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 1100

things to do in Summerland Key, FL

Showing 337-360 of 1,100 results
Key West Backcountry Mangrove Kayak Tour & Sandbar

Key West Backcountry Mangrove Kayak Tour & Sandbar

Explore Key West’s remote backcountry with guided paddling and sandbar time

4.8 • 24.1K reviews
$148/ person
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
Dolphin Watching, Snorkel & Sunset Cruise in Key West

Dolphin Watching, Snorkel & Sunset Cruise in Key West

Cruise to spot dolphins, snorkel a reef, then enjoy sunset drinks

4.8 • 24.1K reviews
$79/ 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
Key West Golf Cart Rental at Casa Marina

Key West Golf Cart Rental at Casa Marina

Explore Key West and Stock Island with a 4-person golf cart

4.8 • 24.1K reviews
$125& up
6-Seat Golf Cart Rental in Key West

6-Seat Golf Cart Rental in Key West

Rent a 6-passenger golf cart to explore Key West roads up to 35 MPH

4.8 • 24.1K reviews
$216/ golf-cart
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 Dinner Cruise in Key West

Sunset Dinner Cruise in Key West

Sail into the Key West sunset with a tropical buffet and open well bar

4.8 • 24.1K reviews
$68/ 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
Smathers Beach Wedding Ceremony

Smathers Beach Wedding Ceremony

Plan a beach wedding ceremony with décor, florals, and an officiant included

4.8 • 24.1K reviews
$1,798
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 Dolphin Watching & Snorkeling Cruise in the Keys

3-Hour Dolphin Watching & Snorkeling Cruise in the Keys

Cruise the Keys waters and watch dolphins, with time to snorkel

5.0 • 29 reviews
$158/ person
1…141516…46
Fishing Charters217Boat Tours114Snorkeling96Boat Rentals95Yacht 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