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Best results for

Water Activities in Sugarloaf Shores, FL

Showing 121-144 of 821 results
28-Mile Guided Jet Ski Tour of Key West

28-Mile Guided Jet Ski Tour of Key West

Circle Key West by jet ski with guided landmark stops and swim time

5.0 • 59 reviews
$237/ jet ski
Clear Kayak Mangrove Eco-Tour in Marathon, Florida Keys

Clear Kayak Mangrove Eco-Tour in Marathon, Florida Keys

See beneath the surface as you paddle the natural side of the Florida Keys

4.9 • 391 reviews
$116/ person
Private Key West Sunset Sailing Charter

Private Key West Sunset Sailing Charter

Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included

4.9 • 5.9K reviews
$3,500
Private Boat Charter in Key West

Private Boat Charter in Key West

Customize a private day on the water with lunch, drinks and watersports

4.9 • 1K reviews
$3,235/ boat
Dolphin Watch & Backcountry Snorkel Tour in Key West

Dolphin Watch & Backcountry Snorkel Tour in Key West

Dolphin watch and backcountry snorkel with complimentary drinks

4.9 • 12.7K reviews
$73/ person
Key West Private Sailing Charter

Key West Private Sailing Charter

Sail, snorkel, and seek sandbars aboard a private catamaran

4.9 • 635 reviews
$1,470& up
Shared Party Boat Fishing Charter in Key West

Shared Party Boat Fishing Charter in Key West

Split a 4-hour party fishing charter with up to 14 people

4.9 • 287 reviews
$101/ person
Half-Day Key West Snorkel & Sandbar Charter

Half-Day Key West Snorkel & Sandbar Charter

See reefs below the surface and relax at a Key West sandbar

5.0 • 59 reviews
$793
Guided 28-Mile Jet Ski Tour Around Key West

Guided 28-Mile Jet Ski Tour Around Key West

Circle Key West by Yamaha WaveRunner with landmark and sandbar stops

5.0 • 59 reviews
$215/ jet ski
Key West Patch Reef Fishing Charter

Key West Patch Reef Fishing Charter

Private light-tackle fishing aboard a 30-foot Jeanneau with a licensed captain

5.0 • 74 reviews
$1,479& up
Half-Day Backcountry Fishing Charter in Key West

Half-Day Backcountry Fishing Charter in Key West

Fish Key West backcountry waters on a 4-hour charter

5.0 • 59 reviews
$795
Private 10-Hour Dry Tortugas Snorkel & Dive Charter

Private 10-Hour Dry Tortugas Snorkel & Dive Charter

Ride in comfort on the gyro-stabilized Park Shark to Dry Tortugas

4.9 • 330 reviews
$3,971
Freestyle Jet Ski Ride in Key West

Freestyle Jet Ski Ride in Key West

Open the throttle in Key West’s open-water freeride zones

5.0 • 59 reviews
$182/ jet ski
23' Tritoon Pontoon Rental with Delivery in Cudjoe Key
Up to 12

23' Tritoon Pontoon Rental with Delivery in Cudjoe Key

GPS-guided tritoon cruising with walk-up water access

5.0 • 58 reviews
$624/ boat
Sandbar, Snorkel & Sunset Schooner Sail in Key West

Sandbar, Snorkel & Sunset Schooner Sail in Key West

Relax on a schooner with snorkeling, sandbar time, snacks, and drinks

4.9 • 5.9K reviews
$132/ person
Small-Group Dry Tortugas Boat Tour

Small-Group Dry Tortugas Boat Tour

Discover Fort Jefferson and Dry Tortugas waters by captained boat

5.0 • 55 reviews
$793/ person
2-Stop Coral Reef Snorkel Trip in Key West

2-Stop Coral Reef Snorkel Trip in Key West

Snorkel two reef sites on a fast catamaran with drinks after the swim

4.9 • 12.7K reviews
$73/ person
Key West Private Day Sailing Charter

Key West Private Day Sailing Charter

Private Key West sailing with snorkeling, sandbars, and dolphin searches

4.9 • 635 reviews
$1,356& up
Shared 3/4-Day Fishing Charter in Key West

Shared 3/4-Day Fishing Charter in Key West

Share a captain-led fishing trip tailored to the day’s bite

4.9 • 287 reviews
$292/ person
Key West Full-Day Snorkel & Sandbar Charter

Key West Full-Day Snorkel & Sandbar Charter

Design your own reef and sandbar escape aboard a glass-bottom boat

5.0 • 59 reviews
$1,362
Private Sandbar Boat Charter in Key West
Up to 6

Private Sandbar Boat Charter in Key West

Private Key West sandbar charter for up to 6 guests on a 25 ft tritoon

5.0 • 54 reviews
$568& up
Private Bachelor & Bachelorette Sandbar Charter in Key West

Private Bachelor & Bachelorette Sandbar Charter in Key West

Build a private Key West celebration around your group's ideal day on the water

5.0 • 74 reviews
$1,479& up
2-Hour Key West Swim Stop Cruise

2-Hour Key West Swim Stop Cruise

Cruise to a Gulf swim stop on a tiki boat

4.9 • 192 reviews
$85/ person
Dry Tortugas Private Snorkel & Dive Charter From Key West

Dry Tortugas Private Snorkel & Dive Charter From Key West

Spend 10 hours exploring Fort Jefferson and snorkel or dive Dry Tortugas sites

4.9 • 330 reviews
$3,404
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Sugarloaf Shores Things To Do
Fishing Charters166Boat Tours143Yacht Charters92Boat Rentals91Snorkeling89
More
  • Sailing77
  • Scuba Diving65
  • Car Rentals47
  • Sunrise and Sunset Tours42
  • Bike Rentals32
  • Private Fishing Charters26
  • Dolphin Watching22

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.

  • Kayaking Tours16
  • Jet Skiing14
  • Ghost and Haunted8
  • Scavenger Hunts8
  • Scooter Rentals8
  • Scenic Flights7
  • Bar and Pub Crawl6
  • Dinner Cruises6
  • Parasailing6
  • Private Boat Charters6
  • Helicopter Tours5
  • Historical Tours5
  • Bike Tours4