Private Sunset Cruise around Key West in Key West
Key West, United States

Private Sunset Cruise around Key West

Outty Ranking 67 5.0 · 66 traveler reviews2 hoursFrom $400

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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$400
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Outty Ranking

67/100

Solid Choice. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 66 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private Sunset Cruise around Key West worth booking?

Private Sunset Cruise around Key West is a 2-hour experience in Key West, United States, from $400 per person. It scores 67 out of 100 on the Outty Ranking, which we label “Solid Choice, based on a 5/5 rating across 66 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
67 / 100
Rating
5/5 (66)
Duration
2 hours
From
$400 per person

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour around the island of Key West on our 20 foot pioneer center console. Your guide will be talking you through many points of i

What you get

    About this experience

    *Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour around the island of Key West on our 20 foot pioneer center console. Your guide will be talking you through many points of interest around the island. Make sure to keep an eye out for wildlife throughout the tour. About 20 minutes before the sunset, your captain will find a quiet and private spot to watch the sun drop into the water uninterrupted by other boats, people, or land!

    What's included

    Included

    • Bottled water

    What you'll see and do

    1. Southernmost Point

      Drive past the southernmost point buoy

      Pass by without stopping

    2. cruise around sunset key to admire the beauty of the islands mansions and beaches

      Pass by without stopping

    3. Mallory Square

      cruise by mallory square to see all thee people waiting for the sunset, along with the live music and street performers.

      Pass by without stopping

    Where it starts and ends

    Meeting point

    Key West

    will pick up guests on the sea wall next to the gas dock

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    will pick up guests on the sea wall next to the gas dock

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 15 travelers per booking
    Operated by
    Stock Island Charters

    Know before you go

    • Infants and small children can ride in a pram or stroller
    • Service animals allowed
    • Public transportation options are available nearby
    • Suitable for all physical fitness levels

    Photos

    Private Sunset Cruise around Key West in Key West, photo 2Private Sunset Cruise around Key West in Key West, photo 3Private Sunset Cruise around Key West in Key West, photo 4Private Sunset Cruise around Key West in Key West, photo 5Private Sunset Cruise around Key West in Key West, photo 6

    What travelers are saying

    Outty’s summary of the themes that recur across 66 traveler reviews. Written by us, not quoted from reviewers.

    Knowledge and storytelling

    6 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Photo opportunities

    4 mentions

    The views and photo stops come up again and again.

    Small groups

    3 mentions

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

    The guide

    2 mentions

    Travelers single out the guide as the reason the experience works.

    Good for families

    2 mentions

    Reviewers traveling with kids report it landed well with their group.

    Traveler reviews

    66 verified traveler reviews for Private Sunset Cruise around Key West. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    65
    4 star
    0
    3 star
    0
    2 star
    1
    1 star
    0
    Sort
    Tina_K · April 2026

    Must do!!!

    It was better than expected. Very informative and breathtaking. We Learned and saw a lot of the area.

    via Viator

    Jordan_I · April 2026

    Great sunset view with a great guide

    Don was an excellent guide. He was fun, and gave a lot of great information during tour. He also knew when to be quiet and let us enjoy the sunset.

    via Viator

    Meander151332 · March 2026

    Great Communication leading up to Sunset Cruise…Excelent local knowledge…Perfect location to watch the sunset!!!

    Don runs a top notch service for a family/group of 5-6 people. He communicated well leading up to the cruise and gives straightforward directions. He has very thorough knowledge of the area and is very personable. His prices are very reasonable for the services he provides and he’s great for families who don’t want to deal with large groups and prefer a more intimate experience. We recommend using him, if he’s available. Book early!!

    via Tripadvisor

    Daydream33413519350 · March 2026

    Small sunset cruise

    If you like small group tours this is the experience you are looking for. We were hoping for an experience that would be memorable and Captain Don delivered. When an owner/operator is running the tour it always shows. His local knowledge was on display and he was a very personable fellow. We enjoyed talking with him while seeing the sights. He really enjoys doing these tours and it shows. We had a group of four (two couples) and split with one couple up front and one in the back of the boat. The views were amazing and Capt. Don answered all of our questions. The sunset was amazing as well! Weather was perfect, which was helpful too. We would recommend this tour to everyone.

    via Tripadvisor

    Scott_C · February 2026

    Private sunset cruise - first time to Key West

    Stock Island Charters and Captain Donnie showed us a great time. His local knowledge and friendly engagement was the perfect complement to a great private sunset cruise. Highly recommended.

    via Viator

    Good to know

    Duration
    2 hours
    Free cancellation
    Up to 24h before
    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
    23
    Verdict
    Solid Choice

    Why this scores 67

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

    Traveler sentiment (30% weight)95
    Review evidence (18% weight)55
    Booking momentum (14% weight)48
    Value for money (12% weight)0
    Listing quality (10% weight)73
    Local standing (8% weight)81
    Booking flexibility (8% weight)100

    Private Sunset Cruise around Key West: questions travelers ask

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

    How much does Private Sunset Cruise around Key West cost?

    +

    Prices start at $400 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 Sunset Cruise around Key West 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 Sunset Cruise around Key West worth it?

    +

    It holds an Outty Ranking of 67 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 66 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Key West, and how flexible the cancellation terms are.

    Can I cancel or reschedule Private Sunset Cruise around Key West?

    +

    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is Private Sunset Cruise around Key West 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 Sunset Cruise around Key West?

    +

    Around 23 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 Sunset Cruise around Key West 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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