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Best results for

Water Activities in Summerland Key, FL

Showing 649-672 of 834 results
Sandbar Charter in Key West

Sandbar Charter in Key West

Private shallow-draft boating for sandbars, swings and wildlife watching

$1,219
4-Hour Shared Charter in Key West

4-Hour Shared Charter in Key West

Head to the sandbar or reef on a shared Key West charter

$398/ person
42' Sailing Catamaran Charter in Key West

42' Sailing Catamaran Charter in Key West

Private sailing with a full bathroom and kitchen

$1,709
42' Sailing Catamaran Charter in Key West

42' Sailing Catamaran Charter in Key West

Sail Key West waters privately with an onboard kitchen and full bathroom

$1,817
Sunrise & Sunset Catamaran Charter in Key West

Sunrise & Sunset Catamaran Charter in Key West

Sail Key West waters on a private catamaran timed for sunrise or sunset

$1,375
42' Sailing Catamaran Charter in Key West

42' Sailing Catamaran Charter in Key West

Sail the ocean on a private catamaran with a full bathroom and kitchen

$1,693
4-Hour Boat Charter in Key West

4-Hour Boat Charter in Key West

Shallow-draft sandbar hopping with dolphin and turtle watching

$1,219
Private Sailing Catamaran Charter in Key West

Private Sailing Catamaran Charter in Key West

Spend the day sailing Key West waters aboard a private catamaran

$2,567
Key West Offshore & Reef Fishing Charter

Key West Offshore & Reef Fishing Charter

Troll offshore or fish reefs and wrecks with a captain and deckhand

$1,219& up
Light Tackle Fishing Charter in Key West

Light Tackle Fishing Charter in Key West

Fish offshore, reefs, and wrecks with lighter tackle from a center-console boat

$1,113& up
Private Tiki Boat Sandbar Party in Key West

Private Tiki Boat Sandbar Party in Key West

Private tiki boat time for swimming, floating, and relaxing with your crew

$426
6-Hour Deep Sea Fishing Charter in Key West

6-Hour Deep Sea Fishing Charter in Key West

Cast off aboard an air-conditioned sportfishing boat

$1,484
Full-Day Key West Deep Sea Fishing Charter

Full-Day Key West Deep Sea Fishing Charter

Head offshore aboard an air-conditioned sportfishing boat for a private day on the water

$1,802
Key West 4-Hour Deep Sea Fishing Charter

Key West 4-Hour Deep Sea Fishing Charter

Cast off aboard an air-conditioned sportfishing boat

$1,166
Key West Sandbar Boat Charter

Key West Sandbar Boat Charter

Swim, snorkel, and unwind at secluded Florida Keys sandbars

$954/ boat
Reef Fishing Charter in Marathon

Reef Fishing Charter in Marathon

Fish patch reefs and bridges with gear, licenses, and catch cleaning included

$981
6-Hour Wreck Fishing Charter in Marathon

6-Hour Wreck Fishing Charter in Marathon

Fish sunken wrecks with jigging and trolling techniques

$1,113
Private Offshore Fishing Charter in Marathon

Private Offshore Fishing Charter in Marathon

Chase tuna, mahi-mahi, sailfish, wahoo, and grouper in Marathon's deep waters

$1,325
64' Power Catamaran Charter in Key West

64' Power Catamaran Charter in Key West

Stretch out across teak decks, lounges, and a spacious salon on the water

$6,810
8-Hour Key West Yacht Charter

8-Hour Key West Yacht Charter

Cruise aboard a sleek Sea Ray with a bright, high-end cabin

$2,838
Sunset Cruise in Key West

Sunset Cruise in Key West

Sail into the evening aboard a sleek Sea Ray 420 Sundancer

$1,135
Key West Big Fish Fishing Charter

Key West Big Fish Fishing Charter

Cast for big fish with a seasoned Key West captain

$1,007
Key West 6-Hour Fishing Charter

Key West 6-Hour Fishing Charter

Fish South Florida waters with Captain Magnus aboard the Ultra Grand Slam

$1,272
Marathon 25' Center Console Boat Rental
Up to 9

Marathon 25' Center Console Boat Rental

Twin-engine boat for fishing, sandbars, and offshore exploring

$437/ boat
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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 Charters212Boat Tours111Snorkeling96Boat 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