Private Key West Sunset Sail in Key West
Key West, United States

Private Key West Sunset Sail

Outty Ranking 51 4.7 · 52 traveler reviews2 hoursFrom $695

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September 2026

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Adults

Age 13 and over

2

Children

Age 12 and under

0

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From, per person$695
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Outty Ranking

51/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

4.7/5

Based on 52 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private Key West Sunset Sail worth booking?

Private Key West Sunset Sail is a 2-hour experience in Key West, United States, from $695 per person. It scores 51 out of 100 on the Outty Ranking, which we label “Worth a Look, based on a 4.7/5 rating across 52 reviews. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.

Outty Ranking
51 / 100
Rating
4.7/5 (52)
Duration
2 hours
From
$695 per person

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West

What you get

    About this experience

    2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for the perfect Key West sunset sail Peaceful, private and exclusive! Your captain and mate will take you out to watch the sunset from your own private classic sailing vessel, with soft drinks, bottled water and coolers stocked with ice provided for any adult beverages you choose to bring. Reserve ahead, there is after all, only one High Tide sunset sail per day! Price is for up to 6 guests, 12 guests max!.

    What's included

    Included

    • Light refreshments
    • Bottled water
    • Captain and mate
    • Soft drinks
    • Private cruise

    Not included

    • Gratuities
    • Hotel pickup and drop-off

    What you'll see and do

    1. Sail out of the Key West Historic Seaport at 202 William St. Key West, FL on Key West's original sailing charter boat, High Tide. The vessel is docked in front of the schooner wharf bar on the floating dock that begins underneath our Sunset Sail Key West sign.

      Pass by without stopping

    2. Mallory Square

      Sail past Key West's nightly sunset celebration while toasting the sunset from your own private sunset sail charter

      Pass by without stopping

    Where it starts and ends

    Meeting point

    Key West

    On the dock in front of the Schooner Wharf Bar. You will see our Sunset Sail Key West sign. Go down that floating dock and you will see the pretty green sailboat named High Tide. We will be prepared to welcome you aboard 15 minutes prior to the scheduled departure.

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    On the dock in front of the Schooner Wharf Bar. You will see our Sunset Sail Key West sign. Go down that floating dock and you will see the pretty green sailboat named High Tide. We will be prepared to welcome you aboard 15 minutes prior to the scheduled departure.

    Options you can book

    • 6pm Sunset Departure

      6pm Sunset Sail Private Charter

    • 4:30pm Sunset Departure

      4:30pm Sunset Sail Private Charter

    • 6:30pm Sunset Departure

      6:30pm Sunset Sail Private Charter

    Before you book

    Cancellation
    All sales are final. No refund is available for cancellations.
    Languages
    en, es
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 15 travelers per booking
    Operated by
    Sunset Sail Key West

    Know before you go

    • Infants and small children can ride in a pram or stroller
    • Service animals allowed
    • Public transportation options are available nearby
    • Infants are required to sit on an adult’s lap
    • Suitable for all physical fitness levels
    • Children must be accompanied by an adult
    • Pricing is per boat/charter
    • Private Charter Capacities Vary by Boat. 6, 12 or Up to 32 Guests

    Photos

    Add on a gourmet cheese boardKey West offers spectacular sailing weatherPrivate Key West Sunset Sail in Key West, photo 4Private Key West Sunset Sail in Key West, photo 5Private Key West Sunset Sail in Key West, photo 6

    What travelers are saying

    Outty’s summary of the themes that recur across 52 traveler reviews. Written by us, not quoted from reviewers.

    Knowledge and storytelling

    4 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Small groups

    3 mentions

    The group size is repeatedly described as intimate rather than packed.

    Photo opportunities

    2 mentions

    The views and photo stops come up again and again.

    Traveler reviews

    52 verified traveler reviews for Private Key West Sunset Sail. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    46
    4 star
    2
    3 star
    1
    2 star
    1
    1 star
    2
    Sort
    csshads · May 2026

    When and If Sunset Sail

    This sail was fantastic, staff was very knowledgeable and accommodating. We took 25 family members, staying at the Perry Hotel on Stock Island for a wedding and everyone raved about this sail. Sailboat was very cool and history was interesting. Would do it again in a heartbeat!

    via Tripadvisor

    dominicrQ147DV · April 2026

    Private sunset and how great it was!

    The experience was truly amazing. Despite it being in harsh weather, the crew managed to make the best of the situation. It was also interactive and we got to set the sails. You got to talk to the crew one on one and really interact with them as a person. There was tons of beverages and even a cheese plate. One the the crew members named Koss was really amazing, she was able to interact while also preforming her job. She was able to keep the mood light despite the weather being not so light. She made us feel involved and engaged.

    via Tripadvisor

    Linda S · March 2026

    The best thing to do on a windy day!

    We had a great sail with Captain Will and First Mate Cameron. Because the day had gusts up to 26 mph we had great sailing on a wonderful boat. Plan to do it again!

    via Tripadvisor

    Rcs3288 · January 2026

    A wonderful sunset sail experience !

    We set sail for my brother’s 40th birthday on a sunset cruise, and it could not have been more perfect. The boat itself was absolutely beautiful—clean, comfortable, and clearly well cared for. From the moment we stepped aboard, the captain and first mate made us feel welcome. They were incredibly knowledgeable, genuinely kind, and effortlessly friendly, sharing great insights while keeping the experience relaxed and fun. The sunset was stunning, the ride was smooth, and the entire trip felt both special and seamless. A huge bonus was the convenience—they picked us up directly at Sunset Key and dropped us off in Key West, which made the evening completely stress-free. An unforgettable experience from start to finish. 5/5 stars, and I would absolutely recommend this cruise to anyone looking for a memorable time on the water.

    via Tripadvisor

    Nemolly · November 2025

    Sun, wind , and rain all wrapped into a birthday party

    Pretty boat high end services, even an opera singer. This boat has it all. Small and intimate. Had a birthday sail, which didn’t disappoint. Loads of rain , a waterspout, and an amazing sunset.

    Response from the operator: What a memorable trip! we had all types of weather on the trip! It started as a small sun shower that wasn't even showing up on radar and it just dumped rain all while the sun and rainbows were out in the west. I'm happy that guests that wanted to could go down below and experience how beautiful and comfortable the interior of the yacht is! I had to stay at the helm and definitely shouldn't have chosen a white shirt that day but someone has to drive the boat! Rain cleared out for the second half of the trip and we had a stunning sunset and a happy birthday serenade from our musically talented mate. Thank you for joining us and your group helped to make it extremely memorable and fun for us as well. Thank you!

    via Tripadvisor

    Good to know

    Duration
    2 hours
    Free cancellation
    Non-refundable
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    18
    Verdict
    Worth a Look

    Why this scores 51

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)78
    Review evidence (18% weight)52
    Booking momentum (14% weight)44
    Value for money (12% weight)0
    Listing quality (10% weight)83
    Local standing (8% weight)52
    Booking flexibility (8% weight)0

    Private Key West Sunset Sail: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Key West.

    How much does Private Key West Sunset Sail cost?

    +

    Prices start at $695 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Key West usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Private Key West Sunset Sail take?

    +

    Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Key West is not rushed.

    Is Private Key West Sunset Sail worth it?

    +

    It holds an Outty Ranking of 51 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.7/5 across 52 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable culture & history in Key West, and how flexible the cancellation terms are.

    Can I cancel or reschedule Private Key West Sunset Sail?

    +

    No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.

    Is Private Key West Sunset Sail suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Private Key West Sunset Sail?

    +

    Around 18 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Key West can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

    +

    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Key West and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.

    Where does Private Key West Sunset Sail start and how do I get there?

    +

    The exact meeting point and directions are on your voucher once you book, and they sit in central Key West within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Key West?

    +

    Key West is a boat town. The only living coral barrier reef in the continental US sits seven miles offshore, and reef trips, sunset catamarans and backcountry kayak runs are the core bookings, alongside Hemingway house and Duval history walks. Our ranking weighs boat capacity and reef site rotation, which separates the good operators from the party cruises. On Outty we rank every Key West experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Shark and Wildlife Viewing Adventure in Key West, Southernmost Food & Cultural Walking Tour by Key West Food Tours, Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Key West?

    +

    December to April, dry season and calm reef water. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Key West?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

    +

    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

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