Free Concierge Service
    Text or call (650) 414-7338
    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
    [email protected](650) 414-7338

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Free Concierge Service
    Text or call (650) 414-7338
    Ask AIAI
    Ask AIAI
    1. Local experiences/
    2. All experiences/
    3. Sugarloaf Key FL

    Best 191 things to do in Sugarloaf Key, FL

    Showing 121-144 of 191 results
    Private Tiki Boat Cruise Around John's Pass
    Boat Tours

    Private Tiki Boat Cruise Around John's Pass

    Book your own private tiki boat near John’s Pass for 2, 3, or 4 hours

    Book your own private tiki boat near John’s Pass for 2, 3, or 4 hours
    4.9 • 214 reviews
    $67/ person
    Cruise Madeira Beach on a Captained 26' Tritoon
    Boat Tours

    Cruise Madeira Beach on a Captained 26' Tritoon

    Cruise to Shell Key Island and Egmont Key for shelling, snorkeling, and dolphin spotting

    Cruise to Shell Key Island and Egmont Key for shelling, snorkeling, and dolphin spotting
    4.9 • 214 reviews
    $446& up
    Sunset Tiki Cruise In Madeira Beach
    Boat Tours

    Sunset Tiki Cruise In Madeira Beach

    Cruise Madeira Beach for 2 hours on a tiki boat at sunset

    Cruise Madeira Beach for 2 hours on a tiki boat at sunset
    4.9 • 214 reviews
    $73/ person
    Cruise Gulf Blvd. With a Bicycle Rental
    Bike Rentals

    Cruise Gulf Blvd. With a Bicycle Rental

    Rent an adult bike and ride Gulf Blvd. for 4 hours to 7 days

    Rent an adult bike and ride Gulf Blvd. for 4 hours to 7 days
    4.9 • 214 reviews
    $23/ bike
    Paddleboard Rental in Madeira Beach
    Paddleboarding

    Paddleboard Rental in Madeira Beach

    Rent a paddle board in Madeira Beach for 2–8 hours

    Rent a paddle board in Madeira Beach for 2–8 hours
    4.9 • 214 reviews
    $40& up
    Kayak Rental
    Kayaking Tours

    Kayak Rental

    Get out on the water with flexible 2–8 hour kayak rentals

    Get out on the water with flexible 2–8 hour kayak rentals
    4.9 • 214 reviews
    $40/ kayak
    Paddleboard Rental With 2-, 4- & 8-Hour Options
    Stand Up Paddle Boarding

    Paddleboard Rental With 2-, 4- & 8-Hour Options

    Get on the water with flexible 2–8 hour paddle board rentals

    Get on the water with flexible 2–8 hour paddle board rentals
    4.9 • 214 reviews
    $40& up
    3-Hour Private Downtown Waterfront Cruise in St. Petersburg
    Boat Tours

    3-Hour Private Downtown Waterfront Cruise in St. Petersburg

    Private 3-hour cruise with downtown St. Petersburg views and a relaxed pace

    Private 3-hour cruise with downtown St. Petersburg views and a relaxed pace
    5.0 • 5 reviews
    $559
    Private 3-Hour Gulfport Sunset Cruise
    Sunrise and Sunset Tours

    Private 3-Hour Gulfport Sunset Cruise

    Private sunset cruise with golden hour and Skyway Bridge night views

    Private sunset cruise with golden hour and Skyway Bridge night views
    5.0 • 5 reviews
    $559
    Private 2-Hour St. Petersburg Sunset Cruise
    Sunrise and Sunset Tours

    Private 2-Hour St. Petersburg Sunset Cruise

    Private sunset cruise with dolphin watching near Shell Key

    Private sunset cruise with dolphin watching near Shell Key
    5.0 • 5 reviews
    $503
    4-5 Hour Private Daytime Sail in St. Petersburg
    Sailing

    4-5 Hour Private Daytime Sail in St. Petersburg

    Private daytime sail with dinghy access for island exploring

    Private daytime sail with dinghy access for island exploring
    $1,356& up
    Dolphin Watching Cruise in John's Pass
    Dolphin Watching

    Dolphin Watching Cruise in John's Pass

    Cruise upper Boca Ciega Bay on a narrated dolphin and wildlife eco tour

    Cruise upper Boca Ciega Bay on a narrated dolphin and wildlife eco tour
    4.8 • 12.7K reviews
    $34/ person
    Egmont Key Ferry From Fort De Soto With Snorkeling
    Boat Tours

    Egmont Key Ferry From Fort De Soto With Snorkeling

    Ride the ferry from Fort De Soto to Egmont Key, with snorkeling available

    Ride the ferry from Fort De Soto to Egmont Key, with snorkeling available
    4.8 • 12.7K reviews
    $48/ person
    Ride a Ferry From Fort De Soto to Shell Key
    Boat Tours

    Ride a Ferry From Fort De Soto to Shell Key

    Take a narrated ferry to Shell Key for beach time and shelling

    Take a narrated ferry to Shell Key for beach time and shelling
    4.8 • 12.7K reviews
    $37/ person
    Sail a 1.5-Hour Pirate Adventure Cruise at John’s Pass
    Boat Tours

    Sail a 1.5-Hour Pirate Adventure Cruise at John’s Pass

    Cruise John’s Pass on a 90-minute pirate ship adventure

    Cruise John’s Pass on a 90-minute pirate ship adventure
    4.8 • 12.7K reviews
    $47/ person
    Dolphin Watching Cruise in John’s Pass
    Dolphin Watching

    Dolphin Watching Cruise in John’s Pass

    Cruise Boca Ciega Bay and learn about local dolphins with your crew

    Cruise Boca Ciega Bay and learn about local dolphins with your crew
    4.8 • 12.7K reviews
    $33/ person
    Sunset Cruise in Madeira Beach via John’s Pass
    Boat Tours

    Sunset Cruise in Madeira Beach via John’s Pass

    Cruise Boca Ciega Bay at sunset via John’s Pass

    Cruise Boca Ciega Bay at sunset via John’s Pass
    4.8 • 12.7K reviews
    $40/ person
    Fish on a 5-Hour Half-Day Trip in Madeira Beach
    Fishing Charters

    Fish on a 5-Hour Half-Day Trip in Madeira Beach

    Fish for snapper and sea bass on a 5-hour trip close to shore from John’s Pass

    Fish for snapper and sea bass on a 5-hour trip close to shore from John’s Pass
    4.8 • 12.7K reviews
    $96/ person
    Take a Sunset Cruise From John’s Pass
    Sunrise and Sunset Tours

    Take a Sunset Cruise From John’s Pass

    Cruise John’s Pass at sunset with free beer and wine

    Cruise John’s Pass at sunset with free beer and wine
    4.8 • 12.7K reviews
    $40/ person
    Fish on a 10-Hour Deep Sea Trip From Madeira Beach
    Fishing Charters

    Fish on a 10-Hour Deep Sea Trip From Madeira Beach

    Spend 6–7 hours fishing offshore from Madeira Beach

    Spend 6–7 hours fishing offshore from Madeira Beach
    4.8 • 12.7K reviews
    $158/ person
    Ride a 12-Hour Deep Sea Fishing Trip in Madeira Beach
    Fishing Charters

    Ride a 12-Hour Deep Sea Fishing Trip in Madeira Beach

    Cruise 70–100 miles offshore for 7–8 hours of deep-water fishing

    Cruise 70–100 miles offshore for 7–8 hours of deep-water fishing
    4.8 • 12.7K reviews
    $451/ person
    Shell Key Shelling Cruise From John's Pass
    Boat Tours

    Shell Key Shelling Cruise From John's Pass

    Cruise from John’s Pass to Shell Key for island shelling

    Cruise from John’s Pass to Shell Key for island shelling
    4.8 • 12.7K reviews
    $45/ person
    12-Hour Night Fishing Trip in Madeira Beach
    Fishing Charters

    12-Hour Night Fishing Trip in Madeira Beach

    Fish offshore at night with 7–9 hours of lines-in time

    Fish offshore at night with 7–9 hours of lines-in time
    4.8 • 12.7K reviews
    $209/ person
    Fish for Trophy Sharks Near John's Pass on a 5-Hour Trip
    Fishing Charters

    Fish for Trophy Sharks Near John's Pass on a 5-Hour Trip

    Fish for trophy sharks with rod, reel, and heavy shark gear provided

    Fish for trophy sharks with rod, reel, and heavy shark gear provided
    4.8 • 12.7K reviews
    $203/ person
    1…45678