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Best results for

Water Activities in Summerland Key, FL

Showing 265-288 of 834 results
3-Hour Afternoon Snorkel Cruise in Key West

3-Hour Afternoon Snorkel Cruise in Key West

Snorkel Key West’s reef, then sip from the open well bar

4.8 • 24.1K reviews
$57/ person
Do 10 Watersports Activities in Key West

Do 10 Watersports Activities in Key West

6-hour Key West watersports combo with 10 activities plus lunch and drinks

4.8 • 24.1K reviews
$159/ person
Morning Dolphin Watching & Reef Snorkel Tour in Key West

Morning Dolphin Watching & Reef Snorkel Tour in Key West

Cruise to spot dolphins, then snorkel a Key West reef with drinks on the ride back

4.8 • 24.1K reviews
$74/ person
Key West Sandbar Cruise at Sunset

Key West Sandbar Cruise at Sunset

Guided mangrove kayaking, paddleboarding and dolphin watching in Key West

4.8 • 24.1K reviews
$148/ person
Guided Jet Ski Island Tour in Key West

Guided Jet Ski Island Tour in Key West

Ride a jet ski around Key West with 5–6 guided stops

4.8 • 24.1K reviews
$204/ person
Sunset Sailing Cruise in Key West With Live Music

Sunset Sailing Cruise in Key West With Live Music

Sip and sail into the Key West sunset with live music and an open well bar

4.8 • 24.1K reviews
$60/ person
Sunset Snorkel Cruise in Key West

Sunset Snorkel Cruise in Key West

Snorkel two reef sites, then sail back at sunset

4.8 • 24.1K reviews
$51/ person
4-Hour Private Boat Charter in Key West
Up to 6

4-Hour Private Boat Charter in Key West

Build your own Key West private boat charter with a licensed local captain

4.8 • 24.1K reviews
$851
Private Full-Day Custom Boat Charter in Key West

Private Full-Day Custom Boat Charter in Key West

Customize your Key West private charter with a captain and your choice of 3 activities

4.8 • 24.1K reviews
$1,078
6-Hour Offshore Fishing Charter in Key West

6-Hour Offshore Fishing Charter in Key West

Fish lesser-fished offshore waters for mutton snapper and grouper on a 6-hour charter

5.0 • 30 reviews
$1,272
12-Hour Dry Tortugas Fishing Charter From Key West

12-Hour Dry Tortugas Fishing Charter From Key West

Fish and explore Fort Jefferson on a 12-hour Dry Tortugas charter

5.0 • 30 reviews
$2,968
4-Hour Reef & Wreck Fishing Charter in Key West

4-Hour Reef & Wreck Fishing Charter in Key West

Fish Key West reefs and wrecks on a 4-hour morning charter

5.0 • 30 reviews
$954
10-Hour Swordfishing Charter In Key West

10-Hour Swordfishing Charter In Key West

Fish the continental shelf for Broadbill Swordfish from Key West

5.0 • 30 reviews
$2,120
Key West Night Snapper Fishing Charter

Key West Night Snapper Fishing Charter

Fish after dark for snapper when they feed

5.0 • 30 reviews
$897
8-Hour Fishing Charter in Key West

8-Hour Fishing Charter in Key West

Fish offshore for mahi and stop at the reef for yellowtail action

5.0 • 30 reviews
$1,590
Key West Night Fishing Charter

Key West Night Fishing Charter

Target tarpon or sharks when nocturnal activity picks up

5.0 • 30 reviews
$530/ boat
Key West 6-Hour Reef Fishing Trip

Key West 6-Hour Reef Fishing Trip

Reef fishing with tackle, bait, a license, and crew assistance

4.8 • 1.7K reviews
$85/ person
3-Hour Key West Sandbar Charter

3-Hour Key West Sandbar Charter

Cruise to shallow sandbars and glide through mangroves in the Florida Keys

5.0 • 29 reviews
$112/ person
Private Charter or Rental in San Jose

Private Charter or Rental in San Jose

Customize a private outing for up to 9 people

5.0 • 29 reviews
$737& up
Full-Day Private Yacht Charter & Reef Snorkeling in Key West

Full-Day Private Yacht Charter & Reef Snorkeling in Key West

Charter a private sailing catamaran or power yacht for 8 hours of snorkeling and island stops

4.9 • 56 reviews
$6,867
Private Sunset Yacht Cruise & Snorkel in Key West

Private Sunset Yacht Cruise & Snorkel in Key West

Sail, snorkel, and toast the sunset on your own Key West yacht

4.9 • 56 reviews
$2,088& up
Private Half-Day Yacht Charter & Snorkeling in Key West

Private Half-Day Yacht Charter & Snorkeling in Key West

Charter a private yacht for 4 hours with snorkeling or sailing options

4.9 • 56 reviews
$4,029
Key West 6-Hour Private Yacht Charter

Key West 6-Hour Private Yacht Charter

Choose your yacht for private snorkeling, swimming, and Key West Harbor cruising

4.9 • 56 reviews
$5,732
Kayak Through Mangroves & Spot Marine Life

Kayak Through Mangroves & Spot Marine Life

Paddle serene mangrove waterways with an expert guide and spot vibrant marine life.

4.8 • 996 reviews
$70/ person
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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.

Summerland Key Things To Do
Fishing Charters214Boat Tours112Snorkeling96Boat Rentals92Yacht Charters92
More
  • Sailing72
  • Scuba Diving68
  • Car Rentals49
  • Sunrise and Sunset Tours44
  • Private Fishing Charters27
  • Bike Rentals25
  • Dolphin Watching22
  • Kayaking Tours19
  • Jet Skiing17
  • Scenic Flights9
  • Scavenger Hunts8
  • Dinner Cruises7
  • Ghost and Haunted7
  • Scooter Rentals7
  • Bar and Pub Crawl6
  • Paddleboarding6
  • Parasailing6
  • Private Boat Charters6
  • Helicopter Tours5
  • Historical Tours5