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Explore the countries and island that make up the Caribbean with expert tips for an unforgettable journey
Published on 24 Jun 2025
A Caribbean cruise is often high on many travellers’ wish lists. Imagine sun-drenched days spent on soft, white-sand beaches, the soothing rustle of palm trees in the breeze, and taking a dip in the invitingly warm, turquoise waters. With a diverse range of islands and countries comprising this remarkable region, there is so much to see, do, and explore. Your dream holiday might involve wandering through the vibrant streets of Havana, admiring the breathtaking beauty of the iconic Pitons in St. Lucia, exploring the lush rainforests of Costa Rica, or beach-hopping in Antigua.
Many travellers wonder exactly which countries are part of this iconic region and which are the most captivating to visit by cruise. In this guide, we’ll take you on a journey through these fascinating locations, sharing travel tips to ensure you make the most of your adventure in paradise.
The Caribbean is a vibrant region located in the tropics, nestled between North and South America and bordered by the Caribbean Sea. It comprises a diverse mix of island nations and mainland countries with Caribbean coastlines, all sharing deep cultural, historical, and geographical ties. There are around 40 locations that are commonly considered to be part of the Caribbean region.
Caribbean territories are islands or island groups located in the Caribbean that are not sovereign nations, but are instead overseas territories or departments governed by other countries, such as the United Kingdom, France, the Netherlands, and the United States. Despite their political status, they are widely regarded as an integral part of the Caribbean region due to their geography, culture, and shared history.
For those craving adventure, ancient ruins, vibrant culture, and stunning beaches, a cruise to the Western Caribbean could be the perfect choice. Thrillseekers might choose to spend their days diving into the crystal-clear waters of Cozumel or Roatán, renowned for their world-class snorkelling and diving. Depending on your itinerary and cruise line, you may find shore excursions that feature visits to Mayan ruins at awe-inspiring sites like Chichén Itzá and Tulum, offering a glimpse into the region’s rich past. Prefer a slower pace? Opt for an itinerary that includes Grand Cayman or Jamaica, where laid-back island life and postcard-worthy beaches await.
By contrast, the Eastern Caribbean is best known for its pristine beaches, lush landscapes, and relaxed island-hopping charm. Unwind on the white sands of Antigua, explore the natural beauty of St. Lucia, or experience the vibrant culture of Barbados. This part of the Caribbean is ideal for watersports and sailing, with calm, crystal-clear waters, especially around the British and U.S. Virgin Islands. Altogether, the Eastern Caribbean offers an inviting and unforgettable escape for those seeking a more laid-back and scenic cruising experience.
Once you have chosen your ideal itinerary, it’s well worth spending a little time researching the ports of call. Learning more about each destination in advance allows you to personalise your trip to match your interests. You might discover charming local eateries, lively bars, or bustling markets just a short distance from the port. Doing your own research and uncovering these hidden gems help you make the most of every top, ensuring you don’t miss a moment of what makes each place special.
Cruise lines offer a wide range of shore excursions designed to help you make the most of every destination. Whether you’re drawn to water sports like snorkelling, kayaking, or paddleboarding, or prefer a guided tour of historical landmarks, there’s something for everyone. Adventurous travellers might choose to hike through lush rainforests, while food lovers can savour the flavours of local culture through immersive tasting experiences. With so many opportunities to explore, discover, and connect, shore excursions are a fantastic way to enrich your journey and create unforgettable memories.
For some, there’s nothing better than simply relaxing on board and soaking up the ever-changing scenery of the Caribbean. Sea days offer the perfect opportunity to unwind, you might choose to get lost in a good book, sip on a refreshing cocktail as you lounge by the pool, or take a blissful trip to the spa. For those craving a little enrichment, you might like to attend a fascinating lecture on the region’s history and cultural traditions. Or, if you’re feeling inspired, take part in a dance class, unleash your creativity in a water colour painting session, or explore the rich flavours of the Caribbean with a hands-on cooking demonstration.
When it comes to choosing the best time to cruise the Caribbean, it all comes down to what suits you. Whether you're looking for a winter escape from the chilly UK weather or a summer adventure in the sun, the Caribbean promises warm temperatures and sunshine all year round. The region experiences two main cruising periods: high season and low season. The high season, typically from mid-December to mid-April, is the most popular time to visit, offering the driest weather and a lively holiday atmosphere—ideal for those seeking classic Caribbean charm at its peak. Here’s a closer look at what the Caribbean offers in each season.
Winter is one of the best times to visit the Caribbean, offering warm, dry, and sunny weather. This period brings ideal conditions for beach days, sightseeing and outdoor adventures. This is the Caribbean’s high season, particularly from mid-December through to February. The weather is generally settled, with little rainfall and calm seas.
In spring, the Caribbean typically sees warm, pleasant weather with plenty of sunshine and lower levels of humidity compared to the peak of summer. March is a fantastic time to visit the Caribbean, offering some of the best weather of the year. It falls firmly within the high season, meaning dry, sunny days, low humidity, and pleasant temperatures. April is generally dry and sunny, especially in the northern and eastern Caribbean islands, making it a popular shoulder-season month. By May and June, temperatures begin to rise slightly and short rain showers become more common.
The Caribbean in July and August is hot, sunny, and full of energy. While this period falls within the low season, meaning fewer crowds and more relaxed shores, it also coincides with the early part of hurricane season. As a result, you may encounter brief tropical showers and the occasional storm, particularly in August. Still, many islands enjoy plenty of sunshine, and the season comes alive with colourful festivals and local celebrations, making it a lively and culturally rich time to visit.
Autumn is the quietest time of year in the Caribbean, largely due to the increased likelihood of rain and tropical storms. Despite this, temperatures remain consistently warm, often accompanied by high humidity and occasional afternoon showers. While September and October tend to be the wettest months, conditions begin to improve in late November, as the region transitions into drier, more settled weather, marking the approach of the high season once again.