Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Key West…
    3. /Water Activities
    4. /Sailing
    5. /Private Sailing Charter in Key West
    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
    Product image 1
    Gallery image

    Private Sailing Charter in Key West

    Charter the 54-foot Schooner Valora for a private sail in Key West

    4.9 stars• 3K reviews
    From$1,340incl. taxes and fees

    Duration

    3 Hours

    Ideal For

    Up to 6 people

    Includes

    Beer, wine, soft drinks

    Highlights

    Set sail in Key West aboard the 54-foot Schooner Valora on a private, customizable charter. Choose a small-group sail for up to six guests or a private bareboat charter for up to twelve.

    • Choose a private charter for up to 6 or 12 passengers
    • Customize your itinerary with sightseeing, snorkeling, or a sunset sail
    • Enjoy flexible start times and trip durations
    • Plan a cruise for corporate events, weddings, birthdays, or anniversaries
    • Add optional food and beverage upgrades

    What's Included

    • Beer
    • Wine
    • Champagne
    • Soft drinks
    • Water

    Cancellation Policy

    Full refund or rebook if cancelled due to captain's discretion and/or weather. Cancel 7 days or more before departure for a full refund or rebook. Cancel less than 7 days before departure: no refund; you forfeit 100% of payment.

    FAQs

    Check in 30 minutes prior to departure.

    Yes. Every member of your party must be present at check-in to sign a waiver and receive a boarding pass.

    Yes. It is customary to tip your crew; a 15–20% tip is suggested.

    Meeting details

    Key West, FL

    Experience provided by Appledore - Key West

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #GVW476

    Private Dolphin Watch Sail

    $1,340.26

    3 Hours | Up to 6 Passengers

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    3K reviews•Google Maps
    2,854
    65
    20
    11
    20

    The schooner draws near-universal praise, and it's easy to see why. Captains and crew, including frequently mentioned Joe, Christina, and Marison, consistently earn compliments for being professional, knowledgeable, and genuinely fun to spend a day with. The boat itself is described as beautiful and immaculately maintained, adding to an overall sense that this operation takes real pride in what they do. The two main offerings, a sunset sail and a daytime ecotour with snorkeling and kayaking, both deliver strong experiences, though in different ways. The sunset cruise focuses on the magic of being out on the water with drinks flowing and appetizers to snack on, while the ecotour leans into wildlife encounters and mangrove exploration. Dolphins, sea turtles, and even the occasional shark have made appearances on multiple trips, which travelers clearly love. Food and drinks are included and repeatedly praised, which seems to be a pleasant surprise for many guests. With a near-perfect rating across thousands of reviews, this is about as close to a sure thing as you'll find in Key West. Booking early makes sense, especially during busy seasons.

    What people are saying

    Review 1 of 5
    5/5

    Joe and Christina were amazing. We had so much fun at our sunset cruise!

    Photo of Monet Bechtold

    Monet Bechtold

    July 4, 2026

    Review 1 of 1
    5/5

    Joe and Christina were amazing. We had so much fun at our sunset cruise!

    Photo of Monet Bechtold

    Monet Bechtold

    July 4, 2026

    Nearby activities

    Sail a Key West Champagne Sunset Cruise
    Sailing

    Sail a Key West Champagne Sunset Cruise

    Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included

    Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included
    4.9 • 3K reviews
    $134/ person
    Sailing, Kayaking & Snorkeling Tour of Key West Backcountry
    Snorkeling

    Sailing, Kayaking & Snorkeling Tour of Key West Backcountry

    Explore mangrove islands by schooner, kayak and snorkel

    Explore mangrove islands by schooner, kayak and snorkel
    4.9 • 3K reviews
    $146/ person
    3.5-Hour Key West Sandbar Cruise
    Boat Tours

    3.5-Hour Key West Sandbar Cruise

    Spend the day at a Key West sandbar aboard the 53-foot tiki boat Lazy Lady

    Spend the day at a Key West sandbar aboard the 53-foot tiki boat Lazy Lady
    4.7 • 8.1K reviews
    $115/ person
    2-Hour Key West Sunset Catamaran Sail With Live Music
    Sunrise and Sunset Tours

    2-Hour Key West Sunset Catamaran Sail With Live Music

    Sunset catamaran sail with live music, full bar, and appetizers

    Sunset catamaran sail with live music, full bar, and appetizers
    4.7 • 8.1K reviews
    $76/ person
    Afternoon Snorkeling Cruise at Florida Keys Reef
    Snorkeling

    Afternoon Snorkeling Cruise at Florida Keys Reef

    Sail to a coral reef with snorkeling gear, instruction, and complimentary drinks

    Sail to a coral reef with snorkeling gear, instruction, and complimentary drinks
    4.7 • 8.1K reviews
    $51/ person
    Mimosa Snorkel Sail in Key West
    Snorkeling

    Mimosa Snorkel Sail in Key West

    Sail to the Florida Keys Reef for guided snorkeling, lunch, and drinks

    Sail to the Florida Keys Reef for guided snorkeling, lunch, and drinks
    4.7 • 8.1K reviews
    $51/ person