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

    Concierge Support

    • Help Center
    concierge@greetwell.com1-877-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 Siesta Key, FL

    Showing 1-24 of 92 results
    Soar Siesta: Parasailing Adventure
    Parasailing

    Soar Siesta: Parasailing Adventure

    Experience Siesta Key like never before—from 400 feet above the ocean!

    Experience Siesta Key like never before—from 400 feet above the ocean!
    5.0 • 9.9K reviews
    $112/ person
    Siesta Key Tiki Boat Tour with Music & Drinks
    Boat Tours

    Siesta Key Tiki Boat Tour with Music & Drinks

    Cruise Siesta Key’s waterways on a 2024 tiki boat with music, drinks and coastal wildlife views.

    Cruise Siesta Key’s waterways on a 2024 tiki boat with music, drinks and coastal wildlife views.
    5.0 • 9.9K reviews
    $53/ person
    Siesta Key Parasailing with Dolphin Watching
    Parasailing

    Siesta Key Parasailing with Dolphin Watching

    Soar above Florida's top-rated beach and spot dolphins during a 12–15 minute parasail flight.

    Soar above Florida's top-rated beach and spot dolphins during a 12–15 minute parasail flight.
    5.0 • 9.9K reviews
    $123/ person
    Siesta Key Sunset Tiki Boat Cruise with Dolphins
    Boat Tours

    Siesta Key Sunset Tiki Boat Cruise with Dolphins

    Enjoy a relaxed evening cruise along Siesta Key with music, LED lights and possible dolphin sightings.

    Enjoy a relaxed evening cruise along Siesta Key with music, LED lights and possible dolphin sightings.
    5.0 • 9.9K reviews
    $73/ person
    Siesta Key Boat Tour to Sandbars & Shell Beaches
    Boat Tours

    Siesta Key Boat Tour to Sandbars & Shell Beaches

    Explore pristine sandbars, collect shells, and relax on a fun 3-hour boat excursion

    Explore pristine sandbars, collect shells, and relax on a fun 3-hour boat excursion
    4.9 • 1.2K reviews
    $113/ person
    Private Boat Charter in Anna Maria Island
    Boat RentalsUp to 20

    Private Boat Charter in Anna Maria Island

    Charter a private boat for your group from Anna Maria Island

    Charter a private boat for your group from Anna Maria Island
    4.9 • 1.2K reviews
    $1,342& up
    Private Sunset & Sandbar Boat Charter in Anna Maria Island
    Boat RentalsUp to 12

    Private Sunset & Sandbar Boat Charter in Anna Maria Island

    Charter a private FunBoat on Anna Maria Island with paddleboards and beach games

    Charter a private FunBoat on Anna Maria Island with paddleboards and beach games
    4.9 • 1.2K reviews
    $939& up
    Private Boat Charter From Anna Maria Island
    Boat RentalsUp to 40

    Private Boat Charter From Anna Maria Island

    Charter the FunBoat with crew, paddleboards, and beach games

    Charter the FunBoat with crew, paddleboards, and beach games
    4.9 • 1.2K reviews
    $1,879& up
    Private Sunset Charter In Siesta Key
    Yacht Charters

    Private Sunset Charter In Siesta Key

    Private boat charter for up to 20 with paddleboards, beach games, and crew

    Private boat charter for up to 20 with paddleboards, beach games, and crew
    4.9 • 1.2K reviews
    $1,610& up
    Private FunBoat Charter In Sarasota
    Boat RentalsUp to 12

    Private FunBoat Charter In Sarasota

    Charter a FunBoat with paddleboards and beach games for your group

    Charter a FunBoat with paddleboards and beach games for your group
    4.9 • 1.2K reviews
    $1,074& up
    Siesta Key Dolphin Cruise with Mimosas
    Boat Tours

    Siesta Key Dolphin Cruise with Mimosas

    Enjoy a morning cruise with complimentary drinks while spotting dolphins in Siesta Key.

    Enjoy a morning cruise with complimentary drinks while spotting dolphins in Siesta Key.
    4.9 • 7.9K reviews
    $68/ person
    Parasailing in Siesta Key with Dolphin Viewing
    Parasailing

    Parasailing in Siesta Key with Dolphin Viewing

    Soar above Siesta Key and spot dolphins on a safe, family-friendly 2.5-hour parasailing cruise

    Soar above Siesta Key and spot dolphins on a safe, family-friendly 2.5-hour parasailing cruise
    4.9 • 7.9K reviews
    $123/ person
    Sarasota Dolphin Cruise with Sandbar & Drinks
    Boat Tours

    Sarasota Dolphin Cruise with Sandbar & Drinks

    Spot playful dolphins and relax at a scenic sandbar while enjoying complimentary drinks

    Spot playful dolphins and relax at a scenic sandbar while enjoying complimentary drinks
    4.9 • 7.9K reviews
    $85/ person
    Siesta Key Jet Ski Rental in Sarasota FL
    Jet Skiing

    Siesta Key Jet Ski Rental in Sarasota FL

    Ride new Yamaha jet skis across Florida's largest riding area at your own pace

    Ride new Yamaha jet skis across Florida's largest riding area at your own pace
    4.9 • 7.9K reviews
    $123& up
    Private Pontoon Boat Rental in Sarasota
    Boat RentalsUp to 12

    Private Pontoon Boat Rental in Sarasota

    Cruise Sarasota’s Gulf waters on a spacious pontoon with flexible 4- or 8-hour options.

    Cruise Sarasota’s Gulf waters on a spacious pontoon with flexible 4- or 8-hour options.
    4.9 • 7.9K reviews
    $496& up
    Siesta Key Private Catamaran Charter
    Private Boat ChartersUp to 49

    Siesta Key Private Catamaran Charter

    Customize your day exploring sandbars, islands, and marine life on a private catamaran.

    Customize your day exploring sandbars, islands, and marine life on a private catamaran.
    4.9 • 7.9K reviews
    $750
    Guided Kayak Tour to Midnight Pass Beach in Siesta Key
    Kayaking Tours

    Guided Kayak Tour to Midnight Pass Beach in Siesta Key

    Paddle Jim Neville Marine Preserve to water-only Midnight Pass Beach

    Paddle Jim Neville Marine Preserve to water-only Midnight Pass Beach
    5.0 • 3.1K reviews
    $61/ kayak
    Kayak & Paddleboard Rental to Midnight Pass
    Stand Up Paddle Boarding

    Kayak & Paddleboard Rental to Midnight Pass

    Launch from Turtle Beach and paddle to Midnight Pass

    Launch from Turtle Beach and paddle to Midnight Pass
    5.0 • 3.1K reviews
    $51/ kayak
    Mangrove Tunnel Kayak & Paddleboard Tour in Sarasota
    Kayaking Tours

    Mangrove Tunnel Kayak & Paddleboard Tour in Sarasota

    Paddle the mangrove tunnels of Ted Sperling Park with a local guide

    Paddle the mangrove tunnels of Ted Sperling Park with a local guide
    5.0 • 3.1K reviews
    $61& up
    Private 2-Hour Mangrove Tunnel Kayak & Paddleboard Tour
    Kayaking Tours

    Private 2-Hour Mangrove Tunnel Kayak & Paddleboard Tour

    Paddle Lido Key mangrove tunnels with a private guide

    Paddle Lido Key mangrove tunnels with a private guide
    5.0 • 3.1K reviews
    $91/ kayak
    2.5-Hour Lido Key Mangrove Tunnel Kayak Rental
    Kayaking Tours

    2.5-Hour Lido Key Mangrove Tunnel Kayak Rental

    Paddle Lido Key’s mangrove tunnels from Ted Sperling Park

    Paddle Lido Key’s mangrove tunnels from Ted Sperling Park
    5.0 • 3.1K reviews
    $51/ kayak
    Private Kayak or Paddleboard Tour in Siesta Key
    Kayaking Tours

    Private Kayak or Paddleboard Tour in Siesta Key

    Paddle Midnight Pass on a private Siesta Key kayak or paddleboard tour

    Paddle Midnight Pass on a private Siesta Key kayak or paddleboard tour
    5.0 • 3.1K reviews
    $91/ person
    Surf Lesson in Sarasota
    Surfing Lessons

    Surf Lesson in Sarasota

    Learn to surf in Sarasota with a coach-led lesson

    Learn to surf in Sarasota with a coach-led lesson
    5.0 • 3.1K reviews
    $123& up
    Pedal Kayak Eco Tour in Sarasota Bay
    Kayaking Tours

    Pedal Kayak Eco Tour in Sarasota Bay

    Pedal kayak Sarasota Bay to seagrass beds and mangrove tunnels

    Pedal kayak Sarasota Bay to seagrass beds and mangrove tunnels
    4.7 • 1.7K reviews
    $78/ kayak
    1234