Sail Away in Montego Bay on a Private Catamaran in Montego Bay
Montego Bay, Jamaica

Sail Away in Montego Bay on a Private Catamaran

Outty Ranking 66 5.0 · 20 traveler reviews3 hoursFrom $1850

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September 2026

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Adults

Age 13 and over

2

Children

Age 12 and under

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From, per person$1850
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Outty Ranking

66/100

Solid Choice. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 20 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Sail Away in Montego Bay on a Private Catamaran worth booking?

Sail Away in Montego Bay on a Private Catamaran is a 3-hour experience in Montego Bay, Jamaica, from $1850 per person. It scores 66 out of 100 on the Outty Ranking, which we label “Solid Choice, based on a 5/5 rating across 20 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
66 / 100
Rating
5/5 (20)
Duration
3 hours
From
$1850 per person

Sailing along the coastline of Montego Bay offers breathtaking views and turquoise waters. You’ll have the opportunity to indulge in snorkeling and swimming, explore the vibrant underwater world, and enjoy the crystal-cl

What you get

    About this experience

    Sailing along the coastline of Montego Bay offers breathtaking views and turquoise waters. You’ll have the opportunity to indulge in snorkeling and swimming, explore the vibrant underwater world, and enjoy the crystal-clear waters. In addition, there’s the added pleasure of an open bar, fresh fruit, chips, and savory Jamaican patties. Our signature drink the “Tipsy Gypsy” is a must try! For your listening pleasure, we also have a Bluetooth sound system, allowing you to sync your favorite playlist. We look forward to providing an unforgettable experience immersed in the natural beauty of Jamaica!

    What travelers are saying

    Outty’s summary of the themes that recur across 20 traveler reviews. Written by us, not quoted from reviewers.

    Good for families

    4 mentions

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

    Knowledge and storytelling

    3 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Photo opportunities

    2 mentions

    The views and photo stops come up again and again.

    Small groups

    2 mentions

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

    Traveler reviews

    20 verified traveler reviews for Sail Away in Montego Bay on a Private Catamaran. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    20
    4 star
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    W9647WVerica · February 2025

    This is the One!!!

    After researching several Charters we settled on Gypsy Sails due to the excellent communication, affordability for services offered and online reviews….and boy did they deliver! Just like in every other review we too had an incredible experience. The crew was very welcoming, friendly, talkative, and knowledgeable, The boat is extremely comfortable and the Captain had charted a beautiful cruise and tour of the harbor front. The snorkelling was beautiful, in crystal clear, calm waters, And the provided lunch and drinks were delicious and filling. We were a combined family of 16 ranging from 80 to 9 years old, and everyone felt comfortable and thoroughly enjoyed the experience. Highly recommend!

    via Tripadvisor

    rileybB5525QT · December 2024

    Unforgettable Experience with an Amazing Crew

    If you're looking for an amazing catamaran experience, Gypsy Sails is the way to go! The crew was incredibly friendly, fun, and professional, making sure everyone felt welcome and had a blast. We were with Peter, Andy, and Peta-Gaye. They were knowledgeable, attentive, and went above and beyond to ensure we had an unforgettable time. Highly recommend!

    Response from the operator: Awwww this is awesome! We truly appreciate you taking the time to share your experience with us! Thank you, thank you, thank you! And we hope to see you again!

    via Tripadvisor

    kristinap36 · December 2024

    Fantastic Time!

    The boat was nice & the crew was amazing! I would definitely book again & recommend to anyone needing private charter for their Jamaican fun!

    Response from the operator: Hiiii Kristina! Thank you so much for sharing your experience with us! It means a lot, and we appreciate it! We hope to see you again!

    via Tripadvisor

    Z7453OTsarahc · December 2024

    Great for a family excursion

    We had the best time on Gypsy Sails! We went with our 5 kids (15 yrs to 6 months) and it was the perfect activity for all ages. Andy was a wonderful guide for an hour long snorkel session and Captain Peter was great in leading us around. The boat is spacious and in great condition. Highly recommend!

    Response from the operator: Thank you SO MUCH for taking the time to share your experience! And thank you for trusting us with your beautiful family! Hope to see you again!

    via Tripadvisor

    tsombat · November 2024

    The BEST time w Gypsy Sails!

    Our private catamaran cruise with Gypsy Sails was the highlight of our MB trip!! Stacey was so responsive from the booking to the excursion, even being flexible with the timing of the cruise to accommodate for the weather forecast. It was a birthday celebration and the whole crew went above and beyond with balloons and cake :) No better way to spend the day than cruising around the island sipping on tipsy gypsies, dancing in the sun, and jumping in the water! I would absolutely book this trip again.

    Response from the operator: We’re so happy to hear you enjoyed your time with us! Thank you for taking the time to share your experience, we do appreciate it! We’ll have the Tipsy Gypsy’s ready for you when you return!

    via Tripadvisor

    Good to know

    Duration
    3 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Booked in 30 days
    7
    Verdict
    Solid Choice

    Why this scores 66

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

    Traveler sentiment (30% weight)92
    Review evidence (18% weight)57
    Booking momentum (14% weight)49
    Value for money (12% weight)0
    Listing quality (10% weight)77
    Local standing (8% weight)65
    Booking flexibility (8% weight)100

    Sail Away in Montego Bay on a Private Catamaran: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Montego Bay.

    How much does Sail Away in Montego Bay on a Private Catamaran cost?

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    Prices start at $1850 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Montego Bay usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Sail Away in Montego Bay on a Private Catamaran take?

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    Plan for about 3 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 Montego Bay is not rushed.

    Is Sail Away in Montego Bay on a Private Catamaran worth it?

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    It holds an Outty Ranking of 66 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 20 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Montego Bay, and how flexible the cancellation terms are.

    Can I cancel or reschedule Sail Away in Montego Bay on a Private Catamaran?

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    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 Sail Away in Montego Bay on a Private Catamaran suitable for kids and families?

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    Yes, all ages are welcome. Families should still weigh the 3-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Sail Away in Montego Bay on a Private Catamaran?

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    Around 7 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 Montego Bay 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?

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    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Montego Bay and add a light layer if any part of the 3-hour experience runs outdoors or after sunset.

    Where does Sail Away in Montego Bay on a Private Catamaran start and how do I get there?

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    The exact meeting point and directions are on your voucher once you book, and they sit in central Montego Bay 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 Montego Bay?

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    On Outty we rank every Montego Bay experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Private Montego Bay Airport Transfer to Negril, Blue Hole and Dunn's River Falls Private Tour from Montego Bay, Appleton Estate Admission Ticket & Distillery Tour with Tastings. 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 Montego Bay?

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    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 Montego Bay?

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    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?

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    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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