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 Summerland Key, FL

    Showing 457-480 of 611 results
    Sail, Snorkel & Kayak Charter in Key West
    Sailing

    Sail, Snorkel & Kayak Charter in Key West

    Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks

    Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks
    4.9 • 5.8K reviews
    $2,409
    4.5-Hour Sail, Snorkel & Kayak Tour in Key West
    Snorkeling

    4.5-Hour Sail, Snorkel & Kayak Tour in Key West

    Sail, snorkel, and kayak on a historic schooner with drinks and snacks included

    Sail, snorkel, and kayak on a historic schooner with drinks and snacks included
    4.9 • 5.8K reviews
    $136/ person
    Private 1.5-Hour Schooner Sailing Charter in Key West
    Sailing

    Private 1.5-Hour Schooner Sailing Charter in Key West

    Charter a private historic schooner sail with drinks and snacks included

    Charter a private historic schooner sail with drinks and snacks included
    4.9 • 5.8K reviews
    $1,713
    Sail, Snorkel & Kayak Key West Sunset Cruise
    Sailing

    Sail, Snorkel & Kayak Key West Sunset Cruise

    Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset

    Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset
    4.9 • 5.8K reviews
    $149/ person
    Private Key West Sunset Sailing Charter
    Sailing

    Private Key West Sunset Sailing Charter

    Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included

    Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included
    4.9 • 5.8K reviews
    $3,500
    Key West Sunset Sandbar & Snorkel Sail
    Snorkeling

    Key West Sunset Sandbar & Snorkel Sail

    Relax on a schooner with snorkeling, sandbar time, snacks, and drinks

    Relax on a schooner with snorkeling, sandbar time, snacks, and drinks
    4.9 • 5.8K reviews
    $149/ person
    Private Sunset Cruise in Key West
    Boat Tours

    Private Sunset Cruise in Key West

    Cruise Key West harbor at sunset with your group and captain

    Cruise Key West harbor at sunset with your group and captain
    4.9 • 5.8K reviews
    $457
    6-Hour Marquesas Islands Snorkeling Charter
    Snorkeling

    6-Hour Marquesas Islands Snorkeling Charter

    Private island cruising with snorkeling and guided narration

    Private island cruising with snorkeling and guided narration
    5.0 • 20 reviews
    $3,133
    Key West Sandbar & Dining Charter
    Boat Tours

    Key West Sandbar & Dining Charter

    Dine at Kiki's and unwind at a local sandbar

    Dine at Kiki's and unwind at a local sandbar
    5.0 • 20 reviews
    $5,244
    Pittsburgh 4-Hour Sandbar Charter
    Yacht Charters

    Pittsburgh 4-Hour Sandbar Charter

    Relax and explore local sandbars aboard a 37-foot Edgewater

    Relax and explore local sandbars aboard a 37-foot Edgewater
    5.0 • 20 reviews
    $2,452
    Key West Private Sunset Cruise
    Yacht Charters

    Key West Private Sunset Cruise

    Celebrate with champagne, hors d'oeuvres, and sunset views on a private charter

    Celebrate with champagne, hors d'oeuvres, and sunset views on a private charter
    5.0 • 20 reviews
    $3,923
    Charter to Dry Tortugas 10-Hour
    Yacht Charters

    Charter to Dry Tortugas 10-Hour

    Explore Fort Jefferson and the Dry Tortugas aboard a private 37-foot boat

    Explore Fort Jefferson and the Dry Tortugas aboard a private 37-foot boat
    5.0 • 20 reviews
    $4,425
    Pittsburgh Sunset Cruise
    Boat Tours

    Pittsburgh Sunset Cruise

    Raise a champagne toast as you cruise into the evening aboard a private boat

    Raise a champagne toast as you cruise into the evening aboard a private boat
    5.0 • 20 reviews
    $2,656
    Pittsburgh Private Sunset Cruise
    Yacht Charters

    Pittsburgh Private Sunset Cruise

    Champagne and hors d'oeuvres aboard a classic yacht at sunset

    Champagne and hors d'oeuvres aboard a classic yacht at sunset
    5.0 • 20 reviews
    $999
    Fort Jefferson Charter in Dry Tortugas
    Yacht Charters

    Fort Jefferson Charter in Dry Tortugas

    Private access to Fort Jefferson and Loggerhead Key

    Private access to Fort Jefferson and Loggerhead Key
    5.0 • 20 reviews
    $15,527& up
    Pittsburgh Sunset Dock & Dine Cruise
    Boat Tours

    Pittsburgh Sunset Dock & Dine Cruise

    Pair a waterfront meal with a narrated sunset cruise and champagne

    Pair a waterfront meal with a narrated sunset cruise and champagne
    5.0 • 20 reviews
    $2,452
    6-Hour Offshore Fishing Charter in Marathon
    Fishing Charters

    6-Hour Offshore Fishing Charter in Marathon

    Private offshore fishing with trolling and live-bait techniques

    Private offshore fishing with trolling and live-bait techniques
    4.5 • 1.4K reviews
    $1,343
    6-Hour Wreck Fishing Charter in Marathon
    Fishing Charters

    6-Hour Wreck Fishing Charter in Marathon

    Private reef, bay & wreck fishing with gear and licenses included

    Private reef, bay & wreck fishing with gear and licenses included
    4.5 • 1.4K reviews
    $1,567
    6-Hour Reef Fishing Charter in Marathon
    Fishing Charters

    6-Hour Reef Fishing Charter in Marathon

    Private bottom fishing across reefs, bays and wrecks

    Private bottom fishing across reefs, bays and wrecks
    4.5 • 1.4K reviews
    $1,567
    Offshore Fishing Charter in Duck Key for 6 Hours
    Fishing Charters

    Offshore Fishing Charter in Duck Key for 6 Hours

    Private offshore fishing with gear, fuel and fishing licenses included

    Private offshore fishing with gear, fuel and fishing licenses included
    4.5 • 1.4K reviews
    $1,343
    Wreck Fishing Charter in Duck Key
    Fishing Charters

    Wreck Fishing Charter in Duck Key

    Private reef and wreck fishing with gear, licenses and a captain included

    Private reef and wreck fishing with gear, licenses and a captain included
    4.5 • 1.4K reviews
    $1,567
    Duck Key 6-Hour Reef Fishing Charter
    Fishing Charters

    Duck Key 6-Hour Reef Fishing Charter

    Bottom-fish reefs, bays, and wrecks with a captain and gear included

    Bottom-fish reefs, bays, and wrecks with a captain and gear included
    4.5 • 1.4K reviews
    $1,567
    6-Hour Offshore Fishing Charter in Marathon
    Fishing Charters

    6-Hour Offshore Fishing Charter in Marathon

    Private offshore fishing with trolling and live-bait techniques

    Private offshore fishing with trolling and live-bait techniques
    4.5 • 1.4K reviews
    $1,343
    6-Hour Wreck Fishing Charter in Marathon
    Fishing Charters

    6-Hour Wreck Fishing Charter in Marathon

    Private wreck fishing with captain, gear, and fishing license included

    Private wreck fishing with captain, gear, and fishing license included
    4.5 • 1.4K reviews
    $1,567
    1…192021…26

    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.