Trelawny, Jamaica, is a fantastic spot for sailing. Unlike the busier parts of the island, Trelawny offers a relaxed yet lively atmosphere with plenty of options for those who want to enjoy the Caribbean waters. Whether you’re after a quick snorkel, a full-day adventure, or a private family outing, there’s something here for everyone. We especially like the Montego Bay Catamaran Cruise and Snorkeling Tour from Falmouth, which combines reggae music, open bar, and coral reefs into a lively half-day trip. It’s perfect if you want to experience the island’s vibrant vibe without spending all day at sea.
If your schedule is flexible and you want a more relaxed, all-day experience, the Full Day Catamaran Cruise to Rick’s Café offers a scenic trip with snorkeling, authentic Jamaican food, and one of the best sunset views on the island. For a family-friendly, extensive day out that includes both snorkeling and climbing Dunn’s River Falls, the Half-Day Private Catamaran And Dunn’s River Falls Tour in Ocho delivers a personalized experience with lots of water fun.
Below, I’ll walk you through each of these top options, explaining what makes each a worthy choice for different types of travelers.
1. Montego Bay Catamaran Cruise and Snorkeling Tour from Falmouth
At number one, this Montego Bay Catamaran Cruise and Snorkeling Tour from Falmouth makes for a lively, half-day outing perfect for travelers wanting a taste of Jamaica’s marine life and island music. You’ll hop aboard a luxury catamaran that cruises along the Montego Bay coastline, playing reggae tunes and serving up unlimited drinks from the open bar. The highlight? Snorkeling in the Caribbean Sea among colorful corals and tropical fish. The boat anchors at a good snorkeling spot where gear is included, making it easy even for beginners.
What makes this trip stand out is its laid-back party atmosphere combined with comfort. The crew is said to be friendly and organized, with reviews praising the clean boat and great music. Children and families can enjoy the Jimmy Buffett Margaritaville stop, where there’s a water slide and casual fun. Although some wish for a longer snorkeling stop or a visit to a sandbar rather than Margaritaville, it remains a popular choice for those who want a quick, fun, and social day on the water.
Bottom Line: A lively, affordable choice for travelers wanting reggae beats, snorkeling, and a social vibe in just a few hours.
$250.00 per person
2. Full Day Catamaran Cruise to Rick’s Café including Lunch
The second spot goes to the Full Day Catamaran Cruise to Rick’s Café, which offers a longer, more relaxed experience perfect for those who want to soak in the scenery and enjoy a full day on the water. This 8-hour round-trip adventure starts in Montego Bay, sailing along the coast while you relax with drinks and listen to music. The cruise includes snorkeling in clear waters, followed by a delicious Jamaican jerk lunch and drinks from the open bar—the kind of meal that makes you appreciate island life.
The highlight, of course, is arriving at Rick’s Café in Negril for sunset. This legendary spot perched on a cliff offers stunning views and the chance to watch brave souls jump into the sea below. The vibe is laid-back, with a live reggae band and a pool for lounging. Reviews note that the trip is a bit expensive, but the combination of snorkeling, good food, and sunset views makes it a worthwhile splurge.
Bottom Line: Ideal for travelers wanting an all-day cruise with scenic sunsets and a taste of Jamaica’s famous cliffside bar scene.
$200.00 per person
3. Negril Catamaran Cruise with Snorkeling – From Falmouth Resorts
At number three, the Negril Catamaran Cruise with Snorkeling from Falmouth Resorts offers a full-day, family-friendly adventure. It’s a longer tour—around 9 to 11 hours—and perfect if you want to explore the west coast’s beaches, snorkel among reefs, and enjoy a scenic drive through Jamaica’s countryside.
The trip begins with private transportation, making for a comfortable start. En route, you’ll pass by familiar landmarks like the Hip Strip, Margaritaville, and Lucea. Once in Negril, you’ll have free time at Margaritaville, where you can relax with cocktails and finger foods. The cruise itself begins around 2 pm, providing plenty of time for swimming, snorkeling, and lounging on the boat. The day wraps up with a visit to Rick’s Café, famous for its cliff jumps at sunset.
While there are no reviews available, the itinerary offers a great mix of beach time, water activities, and sightseeing. This trip suits travelers with a full day to spare who want a relaxed experience with optional adventure.
Bottom Line: Best for families or groups wanting a comprehensive day out on the water combined with sightseeing and beach time.
$270.00 per person
4. Half-Day Private Catamaran And Dunn’s River Falls Tour in Ocho
Finally, the Half-Day Private Catamaran And Dunn’s River Falls Tour in Ocho is the most exclusive choice. This private group tour costs $3,400 for up to 15 people but offers a personalized experience with flexibility in timing and activities.
The tour combines a scenic cruise with snorkeling at a coral reef, followed by a visit to Dunn’s River Falls. The climb up the terraced waterfalls, guided by locals, is a highlight — a physical activity suitable for most fitness levels. The boat trip includes a beachside Jamaican buffet and open bar, making it perfect for celebrating a special occasion or family gathering.
Although there are no reviews, the tour’s private nature and combination of land and water activities make it stand out. It’s best suited for families, groups, or couples wanting a tailored, memorable experience.
Bottom Line: For those seeking exclusivity, personalized service, and a mix of adventure and relaxation, this private tour fits the bill.
$3,400.00 per group (up to 15)
How to Choose the Right Sailing Experience in Trelawny
When deciding among these options, consider your time, budget, and interests. If you want a quick, lively party with snorkeling, the Montego Bay Catamaran Cruise is perfect. For a full day of scenic cruising, snorkeling, and sunset views, the Rick’s Café cruise offers excellent value. Families or those seeking a comprehensive day might prefer the Negril cruise from Falmouth resorts, while groups celebrating special occasions should consider the private Dunn’s River Falls tour.
Booking early is always wise, especially during peak season, to secure your preferred dates and any special requests.
In summary, Trelawny offers a range of sailing experiences from lively party cruises to private family outings. If you value a social atmosphere with reggae jams and snorkeling, the first tour hits the spot. For those wanting a longer, scenic adventure with sunset views, the second is perfect. Families or groups looking for a full day of fun will find the third ideal, and for a tailored, exclusive experience, the private tour provides unmatched flexibility. No matter your preference, these options ensure you’ll make the most of Jamaica’s beautiful waters. Book early, and get ready to enjoy some of the best sailing trips on the island.