Retire in the Caribbean

I sometimes dream of retiring to an island and basking in the romanticism of the Caribbean. I currently live in south Florida, in a location that many of my friends up north think of when they are planning their vacations. In fact, this past February I knew five different families who spent a week vacationing in the warmth down here. I’m lucky enough to live within a few minutes drive of world-famous relaxation destinations, yet I still covet what I don’t have. I guess when you want to retire in the Caribbean, the grass is always greener…

My wife and I have talked many times about where we would like to visit, or eventually retire to. Although I’m not ready to say I want to retire to an island yet, I would like to spend some time exploring different Caribbean locales to get a feel for what island retirement might be like. I plan on using this space to document and share my research, in case it might help you when you’re planning your own visit. I’m going to cover touristy/vacation-type of information here, since that is stage of life I’m currently in. The learnings I gain here will be used to plan future vacations, where I’ll be able to share more first-hand knowledge about the snowbird life in the Caribbean.

So, where can I go? The Caribbean can be divided into island groups called the Great Antilles and Lesser Antilles. The Lesser Antilles can then be divided into two (or three, depending upon who you ask) subgroups – the Windward Islands and Leeward Islands. I’ll focus on the destination islands, ignoring places that I probably wouldn’t want to travel to, such as Haiti.

Greater Antilles

Cayman Islands
Turks and Caicos
Dominican Republic
Puerto Rico

Lesser Antilles (Windward Islands)

U.S. Virgin Islands (St. Croix, St. John, St. Thomas, and other minor surrounding islands)
British Virgin Islands (Tortola, Virgin Gorda, Anegada, Jost Van Dyke, and 50+ other smaller islands and cays)
St. Maarten/St. Martin
St. Barthelemy
Antigua & Barbuda
St. Eustatius
St. Kitts & Nevis

Lesser Antilles (Leeward Islands)

St. Lucia
St. Vincent & the Grenadines
Trinidad & Tobago

The islands differ in their offerings and the cost to visit. In general, I have discovered the following:

Least Expensive:  Dominica, Dominican Republic, Montserrat, Saba, St. Croix (USVI)
Most Expensive:  Barbados, Virgin Gorda (BVI), St. Barthelemy, Parrot Cay (Turks & Caicos)
Beautiful Beaches:  Anguilla, Antigua, BVI, Cayman Islands, Dominican Republic, The Grenadines, Turks & Caicos, USVI
Fine Dining:  Antigua, Barbados, St. Barthelemy, St. Maarten/St. Martin
Shopping:  Cayman Islands, St. Barthelemy, St. Thomas (USVI)
Nightlife:  Aruba, Puerto Rico, Trinidad
Diving:  Bonaire, Dominica, Saba, St. Kitts, The Grenadines, Turks & Caicos
Golf:  Barbados, Curaçao, Dominican Republic, Jamaica, Nevis, The Grenadines
Eco-tourism:  Dominica, Guadeloupe, Jamaica, Puerto Rico, Saba, St. Eustatius, St. Kitts, Nevis, St. Lucia, St. Vincent
Family-friendly:  Jamaica, Puerto Rico, St. Kitts, Nevis, St. John (USVI)

Things to consider when visiting the Caribbean:

How to get there (logistics)
Where to stay (lodging)
What to do (experiences)
What to eat (dining options)
What to learn (history/culture)
Who will be traveling (kids & families)
When to go (seasons, including hurricanes)

If you do a quick search on the Internet, you’ll find enough “best of” Caribbean lists to keep you busy reading for a week. I’ve already done that research and created a simplified compilation of the top Caribbean experiences. Here is the Caribbean bucket list:

Birding:  Trinidad
Boating:  Grenadines, St. Martin
Caving:  Puerto Rico
Diving:  Bonaire, Dominica, British Virgin Islands
Eating:  St. Martin
Eco-tenting:  St. John
Golfing:  Barbados
Hiking:  Dominica, Cayman Islands, Grenada, Puerto Rico, St. Kitts, St. Lucia
Shopping:  St. Thomas
Snorkeling:  Cayman Islands
Surfing:  Barbados
Swim with rays:  Cayman Islands, Tobago
Tour a rum distillery:  Barbados, Jamaica, St. Kitts
View colonial architecture:  Puerto Rico
Whale-watching:  Dominican Republic, Turks and Caicos

Another Option

If Central America isn’t for you, but you enjoy the thought of being a snowbird in an international location, consider the option to snowbird in Mexico, or take a look at our snowbird in Central America summary. Maybe you’ll find some location ideas that better appeal to your lifestyle and interests.

Check back here often for updated links to my research related to retiring in the Caribbean.

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