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  • 15 Best Stuff to Do in Boston in 2026 (Local Favorites + Hidden Gems)
  • Best results for

    Hillsborough

    Showing 1-24 of 321 results
    Shell Key Shelling Cruise

    Shell Key Shelling Cruise

    Cruise to Shell Key for beachcombing, shore snorkeling, and wildlife watching

    4.9 • 769 reviews
    $67/ person
    Waterfront Segway Tour in Downtown St. Petersburg

    Waterfront Segway Tour in Downtown St. Petersburg

    Glide through waterfront scenery with a guide who calls St. Petersburg home

    4.9 • 72 reviews
    $64/ person
    Downtown Tampa Tiki Boat Cruise

    Downtown Tampa Tiki Boat Cruise

    Bring your own drinks for a floating tiki bar cruise on the Hillsborough River

    4.8 • 195 reviews
    $58/ person
    Tampa Bay Wildlife Boat Tour With Fisheries Trawl

    Tampa Bay Wildlife Boat Tour With Fisheries Trawl

    Cruise Tampa Bay on a floating classroom with a fisheries trawl

    4.7 • 258 reviews
    $30/ person
    Mangrove Kayak Rental with Delivery Near St. Petersburg

    Mangrove Kayak Rental with Delivery Near St. Petersburg

    Choose your launch point with kayak delivery and pickup

    5.0 • 1 reviews
    $51/ person
    Vintage Open-Air Train Ride Through Parrish

    Vintage Open-Air Train Ride Through Parrish

    Ride a 13-mile historic railroad excursion in open-air or air-conditioned cars.

    4.5 • 1.9K reviews
    $26/ person
    Kids Jelly Ball Party in Clearwater

    Kids Jelly Ball Party in Clearwater

    Enjoy a private-field party with referee-run games and unlimited ammo

    4.1 • 398 reviews
    $452
    Private Tiki Boat Cruise in Tampa

    Private Tiki Boat Cruise in Tampa

    Design a private tiki boat outing for your celebration

    4.8 • 195 reviews
    $349/ boat
    St. Petersburg Sunset Cruise

    St. Petersburg Sunset Cruise

    Explore Tampa Bay wildlife and skyline views on a sunset eco-cruise

    4.7 • 258 reviews
    $30/ person
    Private Boat Charter in Clearwater

    Private Boat Charter in Clearwater

    Set your own Clearwater-area boating day with a private captain

    5.0 • 753 reviews
    $1,017& up
    St. Petersburg Sunset Yacht Charter

    St. Petersburg Sunset Yacht Charter

    Private Regal 4160 cruises for celebrations, relaxing outings, and time on the Gulf

    5.0 • 524 reviews
    $1,310& up
    Guided Rydable Tour of Tampa

    Guided Rydable Tour of Tampa

    Ride a Rydable through Tampa’s waterfront, parks, and pirate history

    5.0 • 473 reviews
    $84/ person
    Personalized Private Boat Charter in Gulfport

    Personalized Private Boat Charter in Gulfport

    Customize a private cruise for island beaches, dolphin viewing, or a St. Pete sunset

    5.0 • 390 reviews
    $345& up
    4-Seat Slingshot Rental in St. Petersburg

    4-Seat Slingshot Rental in St. Petersburg

    Take the wheel—no motorcycle endorsement needed

    5.0 • 207 reviews
    $277/ slingshot
    4-Hour Tampa Bay Island-Hopping Party Boat Charter

    4-Hour Tampa Bay Island-Hopping Party Boat Charter

    Cruise Tampa Bay’s islands and skyline aboard a private party boat

    5.0 • 192 reviews
    $1,007
    Family-Friendly Horseback Trail Ride in Pinellas Park

    Family-Friendly Horseback Trail Ride in Pinellas Park

    Ride a gentle guided route through Pinellas Park’s equestrian trails

    5.0 • 147 reviews
    $106
    Daytime Hillsborough River Boat Tour in Downtown Tampa

    Daytime Hillsborough River Boat Tour in Downtown Tampa

    See downtown Tampa from a floating tiki bar

    5.0 • 135 reviews
    $477
    Tampa Bay Flats & Backcountry Fishing Charter

    Tampa Bay Flats & Backcountry Fishing Charter

    Fish Tampa Bay’s flats and backcountry with local guidance, gear, and bait included

    5.0 • 113 reviews
    $689& up
    Tampa 37' Luxury Adventure Boat Charter

    Tampa 37' Luxury Adventure Boat Charter

    Customize your day on a 37-foot boat with air-conditioned cabin comfort

    5.0 • 91 reviews
    $907& up
    Big Cat & Bear Sanctuary Walking Tour in Wimauma

    Big Cat & Bear Sanctuary Walking Tour in Wimauma

    See exotic animals up close and watch the volunteers who care for them

    5.0 • 88 reviews
    $21/ person
    2.5-Hour Booze Cruise in Gulfport

    2.5-Hour Booze Cruise in Gulfport

    Cruise the intracoastal on a 21+ party boat with optional open bar

    4.9 • 3.5K reviews
    $62/ person
    Private Captained Boat Charter in Clearwater

    Private Captained Boat Charter in Clearwater

    Private captain-led time on Clearwater's waterways, beaches, and barrier islands

    5.0 • 753 reviews
    $904& up
    Private 41' Sea Ray Yacht Charter in St. Petersburg

    Private 41' Sea Ray Yacht Charter in St. Petersburg

    Private yacht cruising with space to relax, celebrate, or visit a sandbar

    5.0 • 524 reviews
    $1,146/ boat
    Private Shell Key Dolphin & Shelling Tour

    Private Shell Key Dolphin & Shelling Tour

    Explore Shell Key's shores for shells and Gulf wildlife

    4.9 • 769 reviews
    $509
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