If you’re thinking about booking a Caribbean cruise for some winter sunshine, choosing where to go can seem surprisingly complicated.

At first glance, Caribbean itineraries can look quite similar. Beautiful islands, warm weather and plenty of beaches. Start comparing cruises, however, and you’ll soon find Eastern, Western and Southern Caribbean itineraries, different embarkation ports, private islands and an enormous choice of places to visit.

So how do you choose the right Caribbean cruise?

Some islands are perfect if your idea of a great day involves little more than a beautiful beach and somewhere for lunch. Others offer rainforest, wildlife, historic towns, spectacular scenery and some brilliant shore excursions. There are ports where you can simply walk off the ship and explore, while elsewhere it pays to plan your day in advance.

The cruise you choose matters too. An itinerary with several relaxing sea days can feel completely different from one where you wake up somewhere new almost every morning.

Having cruised extensively around the Caribbean on a variety of cruise lines, I’ve experienced everything from busy island hopping itineraries to wonderfully lazy Caribbean sea days. The right itinerary really can make an enormous difference to your holiday.

This guide will help you understand the different Caribbean cruise regions, when to go, how to choose between the islands and what to consider before booking, so you can find the Caribbean cruise that suits you.

When Is the Best Time to Cruise the Caribbean?

One of the reasons the Caribbean is such a popular cruise destination is that ships sail there throughout the year. However, if you are looking for some winter sunshine, the months between December and April are particularly appealing.

This is generally the Caribbean’s drier season, with warm temperatures and lower humidity than you are likely to experience during the summer months. Rain is still possible, of course. This is the tropics, and a beautiful blue sky can suddenly disappear behind a passing shower.

The good news is that Caribbean showers are often short lived. The rain can arrive incredibly quickly, disappear just as fast and leave you with an amazing rainbow stretching across the sea.

Winter is also one of the busiest times for Caribbean cruising, with a huge choice of ships and itineraries. You’ll find everything from shorter cruises from Florida to longer voyages exploring the islands further south.

It is also a popular time to visit. Cruise fares can be higher around Christmas, New Year and school holidays, and some of the busiest Caribbean ports can have several ships visiting on the same day.

What About Hurricane Season?

The Atlantic hurricane season officially runs from 1 June to 30 November, with activity typically peaking between August and October.

That doesn’t mean you cannot cruise the Caribbean during these months. Cruise ships can alter their routes when severe weather threatens, so ports may be changed or missed to keep the ship away from affected areas.

You simply need to be more flexible. If visiting a particular island is the main reason you have chosen your cruise, hurricane season may not be the best time to travel because itineraries can change.

Is Winter a Good Time for a Caribbean Cruise?

For many travellers, absolutely.

If you are looking for warm weather during the British winter, a huge choice of ships and itineraries and plenty of opportunities to spend your days outside, it is an excellent time to cruise the Caribbean.

The next decision is which part of the Caribbean to choose.

Eastern, Western and Southern Caribbean itineraries can offer surprisingly different holidays, so understanding the differences between them is a very good place to start before you book.

Eastern, Western or Southern Caribbean: Which Should You Choose?

One of the first things you’ll notice when comparing Caribbean cruises is that itineraries are often described as Eastern, Western or Southern Caribbean.

Those labels can make the itineraries sound fairly interchangeable. They aren’t. The region you choose can have a big impact on the islands you visit, what you can do ashore and how much time you spend at sea.

What Is an Eastern Caribbean Cruise?

Eastern Caribbean itineraries commonly include islands such as St Maarten, St Thomas, Puerto Rico and the British Virgin Islands, although the exact ports vary between cruise lines.

This can be a particularly good choice if beautiful beaches are high on your wish list. You’ll also find plenty of opportunities for boat trips, snorkelling and exploring smaller islands.

What Is a Western Caribbean Cruise?

Western Caribbean cruises often combine destinations such as Mexico, Grand Cayman, Jamaica and Belize.

These itineraries can be a great choice if you want to mix beach days with more active sightseeing. Depending on your ports, you might have opportunities to visit Mayan ruins, explore caves, snorkel or head inland rather than spending every day beside the sea.

It is worth looking beyond the destination names when comparing cruises. Two Western Caribbean itineraries can offer very different experiences depending on the individual ports and how long your ship spends in each one.

What Is a Southern Caribbean Cruise?

Southern Caribbean itineraries venture towards islands such as Aruba, Curaçao, Bonaire, Barbados, St Lucia and Grenada.

If you have cruised the Caribbean before, this is where you can start finding some really interesting itineraries and a greater variety of islands.

These cruises can also be more port intensive. Depending on where your cruise begins, you could visit a different island on several consecutive days, which is wonderful if exploring is your priority.

The distances involved mean Southern Caribbean cruises can be longer when sailing from Florida. Alternatively, some cruises begin in ports such as Barbados or Puerto Rico, allowing you to reach the southern islands more quickly.

So Which Caribbean Region Is Best?

There really isn’t one Caribbean region that is best for everyone.

If beaches and easygoing island days are your priority, an Eastern Caribbean itinerary may appeal. If you want to combine beach time with history, adventure and more varied excursions, look closely at Western Caribbean options. If your priority is visiting lots of different islands, particularly if you have cruised the Caribbean before, the Southern Caribbean can be particularly tempting.

My biggest tip is not to choose purely because an itinerary says Eastern, Western or Southern Caribbean. Open the actual itinerary and look at every port individually. That is where you begin to see whether the cruise really suits you.

How Do You Choose the Right Caribbean Cruise Itinerary?

Once you start comparing individual itineraries, it can be tempting to assume that the cruise visiting the most islands offers the best value. However, more ports do not necessarily mean a better Caribbean cruise.

Think About How Many Sea Days You Want?

Sea days can sometimes look like empty spaces on an itinerary when you are comparing cruises online, however they are an important part of the holiday.

If you are choosing a ship with fantastic pools, restaurants, entertainment or other facilities, a sea day gives you time to enjoy everything onboard without feeling that you should be ashore.

If exploring the Caribbean is your priority, an itinerary visiting five or six islands may appeal far more than one with several days at sea.

Think about the pace you actually enjoy. Waking up somewhere new every morning sounds wonderful, however several consecutive port days can be surprisingly tiring.

Look at How Long You Have in Each Port

Don’t just look at where the ship goes. Look at when it arrives and leaves.

A long day in port gives you much more freedom, particularly if you want to take a boat trip, travel across an island or combine sightseeing with some time at the beach.

A shorter visit can still be brilliant if the port is easy to explore, however it may limit what you can comfortably fit into your day.

This is particularly useful when comparing two cruises with similar itineraries. One might visit exactly the same island while giving you several more hours to enjoy it.

Don’t Assume You Need an Excursion in Every Port

One of the joys of Caribbean cruising is that your days ashore can be completely different from one another.

You might book a boat trip on one island, spend the next day exploring independently and then decide that all you want from the following port is a taxi to a beautiful beach.

Booking a full day excursion in every destination can quickly make the cruise both tiring and expensive.

Before booking excursions, find out what there actually is to do close to the ship. Some Caribbean ports are much easier to explore independently than others.

Look Beyond the Famous Islands

A recognisable island name can make an itinerary immediately attractive, however some of your favourite days may end up being somewhere you knew very little about before you arrived.

This is where researching the individual ports really pays off.

A smaller island might offer an incredible beach, a memorable boat trip or a much quieter day than one of the Caribbean’s busiest cruise destinations.

Consider the Ship as Well as the Islands

This is particularly important in the Caribbean because you are likely to spend a considerable amount of time outside onboard.

Look at the pools, outdoor decks and places where you can sit with a view. If your itinerary includes several sea days, these become even more important.

The right Caribbean cruise is really a combination of the ship and the itinerary.

A fantastic ship won’t necessarily compensate for an itinerary that doesn’t interest you. Equally, six wonderful islands won’t necessarily make up for choosing a ship that doesn’t suit the way you like to travel.

The sweet spot is finding a cruise where you’re excited about both.

Which Caribbean Islands Should You Choose?

One of the hardest parts of choosing a Caribbean cruise is deciding which islands you actually want to visit. They can look deceptively similar when you are scrolling through itineraries, however the experience ashore can be completely different from one island to the next.

Rather than simply looking for the itinerary with the most recognisable names, think about what you actually want to do when you get there.

If You Want Beautiful Beaches

You are certainly not going to struggle to find a beach in the Caribbean, however some islands make a beach day particularly easy.

Anguilla is a wonderful example. Its beaches are absolutely beautiful, with powdery pale sand and incredibly clear Caribbean water. If your cruise offers an excursion across to Anguilla, it can be a fantastic way to spend the day.

Jost Van Dyke in the British Virgin Islands is another brilliant choice if your idea of the Caribbean involves sand, sea and very little rushing around. White Bay is home to the famous Soggy Dollar Bar and is exactly the sort of place where the journey there can be as much fun as the destination.

If You Want Dramatic Scenery

St Lucia is one of those islands where it is worth looking beyond the nearest beach.

The Pitons give the island one of the Caribbean’s most recognisable landscapes, and exploring more of St Lucia can give you a completely different day from simply heading to a stretch of sand.

This is a good example of an island where researching excursions before you arrive can really pay off.

If You Want a Memorable Cruise Line Experience

Sometimes the island isn’t the only reason a particular day stands out.

On Seabourn, Caviar in the Surf at Carambola Beach in St Kitts turns a Caribbean beach day into something rather unusual. The crew wade into the water to serve Champagne and caviar while guests gather in the sea.

It is a good reminder to look at what your cruise line offers in the Caribbean, rather than judging an itinerary entirely by its list of ports.

If You Want More Than Beaches

Not every Caribbean day needs to involve a sun lounger.

Depending on the island, you can find colourful towns, historic sites, rainforest, wildlife, local food and plenty of opportunities to explore inland.

This is where shore excursions can be particularly worthwhile. An island may look small on a map, however reaching some of its most interesting places can involve a surprisingly long drive.

Don’t Dismiss an Island You’ve Visited Before

Seeing the same port on another itinerary isn’t necessarily a reason to reject the cruise.

One of the advantages of returning to a Caribbean island is that you don’t feel the same pressure to see its major sights. Your first visit might involve a full day excursion, while your second could be spent finding a beach, taking a boat trip or simply wandering somewhere independently.

You can have two completely different days on the same island.

And that is worth remembering when you compare itineraries. You aren’t really choosing a list of Caribbean islands. You’re choosing what you could do on each of those days.

Caribbean Shore Excursions or Exploring Independently?

You certainly don’t need to book a cruise line excursion every time you step ashore in the Caribbean.

In fact, some of the best Caribbean days can be remarkably simple. Find a taxi, head to a beautiful beach, agree a time for your driver to collect you and spend a few hours swimming, having lunch and enjoying the sunshine. Other islands reward a little more planning.

When Is a Cruise Line Excursion Worth Booking?

A cruise line excursion can make sense when you want to travel a significant distance from the ship, take a boat trip or visit somewhere where transport is more complicated.

There is also one important advantage. If an official cruise line excursion is delayed, the ship knows where you are and will make the necessary arrangements. When you arrange your own day ashore, it is your responsibility to be back onboard in time. That doesn’t mean you should be nervous about exploring independently. Simply allow plenty of time and know your ship’s all aboard time, not just its departure time.

You Don’t Have to Spend a Fortune Ashore

Shore excursions can quickly add a considerable amount to the cost of a Caribbean cruise, particularly if you are travelling as a couple or family and booking something in every port. Mixing things up can work really well.

Spend money on a special boat trip or excursion somewhere you particularly want to explore, then have a much cheaper independent beach day at your next port.

You can also simply walk around some destinations, stop somewhere for a drink or lunch and return to the ship whenever you are ready. Every port day doesn’t need to be packed with activities.

Check Where Your Ship Actually Docks

This is worth researching before you sail. Seeing the name of an island on your itinerary doesn’t necessarily tell you how easy it will be to explore. Some ships dock within easy reach of shops, bars and places you can wander independently. Other calls may involve a tender, a more isolated cruise terminal or a taxi ride before you reach somewhere you actually want to spend the day.

Knowing this in advance makes it much easier to decide which ports deserve some of your excursion budget and which could become your inexpensive days ashore.

Be Sensible With Independent Tours

If you book independently, check reviews, understand exactly where you are meeting your guide and leave a generous margin for getting back to the ship. I would never plan an independent excursion that gets you back to port only minutes before all aboard. Saving money is lovely. Watching your cruise ship sail away without you really isn’t.

How Much Does a Caribbean Cruise Cost?

The good news is that Caribbean cruising can suit a surprisingly wide range of budgets.

You can certainly spend a considerable amount on a small ship or luxury cruise line, however you absolutely don’t need to. Larger mainstream cruise ships can offer some cracking entry level options, particularly if your priority is winter sunshine and exploring the islands rather than having lots of extras included in your fare.

Look at Mainstream Cruise Lines for Good Value

For UK travellers, P&O Cruises is particularly worth considering. It offers Caribbean fly cruises as well as longer cruises sailing from Southampton, so there are options even if you would rather avoid flying altogether.

A fly cruise gets you into the Caribbean much more quickly, giving you more of your holiday to spend exploring the islands. Packages that include your flights and transfers can also make getting there considerably easier.

Compare What Is Actually Included

The cheapest advertised cruise fare isn’t necessarily the cheapest holiday. When comparing cruises, look at what you are likely to spend once onboard. Drinks, speciality dining, WiFi, gratuities, excursions and transfers can all make a substantial difference to the final cost.

Equally, don’t assume a more expensive cruise offers poor value. Premium and luxury cruise lines may include considerably more in the fare, and smaller ships can sometimes visit ports that the largest ships cannot. The important thing is to compare the holiday you are actually getting for your money, rather than simply comparing the headline price.

A Caribbean cruise can certainly be a luxury holiday, however it doesn’t have to be one. There are options at very different price points, which is one of the reasons the Caribbean can work just as well for a first cruise as it does for someone looking for something rather special.

Fly Cruise or Sail to the Caribbean From the UK?

For UK cruisers, one of the biggest decisions is whether to fly straight to the Caribbean or choose a longer cruise sailing from the UK.

Neither is necessarily better. They simply suit different travellers and different amounts of annual leave / time off.

Why Choose a Caribbean Fly Cruise?

If your annual leave is limited, flying is the easiest way to maximise your time in the Caribbean.

Instead of spending several days crossing the Atlantic in each direction, you can arrive in the region and begin exploring almost immediately. This makes a two week Caribbean cruise much more achievable if you don’t have several weeks available for your holiday.

Fly cruises can also offer wonderfully port intensive itineraries. If your cruise begins somewhere such as Barbados, you could find yourself visiting a different island on several consecutive days.

The downside, of course, is the long haul flight. I would also always recommend arriving at least a day before your cruise if your flights aren’t part of a cruise line package. It gives you some breathing room if anything disrupts your journey.

Why Choose a Caribbean Cruise From Southampton?

If you have more time available and enjoy sea days, sailing from the UK can be a very appealing alternative.

There is something rather lovely about boarding your ship in Southampton during the British winter and gradually feeling the temperature rise as you sail south.

The Atlantic crossings become part of the holiday, giving you plenty of time to enjoy the ship before and after a much busier period of island hopping once you reach the Caribbean.

If airports are something you would happily avoid, there is an obvious appeal too. You board in Southampton and your holiday begins immediately, without a long haul flight at either end.

Don’t Expect Caribbean Weather From Southampton

This sounds obvious, however it is worth remembering when you pack. A winter cruise from Southampton won’t suddenly become tropical the moment you leave the English Channel. The first and last few days can be cool, and conditions on the Atlantic can feel very different from the warm Caribbean weather you are travelling towards.

Pack for both parts of the journey. You will want layers for those cooler sea days as well as all your Caribbean clothes.

Which Is Right for You?

Think about time as well as price. If you have around two weeks available and want to spend as much of that time as possible in the Caribbean, a fly cruise will probably make more sense.

If you have several weeks available, enjoy sea days and love the idea of avoiding airports altogether, sailing from Southampton can turn the journey itself into a significant part of your holiday. For UK cruisers, having the choice of both is one of the Caribbean’s great advantages.

What Is a Caribbean Cruise Actually Like?

A Caribbean cruise has a very different feel from cruising somewhere such as Alaska, Norway or the polar regions.

Much of the holiday happens outdoors. You might have breakfast on deck as you sail towards another island, spend the afternoon swimming or exploring ashore and still be sitting outside long after the sun has gone down.

Wake Up Somewhere Different

One of my favourite things about Caribbean cruising is waking up, opening the curtains and discovering a completely different island outside. Ships often arrive early in the morning, so try watching the sail in at least once during your cruise. Depending on the island, you might approach a colourful waterfront town, a lush mountainous coastline or a harbour filled with small boats.

And you don’t need to be first off the ship every morning. If you haven’t booked an early excursion, you can enjoy breakfast and let the initial rush disappear before heading ashore.

Staying Onboard in Port Can Be Brilliant

If you have already visited an island or simply fancy a quieter day, staying onboard can be a lovely option.

When most passengers head ashore, the pools and outdoor decks can become wonderfully peaceful. You can enjoy the ship while it is quiet and still head ashore later if you change your mind.

Enjoy the Evenings Outside Too

The Caribbean isn’t only about what you do during the day. Warm evenings are one of the loveliest parts of cruising here. Rather than automatically heading inside after dinner, take a walk around the outside decks, find somewhere to sit with a drink or simply watch the lights of an island disappear as you sail away.

That feeling of spending so much of your holiday outside is one of the things that makes a Caribbean cruise feel completely different from a winter cruise closer to home.

Don’t Expect Every Day to Look Like a Postcard

The Caribbean is beautiful, however that doesn’t guarantee uninterrupted blue skies every day. You may have cloud, wind or one of those sudden tropical downpours. Caribbean showers can disappear almost as quickly as they arrive, and sometimes you get that amazing rainbow afterwards.

Perhaps the best thing about a Caribbean cruise is the variety. One day can involve snorkelling or a boat trip, the next exploring an island, and the following day doing very little at all. You can make a Caribbean cruise as busy or as relaxing as you want it to be.

What Should You Pack for a Caribbean Cruise?

Packing for a Caribbean cruise is generally straightforward, however a few things can make your days ashore much more comfortable.

You’ll spend plenty of time moving between strong sunshine, air conditioned interiors, beaches, boats and restaurants, so pack for all of them.

Take Sun Protection Seriously

Caribbean sunshine can be much stronger than it feels, particularly when a lovely sea breeze is keeping you cool. Take high factor sunscreen, sunglasses and a hat, and remember to reapply sunscreen after swimming.

It is also worth checking the sunscreen rules for the individual islands on your itinerary. Some Caribbean destinations have restrictions on particular sunscreen ingredients to help protect their marine environment.

Pack Something to Cover Up With

A lightweight shirt, kaftan or cover up is incredibly useful. You can throw it over your swimwear when you leave the beach, use it to protect your shoulders from the sun and keep it with you for heavily air conditioned spaces onboard.

If you are visiting churches or religious sites, check whether you need to dress more conservatively too.

Take Comfortable Shoes

Flip flops are perfect for the pool and beach, however don’t make them your only footwear. Caribbean port days can involve far more walking than you expect, particularly if you are sightseeing. If you have booked an excursion involving hiking, waterfalls or other adventurous activities, check the footwear requirements before leaving home.

Take a Small Bag Ashore

A small backpack or beach bag is useful for sunscreen, water, your camera and anything else you need during the day. A waterproof pouch or small dry bag can also be useful for boat trips and beach days, particularly for keeping your phone and other essentials dry.

Don’t Forget Insect Repellent

Mosquitoes can be a nuisance, particularly around vegetation and around dawn and dusk. Insect repellent takes up very little room in your luggage and is worth having with you even if you don’t need it every day.

What Should You Wear in the Evening?

This depends much more on your cruise line than the Caribbean itself. Some ships are very relaxed in the evenings, while others have formal or elegant nights and restaurants with particular dress requirements. Check your cruise line before you pack. Also do not assume you will always be warm! Restaurants and theatres can be surprisingly cool with the air conditioning, so a light layer can be useful even in the Caribbean.

Sailing From Southampton?

Remember that you are packing for two very different climates. If you are sailing from Southampton during winter, you’ll need warmer clothes for the first and last few days of your Atlantic crossing as well as everything you need once you reach the Caribbean.

Things to Know Before Your First Caribbean Cruise

A Caribbean cruise is a relatively easy holiday, however there are a few practical things worth knowing before you go.

Don’t Assume Every Island Uses US Dollars

US dollars are widely accepted in many Caribbean destinations, particularly in areas regularly visited by cruise ships, however the Caribbean is made up of different countries and territories with different currencies.

Check the individual islands on your itinerary before you travel. If you plan to use taxis, visit smaller businesses or buy something at a beach bar, carrying some cash in small denominations can be useful.

Agree Your Taxi Fare Before You Leave

Taxis are one of the easiest ways to explore many Caribbean islands independently. Before setting off, confirm the fare with your driver, which currency you are paying in and whether the price is per person or for the whole vehicle. If you want your driver to collect you later, agree a time and meeting point too.

Always Check Ship Time

Your phone may automatically change time zones when you arrive at a new island. Your ship’s clocks may or may not.

Your cruise line will tell you whether you need to follow ship time or local time. Always use the time specified by your ship and make a note of the all aboard time before heading away from the port.

Watch Your Mobile Roaming

Don’t assume your normal mobile allowance will work throughout the Caribbean. You can move between several different countries and territories during a single cruise, and roaming charges can vary considerably between them.

Check your provider before travelling and be particularly careful when you’re at sea. Your phone can connect to a maritime mobile network, which may be considerably more expensive than ordinary roaming ashore. If you want to stay in touch with back home, it may be worth considering an esim.

Check How Many Ships Are in Port

Some of the Caribbean’s most popular ports can become very busy when several large cruise ships arrive on the same day. It can be worth checking the port schedule when planning an independent day ashore. If several ships are visiting, popular beaches and attractions may be considerably busier than you expect.

Sometimes travelling a little further from the cruise terminal or choosing somewhere less obvious can give you a completely different experience.

Check Your Entry Requirements

A Caribbean cruise can visit several different countries and territories in a single holiday, so don’t assume the same entry requirements apply everywhere. Check the requirements for your nationality and every destination on your itinerary before travelling, including any passport validity or visa requirements that apply to you.

Is a Caribbean Cruise Worth It?

If you are looking for winter sunshine, a huge choice of ships and the opportunity to visit several very different destinations without repeatedly packing and unpacking, a Caribbean cruise is difficult to beat. One of its biggest advantages is choice.

You can choose an affordable mainstream cruise, a huge resort style ship packed with things to do, something smaller and more intimate or a luxury cruise with more included in the fare.

Who Is a Caribbean Cruise Best For?

A Caribbean cruise is particularly appealing if you enjoy warm weather, being outdoors and having plenty of choice over how you spend your days.

It can be a great option for a first cruise because there is such a wide choice of ships, itineraries and prices. It also works brilliantly if you have cruised the Caribbean before because returning doesn’t necessarily mean repeating the same holiday. You can choose different islands or experience familiar ones in a completely different way.

Is a Caribbean Cruise for Everyone?

Perhaps not. If you prefer cooler destinations, dramatic scenic cruising or holidays centred around spending long days exploring historic cities, another cruise region may suit you better.

Some of the larger Caribbean ports can also feel busy when several ships are visiting at once, which makes researching the individual ports particularly worthwhile. Ultimately, a Caribbean cruise is worth it if the itinerary and ship suit the way you like to travel.

Final Thoughts on Choosing a Caribbean Cruise

The Caribbean isn’t one destination, and perhaps that is the most important thing to remember when choosing your cruise.

Start with the amount of time you have and your budget. Decide whether you want to fly or sail from the UK, think about how many sea days you enjoy and then look closely at the individual islands rather than choosing purely because an itinerary is labelled Eastern, Western or Southern Caribbean.

Don’t assume you need the most expensive ship, the longest list of ports or an excursion booked for every day. The right Caribbean cruise is simply the one that gives you the combination of ship, islands and experiences that suits you.

There is something rather wonderful about waking up, opening the curtains and finding another Caribbean island waiting outside. If you are booking now for some winter sunshine, choosing which one you want to wake up to is a rather lovely problem to have.