Your Paradise Plan - Start Your Road Map

1: Pick your Paradise.

Imagine you are in your version of paradise. Start with what the country, city or island looks and feels like. You’ll want to consider the weather, the time of year, what you’re wearing, who you’re talking to, what language you’re speaking, what you’re eating, and what you’re doing with your time there. The more details you consider, the more specific your search will become and this is key. Then, move on to what your own space looks and feels like. Are you living in an old house, an apartment near the beach or a cottage in woods? What will you be doing in this property? Is this your full time home or a vacation home? Do you live alone? Do you have a space for guests and rental income? Finish with a list of criteria, describing your unique vision of your paradise.

If you’re looking for a Caribbean paradise like mine, I included 33 items on that list and it started like this:

  • a heritage home needing renovation.

  • extra space for guests and rental income.

  • business potential for the building and area.

  • budget of 150K.

  • home is close to heritage and tourist sites.

  • a growing economy in more ways than one.

  • close to the beach… + 22 more items.

  • warm weather year round so I can visit and rent out my vacation home any time.

  • an island with European architecture to admire and explore.

  • friendly culture - where people say “hello” to strangers in the street.

  • a view of the ocean.

2: Map it out.

Once you know how your paradise will look and feel, begin searching for where the key elements of your paradise can be found.

When searching for an old house on a tropical island, it didn’t take long to find out which islands have European architecture, where the weather and temperature is stable year round. From there, I thought about where would be easiest to travel to, considering my citizenship and home base. I started researching which islands are prime for real estate investment, tourism, etc. The more I could find out about what’s happening in the Caribbean, the better. Finally, I researched the median home price on each island to figure out where I could afford.

A quick search online can produce a wealth of information and it’s FREE.

3: Focused Research

Next, get connected with the places you’re most interested in. It is incredibly helpful to connect with local communities via email newsletters, websites, articles, facebook groups and by reaching out to people you can relate to. For me, that meant starting with the following:

  • join facebook groups about new comers, being a landlord, art galleries, special events, business, news, etc.

  • Reach out to local heritage societies, art galleries, tourist offices.

  • check out tripadvisor, airbnb,, etc. to find out about current tourism industry.

  • Google street view areas of interest…

4: Check it out

Once you’ve found out everything you can about the places or place you’re interested in without leaving home, it might be time to visit. If you feel you know A LOT about the place you have in mind, even though you’ve never been there, book a trip and find out if your research was correct and if what you’ve found, is really paradise for you.

When I decided to go to St.Croix in the USVI, I felt confident that I knew what the island looked like, what the house I wanted to buy looked like, I knew how recent galleries had just opened, I knew what local hopes and frustrations were. I had spoken with several people who were from the island or had relocated there…

When I arrived in St. Croix, it really did feel like the images in my mind and the research I had completed, came to life.