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Best results for

Water Activities in Sugarloaf Shores, FL

Showing 697-720 of 821 results
Key West Sunset Snapper Fishing Trip

Key West Sunset Snapper Fishing Trip

Fish for snapper as twilight settles over Key West waters

5.0 • 841 reviews
$77/ person
Bottomless Mimosa Brunch Sail & Swim in Key West

Bottomless Mimosa Brunch Sail & Swim in Key West

Brunch, drinks, and a swim stop aboard a Key West sail

5.0 • 375 reviews
$153/ person
Key West Sunday Brunch Sail

Key West Sunday Brunch Sail

Sunday sailing with brunch bites and bottomless mimosas

5.0 • 375 reviews
$124/ person
Christmas Brunch Sail in Key West

Christmas Brunch Sail in Key West

Sail into Christmas morning with brunch, mimosas, and Key West views

5.0 • 375 reviews
$227/ person
Key West Powerboat Races VIP Boat Charter
Up to 12

Key West Powerboat Races VIP Boat Charter

Shape your own day on the water with spacious seating and upscale comfort

5.0 • 188 reviews
$1,272/ boat
2-Hour Sandbar Boat Cruise

2-Hour Sandbar Boat Cruise

Cruise to JewFish Basin Sandbar or Mud Keys for a 2-hour hangout

5.0 • 183 reviews
$462
Cruise Key West Backcountry Sandbars

Cruise Key West Backcountry Sandbars

Key West sandbar cruise for up to 6 guests with captain and drinks included

5.0 • 183 reviews
$488
Key West 2-Hour Sandbar Charter

Key West 2-Hour Sandbar Charter

Cruise to a backcountry sandbar with a captain, cooler, and floats

5.0 • 183 reviews
$510
Private Florida Keys Shelling & Snorkeling Charter

Private Florida Keys Shelling & Snorkeling Charter

Snorkel and shell with your private group in the Lower Keys

5.0 • 136 reviews
$1,120& up
6-Hour Florida Keys Shelling & Snorkeling Tour

6-Hour Florida Keys Shelling & Snorkeling Tour

Explore secluded Florida Keys waters with guided shelling and shallow-water snorkeling

5.0 • 136 reviews
$392/ person
Spearfishing Charter With Instruction

Spearfishing Charter With Instruction

Learn spearfishing with Captain Amy on a private charter

5.0 • 115 reviews
$848& up
Private Key West Sandbar Tour with Kayak or Paddleboard

Private Key West Sandbar Tour with Kayak or Paddleboard

Cruise to a Key West sandbar for independent paddling and floating fun

4.9 • 8K reviews
$681
Sombrero Reef Snorkel & Sandbar Cruise

Sombrero Reef Snorkel & Sandbar Cruise

Snorkel Sombrero Reef, then float and relax at Molasses Key Sandbar

4.9 • 12.7K reviews
$103/ person
Powerboat Race Viewing Cruise in Key West

Powerboat Race Viewing Cruise in Key West

Watch the Powerboat Races from a captain-led spot on the water

4.9 • 5.9K reviews
$149/ person
Key West Sunset Sail

Key West Sunset Sail

Sail Key West’s historic waterfront aboard a hand-built 86-foot schooner

4.9 • 3K reviews
$91/ person
Key West Tall Ship Sailing Cruise

Key West Tall Ship Sailing Cruise

Hoist sails and take the wheel aboard a 2-masted schooner

4.9 • 3K reviews
$57/ person
8-Hour Key West Sandbar Charter

8-Hour Key West Sandbar Charter

Build a flexible day of sandbars, mangroves, and island stops

5.0 • 76 reviews
$1,272
Historic Harbor Cruise in Key West

Historic Harbor Cruise in Key West

Cruise Key West’s waterfront with local history narrated by a licensed captain

5.0 • 74 reviews
$1,055
Snorkel Sombrero Reef & Sandbar Cruise in Marathon

Snorkel Sombrero Reef & Sandbar Cruise in Marathon

Snorkel Sombrero Reef, then relax at Molasses Key sandbar

4.9 • 934 reviews
$147/ person
Holiday Party Sailing Charter Key West

Holiday Party Sailing Charter Key West

Private catamaran celebration with bubbly, wines, and party platters

4.9 • 635 reviews
$1,340
Key West 1.5-Hour Classic Day Sailing Cruise

Key West 1.5-Hour Classic Day Sailing Cruise

Sail Key West on Schooner America 2.0 with complimentary soft drinks

4.9 • 593 reviews
Contact for pricing
Sail Key West on a 2-Hour Champagne Sunset Cruise

Sail Key West on a 2-Hour Champagne Sunset Cruise

Sail into the Key West sunset with drinks and hors d'oeuvres included

4.9 • 593 reviews
$127/ person
Key West Full Moon Sailing Cruise

Key West Full Moon Sailing Cruise

Sail Key West's night waters beneath the full moon aboard a 105-foot schooner

4.9 • 593 reviews
$73/ person
Key West Christmas Brunch Sail

Key West Christmas Brunch Sail

Sail Key West’s waters aboard a 105-foot schooner with Christmas brunch and drinks

4.9 • 593 reviews
$236/ person
1…293031…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