Retiring can mean going somewhere to do less — to be less active. And there’s nothing wrong with that — especially in the Caribbean, one of the most relaxing places on earth. But some people want a different level of activity for their retirement — they’re seeking a different energy. That’s where these places come in — they’re young, hip and off-the-beaten path — and this kind of positioning offers a totally different experience — a raw, thrilling, sometimes “frontier” type of existence. These are the coolest places to retire in the Caribbean.
St John, US Virgin Islands
A haven for artists, creative types, beach lovers and sailors, St John is an eclectic place with beautiful beaches, a massive national park system and a very artsy, funky vibe. It’s also in the US, meaning Americans simply have to buy a plane ticket and find a house. It’s not cheap, but you’re paying to be a part of a very unique community.
Rincon, Puerto Rico
One of the Caribbean’s surfing capitals, this is the Wild West of Puerto Rico, a hip, lush corner on the far west of the island. There’s a regional airport with JetBlue flights, the benefits of American regulation and laws, and real estate that’s very competitive for the Caribbean region.
Bocas del Toro, Panama
The hippest spot on the Caribbean coast of Panama, this is an adventurous destination for people who want to retire without sitting down. While it’s getting more expensive, there’s still a large portfolio of real estate available, particularly with waterfront. That, along with the fact that Panama has the most attractive retirement incentives in the region — including freedom from property tax, discounts on food and professional services and import incentives. And the cost of living is substantially lower than much of the Caribbean, too.
Cabarete
Sports like windsurfing, kitesurfing and other adventure activities draw a hip kind of traveler — that makes it a unique kind of active destination in the Caribbean, with a robust real estate offering and a lot of beachfront properties.
Bequia
Tucked far away in the heart of the Grenadines chain is a remarkable island with a diverse character. This is a place for artists, for adventurers, for those seeking a different kind of quiet. And as a former whaling community, Bequia has a special kind of New England feel in the middle of the Caribbean.
Bonaire
The coolest spot in the Dutch Caribbean is a bit like a small town that has its own island. It’s long been a haven for divers (rightfully so, this is the best place for shore diving in the Caribbean), and that’s created a mix of friendly, sea-loving people, a kind of beach colony with a common bond. The food scene here is also among the Caribbean’s best.
St Barth
For sheer coolness, it doesn’t get any cooler than St Barth, the ultimate tony Caribbean estate. It’s expensive, it’s hard to reach and it’s beautiful, but that’s precisely why people come here — to assure privacy, luxury and the feeling of exclusivity.
Roatan
Part of the Bay Islands chain on the Caribbean coast of Honduras, Roatan has long been a well-kept secret both for Caribbean travelers and retirees. That’s because it has long had a strong position of affordability, both for real estate and cost of living. It also has fascinating cultural mix of indigenous, Garifuna and foreigners from around the world seeking Caribbean tranquility.
Puerto Morelos
This little fishing village a short drive from both Cancun and Playa del Carmen is a lovely, charming town that’s increasingly drawn interest from expatriates for its close-to-the-beach lifestyle. It’s a place for beach, culture and a developing food scene, buoyed by the launch of the nearby Grand Residences resort.
Placencia, Belize
At the tip of a long, narrow peninsula off the Caribbean coast of Belize is Placencia filled with beaches. It offers great access to Belize’s incredible reef system, and its developed tourism sector has created a relatively easy, English-speaking retirement destination. This is a quiet place but one designed for active people. It’s also home to one of the Caribbean’s coolest new residential projects, Itz’ana.