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Best results for

Water Activities in Sugarloaf Shores, FL

Showing 721-744 of 821 results
Key West Wrecker's Race Sailing Cruise

Key West Wrecker's Race Sailing Cruise

Join Key West schooners in a monthly race to Sand Key Lighthouse

4.9 • 593 reviews
$127/ person
Key West Christmas Day Sunset Sail

Key West Christmas Day Sunset Sail

Sail into Key West sunset views with holiday treats aboard a 105-foot schooner

4.9 • 593 reviews
$150/ person
23' WorldCat Boat Rental in Cudjoe Key

23' WorldCat Boat Rental in Cudjoe Key

Cruise the Keys on a 23-foot dual-hull World Cat for three days or more

5.0 • 58 reviews
$3,405/ boat
Cudjoe Key 24' Center Console Boat Rental
Up to 8

Cudjoe Key 24' Center Console Boat Rental

GPS-guided center console for Keys exploration

5.0 • 58 reviews
$624/ boat
Double Slide Pontoon Boat Rental in Cudjoe Key
Up to 10

Double Slide Pontoon Boat Rental in Cudjoe Key

Cruise at your own pace with double slides and GPS-marked routes

5.0 • 58 reviews
$681/ boat
Reef, Bay & Wreck Fishing Charter in Cudjoe Key

Reef, Bay & Wreck Fishing Charter in Cudjoe Key

Fish reefs, bays, and wrecks from Cudjoe Key with Capt. Craig

4.9 • 189 reviews
$424& up
Shark & Goliath Grouper Fishing Charter in Cudjoe Key

Shark & Goliath Grouper Fishing Charter in Cudjoe Key

Fight sharks and Goliath grouper with heavy tackle in the Lower Keys

4.9 • 189 reviews
$424& up
Tarpon Fishing Charter in Cudjoe Key

Tarpon Fishing Charter in Cudjoe Key

Target tarpon with Capt. Craig on a 2–6 hour charter for up to 4 anglers

4.9 • 189 reviews
$424& up
Fish an Inshore Patch Reef Charter in Cudjoe Key

Fish an Inshore Patch Reef Charter in Cudjoe Key

Fish an inshore patch reef charter in Cudjoe Key (2–6 hours, up to 4 fishermen)

4.9 • 189 reviews
$424& up
Paddleboard Fishing Charter in Cudjoe Key

Paddleboard Fishing Charter in Cudjoe Key

Paddleboard fishing in Cudjoe Key with flexible 2–6 hour options

4.9 • 189 reviews
$371& up
2-Hour Key West Seaport Cruise

2-Hour Key West Seaport Cruise

Cruise Key West’s seaport by tiki boat with captain-guided local stories

4.9 • 192 reviews
$85/ person
6-Hour Flats & Backcountry Fishing Charter in Key West

6-Hour Flats & Backcountry Fishing Charter in Key West

Fish the flats and backcountry on a 6-hour private charter

5.0 • 50 reviews
$1,060
Fish The Flats & Backcountry In Key West

Fish The Flats & Backcountry In Key West

Fish the flats and backcountry on an 8-hour private charter

5.0 • 50 reviews
$1,272
Fish For Tarpon In Key West Morning & Evening

Fish For Tarpon In Key West Morning & Evening

Target tarpon twice in one day with morning and evening sessions

5.0 • 50 reviews
$1,378
Sunset Tarpon Fishing Charter in Key West

Sunset Tarpon Fishing Charter in Key West

Private sunset tarpon charter that departs around dusk

5.0 • 50 reviews
$583
Key West Catch & Release Fishing Charter

Key West Catch & Release Fishing Charter

Private, light-tackle fishing in the calm Florida Keys backcountry

4.9 • 137 reviews
$795& up
Key West Pirate Treasure Hunt Charter

Key West Pirate Treasure Hunt Charter

Follow pirate clues to hidden Key West sandbar treasure

5.0 • 39 reviews
$525
Key West Sunset Charter

Key West Sunset Charter

Cruise the Historic Seaport as the sun sets

5.0 • 34 reviews
$448
Sunset Snorkeling Tour at Sand Key

Sunset Snorkeling Tour at Sand Key

Snorkel Sand Key, then watch the Gulf sunset from the water

4.9 • 63 reviews
$423/ person
Key West 6-Hour Reef Fishing Trip

Key West 6-Hour Reef Fishing Trip

Reef fishing with tackle, bait, a license, and crew assistance

4.8 • 1.7K reviews
$85/ person
Night Fishing Party Boat Trip in Key West

Night Fishing Party Boat Trip in Key West

Fish Key West at night on a 5.5-hour party boat trip

4.8 • 1.7K reviews
$89/ person
3-Hour Charter in San Jose

3-Hour Charter in San Jose

Shape a private boat outing around your group's interests

5.0 • 29 reviews
$737
Sunset Fishing Charter in Key West

Sunset Fishing Charter in Key West

Fish Key West’s evening bite for snapper and grouper under the stars

4.8 • 1K reviews
$1,305
Key West Jet Ski Tour: 26-Mile Island Circle

Key West Jet Ski Tour: 26-Mile Island Circle

Circle Key West in 90 minutes on a thrilling 26-mile guided jet ski ride.

4.8 • 782 reviews
$170
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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