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Best results for

Water Activities in Sugarloaf Shores, FL

Showing 73-96 of 819 results
Lobster Mini Season Charter in Key West

Lobster Mini Season Charter in Key West

Catch lobsters during Key West's July Mini Season

5.0 • 101 reviews
$1,060& up
Key West Sunset Charter

Key West Sunset Charter

Explore a sandbar, watch for dolphins, and cruise into the Key West sunset

5.0 • 278 reviews
$583
Sail, Snorkel & Kayak Charter in Key West

Sail, Snorkel & Kayak Charter in Key West

Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks

4.9 • 5.9K reviews
$2,409
Adults-Only Snipes Key Sandbar Cruise from Key West

Adults-Only Snipes Key Sandbar Cruise from Key West

An adults-only sandbar outing with lunch, drinks and water toys

4.9 • 1K reviews
$138/ person
Key West Jet Ski Tour Past the Southernmost Point

Key West Jet Ski Tour Past the Southernmost Point

Ride your own jet ski on a 28-mile guided loop around Key West

4.9 • 12.7K reviews
$151/ jet-ski
Adults-Only Champagne Sunset Sail in Key West

Adults-Only Champagne Sunset Sail in Key West

Adults-only Key West sunset sail with champagne and gourmet cheese

4.9 • 635 reviews
$112/ person
5-Hour Key West Sandbar Charter

5-Hour Key West Sandbar Charter

Relax at Key West sandbars with lunch, drinks, and a captain

5.0 • 183 reviews
$847
Key West 2-Hour Paddleboard Rental

Key West 2-Hour Paddleboard Rental

Paddle mangrove creeks with an included lesson and area map

4.9 • 8K reviews
$45/ person
4-Hour Key West Light Tackle Fishing Charter

4-Hour Key West Light Tackle Fishing Charter

Private 4-hour light tackle fishing charter for up to 4 guests

5.0 • 76 reviews
$689
Key West Private Sunset Cruise

Key West Private Sunset Cruise

A private evening on the water for toasts, music and horizon views

5.0 • 74 reviews
$1,055
Key West Private 3-Hour Bottom Fishing Charter

Key West Private 3-Hour Bottom Fishing Charter

Private inshore fishing with captain guidance tailored to your group

5.0 • 101 reviews
$848
Key West Backcountry Schooner Sail, Kayak & Snorkel Tour

Key West Backcountry Schooner Sail, Kayak & Snorkel Tour

Explore mangrove islands by schooner, kayak and snorkel

4.9 • 3K reviews
$146/ person
4-Hour Private Cruise Charter in Key West

4-Hour Private Cruise Charter in Key West

Charter Cowfish for a 4-hour private cruise with any two water activities

4.9 • 414 reviews
$847
Guided Clear Kayak Eco-Tour in Marathon

Guided Clear Kayak Eco-Tour in Marathon

Paddle Marathon’s mangroves and seagrass flats in a clear tandem kayak with a guide

4.9 • 391 reviews
$116/ person
4.5-Hour Sail, Snorkel & Kayak Tour in Key West

4.5-Hour Sail, Snorkel & Kayak Tour in Key West

Sail, snorkel, and kayak on a historic schooner with drinks and snacks included

4.9 • 5.9K reviews
$120/ person
Snipes Key Sandbar Boat Tour from Key West

Snipes Key Sandbar Boat Tour from Key West

Paddle, float, and relax at Snipes Key Sandbar with lunch and drinks included

4.9 • 1K reviews
$128/ person
Key West 28-Mile Guided Jet Ski Tour

Key West 28-Mile Guided Jet Ski Tour

Ride Key West waters with a guide and views of island landmarks

4.9 • 12.7K reviews
$151/ Jet Ski
Key West Champagne Dolphin Sail & Reef Snorkel

Key West Champagne Dolphin Sail & Reef Snorkel

Sail, snorkel, and toast with included drinks aboard a spacious catamaran

4.9 • 635 reviews
$112/ person
Private Full-Day Captained Boat Charter in Key West

Private Full-Day Captained Boat Charter in Key West

Private captained day on the water with lunch, floats, and refreshments

5.0 • 183 reviews
$1,304
Private Sandbar Charter in Key West

Private Sandbar Charter in Key West

Private Key West sandbar charter with snorkel gear, drinks, and snacks

4.9 • 384 reviews
$850
Private Backcountry Sandbar Boat Tour in Key West

Private Backcountry Sandbar Boat Tour in Key West

Choose your sandbar stops and explore Key West’s mangroves by private boat

5.0 • 76 reviews
$610
Key West 4-Hour Private Sandbar Charter

Key West 4-Hour Private Sandbar Charter

Trade crowded boat routes for secluded Lower Keys sandbars

5.0 • 74 reviews
$1,267
6-Hour Fishing Charter in Key West

6-Hour Fishing Charter in Key West

Flexible fishing from offshore waters to the reef

5.0 • 101 reviews
$1,378
Private Sunset Sail in Key West

Private Sunset Sail in Key West

Settle into a classic schooner for an intimate Key West sunset

4.9 • 3K reviews
$125
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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