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 576

things to do in Osprey, FL

Showing 265-288 of 576 results
90+ Mile Deep Sea Fishing Charter From Holmes Beach

90+ Mile Deep Sea Fishing Charter From Holmes Beach

Chase Seasonal Snapper and Grouper Far Offshore

4.9 • 64 reviews
$3,180
Bradenton Bay Horseback Swim Tour

Bradenton Bay Horseback Swim Tour

Ride your own horse through bay water with guided swims to shore

4.8 • 1.3K reviews
$175/ person
Bradenton Sunset Horseback Swim

Bradenton Sunset Horseback Swim

Ride into Palma Sola Bay for a guided sunset swim on horseback

4.8 • 1.3K reviews
$191/ person
Siesta Key 24' Pontoon Boat Rental
Up to 10

Siesta Key 24' Pontoon Boat Rental

Cruise Sarasota Bay waterways with shade, storage, and room to fish or relax

4.8 • 1.2K reviews
$451/ boat
24' Pontoon Boat Rental in Sarasota
Up to 10

24' Pontoon Boat Rental in Sarasota

Cruise Sarasota Bay’s mangroves, sandbars, and beaches by pontoon

4.8 • 1.2K reviews
$620/ boat
Siesta Key 27' Pontoon Boat Rental
Up to 14

Siesta Key 27' Pontoon Boat Rental

Cruise Sarasota Bay and the Intracoastal on a roomy pontoon

4.8 • 1.2K reviews
$507/ boat
Siesta Key 27' Pontoon Boat Rental
Up to 14

Siesta Key 27' Pontoon Boat Rental

Cruise Sarasota Bay and the Intracoastal with room for up to 14

4.8 • 1.2K reviews
$677/ boat
Siesta Key 4-Hour Pontoon Boat Rental
Up to 8

Siesta Key 4-Hour Pontoon Boat Rental

Cruise Sarasota’s Intracoastal waterways on a shaded pontoon

4.8 • 1.2K reviews
$371/ boat
Siesta Key 22' Center Console Boat Rental
Up to 8

Siesta Key 22' Center Console Boat Rental

Cruise Sarasota’s bays and waterways with fishing-ready gear

4.8 • 1.2K reviews
$451/ boat
Siesta Key 22' Center Console Boat Rental
Up to 8

Siesta Key 22' Center Console Boat Rental

Cruise or fish Sarasota Bay on a 22-foot center console

4.8 • 1.2K reviews
$620/ boat
Siesta Key 4-Hour Southwind Boat Rental
Up to 8

Siesta Key 4-Hour Southwind Boat Rental

Cruise Sarasota Bay and Intracoastal waterways on a shaded sportdeck boat

4.8 • 1.2K reviews
$394/ boat
Siesta Key 9-Hour Sportdeck Boat Rental
Up to 8

Siesta Key 9-Hour Sportdeck Boat Rental

Cruise Sarasota’s Intracoastal waterways for fishing or beachside exploring

4.8 • 1.2K reviews
$564/ boat
4-Hour Sport Deck Boat Rental in Siesta Key
Up to 10

4-Hour Sport Deck Boat Rental in Siesta Key

Cruise Sarasota Bay on a roomy SportDeck boat

4.8 • 1.2K reviews
$507/ boat
Siesta Key 2400 SportDeck Boat Rental
Up to 10

Siesta Key 2400 SportDeck Boat Rental

Cruise Sarasota Bay and Intracoastal waterways on a shaded SportDeck

4.8 • 1.2K reviews
$677/ boat
Anna Maria Island 22' Pontoon Boat Rental
Up to 10

Anna Maria Island 22' Pontoon Boat Rental

Cruise Anna Maria Island waters with a paddle board and kids kayak included

4.8 • 794 reviews
$331/ boat
Anna Maria Island 24' Pontoon Boat Rental
Up to 15

Anna Maria Island 24' Pontoon Boat Rental

Cruise Anna Maria Island waters with a paddleboard and kids kayak included

4.8 • 794 reviews
$411/ boat
Shark Tooth Snorkel & Huka Dive Boat Tour in Venice

Shark Tooth Snorkel & Huka Dive Boat Tour in Venice

Find prehistoric shark teeth while exploring Venice’s Boneyard

4.8 • 466 reviews
$112/ person
Venice 4-Hour Scuba Refresher Course

Venice 4-Hour Scuba Refresher Course

Rebuild scuba confidence with a skills refresher tailored to you

4.8 • 466 reviews
$338/ person
Guided Megalodon Fossil Shore Dive in Venice

Guided Megalodon Fossil Shore Dive in Venice

Guided beach dive to search for Megalodon fossils

4.8 • 466 reviews
$191/ person
Beginner 2-Tank Scuba Diving in Nokomis, FL

Beginner 2-Tank Scuba Diving in Nokomis, FL

Learn scuba fundamentals with guided land and water training

4.8 • 466 reviews
$338/ person
Venice Sunset Cruise

Venice Sunset Cruise

Sunset stories of Megalodon and Venice's fossil-rich waters

4.8 • 466 reviews
$112/ person
No-Certification Shark Tooth Reef Dive in Venice

No-Certification Shark Tooth Reef Dive in Venice

Dive the reef with a Divemaster—no scuba certification needed

4.8 • 466 reviews
$157/ person
Private Snorkeling Boat Trip on Anna Maria Island

Private Snorkeling Boat Trip on Anna Maria Island

Family-friendly snorkeling on Anna Maria Island with gear included

4.8 • 382 reviews
$578
Private Egmont Key Boat Tour to Fort Dade & Lighthouse

Private Egmont Key Boat Tour to Fort Dade & Lighthouse

Cruise to Egmont Key State Park to explore Fort Dade and beachcomb for shells

4.8 • 382 reviews
$555
1…111213…24
Boat Tours83Boat Rentals71Yacht Charters62Kayaking Tours58Fishing Charters37
More
  • Jet Skiing33
  • Dolphin Watching27
  • Bike Rentals21
  • Sunrise and Sunset Tours17
  • Snorkeling14
  • Car Rentals12
  • Train Tours12
  • Horseback Riding9
  • Parasailing9
  • Equipment Rental8
  • Food Tours8
  • Ferries7
  • Helicopter Tours7
  • Outdoor Picnics7
  • Paddleboarding7
  • Stand Up Paddle Boarding6
  • Trolley Tours6
  • Sailing5
  • Scooter Rentals5
  • Private Boat Charters4