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Best results for

Water Activities in Sugarloaf Shores, FL

Showing 97-120 of 819 results
Private Kayak, Snorkel & Sail Charter in Key West

Private Kayak, Snorkel & Sail Charter in Key West

Sail, kayak, and snorkel Key West's shallow waters on a private cruise

4.9 • 414 reviews
$847
Clear Paddleboard Rental in Marathon

Clear Paddleboard Rental in Marathon

Glide over shallow seagrass flats on a clear paddleboard

4.9 • 391 reviews
$70/ paddleboard
Private Historic Schooner Day Sail in Key West

Private Historic Schooner Day Sail in Key West

Charter a private historic schooner sail with drinks and snacks included

4.9 • 5.9K reviews
$1,713
Key West Sandbar & Sunset Cruise

Key West Sandbar & Sunset Cruise

Lunch, water activities, and a sunset cruise in one Key West afternoon

4.9 • 1K reviews
$148/ person
Snorkel Key West Reef With Margaritas

Snorkel Key West Reef With Margaritas

Snorkel Key West’s coral reef, then relax with complimentary margaritas

4.9 • 12.7K reviews
$57/ person
Key West Adults-Only Champagne Sunset Sail

Key West Adults-Only Champagne Sunset Sail

Sip bubbly and sail into the Key West sunset aboard a spacious catamaran

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

Private Captained Boat Charter in Key West

Cruise Key West waters aboard a private captained Boston Whaler

5.0 • 183 reviews
$900
Private Snorkeling Charter in Key West

Private Snorkeling Charter in Key West

Build your own 3–3.5 hour private boat charter with snorkeling gear, snacks, and drinks

4.9 • 384 reviews
$907
Private Backcountry Sandbar Boat Tour in Key West

Private Backcountry Sandbar Boat Tour in Key West

Design your own sandbar escape among Key West’s mangroves

5.0 • 76 reviews
$477
4-Hour Key West Reef Snorkel Charter

4-Hour Key West Reef Snorkel Charter

Private reef time aboard a 30-foot Jeanneau yacht

5.0 • 74 reviews
$1,267
Private Fishing Charter in Key West

Private Fishing Charter in Key West

Set your own fishing pace with a private captain

5.0 • 101 reviews
$1,060
Key West Wreck Diving: Two-Tank Adventure

Key West Wreck Diving: Two-Tank Adventure

Explore historic shipwrecks guided by a dive master for an unforgettable 4-hour underwater adventure.

4.9 • 330 reviews
$226/ person
Men's Sailing Cruise in Key West

Men's Sailing Cruise in Key West

A clothing-optional all-male sailing trip with snorkeling, sandbar, or kayaking

4.9 • 414 reviews
$146/ person
Single & Double Kayak Rental in Boot Key Harbor, Marathon

Single & Double Kayak Rental in Boot Key Harbor, Marathon

Set your own pace on the water

4.9 • 391 reviews
$47/ kayak
Sail, Snorkel & Kayak Key West Sunset Cruise

Sail, Snorkel & Kayak Key West Sunset Cruise

Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset

4.9 • 5.9K reviews
$132/ person
Private Sunset Cruise in Key West

Private Sunset Cruise in Key West

Design a Key West charter around your group’s occasion

4.9 • 1K reviews
$3,235& up
Sail a Live Music Sunset Cruise in Key West

Sail a Live Music Sunset Cruise in Key West

Sunset catamaran sail with live music, appetizers, and included drinks

4.9 • 12.7K reviews
$101/ person
Private Champagne Sunset Catamaran Sail in Key West

Private Champagne Sunset Catamaran Sail in Key West

Private catamaran sailing with champagne, wines and a gourmet cheese buffet

4.9 • 635 reviews
$1,470
Fish a 4-Hour Split Charter in Key West

Fish a 4-Hour Split Charter in Key West

Share a 4-hour fishing charter and meet fellow anglers in Key West

4.9 • 287 reviews
$227/ person
Half-Day Private Snorkeling Charter in Key West

Half-Day Private Snorkeling Charter in Key West

Customize your private Key West water charter with snorkeling gear, drinks, and snacks included

4.9 • 384 reviews
$1,020
Key West 2-Hour Guided Jet Ski Tour

Key West 2-Hour Guided Jet Ski Tour

Circle Key West by jet ski with guided stops and free-ride time

5.0 • 59 reviews
$237/ jet ski
Marquesas Keys Private Charter

Marquesas Keys Private Charter

Cruise 30 miles offshore to snorkel, explore sandbars, and shape your own day

5.0 • 74 reviews
$2,761& up
Full-Day Backcountry Fishing Charter in Key West

Full-Day Backcountry Fishing Charter in Key West

Spend 8 hours fishing deeper into Key West’s backcountry waters

5.0 • 59 reviews
$1,272
Private Spearfishing Charter in Key West

Private Spearfishing Charter in Key West

Hunt reef fish alongside a professional divemaster and refine your underwater skills.

4.9 • 330 reviews
$1,113
1…456…35
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