St. John is one of those beautiful, unspoiled Virgin Islands that many travelers have sometimes ignored. It is the smallest of the three main U.S. Virgin Islands in the Caribbean. The Virgin Islands National Park, deeded to the island in 1956 by Laurance Rockefeller, occupies more than half the island. Its forests are home to resident and migratory birds, including cuckoos, warblers, and hummingbirds. The mangroves at Hurricane Hole in the east, support coral and anemone. Dolphins inhabit the island’s waters, which also host hawksbill and green turtles. And at Cruz Bay, one can swim in the richly blue waters and encounter a variety of these sea turtles.

It is an exceptional island, with no airport, and the only way to get there is by ferry that goes multiple times a day from St Thomas. Its isolation is a blessing according to the residents, who number between three and four thousand depending on the season. It is an essentially quiet island with the exception of songbirds and soughing trees.

It is no wonder then, that a new co-ownership project has landed there. Called Island Sky Residence Club, it is an equity residence club, where owners are in control of the property, all being overseen by Elite Alliance, a well-respected, well-known residence club management group. The developer is Jason Caraway, a gentleman who has deep connections to St. John. His attachments are not only fiscal, but spiritual, as he has been coming to St. John for years - first as a child with his parents, and now with his wife and two teenage children.

Island Sky St John Rooftop Terrace

We recently spoke with Jason about the Island Sky project:

SherpaReport: Do you remember what first attracted you to St. John?

I visited St John many times when I was a kid, with my family, Then, repeatedly. I developed a love for the island, and its people and its wildlife, it is now our home away from home.

SherpaReport: Are there other residence clubs on St John right now, or will you be the only one?

Island Sky is the only equity residence club on the island. This means it is the only club where owners have full control of the property, making decisions by way of a board, overseeing the management company.

SherpaReport: What is your pricing and annual dues?

Our pricing ranges from $190,000 per 1/10th share for one bedroom, one bathroom, to $220,000 for two bedrooms, two baths.

The annual dues for each residence are approximately $600.00 per month for 1 bedroom, and for the 2 bedroom it is approx. $900.00 per month.

SherpaReport: And the square footage?

The one bedroom / one bath is 716 square feet, plus terrace, and the two bedrooms, two bath is 1,038 square feet plus terrace. The rooftop with pool is called the Sunset Lounge and it open to all members.

SherpaReport: If all goes well, do you plan to buy and build more on St. John in the immediate future?

I do plan to be on St. John, both in business and pleasure, from now on.

SherpaReport: What additional services do you provide that are included in the annual dues -- examples: adventure concierges, private chefs, housecleaners?

A great question! We will offer all of those mentioned, we’ll have a full-time concierge, housecleaning staff, and will be able to assist with transportation, boat charters, meals, shopping, and personal chefs. We’ll have an organization in place which will be able to facilitate most any experience our residents would like on the island.

Island Sky Residence Club

SherpaReport: Are pets allowed?

Yes, we have certain units that are designated as pet friendly.

SherpaReport: What are the major differentiators between Island Sky and others?

I would say that Island Sky is an equity residence club which means that owners have control over the direction of the property and are not at the mercy of a random buyer or management firm that can come in and make unreasonable changes or inadvertently raise costs. This is a comforting thought and does separate us from other properties on the island.

And while there are plenty of great sunset views from different parts of St. John, our rooftop pool lounge, facing west toward is one of the best you can find anywhere.

SherpaReport: What is your timeline for project completion?

We expect to deliver the units in 18 months from now, and we are already selling units now.


Island Sky Residence Club St. John is on a waterfront hillside overlooking Turner Bay, with panoramic views over to St. Thomas and the surrounding islands. The development will include ten one- and two-bedroom fractional residences, designed in a modern coastal style with a touch of West Indies tradition. The location is less than five minutes by car to Wharfside in Cruz Bay, providing easy access to the island's main area where most shopping, passenger ferry docks, bars, and restaurants reside.