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. /2-Hour Private Sailing Lesson 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
    Gallery image
    Gallery image 2
    Gallery image 3

    2-Hour Private Sailing Lesson in Key West

    Learn at your own pace with private instruction on the water

    4.9 stars• 49 reviews

    Duration

    2 Hours

    Includes

    Private lesson, instructor

    Highlights

    Set sail on a private lesson tailored to your skill level. Learn with an experienced instructor and bring friends or family along.

    • Pick the boat you'd like to learn on
    • Learn sailing skills at your own pace
    • Bring friends or family for a private lesson
    • Build skills from beginner to advanced levels
    • Bring a refillable water bottle, shoes or flip-flops, and sunscreen

    What's Included

    • Experienced instructor
    • Personalized sailing lesson

    Important details

    • Ages 5+ only
    • Complete the required waiver before your lesson
    • A member ID is required for member pricing
    • A Florida ID is required for local pricing

    Cancellation Policy

    Full refund for cancellations made more than 48 hours before class. No refund for cancellations made less than 48 hours before class.

    Product ID: QZYCDM

    FAQs

    Bring a refillable water bottle, shoes or flip-flops, and sunscreen. Consider bringing a swimsuit, towel, closed-toe shoes, hat or sunglasses, and a dry change of clothes.

    A signed waiver is required for your sailing lesson.

    Meeting details

    Key West Community Sailing Center, Inc - 705 Palm Ave, Key West, FL 33040

    Experience provided by Key West Community Sailing Center

    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

    Member

    $95.40

    member ID will be required at check-in

    0

    Local

    $137.80

    please bring your Florida ID

    0

    Visitor

    $159

    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
    49 reviews•Google Maps
    45
    3
    0
    0
    1

    This sailing center runs on genuine community spirit, and it shows in nearly every review. Piper, the director, is consistently praised as a patient, knowledgeable, and engaging instructor, and Ben gets similar praise for tailoring lessons to individual skill levels. The instructors here clearly care about what they do, and that enthusiasm tends to be contagious. One of the more surprising perks is the free weekend open sails, where total beginners can get on the water with guidance from qualified instructors at no cost. Private and group lessons are also available for those wanting more structured time. Families with kids are especially well served, with a youth program that focuses on building confidence safely. The vibe is relaxed and welcoming, with a fleet of varied boats, well-maintained facilities, and an old-school Key West atmosphere that feels refreshingly unpretentious. If you are visiting short-term and worried about fitting sailing into a packed schedule, the flexible session options make it easier than you might expect.

    What people are saying

    Review 1 of 4
    5/5

    Good trip, good vibes, nice place and amazing people.!

    Photo of jonathan granados

    jonathan granados

    March 12, 2026

    Review 1 of 1
    5/5

    Good trip, good vibes, nice place and amazing people.!

    Photo of jonathan granados

    jonathan granados

    March 12, 2026

    Great for groups

    Explore Key West on a 23' Fishing Boat Rental
    Boat RentalsUp to 6

    Explore Key West on a 23' Fishing Boat Rental

    Rent a 23' center console and fish Key West your way

    Rent a 23' center console and fish Key West your way
    4.1 • 135 reviews
    $568/ boat
    21' Backcountry Boat Rental in Key West
    Boat Rentals2 to 8

    21' Backcountry Boat Rental in Key West

    Self-guided shallow-water fishing, snorkeling, and sandbar exploring

    Self-guided shallow-water fishing, snorkeling, and sandbar exploring
    4.1 • 135 reviews
    $568/ boat
    Key West Sandbar Boat Rental
    Boat Rentals2 to 8

    Key West Sandbar Boat Rental

    Explore Key West waters with onboard navigation and sandbar-ready comforts

    Explore Key West waters with onboard navigation and sandbar-ready comforts
    4.1 • 135 reviews
    $568/ boat

    Nearby activities

    Private 3-Hour Sailing Lesson in Key West
    Sailing

    Private 3-Hour Sailing Lesson in Key West

    Choose your boat and learn to sail with a private instructor in Key West

    Choose your boat and learn to sail with a private instructor in Key West
    4.9 • 49 reviews
    $143& up
    Cruise Key West at Sunset on a Private Charter
    Sunrise and Sunset Tours

    Cruise Key West at Sunset on a Private Charter

    Private Key West sunset cruise for up to 6 on the Miss Marie

    Private Key West sunset cruise for up to 6 on the Miss Marie
    5.0 • 190 reviews
    $482
    6-Hour Private Charter in Key West
    Yacht Charters

    6-Hour Private Charter in Key West

    Customize your day on Key West’s waters with snorkeling, fishing, or island exploring

    Customize your day on Key West’s waters with snorkeling, fishing, or island exploring
    5.0 • 190 reviews
    $965
    4-Hour Private Charter in Key West
    Yacht Charters

    4-Hour Private Charter in Key West

    Customize your time on the water with snorkeling, fishing, island stops, or a sunset cruise

    Customize your time on the water with snorkeling, fishing, island stops, or a sunset cruise
    5.0 • 190 reviews
    $738
    3-Hour Private Charter in Key West
    Boat Tours

    3-Hour Private Charter in Key West

    Customize a private boat outing with snorkeling, fishing, island stops, and sunset cruising

    Customize a private boat outing with snorkeling, fishing, island stops, and sunset cruising
    5.0 • 190 reviews
    $624
    Key West 23' Fishing Boat Rental
    Boat Rentals2 to 8

    Key West 23' Fishing Boat Rental

    Set your own course for fishing, snorkeling, and sandbars

    Set your own course for fishing, snorkeling, and sandbars
    4.1 • 135 reviews
    $568/ boat