Today we’re heading to the lush island nation of Jamaica. While the country is often associated with beaches and resorts, it’s also a place with a deep and complex history, a strong sense of identity, and a rhythm of life that you feel the moment you arrive.

Joining me today is Kenton Jones, Managing Director of The Tryall Club, a 2,200-acre private villa community just outside Montego Bay. It blends classic Jamaican hospitality with one of the most expansive and personalized resort experiences in the Caribbean.

We discuss what makes Jamaica so culturally rich, how the island’s geography shapes everything from lifestyle to cuisine, and what it’s like to stay in a fully staffed private villa surrounded by golf, beach, and nature.

Book your stay HERE

Listen to hear:

• 02:04 – What is happening around Kenton’s surroundings
• 02:49 – Where the island’s geography comes into focus
• 04:07 – How the landscape shapes the culture
• 05:08 – Why history shows up in daily life
• 06:22 – What to know about Jamaican cuisine
• 08:50 – How music lives in everyday moments
• 10:24 – What first-time visitors get wrong
• 12:19 – Why Jamaican culture stands apart
• 13:22 – How this large property stays intimate
• 16:15 – What keeps each villa experience consistent
• 17:48 – Who makes up each villa’s staff
• 20:20 – Where the spa and wellness fit in
• 20:56 – About the behind-the-scenes details
• 23:27 – What guests love the most on the property
• 25:48 – How to best experience the water here
• 27:35 – Where to explore beyond the resort
• 29:50 – Why it works for multi-generational trips
• 30:58 – What a favorite guest memory reveals about Tryall Club
• 31:53 – How relationships evolve during a stay here
• 34:03 – About a few fun facts on Jamaica
• 36:16 – What you will learn about the world and humanity by visiting Tryall Club

Listener Exclusive Amenities

Complimentary roundtrip private airport transfers (for up to 4 guests per accommodation)

Early Check-In / Late Check-Out, subject to availability

Complimentary Wi-Fi