About the Owners

Hooked on St. John for over 40+ Years

Owners of Great Expectations, Chuck and KristinWe first visited St John in the 1970’s and fell in love with the island (we were already in love with each other). We stayed at Caneel Bay and discovered we could rent a villa for the two of us for the cost of one night at Caneel Bay.

We have returned every year since and for many years brought our favorite chocolate labrador, Caneel, who loved to swim after coconuts in Hart Bay each afternoon.

In 1989, we arrived with a plan to purchase a piece of land to build our own dream villa on – preferably with sunrise & sunset views and of course visuals of water as much as possible. We also wanted to make sure we found a place with plenty of breezes (which meant an easterly exposure) and wanted it convenient to Cruz Bay, but not too close to be bothered by the late night noise. Secondarily we hoped for a short walk to the water and enough land to build and have some privacy. In short, we were set on finding the ultimate piece of land that no one else had discovered yet!

We looked at dozens and dozens of properties. We climbed trees to see what the view would be like. We stood and tried to get a sense of the breezes.  When we got to the parcel that is now Great Expectations, we said “This is it!” Great breezes, great views of the water, a sunrise right out of the movies, and although we didn’t know it when we bought the property because of bushes, sunset views! We made an offer that same day, flew our architect friend and his wife down from Boston for 2 weeks to design the Villa, got a construction loan from a friendly banker and spent a million dollars over two years to build the Villa.

We have been long term members of the St John Accommodations Council and are very committed to many of the St John community initiatives such as the St John Community Foundation, St John Animal Care Center and the Friends of the Virgin Islands National Park.

Great Expectations is our passion, our love, and we hope will be yours too!

Our goal – always – is to meet and exceed your expectations.

How to move to Paradise in 10 not-so-easy steps

  • 1975First Visit to St. John

    Our first vacation on St. John was at Caneel Bay; we haven't miss a year since!
  • 1976Our first villa rental

    We figure out there's more value, privacy, and ease when renting a villa than staying in a resort, even one as wonderful as Caneel Bay
  • 1980 - 1990 Staying in Chocolate Hole

    We fall in love with the south shore of St. John, particularly the spur of land between Chocolate Hole and Hart Bay and rent many different villas
  • 1991Deciding to buy a piece of paradise

    We hunt for land, with and without a realtor, with the literal 'big picture' in mind. After looking at many sites we purchase our piece of paradise. We bring our very good friend and architect to St John, walk the land, and during a two week stay design what is now Great Expectations.
  • 1998Great Expectations completed

    After 2 years and many re-readings of "Don't Stop the Carnival," we finally complete our dream villa and move in to the owner's quarters for the 1st winter.
  • 1999The first vacation rentals

    Back in 1999, while we already had a website many did not so when someone inquired (usually as a result from a magazine ad, we often had to send them a letter (remember those days) which would take several days to arrive in their mailbox. Our very first rentals were pioneers in that our tennis court was not yet ready and our landscaping was still very, very fresh and we really still looked like a construction site. Well, some of our very early rentals have become long time repeat guests!
  • 2005A Property Manager!

    The best way to ensure a great guest experience when not on the island is to find a property manager that goes above and beyond and we have just that person and great team of dedicated people who work hard to ensure your expectations are met and exceeded!
  • 2012A Pool to Infinity

    With our groups getting larger and larger, we decide to invest in expansion of our patio area and build a beautiful infinity pool for future guests
  • 2013Adding a Sunroom gives us more space

    We convert a large storage area under the owner's apartment into a Sunroom. The villa now sleeps 16 adults comfortably!
  • 2015Building a new BBQ area

    We engaged a local artist to design a wonderful tiled mural as the centerpiece for our new BBQ area
  • 2016Responsive Website

    New photos to show off what we have and a website that works well on smaller screens

Want to Sell it all and Move to the Islands?

We joke often about 'island time' and 'limin,' but, looking back on our experience on St. John building our dream villa, we wouldn't change a thing. One piece of advice: Read Don't Stop the Carnival by Herman Wouk. It's more non-fiction than you would believe.