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Best results for

Water Activities in Sugarloaf Shores, FL

Showing 1-24 of 819 results
Key West Guided Night Kayak Tour

Key West Guided Night Kayak Tour

Light up the sea floor on a guided kayak paddle beneath the stars

4.8 • 996 reviews
$93/ kayak
4-Hour Sandbar Cruise in Key West

4-Hour Sandbar Cruise in Key West

Cruise to a Key West sandbar for swimming, relaxing, and wildlife watching

$596
Sombrero Reef Snorkeling Tour from Marathon

Sombrero Reef Snorkeling Tour from Marathon

Snorkel Sombrero Reef with gear included on the Marathon Mermaid

5.0 • 3.9K reviews
$101/ person
5-Hour Reef Fishing Trip in Key West

5-Hour Reef Fishing Trip in Key West

Reef fishing for snapper and grouper, with bait and tackle included

5.0 • 841 reviews
$89/ person
Key West Parasailing with Dry Take-Offs & Landings

Key West Parasailing with Dry Take-Offs & Landings

Parasail above Key West on a 12-passenger boat with tandem flight options

4.9 • 12.7K reviews
$74/ person
Dive 2-Tank Private Charter in Key West

Dive 2-Tank Private Charter in Key West

Charter a private 2-tank dive with an in-water dive master

4.9 • 330 reviews
$1,192
1.5-Hour Key West Parasailing Adventure

1.5-Hour Key West Parasailing Adventure

See Key West and the Florida Keys from above the water

5.0 • 31 reviews
$64/ person
Parasail & Water Sports Day Pass at Smathers Beach

Parasail & Water Sports Day Pass at Smathers Beach

All-day Smathers Beach pass with parasail flight and unlimited watersports

4.8 • 24.1K reviews
$113/ person
Private Deep Sea Fishing Charter in Key West

Private Deep Sea Fishing Charter in Key West

Charter the Linda D V for up to 6 anglers on a 4–8 hour Key West trip

4.8 • 278 reviews
$1,166& up
Dolphin Watch & Guided Snorkel Tour in Key West

Dolphin Watch & Guided Snorkel Tour in Key West

Dolphin watch, snorkel, and visit a sandbar on a small-group Key West tour

5.0 • 1.7K reviews
$124/ person
Clear Kayak Mangrove Tour in Sugarloaf Key Near Key West

Clear Kayak Mangrove Tour in Sugarloaf Key Near Key West

Paddle clear waters and mangrove tunnels with an eco-guide

5.0 • 1.3K reviews
$81/ person
Private Dry Tortugas Boat Charter from Key West

Private Dry Tortugas Boat Charter from Key West

Cruise to Fort Jefferson and swim in Dry Tortugas waters

5.0 • 379 reviews
$2,120
Marathon Sandbar Cruise

Marathon Sandbar Cruise

Sightsee around Marathon, then float and paddle at a local sandbar

5.0 • 281 reviews
$129/ person
Private Sunset Cruise in Key West

Private Sunset Cruise in Key West

Sail turquoise waters as Key West’s sunset colors emerge

5.0 • 278 reviews
$477/ boat
Marathon Sunset Cruise

Marathon Sunset Cruise

An evening cruise with champagne, music, and sunset views from the water

5.0 • 3.9K reviews
$82/ person
Key West Sunset Harbor Charter

Key West Sunset Harbor Charter

Cruise Key West's calm harbor channels on a private sunset charter

5.0 • 841 reviews
$802
6-Hour Private Charter in Key West

6-Hour Private Charter in Key West

Customize your day on Key West’s waters with snorkeling, fishing, or island exploring

5.0 • 199 reviews
$965
Key West Half-Day Sandbar & Snorkel Charter

Key West Half-Day Sandbar & Snorkel Charter

Cruise Key West by private boat with snorkel gear and a sandbar stop

5.0 • 188 reviews
$1,272
Private Key West Sandbar Trip with Lunch & Snorkeling
Up to 6

Private Key West Sandbar Trip with Lunch & Snorkeling

Enjoy a four-hour private cruise to mangrove sandbars with snorkeling, paddle boards, and a catered Cuban lunch.

5.0 • 183 reviews
$780
Guided Backcountry Fishing Charter in Key West

Guided Backcountry Fishing Charter in Key West

Backcountry flats fishing for up to 4 anglers on the ShadowCaster

5.0 • 172 reviews
$742& up
Explore Key West Sandbars Private Charter

Explore Key West Sandbars Private Charter

Choose a 3–6 hour private sandbar charter with floats, snorkel gear, and shade

5.0 • 115 reviews
$530& up
4-Hour Private Sandbar & Snorkel Charter in Key West

4-Hour Private Sandbar & Snorkel Charter in Key West

Charter COWFISH for a Key West sandbar stop and guided snorkel, with snacks and water included

5.0 • 1.7K reviews
$847
Customize Your Key West Private Boat Charter

Customize Your Key West Private Boat Charter

Build your own private Key West day on the water for up to 6 guests

5.0 • 101 reviews
$1,007& up
Key West Private 6-Hour Fishing & Snorkeling Charter

Key West Private 6-Hour Fishing & Snorkeling Charter

Customize a private day of fishing, snorkeling, sandbar stops, or island hopping

5.0 • 379 reviews
$1,007
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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
  • 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
  • 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.