Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Why travelers choose Greetwell

Curated by our team

Every experience is hand selected and approved by Greetwell.

Personal concierge

Real humans available to help before, during, and after your booking.

Intimate & authentic

Including unique in-home experiences you won't find anywhere else.

Easy booking & cancellation

Reserve in minutes with free cancellation on most experiences.

Greetwell

Experiences that stay with you long after the trip

Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

About

  • Our Story
  • For Experience Providers
  • For Hospitality Partners
  • For Developers

Resources

  • Travel Guides
  • Experience Gift Cards
  • Help Center
[email protected]1-877-GREET-WELL

Safe & Secure Payments

© 2026 Greetwell, Inc. All rights reserved.
Privacy PolicyTerms
Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Best results for

Tours And Adventures in Big Pine Key, FL

Showing 553-576 of 1,002 results
Sunset & Night Scuba Dive for Certified Divers in Key West

Sunset & Night Scuba Dive for Certified Divers in Key West

Explore Key West’s underwater world after sunset with lights and gear included

4.6 • 349 reviews
$199/ person
Beginner Scuba Diving in Key West

Beginner Scuba Diving in Key West

Learn scuba basics in a pool, then explore shallow reef areas with an instructor

4.6 • 349 reviews
$280/ person
Key West Reef Dive & Snorkel Trip

Key West Reef Dive & Snorkel Trip

Explore Key West’s barrier reef with diving or snorkeling options

4.6 • 311 reviews
$182/ person
Key West USS Vandenberg Wreck Dive

Key West USS Vandenberg Wreck Dive

Dive the 10-story Vandenberg artificial reef off Key West

4.6 • 311 reviews
$182/ person
Key West Ghost Walking Tour

Key West Ghost Walking Tour

Explore Old Town’s ghost lore with interactive paranormal experiments

4.6 • 207 reviews
$34/ person
Adults-Only Ghost Hunt with Equipment in Key West

Adults-Only Ghost Hunt with Equipment in Key West

Explore Key West's haunted past with local ghost-hunting experts

4.6 • 161 reviews
$51/ person
Offshore & Reef Fishing Charter or Eco Tour in Marathon

Offshore & Reef Fishing Charter or Eco Tour in Marathon

Choose offshore fishing, reef and wreck fishing, or an ocean eco tour from Marathon

4.7 • 15 reviews
$1,873/ boat
Marathon Offshore Fishing Charter

Marathon Offshore Fishing Charter

Fish offshore, explore reefs and wrecks, or enjoy an eco tour from Marathon

4.7 • 15 reviews
$2,043
Key West Naturist Charter

Key West Naturist Charter

Private sandbar charter with dolphin and turtle watching

5.0 • 4 reviews
$1,219
8-Hour Private Sailing Catamaran Charter in Key West

8-Hour Private Sailing Catamaran Charter in Key West

Private sailing, ocean scenery, and a setting built around your comfort

5.0 • 4 reviews
$1,855
Sandbar Charter in Key West

Sandbar Charter in Key West

Cruise shallow waters with sandbar stops and onboard comforts

5.0 • 4 reviews
$1,219
4-Hour Charter in Key West

4-Hour Charter in Key West

Choose a sandbar or reef outing, weather permitting

5.0 • 4 reviews
$371/ person
Key West Sunrise or Sunset Catamaran Charter

Key West Sunrise or Sunset Catamaran Charter

Private catamaran sailing for sunrise or sunset ocean views

5.0 • 4 reviews
$1,007
4-Hour Sailing Catamaran Charter in Key West

4-Hour Sailing Catamaran Charter in Key West

Private sailing with an onboard bathroom and kitchen

5.0 • 4 reviews
$1,219
6-Hour Private Sailing Charter in Key West

6-Hour Private Sailing Charter in Key West

Private catamaran sailing with ocean serenity

5.0 • 4 reviews
$1,590
4-Hour Sandbar or Reef Charter in Key West

4-Hour Sandbar or Reef Charter in Key West

Bring your own drinks for a shared ocean charter to a weather-dependent sandbar or reef

5.0 • 4 reviews
$371/ person
Sunrise & Sunset Catamaran Charter in Key West

Sunrise & Sunset Catamaran Charter in Key West

Enjoy a private catamaran outing in a clothing-optional setting at your comfort level

5.0 • 4 reviews
$1,007
4-Hour Sailing Catamaran Charter in Key West

4-Hour Sailing Catamaran Charter in Key West

Private catamaran sailing with a full bathroom and kitchen

5.0 • 4 reviews
$1,219
Naturist Sailing Catamaran Charter in Key West

Naturist Sailing Catamaran Charter in Key West

Sail privately in a clothing-optional setting shaped around your comfort

5.0 • 4 reviews
$1,590
Naturist Catamaran Charter in Key West

Naturist Catamaran Charter in Key West

Spend a private day on a clothing-optional sailing catamaran

5.0 • 4 reviews
$1,855
4-Hour Private Fishing Charter in Key West

4-Hour Private Fishing Charter in Key West

Fish or relax on a private 4-hour charter with a local captain

5.0 • 2 reviews
$1,060
6-Hour Private Fishing Charter in Key West

6-Hour Private Fishing Charter in Key West

Private 6-hour fishing charter for up to 4 anglers

5.0 • 2 reviews
$1,219
8-Hour Private Fishing Charter in Key West

8-Hour Private Fishing Charter in Key West

Spend 8 hours on the water with a private captain and gear for up to 4 anglers

5.0 • 2 reviews
$1,378
Mangrove Dinghy Bar Hop Tour in Key West

Mangrove Dinghy Bar Hop Tour in Key West

Ride a dinghy through Key West mangroves with waterfront bar stops

5.0 • 2 reviews
$90/ person
1…232425…42
Big Pine Key Things To Do
Fishing Charters212Boat Tours111Boat Rentals98Snorkeling97Yacht Charters92
More
  • Sailing73
  • 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
  • Paddleboarding7
  • Scooter Rentals7
  • Bar and Pub Crawl6
  • Parasailing6
  • Private Boat Charters6
  • Helicopter Tours5
  • Historical Tours5