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Best results for

Water Activities in Osprey, FL

Showing 121-144 of 395 results
Boca Grande Inshore Fishing Charter

Boca Grande Inshore Fishing Charter

Cast for Gulf Coast favorites in Boca Grande’s backcountry waters

5.0 • 56 reviews
$636& up
Bradenton Tiki Bar Boat Charter

Bradenton Tiki Bar Boat Charter

Cruise to island bars and waterfront eateries by boat

5.0 • 55 reviews
$636& up
Neal Preserve 2-Hour Pedal Kayak Tour

Neal Preserve 2-Hour Pedal Kayak Tour

Pedal through seagrass beds and mangrove tunnels on a 2-mile Neal Preserve tour

4.9 • 196 reviews
$78/ kayak
Guided Kayak Tour of Emerson Point Mangroves

Guided Kayak Tour of Emerson Point Mangroves

Paddle mangrove tunnels and explore sandbars in Terra Ceia Bay

4.9 • 169 reviews
$55/ kayak
Boat Rental in Englewood on a 22' Tritoon
Up to 12

Boat Rental in Englewood on a 22' Tritoon

Comfortable tritoon rental with shaded seating and onboard navigation gear

4.9 • 99 reviews
$459/ boat
Cruise Sarasota Bay on a Private Sunset Charter

Cruise Sarasota Bay on a Private Sunset Charter

Book a 3- or 4-hour private sunset cruise on a 38-foot Sea Ray

4.9 • 517 reviews
$1,808
Siesta Key Double Kayak Rental

Siesta Key Double Kayak Rental

Paddle independently through Midnight Pass at your own pace

5.0 • 196 reviews
$65/ kayak
Solo Jet Ski Rental in Sarasota

Solo Jet Ski Rental in Sarasota

Take the controls and cruise a designated riding area at your own pace

5.0 • 37 reviews
$294/ jet ski
2-Hour Sunset Cruise in Sarasota

2-Hour Sunset Cruise in Sarasota

Plan a private coastal cruise with your own food and drinks

4.9 • 691 reviews
$57/ person
6-Hour Offshore Fishing Charter in Bradenton

6-Hour Offshore Fishing Charter in Bradenton

Reef fishing for seasonal offshore species

5.0 • 100 reviews
$953
Anna Maria Island Sound Glow Kayak Tour

Anna Maria Island Sound Glow Kayak Tour

Paddle a clear, LED-lit kayak through Anna Maria Island Sound after dark

5.0 • 43 reviews
$79/ person
Sunset Cruise in Venice

Sunset Cruise in Venice

Private evening cruise on Florida waters with room for your snacks and drinks

5.0 • 41 reviews
$318
Boca Grande Nearshore Fishing Charter

Boca Grande Nearshore Fishing Charter

Cast for snapper, grouper, and more off Boca Grande

5.0 • 56 reviews
$689& up
North Port Dolphin & Sandbar Cruise

North Port Dolphin & Sandbar Cruise

Explore a sandy sandbar and look for dolphins on a private boat outing

4.9 • 80 reviews
$446
6-Hour Private Boat Charter in Siesta Key

6-Hour Private Boat Charter in Siesta Key

Spend 6 hours on the water with a private Siesta Key boat charter

4.9 • 75 reviews
$904
3-Hour Kayak Rental at Emerson Point

3-Hour Kayak Rental at Emerson Point

Choose a single or tandem kayak with free delivery to your location

4.9 • 169 reviews
$48/ kayak
Sarasota Jet Ski Rental

Sarasota Jet Ski Rental

Ride Sarasota Bay and Siesta Key waters with safety gear included

4.9 • 69 reviews
$136/ jet ski
Cruise Sarasota Bay on a 3-Hour Sunset Charter

Cruise Sarasota Bay on a 3-Hour Sunset Charter

Charter the 50' Memory Maker for 3 hours with four lounge areas

4.9 • 517 reviews
$2,463& up
Sarasota Single Kayak Rental

Sarasota Single Kayak Rental

Paddle Midnight Pass at your own pace

5.0 • 196 reviews
$47/ kayak
4-Hour Offshore Fishing Charter in Palmetto

4-Hour Offshore Fishing Charter in Palmetto

Target reef species offshore with AM or PM options

4.9 • 64 reviews
$996
4.5-Hour Cruise in Bradenton Beach

4.5-Hour Cruise in Bradenton Beach

Customize a Gulf Coast cruise with sandbar swims and waterfront stops

4.9 • 691 reviews
$684
Explore Siesta Key by Double Kayak

Explore Siesta Key by Double Kayak

Paddle Midnight Pass on your own schedule

5.0 • 196 reviews
$65/ kayak
Sarasota Private Cruise

Sarasota Private Cruise

Customize a private cruise along Florida's western coast

4.9 • 691 reviews
$114/ person
Half-Day Private 54' Pardo Yacht Charter in Sarasota

Half-Day Private 54' Pardo Yacht Charter in Sarasota

Charter the 54’ Pardo Exit Strategy for 4 hours on Sarasota Bay

4.9 • 517 reviews
$3,532
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Travel guides for Water Activities

13 Stunning Beaches in Florida With Clear Water You Need to Visit
Best of Florida • 2026

13 Stunning Beaches in Florida With Clear Water You Need to Visit

Clarity is geology, not luck: quartz sand, seagrass filtration, and how close the Gulf Stream runs. Thirteen beaches, and the trade-off each one asks of you.

Do You Need a License to Rent a Boat in Florida? Your Complete Guide
Best of Florida • 2026

Do You Need a License to Rent a Boat in Florida? Your Complete Guide

Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.

Osprey Things To Do
Boat Tours82Boat Rentals70Yacht Charters62Kayaking Tours58Fishing Charters37
More
  • Jet Skiing29
  • Dolphin Watching27
  • Bike Rentals21
  • Sunrise and Sunset Tours17
  • Snorkeling14
  • Car Rentals12
  • Train Tours12
Horseback Riding
9
  • Parasailing9
  • Equipment Rental8
  • Food Tours8
  • Helicopter Tours7
  • Outdoor Picnics7
  • Paddleboarding7
  • Stand Up Paddle Boarding6
  • Trolley Tours6
  • Sailing5
  • Scooter Rentals5
  • Private Boat Charters4
  • Scuba Diving4