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
    • 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
    1. Local experiences
    2. /All experiences
    3. /Water Activities

    Best results for Water Activities in Osprey, FL

    Showing 169-192 of 349 results
    4-Hour Yacht Charter in Sarasota
    Yacht Charters

    4-Hour Yacht Charter in Sarasota

    Private Aviara cruising with sandbar-ready comfort

    Private Aviara cruising with sandbar-ready comfort
    4.9 • 513 reviews
    $1,560
    Sarasota Sunset Yacht Charter
    Yacht Charters

    Sarasota Sunset Yacht Charter

    Private evening cruising with lounge seating, bar amenities, and Sarasota Bay views

    Private evening cruising with lounge seating, bar amenities, and Sarasota Bay views
    4.9 • 513 reviews
    $1,559
    3-Hour Sarasota Bay Yacht Charter
    Yacht Charters

    3-Hour Sarasota Bay Yacht Charter

    Cruise Sarasota Bay aboard a private yacht built for relaxed coastal escapes

    Cruise Sarasota Bay aboard a private yacht built for relaxed coastal escapes
    4.9 • 513 reviews
    $1,178
    4-Hour Bachelor & Bachelorette Party Charter
    Yacht Charters

    4-Hour Bachelor & Bachelorette Party Charter

    Reserve a private 4-hour boat party for your bachelor or bachelorette group

    Reserve a private 4-hour boat party for your bachelor or bachelorette group
    $764
    Sarasota 4-Hour Dolphin & Sandbar Cruise
    Boat Tours

    Sarasota 4-Hour Dolphin & Sandbar Cruise

    Cruise Sarasota’s waterways with swimming, sandbar games, and seashell collecting

    Cruise Sarasota’s waterways with swimming, sandbar games, and seashell collecting
    $737
    Dolphin & Sandbar Cruise in Sarasota
    Boat Tours

    Dolphin & Sandbar Cruise in Sarasota

    Cruise sandbars, swim, and bring your own drinks

    Cruise sandbars, swim, and bring your own drinks
    $628
    Sarasota Dolphin & Wildlife Boat Tour
    Boat Tours

    Sarasota Dolphin & Wildlife Boat Tour

    Experience marine life up close on a comfortable pontoon cruise for all ages.

    Experience marine life up close on a comfortable pontoon cruise for all ages.
    4.9 • 431 reviews
    $41/ person
    4.5-Hour Siesta Key Sandbar Charter
    Yacht Charters

    4.5-Hour Siesta Key Sandbar Charter

    Cruise Siesta Key’s western coast with time for dolphins, a sandbar stop, and a swim

    Cruise Siesta Key’s western coast with time for dolphins, a sandbar stop, and a swim
    4.9 • 674 reviews
    $114
    Cruise Siesta Key & Sarasota Sandbar on a 4.5-Hour Charter
    Boat Tours

    Cruise Siesta Key & Sarasota Sandbar on a 4.5-Hour Charter

    Spend 4.5 hours cruising, snorkeling stops, and sandbar time off Siesta Key

    Spend 4.5 hours cruising, snorkeling stops, and sandbar time off Siesta Key
    4.9 • 674 reviews
    $114
    Cruise Sarasota on a Private 2-Hour Charter
    Yacht Charters

    Cruise Sarasota on a Private 2-Hour Charter

    Leisurely 2-hour private cruise from Lido/Longboat Key with coolers and ice onboard

    Leisurely 2-hour private cruise from Lido/Longboat Key with coolers and ice onboard
    4.9 • 674 reviews
    $57
    2-Hour Private Cruise in Siesta Key
    Boat Tours

    2-Hour Private Cruise in Siesta Key

    Cruise Siesta Key’s western coast with your private group

    Cruise Siesta Key’s western coast with your private group
    4.9 • 674 reviews
    $57/ person
    Private 2-Hour Cruise in Siesta Key
    Boat Tours

    Private 2-Hour Cruise in Siesta Key

    Cruise Siesta Key’s western coast on a private 2-hour daytime or sunset boat ride

    Cruise Siesta Key’s western coast on a private 2-hour daytime or sunset boat ride
    4.9 • 674 reviews
    $57
    2-Hour Sunset Cruise in Sarasota
    Boat Tours

    2-Hour Sunset Cruise in Sarasota

    Plan a private coastal cruise with your own food and drinks

    Plan a private coastal cruise with your own food and drinks
    4.9 • 674 reviews
    $57/ person
    4.5-Hour Cruise in Bradenton Beach
    Boat Tours

    4.5-Hour Cruise in Bradenton Beach

    Customize a Gulf Coast cruise with sandbar swims and waterfront stops

    Customize a Gulf Coast cruise with sandbar swims and waterfront stops
    4.9 • 674 reviews
    $684
    Sarasota Private Cruise
    Boat Tours

    Sarasota Private Cruise

    Customize a private cruise along Florida's western coast

    Customize a private cruise along Florida's western coast
    4.9 • 674 reviews
    $114/ person
    2-Hour Cruise in Venice
    Boat Tours

    2-Hour Cruise in Venice

    Private coastal cruising with flexible routes and sunset options

    Private coastal cruising with flexible routes and sunset options
    4.9 • 674 reviews
    $57/ person
    Venice Sandbar Cruise
    Boat Tours

    Venice Sandbar Cruise

    Cruise Venice’s coast with time for dolphin searching, swimming, and waterfront stops

    Cruise Venice’s coast with time for dolphin searching, swimming, and waterfront stops
    4.9 • 674 reviews
    $114/ person
    Sarasota 4.5-Hour Sandbar Cruise
    Boat Tours

    Sarasota 4.5-Hour Sandbar Cruise

    Cruise coastal waters with time for a sandbar swim, waterfront stops, or an eco-focused outing

    Cruise coastal waters with time for a sandbar swim, waterfront stops, or an eco-focused outing
    4.9 • 674 reviews
    $114/ person
    Parasailing Flight in Sarasota
    Parasailing

    Parasailing Flight in Sarasota

    Parasail with an 800 ft line and 14 minutes of flight time

    Parasail with an 800 ft line and 14 minutes of flight time
    5.0 • 322 reviews
    $103/ person
    Private Parasailing Experience in Sarasota
    Parasailing

    Private Parasailing Experience in Sarasota

    Fly parasailing on a private trip for up to 12, with observer spots if space allows

    Fly parasailing on a private trip for up to 12, with observer spots if space allows
    5.0 • 322 reviews
    $683
    LED Night Clear-Bottom Kayak Tour in Sarasota
    Kayaking Tours

    LED Night Clear-Bottom Kayak Tour in Sarasota

    Feed fish and spot marine life beneath LED-lit clear-bottom kayaks

    Feed fish and spot marine life beneath LED-lit clear-bottom kayaks
    $70/ person
    Sandbar Cruise in Sarasota
    Boat Tours

    Sandbar Cruise in Sarasota

    Cruise Sarasota Bay and relax at a sandbar

    Cruise Sarasota Bay and relax at a sandbar
    5.0 • 55 reviews
    $115/ person
    Sarasota Sunset Tiki Boat Cruise
    Boat Tours

    Sarasota Sunset Tiki Boat Cruise

    Watch the Sarasota sunset from a private tiki boat

    Watch the Sarasota sunset from a private tiki boat
    5.0 • 55 reviews
    $876
    Sunset Tiki Boat Cruise in Sarasota
    Boat Tours

    Sunset Tiki Boat Cruise in Sarasota

    Cruise Sarasota’s Gulf Coast as the sun sets from a tiki boat

    Cruise Sarasota’s Gulf Coast as the sun sets from a tiki boat
    5.0 • 55 reviews
    $87/ person
    1…789…15

    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.