Pinehills Golf Club

Two courses, designed by Rees Jones and Jack Nicklaus, are seamlessly sculpted into undulating terrain for spectacular playing conditions

$120 $79

One or Three One-Day Rock-Climbing Passes with Gear Rental or Membership at Rock Spot Climbing (Up to 51% Off)

Rock Spot Climbing

Multiple Locations

Dual climbing facilities sprawl with challenging top-rope, lead-climbing, and bouldering routes

$25 $16

One 18-Hole Round of Golf Including Cart Rental at Atlantic Country Club (Up to 36% Off)

Atlantic Country Club


Bent-grass fairways and greens spread across tree-lined terrain make for challenging rounds of golf at acclaimed course

$76 $49

$49 for "Taste of the Sky" Glider Ride at Stowe Soaring ($99 Off)

Stowe Soaring


Hitch a ride in a glider attached to a traditional plane for the ascent, and then soar over gorgeous scenery during a 10-minute flight

$99 $49

Two or Four Hours of Simulated Golf for Two at The Clubhouse Golf and Entertainment (Up to 66% Off)

The Clubhouse Golf and Entertainment

The Clubhouse Golf and Entertainment

7,000 square-foot center features nine simulators with 14-foot HD projections screens and a library of 85 championship courses

$100 $35

Roller Skating Package for Two or Four at Roll On America (Up to 64% Off)

Roll On America

Fun America at Roll On America

Roller skating facility features snack bar, more than 25 arcade games, and laser tag

$70 $25

Two-Hour Bowling Outing with Shoe Rental for Two, Four, or Six at Brunswick Bowling (Up to 48% Off )

Brunswick Bowling

Brunswick Zone - Lowell

Long-time bowling industry leader with 80 plus locations across the country offers two-hour bowling packages for groups of two, four, or six

$29 $19

Rock-Climbing Pass for Two or Two Groupons, Each Good for a Climb for One at Rock On Adventure (47% Off)

Rock On Adventure


Pick from up to 12 auto-belayed walls with varying difficulty levels that provide fun, total-body workouts

$30 $16

Indoor Surfing or Boogie Boarding for One or Two at Surf's Up (Up to 33% Off)

Surf's Up


Surf waves on a 32-foot-wide wave pool seen on the Discovery Channel, designed to be the biggest on the continent

$45 $30

Paintball Package for 2, 4, 8, or 12 at Merrimack Valley Paintball (Up to 68% Off)

Merrimack Valley Paintball


Just under an hour from Boston, players compete on woodsball and speedball fields using .68-caliber markers

$75 $37

Boston Bruins Tickets

Boston Bruins Tickets

Downtown Boston

Find tickets for sports, concerts and theatre events on FanXchange’s secondary ticket marketplace and get the best seats for live events.

$48 $48

2, 4, 6, or 12 Paintball Passes with Safety Gear and Gun from Paintball USA Tickets (Up to 89% Off)

Paintball USA Tickets

Multiple Locations

Use passes for open play, safety gear, and gun rental at any of 80+ participating locations nationwide, including 6 in New England area

$140 $15

Admission with Equipment and Paintballs for One, Two, or Four People at BOLP Paintball (48% Off)

BOLP Paintball


This paintball facility boasts a speedball field and three woodsball fields, including a lit field that allows for night time play

$40 $21

One, Three, or Five 60-Minute Private Horseback-Riding Lessons at Taylor River Farm (Up to 73% Off)

Taylor River Farm, LLC.

Hampton Falls

Lesson Academy guides riders through lessons under guidance of 25-year veteran rider and trainer

$65 $24

Pre-Sale: Harlem Globetrotters Game on March 5 or 11

Harlem Globetrotters

TD Garden

The Globetrotters celebrate their 91st anniversary with a signature blend of athletic prowess and side-splitting antics

$81.80 $45

One-Hour Lane Rental for Two or Four or 25 Range Visits for Two at New England Airgun (Up to 52% Off)

New England Airgun


Brush up on your marksmanship with realistic airguns that have the weight and feel of real guns without the recoil

$65 $32

All-Day Paintball Session for Two or Four with 250 Paintballs Per Person at AG Paintball (Up to 64% Off)

AG Paintball


Seven fields littered with barrels and wooden spools are regularly updated to host players who lock and load rented equipment

$70 $30

All-Day Paintball Package with Equipment Rental for 4, 6, or 12 from Paintball International (Up to 79% Off)

Paintball International

Multiple Locations

Equipped with rental paintball guns and masks, groups vie for supremacy over outdoor fields

$88 $19

One, Three, or Five Horseback Riding Lessons at Cornerstone Farm (Up to 49% Off)

Cornerstone Farm

Cornerstone Farm

Experienced and friendly instructors teach students of all ages and abilities riding techniques on gentle steeds

$65 $35

Paintball with Equipment Rental for 4, 8, or 12 at BattlegroundZ (Up to 78% Off)



Facemasks and chest protectors swaddle combatants as they clash in objective games in 10,000 sq. ft. indoor area

$120 $39

4 or 10 Kickboxing Classes with Personal-Training Session and Boxing Gloves at ( 74% Off )

Multiple Locations

Kickboxing classes combine boxing and martial arts to help tone and trim physiques, and one-on-one training helps refine style and results

$105 $30

Three or Six 60-Minute Horseback-Riding Lessons for One or Two at Prestige Stables (Up to 55% Off)

Prestige Stables

Prestige Stables

Instructors help students bond with horse, learn riding techniques, and develop coordination skills during 60-minute horseback-riding lesson

$195 $95

Seven-Hour Fishing Trip with Rod and Lunch for One, Two, or Four from Miss Belmar Princess (Up to 51% Off)

Miss Belmar Princess

Belmar Marina

Spend time on the water fishing with a fishing pole and bait; recharge with a hot dog and drink

$79 $42

Admission to Public Skate for Two or Up to Four from FMC Ice Sports (Up to 50% Off)

FMC Ice Sports

Multiple Locations

Socialize on ice with up to three friends during public skating sessions at any one of 24 locations; Skate rental available for $5 per pair

$10 $7

Introduction to Shooting Handguns and Rifles Experience for One or Four at Mass Firearms School (Up to 50% Off)

Mass Firearms School


Students are introduced to shooting handguns and rifles In a fully equipped indoor shooting range.

$75 $45

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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    Gloucester, MA US
  • Essex River Cruises and Charters
    When the Ice Age ended more than 15,000 years ago, melting glaciers created the saltwater estuary that today sustains the Essex River’s myriad boaters, clammers, and fisherman. Amid this naturally beautiful backdrop, Essex River Cruises and Charters floats its two handsome spectator vessels, the Essex River Queen I and the Essex River Queen II. Guides lead daily, narrated cruises through the estuary, navigating the protected waters and pointing out the various local flora and fauna of the salt marsh. Cruises embark daily from May to October and also include weekend cruises accompanied by coffee and muffins, during which passengers are serenaded by the plaintive cries of pelicans begging for the love of a good man. The fleet is also available for group tours and charters for up to 100 passengers at a time, and the staff caters signature clambakes and other events along the tidal beach. The cruise-curators even make big days memorable, transporting wedding parties to any of the many secluded tidal beaches in Essex Bay for ceremonies or receptions.
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    Essex, MA US
  • Capt. Bill & Sons Whale Watch / Captain Bill
    Capt. Bill and Sons Whale Watch started more than 50 years ago, but the late Captain Bill Cunningham can't take full credit for his business' creation. In many ways, the whales themselves founded the company, though they still made Bill do all of the paperwork. Capt. Bill and Sons originally chartered deep sea fishing trips, but the anglers would often get distracted when a humpback or minke whale breached the surface. Seeing how the majestic mammals awed his passengers, the company decided to stow its fishing rods and set out on whale-watching tours instead. Today, the Capt. Bill and Sons team—which includes son Marc—welcome whale-watchers aboard their two-tiered ship, the Miss Cape Ann. Once they head out into the water, the experts share tips on spotting whales and insights into the animals' behavior, biology, and social structure. Passengers should look sharp for other species as well, as the waters around Stellwagen Bank and Jeffreys Ledge are also home to Atlantic white-sided dolphins and harbor seals.
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    Gloucester, MA US
  • 7 Seas Whale Watch
    By the Numbers: 7 Seas Whale Watch 15 species of whales have been spotted off the coast of Gloucester 30 feet—the minimum length of the seven “great whale” species you might see, including the humpback whale, the minke whale, the North Atlantic right whale, and the blue whale (the world’s largest animal!) 99% success rate for whale sightings since 1983; if the trip doesn’t spot one, you’ll be issued a voucher for another cruise 12 miles from Gloucester Harbor to Stellwagen Bank National Marine Sanctuary, so there’s less time spent traveling and more time spent whale watching 149— the maximum number of passengers permitted on The Privateer IV, which accommodates 300, to ensure safer, better views 1 onboard naturalist or marine biologist helps passengers spot whales and other marine animals (such as dolphins, sharks, and seals), then describes the species and the behaviors being observed
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    Gloucester, MA US
  • Cape Ann Whale Watch
    Since 1979, the whale-watching pioneers of Cape Ann Whale Watch have escorted more than half a million spectators fascinated by the sea's magnificent leviathans on three- to four-hour treks 15 miles off the Gloucester coast, earning it a spot on the Top 5 American Whale-Watching Tours by Joshua Horwitz, author of War of the Whales. Aboard the lightning-fast 115-foot Hurricane II, passengers can witness the natural grace of humpback whales, finback whales, dolphins, and pirates disguised as mermaids feeding and frolicking just feet from the boat. In the course of the approximately 30-mile circuit, a naturalist from Whale Cetacean Alliance narrates excursions, illumining the sight of each water dweller by discussing why whales breach, how to recognize individual humpbacks, and various feeding styles.
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    Gloucester, MA US
  • Defiance Sail Charters
    In Focus: Defiance Sail Charters Sailing season: February through May in the Bahamas; June through October in Gloucester Ship: Windfall, a well-equipped 49’ center cockpit ketch Captains: Raffi Kassabian and Lisa Kennedy, who have both been sailing for more than three decades Trips last: as short as three hours or as long as multiple overnight voyages Who’s coming with you: up to 12 passengers for day trips and up to four for overnight trips What you’ll get up to: When you aren’t admiring the views of water and coastline, tune in to an HDTV or XM satellite radio, nap in a hammock, play a board game, or use some of the ship’s complimentary fishing gear.
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    Gloucester, MA US