He’s perhaps best known as the person who first introduced reggae music to the world. In 1959 at the age of 22, Chris Blackwell founded Island Records, which launched many musical careers, most notably Bob Marley’s.

It wasn’t long before the British-born, Jamaican-raised Blackwell became an industry icon. With success came money and the chance to fulfill a childhood dream—to purchase a historic property known as Strawberry Hill, a place his mother took him as a boy for afternoon tea.

Located high in Jamaica’s Blue Mountains and accessed via a long, winding road with 365 bends, the remote and pristine location with its cooler temperatures and unique microclimate obviously made an impression.

Blackwell’s friends, such as the Rolling Stones and Bob Marley (who found shelter here after threats to his life), were among his guests. Today, it still attracts serious talent, as well as discerning travellers desiring a genuine escape and a vibe that is relaxed yet sophisticated. Set amidst tropical gardens, the 12 colonial-style cottages (with muslin-draped four-poster beds) have received many accolades including the Governor General’s Most Beautiful Design Award.

What to Expect

It’s easy to unwind in this paradise-like setting, as you sway in the hammock on the veranda and watch passing clouds at eye level!

Another treat is dining on the Great House terrace. Sample menu items include jerk chicken, spicy crab backs, a signature rum cake and, of course, freshly-brewed Blue Mountain coffee. Sunday brunch is popular and worth the trip for the view alone.

Later, check out the Gold Room, crammed with trophies and awards from artists such as Melissa Etheridge, Traffic, Cat Stevens and Jethro Tull, all of whom Blackwell and Island Records have either produced or nurtured.

Occupied since 1780, Strawberry Hill gets its name from the first owner, Horace Walpole, fourth Earl of Orford, who discovered the elevation was ideal for growing strawberries. His cousin Admiral Lord Nelson was a guest. Were Walpole visiting today, he could take a dip in the resort’s stunning infinity pool or enjoy a spa treatment using locally-sourced lavender and coconut.

The resort can arrange guided nature hikes or a visit to a coffee plantation to learn what makes Blue Mountain coffee so special. In Kingston, the Bob Marley Museum and historic Devon House are both worth touring.

Back at the resort, nature reigns. Keep an eye out for rainbows or watch the sun slide into the mountains. Once night falls at Strawberry Hill, nothing quite compares to the twinkling stars in the velvet sky above competing with the city lights of bustling Kingston far off in the distance below.

Travel Planner

Air Canada (aircanada.com), WestJet (westjet.com) and Caribbean Airlines (caribbean-airlines.com) operate direct flights year-round between Toronto and Kingston, Jamaica. Strawberry Hill (strawberryhillhotel.com), part of the Island Outpost collection, is a 45-minute drive from Kingston. For information on Jamaica, log onto VisitJamaica.com.