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  • 13 Stunning Beaches in Florida With Clear Water You Need to Visit
  • Best results for

    Water Activities in Gloucester, MA

    Showing 25-48 of 143 results
    Private 90-Minute Tiki Boat Cruise in Boston

    Private 90-Minute Tiki Boat Cruise in Boston

    Cruise Boston Harbor on a private tiki boat for your group

    4.9 • 986 reviews
    $2,014
    Private Giant Bluefin Tuna Fishing Charter in Gloucester

    Private Giant Bluefin Tuna Fishing Charter in Gloucester

    Target a giant bluefin and keep 100% of qualifying tuna sale proceeds

    4.8 • 16 reviews
    $5,300
    Bottom Fishing Cruise From Hampton Beach

    Bottom Fishing Cruise From Hampton Beach

    Fish all day with the crew on a 9-hour bottom fishing trip

    4.5 • 1K reviews
    $91/ person
    12-Hour Gloucester Bluefin Tuna Fishing Trip

    12-Hour Gloucester Bluefin Tuna Fishing Trip

    Join the crew for hands-on giant bluefin tuna fishing

    5.0 • 260 reviews
    $337/ person
    Cruise Boston Harbor on a Fall Luncheon Cruise

    Cruise Boston Harbor on a Fall Luncheon Cruise

    See fall foliage on a 1.5-hour Boston Harbor cruise with a gourmet picnic lunch

    4.8 • 693 reviews
    $75/ person
    Private Giant Bluefin Tuna Fishing Charter in Gloucester

    Private Giant Bluefin Tuna Fishing Charter in Gloucester

    Target giant bluefin offshore with Captain Mike and crew

    $1,908
    Private Boston Harbor Sailing Charter from Seaport

    Private Boston Harbor Sailing Charter from Seaport

    Take in Boston's waterfront with harbor history or music on a leisurely private sail

    4.9 • 91 reviews
    $599
    Boston Harbor Sunset Cruise

    Boston Harbor Sunset Cruise

    Watch Boston’s skyline and the USS Constitution glow from the water at sunset

    4.4 • 478 reviews
    $33/ person
    Private Striped Bass Fishing Charter in Boston Harbor

    Private Striped Bass Fishing Charter in Boston Harbor

    Fish with a captain who has known Boston’s waters since childhood

    5.0 • 32 reviews
    $1,060
    Fall Foliage & Lighthouse Cruise in Salem, MA

    Fall Foliage & Lighthouse Cruise in Salem, MA

    Discover five historic lighthouses with fall colors along the shore

    4.6 • 283 reviews
    $45/ person
    Haddock Fishing Charter in Gloucester

    Haddock Fishing Charter in Gloucester

    Bottom fish for haddock with bait and tackle included

    5.0 • 260 reviews
    $247/ person
    80' Yacht Charter in Quincy

    80' Yacht Charter in Quincy

    Celebrate aboard a spacious vessel with a ballroom, two bars, and crew support

    4.6 • 13 reviews
    $1,922& up
    Private Tiki Boat Party Cruise on Boston Harbor

    Private Tiki Boat Party Cruise on Boston Harbor

    Set sail for a personalized tiki cruise through Boston Harbor

    4.9 • 986 reviews
    $2,014
    Private Tiki Boat Cruise on Boston Harbor

    Private Tiki Boat Cruise on Boston Harbor

    Turn your celebration into a private Boston harbor party

    4.9 • 986 reviews
    $2,756
    Private Striped Bass Fishing Charter in Boston Harbor

    Private Striped Bass Fishing Charter in Boston Harbor

    Fish with a captain who has known Boston Harbor's waters since age 5

    5.0 • 32 reviews
    $1,272
    Private 80' Yacht Charter in Quincy

    Private 80' Yacht Charter in Quincy

    Celebrate on the water with a ballroom, two bars, and dedicated crew

    4.6 • 13 reviews
    $3,460& up
    Private Offshore Haddock & Cod Fishing Charter in Gloucester

    Private Offshore Haddock & Cod Fishing Charter in Gloucester

    Fish New England’s deeper waters with your catch cleaned and packed for home

    $1,590
    Private Offshore Shark Fishing Charter in Gloucester

    Private Offshore Shark Fishing Charter in Gloucester

    Take on powerful sharks with custom rods and tackle

    $1,590
    Boston Harbor 1-Hour Narrated Cruise

    Boston Harbor 1-Hour Narrated Cruise

    Take in Boston Harbor’s history on a narrated midday cruise

    4.4 • 478 reviews
    $13/ person
    Full-Day Deep Sea Fishing Trip in Gloucester

    Full-Day Deep Sea Fishing Trip in Gloucester

    Fish Gloucester’s banks with a seasoned captain and crew

    4.2 • 521 reviews
    $85/ person
    3-Hour Sailing Charter From Marblehead

    3-Hour Sailing Charter From Marblehead

    Private sail for up to 6 guests beyond Marblehead Harbor

    $451
    Boston Harbor Morning Mai Tai Cruise

    Boston Harbor Morning Mai Tai Cruise

    Harbor landmarks and a laid-back Tiki Boat morning

    4.9 • 986 reviews
    $43/ person
    80' Yacht Charter in Quincy

    80' Yacht Charter in Quincy

    Private event yacht with a ballroom, two bars, and dedicated crew support

    4.6 • 13 reviews
    $4,485& up
    24' Motorboat Charter in Quincy

    24' Motorboat Charter in Quincy

    Private Boston Harbor outings with a captain, cooler, and bathroom

    4.6 • 13 reviews
    $756/ boat
    123456
    Gloucester Things To Do
    Historical Tours72Sailing39Boat Tours33Fishing Charters33Ghost and Haunted25
    More
    • Food Tours19
    • Yacht Charters14
    • Bike Rentals13
    • Dessert Tours10
    • Scooter Rentals10
    • Kayaking Tours9
    • Architectural Tours8

    Travel guides for Water Activities

    13 Stunning Beaches in Florida With Clear Water You Need to Visit
    Best of Florida • 2026

    13 Stunning Beaches in Florida With Clear Water You Need to Visit

    Clarity is geology, not luck: quartz sand, seagrass filtration, and how close the Gulf Stream runs. Thirteen beaches, and the trade-off each one asks of you.

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide
    Best of Florida • 2026

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide

    Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.

    Movie Location Tours
    8
  • Themed Experiences8
  • Cooking Classes7
  • Heritage Walks7
  • Bike Tours6
  • Bar and Pub Crawl5
  • Whale Watching5
  • Farm Visits4
  • Neighborhood Tours4
  • Photography Tours4
  • Stand Up Paddle Boarding4
  • Culinary Tours3
  • Day Trips3