Strawberry Hill was going to be Chris Blackwell's first hotel, but he got "sidetracked" by South Beach. Atop a mountain with stunning views in every direction, a two-century-old "post-plantation" estate is surrounded by more-recently constructed cottages and villas that seem to hang off the mountainside.
It couldn't be more different from GoldenEye in setting, yet it adheres to Island Outpost's aesthetic and philosophy. The colonial structure of the main house is balanced with Rasta-influenced details carved into ceilings and panels in rooms and public spaces. The landscaping is stunning, and the pool overlooks Kingston, more than 3,000 feet below.
It's a much smaller property than GoldenEye, and there's not much in the way of on-property activity, but the excursions are interesting and very, very Jamaican. Tours to Kingston include visits to the Bob Marley Museum and the Trenchtown neighborhood where he lived. (After Marley was shot and wounded in an assassination attempt in 1976, Blackwell brought him to Strawberry Hill to convalesce.)
I enjoyed a half-day walk to a waterfall-fed swimming pool in the company of Rasta Dave, one of the more entertaining guides I've encountered in the Caribbean. The lush, winding trail -- downhill all the way -- passed through small villages, past subsistence farms and isolated homes until we reached the welcome (and surprising cold) swimming hole. We returned in a local cab.
Guests can walk 10 minutes downhill to a Blue Mountain coffee plantation for a tour of how the coffee is grown.
Another excursion was a short walk to the Craigton Estate Plantation, where Blue Mountain coffee, the most expensive in the world, is grown. (The entire crop of this plantation, and many others in Jamaica, is exported to Japan.) The guide employed by the plantation told the story of coffee, Blue Mountain coffee in particular, in a wonderful narrative, and the mountain scenery provided a beautiful backdrop.
Jenny Wood, who handles trade relations for Island Outpost, said Strawberry Hill and GoldenEye are frequently paired and promoted together as a "two-post Outpost" option.
"Strawberry Hill is a great place to stop for a couple of nights and decompress before heading to the coast," she said. "Both properties, though very different, attract the same type of person."
One difference between the properties is that there are no televisions at Strawberry Hill, something that General Manager Clemens Von Merveldt said requires a leap of faith for some guests. He added that, no matter how skeptical they might be, once guests have stayed a couple of nights on the property, they end up grateful to have had a break from TV for a period of time.
Going further off the grid
On the highway west from GoldenEye, past Montego Bay, a left turn brings you into the rural center of Jamaica. The land rolls, and the road passes former cane fields that now contain orchards. Eventually the pavement ends and the road turns to dirt.
Not long after, you reach Pantrepant, an old sugar plantation. An enormous tree behind a large house dominates the view. A rock/reggae mix plays loudly from the house. A small pack of dogs, alert but friendly, greets visitors.
Pantrepant is both Blackwell's retreat and the site of an ambitious dream. He spends about 80 days a year there and would spend more except, he said, "I hate to leave. That's the biggest problem. If I'm only coming for a day, it's not really satisfying -- you're leaving before you're really settled in."
The pace and vibe of all the Island Outpost properties is mellow, but compared with Pantrepant, GoldenEye bustles. Pantrepant activities include riding an inflated tube down a (mostly) lazy river, eating meals on white linen under that giant tree, hiking to caves and looking for petroglyphs, taking a tour of an organic farm on the grounds or exploring the stone remains of abandoned sugar plantation structures.
And, hanging out with Blackwell, if he's there. ("I'm always interested to meet people.")
The property had offered trail rides on horseback but has put a moratorium on that activity until liability and insurance issues are worked out.
Pantrepant is seen primarily on weekends, as an excursion from GoldenEye, with the promise of a day in the country and a farm-to-table meal, cooked by Mama J, who has worked for Blackwell for decades, and her daughter Aldrene.
There is one spacious cottage for rent to overnight guests, decorated with tasteful local flair by Pantrepant's general manager, Marika Kessler, who also designed the interiors of GoldenEye's beach huts. People who stay there, Blackwell said, tend to be repeat visitors who enjoy its slow tempo.
Blackwell has big plans for Pantrepant, but in keeping with the pace of the property, he's content to let it develop leisurely and incrementally.
"I want to keep it as a country place, simple, and then grow it," he said. "The plan in my mind is to identify some locations where one would build cottages, but I don't want to change the feel of it. We do have a lot of land, and you could place a hundred houses here and no one would see each other. We could do that, though we don't want to do as many as that. I am thinking that perhaps it could be around 50 houses."
But not just any houses.
"What I'm thinking is that they would be off the grid. They could be solar-powered but still hooked up to Internet and everything. If one could own a place like that here, with its privacy and silence and access to good agriculture and an abundance of water, my sense is that there will be a demand for living in such a way."
Especially, he said, if it's managed and connected to a group of properties.
"The problem with getting a cottage in the country is you've got to look after the damn thing. I had done that once, one cottage for me and one for my band Traffic. We had a little farm in the Midlands [in the U.K.] with a rehearsal room, and they lived there. But my cottage, every time I went there it was a nightmare. You open the fridge and it's full of mold and this and that, so the first day is miserable and this isn't working and that isn't working, and then the last day you've got to be closing everything up. At Pantrepant, it would be our responsibility."
His timeline to develop Pantrepant? "I would say in about five years. I'm waiting a bit on the technology, the solar batteries, for it to be feasible."
The reference to Traffic was not the only time Blackwell brought up an Island Records experience to explain what he was doing with Island Outpost.
"It's in our DNA, the record label," he said. "It's still the base of the Island brand."
Butch, Chris and all-inclusives
Chris Blackwell shares two things in common with Jamaica's most prominent hotelier, Butch Stewart, the founder and chairman of Sandals and Beaches Resorts. The first is that they both started their careers in air conditioning sales in Jamaica. They knew each other and competed for business, though Blackwell says Stewart was far better at it than he was.
They remain friends, and Blackwell is quick to say he's not in Stewart's league.
Of Blackwell, Stewart said, "Our relationship goes back many years, and I'm proud of all he does. He has been both an extraordinary friend and an extraordinary Jamaican. Island Outpost's creative blend of native luxury appeals to everyone, and Chris is equally passionate about his music and his hotels. He not only has developed unique hotels, but he's brought unknown artists to prominence. And I know he's proud of the partnership that Sandals now has with the Marley family." (Sandals recently formed a partnership with Bob Marley's grandson, Skip, whose music will be used in Sandals promotions.)
Blackwell's and Stewart's approach to hospitality does overlap in one region and one style: Like Stewart, Blackwell runs an adults-only all-inclusive in Negril.
The Caves has only 13 rooms but -- and by now this should come as no surprise -- Blackwell has a growth plan for it.
"Well, the Caves is another one which needs [more] development," he said. "I've got work to do there."
Blackwell said he has enough surrounding land to "easily have 40 rooms. From the day it opened, it has been successful, really successful. It runs at 80-something-percent occupancy all year. It's the classic 'if it works, don't fix it,' so, the question is how to expand it and not lose the feel. And our audience."
The property is all-inclusive, Blackwell said, because "it's really tiny. But I don't know if it will continue to be when we add rooms."
Pushing out the timeline
The development of Firefly and expansion of GoldenEye, the promotion of Oracabessa Bay into a resort area, the evolution of Pantrepant from a farm to a community and the tripling of the number of rooms at the Caves all add up to a fairly ambitious agenda, even for a septuagenarian who is physically fit and mentally sharp.
"You have to live life as if you're going to live to be 94," he said over dinner at Pantrepant one evening. "It helps you think in the long term." He paused. "Actually, that's getting a bit close. I may have to revise that and push it out further."
His mother, he noted, is still going strong at 103.