ABOUT OUR REVIEWS // We love what we do! We travel often. It’s essential to stay up to date on the hotels we sell. Truth + transparency in travel is our goal, so if we don’t enjoy our stay at a hotel, we won’t write about it. If you’re reading this – the hotel below was a hit! I hope you like our review of how to spend a day at our favorite resort for villa rentals in Jamaica.

FIRST IMPRESSIONS // From the moment I arrived at The Tryall Club, I knew this vacation would be all about true relaxation. As soon as the air-conditioned private van pulls up to your villa (no hotel lobby check-ins here!) and the warm, welcoming staff greets you with smiles, any lingering travel stress instantly melts away. Fast-forward to my parting thoughts, and I can confidently say I was right about my first impression; this was one of the most relaxing vacations I’ve ever had.

There’s something about the privacy of a villa that takes your relaxation to a whole new level. Even the world’s most exclusive beach resorts can’t quite match the feeling you get from a villa vacation. One of the best aspects of private villa rentals in Jamaica is the simplicity it offers—fewer decisions to make and more time to unwind with your family and friends. It’s the perfect contrast to the typical hotel experience, where even luxury can feel a bit less personal.

9 AM // You’ll likely wake up to the sound of songbirds right outside your window—it’s just part of the charm in Jamaica, where their sweet melodies are everywhere. After a great night’s sleep in one of the softest beds you’ve ever had on vacation, you’ll be reminded that this isn’t just any hotel; you’re staying in someone’s private vacation home, and the attention to detail is unmatched.

Coffee is in order because you want to greet the day with all the enthusiasm possible. You can request that a carafe be waiting for you outside your bedroom door at a set time so you can enjoy a private moment on your patio or balcony before finding the rest of your group.

Breakfast is served at your preferred time and prepared by your personal cook and staff, who are dedicated solely to your villa. All of the villas at The Tryall Club operates like a mini-hotel, but with one key difference—you’re the only guest.

10 AM //  Your tee-time is before noon because it’s warm in the Caribbean so this is what we do. The 18-hole championship golf course at The Tryall Club in Montego Bay, Jamaica is one of the most picturesque in the region. You’ll tee off beside a centuries-old water wheel, overlooking a gentle cascade of lush green fairways that stretch down to meet the sparkling ocean.

If you’re not a golfer, your butler can easily arrange for a private yoga instructor to guide you through a session right at your villa, or perhaps you’ll find a class happening at the spa before your massage.

After yoga at the spa, you might not want to leave. The Spa at Tryall “seamlessly blends holistic wellbeing with purposeful, results-driven spa resort treatments.” 

3 PM // After lunch, the best way to relax is by retreating to your luxurious private villa and slipping into your gorgeous swimming pool. With most villa pools at The Tryall Club offering sweeping views of the ocean, the tranquility is unmatched. Picture yourself floating effortlessly, the warm Caribbean sun overhead and the gentle breeze carrying the scent of tropical flowers. Your villa staff remain attentive, ready to top off your chilled rosé as you let time drift by. This is the ultimate way to spend a peaceful afternoon immersed in both serenity and luxury. 

6 PM // One of my favorite rituals at villa rentals in Jamaica is cocktail hour. Your group will gather in the open-air living space, sipping cocktails and enjoying hors d’oeuvres while soaking in the views and discussing what everyone did that day. As the sky darkens, you’ll retreat to your private suites to get ready for dinner.  At Tryall, many of the bathrooms feature outdoor showers, while others are completely open-air, blending luxury with nature. The connection to the outdoors elevates the experience, adding an extra layer of relaxation to your evening routine.

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9 PM // Activities at Tryall after dark are vibrant and varied, influenced by the time of year and the scheduled events. Some evenings, you might find yourself at a themed dinner on the beach, where the soft sounds of waves complement a soulful live band, creating an unforgettable atmosphere under the stars. After dinner, the excitement often continues at the bar, where you can enjoy the sounds of another live band, where you’ll sip on cocktails and mingle with fellow guests.

For a change of scenery, consider dining at the elegant Great House during one of their enchanting piano dinners. Here, you’ll enjoy elevated Jamaican cuisine while a talented pianist sets the mood, making for a very memorable meal.

10 PM //  I highly recommend you convince your group to take a quick dip in the hot tub or heated pool before calling it a night. There’s something incredibly soothing about sinking into warm water, surrounded by the fresh island air, with the only light coming from the stars and the moon above. It’s a serene, almost magical experience that calms the mind and body, making it the perfect way to end the day. This is where unforgettable memories are made—where laughter lingers, conversations flow effortlessly, and the beauty of the island wraps around you making you to start planning your next visit!

FINAL THOUGHTS // What I loved most about my stay at The Tryall Club was how great it was to have the best of both worlds. We stayed in a huge six-bedroom villa that we had all to ourselves, yet there was always something social going on somewhere on property if we wanted to branch out.

Fun fact – I used to own a villa company – you can read that story here. What was true then is still true today… The Tryall Club is one of the top 3 villa rental experiences in the Caribbean.

All this experience makes The Caribbean Journey Team experts on villa vacations… we’d love to help you select the perfect villa for your next vacation! Contact us for full details.

Cheers,

Laura Sangster