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 Historic Schooner Sail 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
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Private Historic Schooner Sail in Key West

    Sail a 1939 wooden schooner and take a turn at the helm

    4.8 stars• 377 reviews
    From$1,344incl. taxes and fees

    Duration

    2 hrs

    Ideal For

    Up to 6 people

    Includes

    Captain, crew, beverages

    Highlights

    Step aboard When And If, a 1939 wooden schooner built for General George S. Patton. Help raise the sails, take the helm, or relax as you sail Key West's Historic Seaport.

    • Help raise the sails and take a turn at the helm
    • Discover the story of a schooner built for General George S. Patton
    • Relax aboard a classic wooden yacht with a captain and crew
    • Take in the sights and sounds of Key West's Historic Seaport
    • Customize your charter with optional extra sailing time, pickup or drop-off locations, or catering

    What's Included

    • Captain and crew
    • Bottled water
    • Seltzer water
    • Wine and select beers

    Important details

    • Arrive at the dock 15 minutes before departure
    • Bring weather-appropriate clothing and sun protection
    • Bring any snacks you would like during the sail
    • Outside adult beverages are not permitted
    • Crew gratuity is not included in the listed price and is customary

    Cancellation Policy

    Cancel 7+ days ahead for a full refund minus a 10% processing fee. No refund within 7 days. If the captain cancels due to weather and cannot rebook you, you'll receive a full refund.

    FAQs

    No. Guests are not permitted to bring their own adult beverages.

    Enjoy bottled water, seltzer water (La Croix), plus complimentary schooner wine and select beers. You can also choose a premium beverage upgrade.

    Bring suitable weather wear (sunscreen, hats, sweaters) and adequate sun protection. It can feel cooler in the breeze on the water, and winter sunsets can be chilly. You may also want a dry bag, a change of clothes, and foul weather gear, plus any snacks you’d like.

    Meeting details

    End of E Dock, Historic Key West Seaport

    Experience provided by Sunset Sail 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 #2BR4RE

    Private Charter

    $1,344.98

    Up to 6 guests (including children)

    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

    4.8
    Excellent
    377 reviews•Google Maps
    327
    26
    7
    3
    10

    Sailing on the historic schooner When & If is genuinely one of those experiences that surprises people. Built for General George Patton in 1939, the vessel carries real history, and the crew, led by captains like Tyler and Zack, clearly love sharing it. Guests can help raise the sails, take a turn at the wheel, or explore the crew quarters below deck. The vibe is intimate and unhurried, with no blaring music, just wind, waves, and a champagne toast as the sun goes down. The crew consistently earns high praise across the board. Veronica, Yann, Amy, and others are called out by name repeatedly for being warm, knowledgeable, and genuinely enthusiastic about the whole experience. Groups, couples, and families with young kids have all had great times, which speaks to how well the crew reads the room. One reviewer did note a dock location change that wasn't communicated when booking through a third-party platform, so it's worth confirming details directly if you're booking elsewhere. That said, it stands out as an isolated situation in an otherwise overwhelmingly positive pattern of reviews. If a sunset sail is on your Key West list, this one is hard to beat.

    What people are saying

    Review 1 of 5
    5/5

    My girlfriend and I (now fiancè) had an absolutely wonderful time on this sunset sail. Captain Bryce and Dawson were the best crew we could have imagined to get! The hors d'oeuvre's were pretty incredible. Our favorite was the smoked mahi with crustinis and cocktail shrimps! And they had my beer on tap (great choice with Bud Light btw). Dawson was extremely knowledgeable about the history of Key West and the geographical location of everything around there. Took us right to where the dolphins were to snap many videos and pictures too! The icing on the cake was right as sunset was approaching, I asked Captain Bryce if he could angle the boat for me in a way that I could have the sunset in the background as I proposed to my girlfriend. With him very recently proposing to his girlfriend (congratulations again brother) he understood the assignment. And my man Dawson after a few moments of talking, also understood the very important assignment of taking the video for us. All in all, 10/10 experience. Amazing crew, amazing food, amazing passengers too everyone on our ship was very nice. Would highly recommend to anyone looking to do a sunset sail in Key West. This is THE choice. Thanks again guys. God bless.

    Photo of Derk Diggler

    Derk Diggler

    June 22, 2026

    Review 1 of 1
    5/5

    My girlfriend and I (now fiancè) had an absolutely wonderful time on this sunset sail. Captain Bryce and Dawson were the best crew we could have imagined to get! The hors d'oeuvre's were pretty incredible. Our favorite was the smoked mahi with crustinis and cocktail shrimps! And they had my beer on tap (great choice with Bud Light btw). Dawson was extremely knowledgeable about the history of Key West and the geographical location of everything around there. Took us right to where the dolphins were to snap many videos and pictures too! The icing on the cake was right as sunset was approaching, I asked Captain Bryce if he could angle the boat for me in a way that I could have the sunset in the background as I proposed to my girlfriend. With him very recently proposing to his girlfriend (congratulations again brother) he understood the assignment. And my man Dawson after a few moments of talking, also understood the very important assignment of taking the video for us. All in all, 10/10 experience. Amazing crew, amazing food, amazing passengers too everyone on our ship was very nice. Would highly recommend to anyone looking to do a sunset sail in Key West. This is THE choice. Thanks again guys. God bless.

    Photo of Derk Diggler

    Derk Diggler

    June 22, 2026

    Nearby activities

    Private Dolphin Watch & Snorkel Sail in Key West
    Snorkeling

    Private Dolphin Watch & Snorkel Sail in Key West

    Sail Key West and snorkel the backcountry on your own private boat

    Sail Key West and snorkel the backcountry on your own private boat
    4.8 • 377 reviews
    $959
    Sail & Swim Lilypad Private Charter in Key West
    Sailing

    Sail & Swim Lilypad Private Charter in Key West

    Private sail to a shallow-water anchorage with time to lounge on a Lilypad float

    Private sail to a shallow-water anchorage with time to lounge on a Lilypad float
    4.8 • 377 reviews
    $789
    Sail a Private Key West Harbor Sunset Charter
    Sailing

    Sail a Private Key West Harbor Sunset Charter

    Private 2-hour Key West sunset sail with captain and mate

    Private 2-hour Key West sunset sail with captain and mate
    4.8 • 377 reviews
    $732
    Key West Sunset Snorkel Cruise
    Snorkeling

    Key West Sunset Snorkel Cruise

    Sail, snorkel and watch the Key West sunset from your private boat

    Sail, snorkel and watch the Key West sunset from your private boat
    4.8 • 377 reviews
    $1,129
    Charter a Private Yacht in Key West
    Yacht Charters

    Charter a Private Yacht in Key West

    Bareboat yacht charter for groups over 6, with snorkel and float gear included

    Bareboat yacht charter for groups over 6, with snorkel and float gear included
    4.9 • 35 reviews
    $1,280& up
    Luxury Private Yacht Charter in Key West
    Yacht Charters

    Luxury Private Yacht Charter in Key West

    Charter a private motor yacht in Key West with flexible 1.5–8 hour options

    Charter a private motor yacht in Key West with flexible 1.5–8 hour options
    4.9 • 35 reviews
    $1,519& up