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Best results for

Water Activities in Sugarloaf Shores, FL

Showing 169-192 of 821 results
Key West Sandbar Charter

Key West Sandbar Charter

Explore Key West waters on a customizable private boat trip

4.9 • 187 reviews
$1,022& up
20' Deck Boat Rental in Cudjoe Key
Up to 10

20' Deck Boat Rental in Cudjoe Key

Cruise local waters with GPS guidance and convenient delivery

5.0 • 58 reviews
$568/ boat
Key West 3.5-Hour Sandbar Kayak & Paddleboard Tour

Key West 3.5-Hour Sandbar Kayak & Paddleboard Tour

Cruise to a Key West sandbar with kayaking, paddleboards, lunch, and drinks

4.9 • 12.7K reviews
$110/ person
Private 2-Tank Reef Dive Charter in Key West

Private 2-Tank Reef Dive Charter in Key West

Book a private reef dive with an in-water divemaster for up to 6 guests

4.9 • 330 reviews
$1,192
4-Hour Sandbar Cruise in Key West

4-Hour Sandbar Cruise in Key West

Share a laid-back Key West sandbar outing with fellow travelers

5.0 • 55 reviews
$284/ person
5-Hour Key West Sandbar & Snorkel Private Charter

5-Hour Key West Sandbar & Snorkel Private Charter

Snorkel the reef, then cruise to a remote Key West sandbar

5.0 • 51 reviews
$795
Key West Private Fishing Charter

Key West Private Fishing Charter

A crewed private charter shaped around your preferences

4.9 • 287 reviews
$1,080/ boat
Private Waterfront Bar Hop Boat Cruise Near Key West

Private Waterfront Bar Hop Boat Cruise Near Key West

Pair Stock Island’s waterfront scenery with marina bars, seafood, and tacos

5.0 • 49 reviews
$722
Florida Keys Night Fishing Charter

Florida Keys Night Fishing Charter

Fish Florida Keys waters after dark aboard a private, fully equipped boat

4.9 • 154 reviews
$1,484& up
90-Minute Guided Jet Ski Tour in Key West

90-Minute Guided Jet Ski Tour in Key West

Ride a 28-mile guided jet ski loop around Key West from Opal Key Marina

4.9 • 12.7K reviews
$142/ jet-ski
17' Center Console Boat Rental in Cudjoe Key
Up to 6

17' Center Console Boat Rental in Cudjoe Key

Take the helm of a GPS-equipped center console for daytime Keys boating

5.0 • 58 reviews
$568/ boat
Key West Tiki Cruise

Key West Tiki Cruise

Cruise Key West's Historic Seaport past Sunset Pier and Mallory Square

4.9 • 192 reviews
$68/ person
Guided 2-Tank Wreck & Reef Dive in Key West

Guided 2-Tank Wreck & Reef Dive in Key West

Dive a guided wreck and shallow reef combo in Key West

4.9 • 330 reviews
$226/ person
22' Deck Boat Rental with Dock Delivery in Cudjoe Key
Up to 12

22' Deck Boat Rental with Dock Delivery in Cudjoe Key

GPS-guided cruising and fishing around Cudjoe Key

5.0 • 58 reviews
$596/ boat
Key West Custom Boat Charter

Key West Custom Boat Charter

Build a private Key West day around snorkeling, fishing, sandbars, or Dry Tortugas

5.0 • 55 reviews
$1,020/ boat
Private Night Dive Charter From Finz Dive Center

Private Night Dive Charter From Finz Dive Center

Dive after dark on a private 2-tank scuba charter with an in-water dive master

4.9 • 330 reviews
$1,225
Key West Sunset Cruise

Key West Sunset Cruise

Set out on a shaded boat for a Key West sunset

5.0 • 55 reviews
$681& up
Snorkel & Sunset Cruise In Key West

Snorkel & Sunset Cruise In Key West

Private 5-hour snorkel and sunset cruise for all ages

5.0 • 51 reviews
$795
Cruise Dry Tortugas On A Private Charter From Key West

Cruise Dry Tortugas On A Private Charter From Key West

Private Dry Tortugas charter with breakfast, picnic lunch, and snacks included

5.0 • 51 reviews
$3,859
Private Captain for Your Own Boat in the Florida Keys

Private Captain for Your Own Boat in the Florida Keys

Put a licensed captain at the helm of your Florida Keys boat

4.9 • 154 reviews
$848& up
Deep-Drop Swordfish Fishing Charter in Cudjoe Key

Deep-Drop Swordfish Fishing Charter in Cudjoe Key

Target daytime swordfish and deepwater species on a private Florida Keys charter

4.9 • 154 reviews
$2,544& up
Dive Key West on a Private Full-Day 4-Tank Charter

Dive Key West on a Private Full-Day 4-Tank Charter

Private 8-hour Key West charter with up to 4 dives

4.9 • 330 reviews
$2,100
18' Pontoon Boat Rental in Cudjoe Key

18' Pontoon Boat Rental in Cudjoe Key

GPS-equipped pontoon rental with boat delivery

5.0 • 58 reviews
$511/ boat
Key West Light Tackle Fishing Charter

Key West Light Tackle Fishing Charter

Set out for Key West fishing with shade, coolers, and optional tackle

5.0 • 55 reviews
$1,270& up
1…789…35

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.

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