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Best 1099

things to do in Summerland Key, FL

Showing 553-576 of 1,099 results
Key West Sunset Tiki Cruise

Key West Sunset Tiki Cruise

Toast Key West's sunset from a 53-foot tiki boat

4.7 • 8.1K reviews
$58/ person
Key West Seafood Boil Snorkel Sail

Key West Seafood Boil Snorkel Sail

Two reef snorkel stops with a seafood boil and open bar

4.7 • 8.1K reviews
$70/ person
Key West Sandbar Tour on a 53' Tiki Boat

Key West Sandbar Tour on a 53' Tiki Boat

Spend the day at a Key West sandbar aboard the 53-foot tiki boat Lazy Lady

4.7 • 8.1K reviews
$93/ person
2-Hour Key West Sunset Catamaran Sail With Live Music

2-Hour Key West Sunset Catamaran Sail With Live Music

Sunset catamaran sail with live music, full bar, and appetizers

4.7 • 8.1K reviews
$76/ person
Afternoon Snorkeling Cruise at Florida Keys Reef

Afternoon Snorkeling Cruise at Florida Keys Reef

Sail to a coral reef with snorkeling gear, instruction, and complimentary drinks

4.7 • 8.1K reviews
$51/ person
Mimosa Snorkel Sail in Key West

Mimosa Snorkel Sail in Key West

Sail to the Florida Keys Reef for guided snorkeling, lunch, and drinks

4.7 • 8.1K reviews
$51/ person
Sunset Dolphin Watch Sail in Key West

Sunset Dolphin Watch Sail in Key West

Sail Key West waters with complimentary drinks and chances to spot dolphins

4.7 • 8.1K reviews
$70/ person
Key West Dolphin Watch Sunset Sail

Key West Dolphin Watch Sunset Sail

Sail in a small group with dolphin watching, Tapas, and drinks

4.7 • 8.1K reviews
$81/ person
Key West Champagne Sunset Sail

Key West Champagne Sunset Sail

Sail into Key West’s sunset with complimentary drinks on board

4.7 • 8.1K reviews
$63/ person
Explore Crane Point Nature Preserve in Marathon

Explore Crane Point Nature Preserve in Marathon

Explore historic grounds, natural trails, and a fish pedicure

4.7 • 1.2K reviews
$23/ person
No-Certification SNUBA Diving Trip in Key West

No-Certification SNUBA Diving Trip in Key West

Go beyond snorkeling with a guided SNUBA® tour—no certification needed

4.7 • 405 reviews
$143/ person
Looe Key 4-Hour Private Charter

Looe Key 4-Hour Private Charter

Snorkel, visit a sandbar, and relax aboard a private center-console charter

4.7 • 405 reviews
$1,078
Private Looe Key Snuba, Scuba & Sandbar Charter

Private Looe Key Snuba, Scuba & Sandbar Charter

Explore Looe Key Reef with guided diving options and time at the sandbar

4.7 • 405 reviews
$1,759
Key West Sunset Cocktail Cruise

Key West Sunset Cocktail Cruise

Private catamaran cocktails with a full open bar

4.7 • 405 reviews
$1,646
Key West Sunset Cocktail Cruise

Key West Sunset Cocktail Cruise

Sunset sailing with craft drinks, island music, and catamaran views

4.7 • 405 reviews
$95/ person
Key West Sunset Cocktail Cruise

Key West Sunset Cocktail Cruise

Evening catamaran cruise with craft drinks and island music

4.7 • 405 reviews
$95/ person
Guided 2-Tank Reef Dive in Key West

Guided 2-Tank Reef Dive in Key West

Explore Florida Keys reefs on a semi-private two-dive charter

4.7 • 405 reviews
$204/ person
Half-Day Shared Fishing Charter in Key West

Half-Day Shared Fishing Charter in Key West

Fish the Florida Keys with gear provided and your catch cleaned at the dock

4.7 • 229 reviews
$93/ person
Explore Key West on a Step-Through E-Bike Rental

Explore Key West on a Step-Through E-Bike Rental

Cruise Key West on a regular-size step-through e-bike with included helmet and lock

4.7 • 210 reviews
$68/ bike
Large Step-Through E-Bike Rental in Key West

Large Step-Through E-Bike Rental in Key West

Rent a large step-thru e-bike and explore Key West on your schedule

4.7 • 210 reviews
$68/ bike
Key West Large E-Bike Rental

Key West Large E-Bike Rental

Explore Key West with torque-sensor assistance and built-in turn signals

4.7 • 210 reviews
$57/ bike
Regular-Size E-Bike Rental in Key West

Regular-Size E-Bike Rental in Key West

Glide through Key West with responsive electric assistance and built-in turn signals

4.7 • 210 reviews
$57/ bike
Key West Beach Cruiser Rental

Key West Beach Cruiser Rental

Relaxed single-speed rides with a helmet, lock, and route map included

4.7 • 210 reviews
$23/ bike
Key West Private Snorkeling Charter

Key West Private Snorkeling Charter

Explore Key West reefs with snorkel gear and onboard refreshments included

4.8 • 26 reviews
$793& up
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Fishing Charters217Boat Tours114Snorkeling96Boat Rentals95Yacht Charters92
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  • 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