The Art of Winter Escapism: Caribbean Islands with Character, Culture and Calm

When winter months feel long and unrelenting, the Caribbean islands, with their laid-back atmosphere, colourful architecture, picture-perfect beaches and warm (literal and metaphorical) welcome, are an obvious choice. Especially, as the area experiences its best weather — bright dry and comfortably warm days, with low humidity and little hurricane risk post-November. But, if you’re offput by all-inclusive resorts, mass tourism, or Caribbean cliches, know that these islands offer much more depth and diversity than the holiday brochures may communicate. It will likely mean an additional short-haul hop on a local airline, once you’ve landed in one of the larger islands’ airports. But the views afforded by these aerial trips are a mini adventure in themselves. Here are some of the best islands to explore, if your aim is to discover rich layers of character, culture and calm this winter season.

Dominica

Those wishing to immerse in ‘real’ Caribbean life should consider a stay on Dominica. With relatively few tourists, the island remains unhurried and oriented around the needs of locals, rather than visitors. Communities are tight-knit, traditions are strong, and the indigenous Kalinago culture is ever-present. Waterfalls, volcanoes, hot and cold springs (including the natural jacuzzi known as Champagne Beach) are waiting to be discovered, with horse riding treks, canyoning, river boat tours and tubing, popular with those travellers who make the journey to Dominica. Five-star accommodation here includes secluded treetop pool villas, refined ecolodges and a boutique spa resort with colonial-style architecture.

Puerto Rico

For Caribbean character, the pulsating capital of San Juan is hard to beat; alive with salsa, reggaetón, murals and street food. But just a few minutes away, in the quieter 16th-century Yoruban settlement of Loíza, you can experience the region’s African heritage with bomba music and local art — take a dance class, trek the mangrove forest, or visit the María de la Cruz Cave Historic Park. Or take a trip to Yauco for some java (Yauco is known as “El Pueblo del Café/Coffee Town” for its role in bean production) and to see some colourful Yaucromatic murals in the island’s large outdoor gallery. Along with caffeinated beverages, the pina colada is an integral part of the culture on Puerto Rico — you may like to stay a few nights at its birthplace, the Caribe Hilton.

Discover our favourite luxury hotels in Puerto Rico

Bonaire

If calm, low-key eco-tourism is your aim, venture just off the Venezuelan coast to the Dutch Caribbean. Bonaire brings a strong commitment to sustainability and a refreshingly uncommercial pace. The island is arguably best known for its exceptional marine life, with protected reefs that begin just metres from the shoreline, making it one of the Caribbean’s most respected diving and snorkelling destinations. Above water, Bonaire excels in conservation and community. Its flamingos (the island airport’s namesake) are a frequent, if surprising sight. And each winter sees the arrival of a month-long carnival with costumed parades and Tumba music. Accommodation styling tends toward small and simple, rather than sprawling, and days are quiet, relaxed and heavily immersed in nature.

Tortola

Tortola is the largest of the British Virgin Islands, a place of understated luxury that’s especially suited to sailing enthusiasts of all levels. Its mountainous interior gives way to sweeping bays and calm shores — a landscape alive with drama, and surprisingly unspoilt. An absence of large-scale resort developments and plenty of luxe villas make it a refuge for those seeking privacy. Tortola is also especially convenient for those visiting by yacht, with easily accessible anchorages. Those keen to learn more about BVI culture can explore the 1780 Lower Estate Sugar Works Museum, Fort Burt, Mount Healthy Windmill, Callwood’s Rum Distillery, J.R. O’Neal Botanic Gardens, Old Government House Museum and the VI Folk Museum.

Grenada

Known as the “Spice Island”, Grenada is home to two nutmeg museums and a bean-to-bar chocolate-making industry. It’s a destination often overlooked by mainstream tourists. But that may change in the near future, with premium brands such as Six Senses taking up residence on the isle, and direct flights from London. Now is therefore an optimum time to book a stay, with access to such high-end resorts becoming available, yet without the abundance of holidaymakers found in many of the more populated islands. Do take a dive to the Molinere Underwater Sculpture Park, see the sulphur springs and the Rainbow Eucalyptus tree (whose bark peels to reveal vibrant colours). And to disappear somewhere even more secluded, take a boat to the neighbouring Southern Grenadine islands of Carriacou or Petite Martinique.

Discover our favourite luxury hotels in Grenada.

Add to wishlist

Sign up for our newsletter for inspiration, exclusive previews & luxury tips