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The Caribbean’s long ribbons of sand and sparkling waters have always been one of our preferred winter sun destinations. But, with more than 700 islands plus numerous reefs and cays, choosing where to go can quickly become overwhelming.

Written by


Stella Matthew

Published on 12/05/2023

Multi-destination luxury cruises to the Caribbean have always been an excellent option for travelers who want to experience as many islands as time allows. By day, you’ll be relaxing with a rum punch and enjoying the archipelago's famed fun in the sun, while by night, you’ll be dining on first-class food, drinking vintage wine, and enjoying onboard amenities, as you drift toward your next sun-drenched destination. The best time to sail is from December to April, with the holiday period being one of the most festive (but also one of the busiest) times.

If you’re still struggling to decide where to go in 2024, here’s our list of the five Caribbean islands that deserve Crystal discovery.

Tortola offers great sailing and RIB experiences
Tortola offers great sailing and RIB experiences

Tortola, British Virgin Islands

Arriving at Tortola from the sea feels like arriving at a hidden gem in the Caribbean’s crown. It’s the archetypal Caribbean dream: turquoise waters, white sand beaches, and secluded coves with romantic names that invite swashbuckling adventure. No resorts can claim ownership of their beaches in the BVI, so the long ribbons of powdery sands are yours for the taking.

Despite being the largest, liveliest, and most developed island in the 60-strong archipelago, Tortola still has a sleepy feel. Tourists are mostly professional and amateur sailors who come here for the balmy winds and the spectacular coastline that has a magical feel when viewed from the sea; don’t hesitate to take a trip around the island. If you prefer your activities on dry land, there’s still plenty to do: the busy markets offer some of the most authentic shopping in the Caribbean while the streets are lined with beautiful 19th-century British Colonial architecture. For the more adventurous, don’t miss a trek through the rain-forested Mount Sage National Park for sweeping views of the island, possibly spotting your ship below.

Best for: sailing excursions

Jost Van Dyke
Jost Van Dyke's small size is perfect for relaxing the day away

Jost Van Dyke, British Virgin Islands

Another BVI beauty that deserves a mention. At just 8 km2 (3 square miles), this little island is the smallest of the four main British Virgin Islands destinations. However, due to its affluent clientele, it has a disproportionately large number of upscale bars and restaurants for its tiny size. These are mostly found nestled in the pretty horseshoe-shaped disembarkation bay, so if your idea of a perfect Caribbean idyll is pulling up a chair and sipping a local rum punch, then you won’t need to go much further than the appropriately named Belle Vue harbor.

The island is lapped by unfeasibly clear waters, which are not tidal, making them very attractive to both novice and experienced snorkelers and scuba divers. Take a trip to nearby Norman Island and plunge into the tropical waters, which teem with kaleidoscopic marine life, for a Caribbean experience that will leave you spellbound.

Best for: relaxing

Montserrat offers a fascinating taste of history
Montserrat offers a fascinating taste of history


Montserrat is an unusual destination for cruisers. Thus, as one of the lesser-visited islands, experiences are authentic, and welcomes are warm. The uncommonness of the island is due to the Soufrière Hills volcano's eruption in 1997, which devastated the south of the island and buried the then-capital Plymouth. Understandably, tourism was severely hit, and ongoing volcanic activity has significantly impacted the island's infrastructure and specific areas.

However, don’t let that put you off. The island has been open to tourism since 2021 and today offers one of the most authentic Caribbean experiences in the archipelago. Take a trip to the ‘Buried City’ of Plymouth, the Caribbean’s answer to Pompeii, to better understand the island's spirit.

Best for: history

French cuisine is widely found all over Les Saintes
French cuisine is widely found all over Les Saintes

Les Saintes, French West Indies

If you like your creole with un café et croissant s’il vous plait, look no further than Les Saintes. Located in the northeastern Caribbean Sea south of Guadeloupe, this nine-island archipelago is made up of seven smaller islands and two larger, inhabited ones. As one of France’s Departments d’Outre Mer, Les Saintes and its governing parent island, Guadeloupe, enjoy a very elegant ambiance. The native language is French (albeit a Creole version), payment is in Euros, and you would be just as likely to find baguettes and patisseries as you would sarongs and spices.

Les Saintes has an under-the-radar reputation, so visitors should not expect the urban charms of some of the bigger Caribbean islands. Instead, this paradise archipelago of the French West Indies is perfect for those looking for deserted beaches (avoid the famous Pain de Sucre beach if you want quiet), verdant landscapes, and a serene atmosphere. Take a culinary tour to sample a Tourment d’amour, a mouth-watering local delicacy made from a pastry base, covered with coconut jam, and topped with a delicious cinnamon-flavored genoise: pure foodie heaven and a superb souvenir for anyone lucky enough to visit.

Best for: food

St. Vincent has amazing marine life
St. Vincent has amazing marine life

St. Vincent and the Grenadines

Saint Vincent was once called Hairoun by the Carib Indians, meaning "land of the blessed," and you would be hard-pressed to find a more appropriate description. However, there is more to stunning natural beauty – of which there is much – to Saint Vincent and the Grenadines.

Even if you are not an underwater person, you cannot help but be mesmerized by the marine life that thrives in Saint Vincent’s warm waters. But it is not the psychedelic fish that is the biggest underwater pull for this little island, but rather the coffee table-sized, beautiful, greyish-green turtles that live in this part of the Caribbean Sea (some of which are believed to be around 200 years old). Saint Vincent and the Tobago Cays have long been a paradise for scuba divers and snorkelers, mainly because the island's south coast has been a protected Marine Park since 1987. This means diving enthusiasts can spy over 500 marine species, including 450 species of finfish, 12 species of whales and dolphins, four species of turtles, nine species of gastropods, 11 species of seaweed, and 30 species of coral reef in the shallow, secluded waters.

Best for: snorkeling and diving

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