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 1095

things to do in Big Pine Key, FL

Showing 169-192 of 1,095 results
Private Sunset Cruise in Key West

Private Sunset Cruise in Key West

Cruise Key West harbor at sunset with your group and captain

4.9 • 5.9K reviews
$427
Key West Private Day Sailing Charter

Key West Private Day Sailing Charter

Private Key West sailing with snorkeling, sandbars, and dolphin searches

4.9 • 635 reviews
$1,356& up
Key West Patch Reef Fishing Charter

Key West Patch Reef Fishing Charter

Private light-tackle fishing aboard a 30-foot Jeanneau with a licensed captain

5.0 • 74 reviews
$1,479& up
Helicopter Tour of Key West & the Backcountry

Helicopter Tour of Key West & the Backcountry

See Key West landmarks and backcountry waters on a 30-minute scenic flight

4.9 • 273 reviews
$329/ person
Snorkel & Sunset Sail Cruise in Key West

Snorkel & Sunset Sail Cruise in Key West

Snorkel the living coral reef, then sail into the Key West sunset with included drinks

4.9 • 12.7K reviews
$57/ person
Key West 3.5-Hour Sandbar Kayak & Paddleboard Tour

Key West 3.5-Hour Sandbar Kayak & Paddleboard Tour

Cruise to a Key West sandbar with kayaking, paddleboards, lunch, and drinks

4.9 • 12.7K reviews
$110/ person
Private Bachelor & Bachelorette Sandbar Charter in Key West

Private Bachelor & Bachelorette Sandbar Charter in Key West

Build a private Key West celebration around your group's ideal day on the water

5.0 • 74 reviews
$1,479& up
Champagne Sunset Sailing Cruise in Key West

Champagne Sunset Sailing Cruise in Key West

Private sunset sailing with bubbly, wines and a gourmet cheese buffet

4.9 • 635 reviews
$1,016
Private 4-Hour Wreck Dive Charter

Private 4-Hour Wreck Dive Charter

Dive the USNS General Hoyt S Vandenberg on a private 2-tank wreck trip

4.9 • 330 reviews
$1,192
4-Hour Light Tackle Fishing Charter in Key West

4-Hour Light Tackle Fishing Charter in Key West

Cast light tackle from Stella Blue in calm nearshore waters

4.9 • 287 reviews
$1,080/ boat
Key West Private Fishing Charter

Key West Private Fishing Charter

A crewed private charter shaped around your preferences

4.9 • 287 reviews
$1,080/ boat
Private 2-Tank Reef Dive Charter in Key West

Private 2-Tank Reef Dive Charter in Key West

Book a private reef dive with an in-water divemaster for up to 6 guests

4.9 • 330 reviews
$1,192
10-Minute Key West Helicopter Tour

10-Minute Key West Helicopter Tour

See Key West landmarks from above on a quick helicopter flight

4.9 • 273 reviews
$113/ person
Key West Reef Snorkeling Charter

Key West Reef Snorkeling Charter

Snorkel coral reefs and relax at a Key West sandbar

5.0 • 59 reviews
$169/ person
Clothing-Optional Private Charter in Stock Island

Clothing-Optional Private Charter in Stock Island

A discreet, captain-led private escape on Florida Keys waters

5.0 • 74 reviews
$1,373& up
Marine Life Aerial Tour in Key West

Marine Life Aerial Tour in Key West

Private 20-minute flight for aerial views of reefs and marine life

4.9 • 273 reviews
$375
90-Minute Guided Jet Ski Tour in Key West

90-Minute Guided Jet Ski Tour in Key West

Ride a 28-mile guided jet ski loop around Key West from Opal Key Marina

4.9 • 12.7K reviews
$142/ jet-ski
Seven Mile Bridge Sunset Cruise

Seven Mile Bridge Sunset Cruise

Watch the sunset over Seven Mile Bridge from the water

4.9 • 12.7K reviews
$57/ person
Key West Memorial Ash-Scattering Charter

Key West Memorial Ash-Scattering Charter

Hold a private, personalized farewell at sea with a caring local captain

5.0 • 74 reviews
$1,055
Sunset Cruise in Key West

Sunset Cruise in Key West

Take in Key West’s sunset with glass-bottom views of marine life

5.0 • 59 reviews
$482
Guided 2-Tank Wreck & Reef Dive in Key West

Guided 2-Tank Wreck & Reef Dive in Key West

Dive a guided wreck and shallow reef combo in Key West

4.9 • 330 reviews
$226/ person
Private Night Dive Charter From Finz Dive Center

Private Night Dive Charter From Finz Dive Center

Dive after dark on a private 2-tank scuba charter with an in-water dive master

4.9 • 330 reviews
$1,225
Private Sunset Helicopter Tour in Key West

Private Sunset Helicopter Tour in Key West

See Key West’s sunset from a helicopter, plus a champagne toast

4.9 • 273 reviews
$421/ person
Dive Key West on a Private Full-Day 4-Tank Charter

Dive Key West on a Private Full-Day 4-Tank Charter

Private 8-hour Key West charter with up to 4 dives

4.9 • 330 reviews
$2,100
1…789…46
Fishing Charters214Boat Tours112Boat 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