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. /Sail Key West Harbor on a 90-Minute Private Charter
    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
    • Experience Gift Cards
    • 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
    Product image 7
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Sail Key West Harbor on a 90-Minute Private Charter

    Private Key West harbor sail with time at the helm

    4.8 stars• 376 reviews

    Duration

    90 Minutes

    Ideal For

    Up to 12 people

    Includes

    Private boat, Captain, Drinks

    Highlights

    Head out from Downtown Key West on a private 90-minute harbor sail with a captain and mate. Relax under sail with the engine off, or get hands-on as you cruise past harbor islands and local landmarks.

    • Set sail on a private boat with captain and mate
    • Steer at the helm or help raise the sails
    • Spot Key West landmarks as you sail the harbor
    • Bring your own adult beverages and snacks
    • Plan for a $75 surcharge per guest after 6, up to 12 total

    What's Included

    • Private use of the vessel
    • Captain and mate
    • Coolers with ice
    • Soft drinks
    • Bottled water

    Things to know

    All ages welcome; children under 12 must be accompanied by an adult. Crew gratuity is customary and not included.

    Cancellation Policy

    Private charters: cancel 7 days or more in advance for a full refund minus a 10% processing fee. No refund within 7 days. If the operator cancels, a full refund will be issued immediately. If the captain cancels due to weather and you can’t rebook, a full refund will be issued immediately.

    Product ID: F5P3TV

    FAQs

    Yes. Bring any adult beverages and/or snacks you want to enjoy during your sail.

    Bring sun protection and suitable weatherwear (for example sunscreen, hats, and a sweater). It can feel cooler in the breeze on the water.

    Yes. All ages are welcome. Children under 12 must be accompanied by an adult.

    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

    Private Charter

    $448.32

    Up to 6 guests (including children)

    0

    Private Charter Promotional Rate

    $0

    Up to 6 Guests

    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
    376 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

    Key West Guided Night Kayak Tour
    Kayaking Tours

    Key West Guided Night Kayak Tour

    Light up the sea floor on a guided kayak paddle beneath the stars

    4.8 • 996 reviews
    $93/ kayak
    Climb Key West Lighthouse & Visit Keeper's Quarters
    Historical Sites and Monuments

    Climb Key West Lighthouse & Visit Keeper's Quarters

    Climb 88 steps for panoramic island views and explore the Keeper’s Quarters Museum

    4.6 • 508 reviews
    $17/ person
    4-Hour Sandbar Cruise in Key West
    Boat Tours

    4-Hour Sandbar Cruise in Key West

    Cruise to a Key West sandbar for swimming, relaxing, and wildlife watching

    $596
    5-Hour Reef Fishing Trip in Key West
    Fishing Charters

    5-Hour Reef Fishing Trip in Key West

    Reef fishing for snapper and grouper, with bait and tackle included

    5.0 • 841 reviews
    $89/ person
    Key West Parasailing with Dry Take-Offs & Landings
    Parasailing

    Key West Parasailing with Dry Take-Offs & Landings

    Parasail above Key West on a 12-passenger boat with tandem flight options

    4.9 • 12.7K reviews
    $74/ person
    Dive 2-Tank Private Charter in Key West
    Scuba Diving

    Dive 2-Tank Private Charter in Key West

    Charter a private 2-tank dive with an in-water dive master

    4.9 • 330 reviews
    $1,192& up