Planning the perfect Caribbean Cruise & Stay holiday: Expert tips & guide

Caribbean cruise and stay holidays are a great solution for many jet-setters keen to make the most of the trip across the pond.

By opting for this type of package holiday, you can island-hop via ship – admiring the amazing shorelines from a distance and visiting multiple fabulous destinations without ever unpacking – before setting down roots in a hotel and exploring the hotspot on foot (or by snorkel, paddleboard, scooter… you get the picture).

If you’re new to cruise and stay, though, it can be tricky to know how to go about planning your getaway.

So, we’ve teamed up with the experts at boutique travel agency Paramount Cruises who shared their wisdom on the top tips and tricks to nailing your Caribbean cruise and stay holiday.

First things first, what is a cruise and stay holiday?

Cruise and stay holidays combine a traditional cruise with a hotel stay on land. Usually, the land-based portion takes place before or after your sailing, giving you more time to explore and relax in one destination.

Most Caribbean cruise and stay packages are fly-cruise itineraries, flying you from the UK to the embarkation point (most often Barbados, Miami, Orlando or San Juan) where you’ll begin or end your journey.

Why book a Caribbean cruise and stay holiday?

• More time to explore! You’ll get to stay longer in destinations like Barbados or St. Lucia, that might otherwise have been a fleeting stop on your itinerary.
• Ease and convenience: Cruise & stay packages often include flights, transfers, and hotels, with everything arranged for you by your travel agent.
• Great value for money: Cruise and stay deals often come with perks like drinks packages, tips, or excursions.
• Total relaxation: By starting your trip with a blissful beach break or ending it with time to wind down, you’re sure to feel fully refreshed before heading home.

– READ MORE: The fun-seeker’s guide to Barbados  –

When is the best time to cruise the Caribbean?

While year-round temperatures of 28C are guaranteed in the Caribbean, cruise season in the region generally runs from November to April, when it’s warm and dry – perfect for winter sun.

Hurricane season is from June to October, and though cruises still operate, there is potential for itinerary changes due to storms. It’s smart to travel during the shoulder season for lower prices, fewer crowds and good weather – November is often a sweet spot.

Which part of the Caribbean is best to cruise?

It’s an age-old question: which is better, a western or eastern Caribbean cruise? Well, the Eastern Caribbean is best for you if you prefer the beach and enjoy island hopping (guilty).

This part of the Caribbean hosts some of the most beautiful, tropical beaches in the world, including the U.S. Virgin Islands, the British Virgin Islands, St. Maarten and Antigua. What’s more, Eastern Caribbean ports are usually the best for duty-free shopping.

However, if you are interested in the history and flora and fauna at your ports of call, the Western Caribbean could well suit you better. Here you will be able to explore ancient ruins or tour a coffee plantation, for instance.

It’s worth considering holiday length, too. If you want a shorter cruise, the Western Caribbean usually offers four to five-night itineraries, whereas the Eastern Caribbean tend to have longer itineraries.

Southern Caribbean cruises provide a great mix of culture with beautiful scenery, with islands including Barbados, Grenada, St. Lucia and the ABC Islands (Aruba, Bonaire, Curaçao).

– READ MORE: 8 unusual Caribbean excursions with P&O Cruises –

What is the cheapest month to cruise the Caribbean?

Typically there are some great deals around September for the Caribbean; however, it does come with the risk of being in the middle of hurricane season.

Depending on cruise line promotions, you may find some great prices throughout other months of the year, so do shop around!

How much does a Caribbean cruise & stay cost?

There will be a cruise line out there for every budget. Those looking for a cheaper deal (i.e £1,200 – £2,000 pp all in!) should look out for the four-star cruise lines such as Royal Caribbean, NCL, Carnival or Princess, while those who want a touch of luxury can cruise with five or six-star lines such as Celebrity, Silversea, Regent Seven Seas or Seabourn.

The Paramount team is always able to advise on which cruise line will meet your needs, so feel free to give them a call to discuss your options – one of the many ways in which going with a travel agent makes things easier!

– READ MORE: Could this be the most affordable way to cruise the Caribbean? –

Is all-inclusive worth it on a Caribbean cruise and stay holiday?

Every cruiser will have a different view on value, but as a general rule, with all cruises being full board, those who do not drink a lot of alcohol may not see the value in an all-inclusive upgrade, while those who do indulge could make a significant saving by upgrading their cruise ahead of time.

Paramount recommends checking with its travel agents and doing some research to make sure you get the best value for your preferences. Also, do check how many days you will have at sea during your cruise as you will spend more onboard those days compared to a day in port.

– READ MORE: Could this be the most affordable way to cruise the Caribbean? –

Is it better to do the cruise before the hotel stay or vice versa?

Ah, the classic surf and turf dilemma – where to begin? This actually depends on the places the cruise is starting and finishing in; for example, if the cruise was to finish in a really exciting destination then it would be best to do your hotel stay after the cruise (just remember to conserve your energy!).

Top tip: When going on cruises starting in the far east, it can be wise to do your cruise stay both before and after the sailing – sometimes flights to and from these sorts of destinations will get you in late at night and therefore often don’t match up with the departing time of the cruise.

In short, when you do the hotel stay depends on the location you are sailing from and to, as well as flight times.

How do shore excursions work on a cruise and stay holiday in the Caribbean?

The Caribbean has so many different experiences to get stuck into when you visit each port, so booking shore excursions is a must if you want to try specific sights or activities such as the El Yunque Rainforest Drive or the Old and New San Juan City Tour in Puerto Rico.

Shore excursions organised with the cruise line can be most convenient as you can be sure you will always be back on the ship on time before it departs. Other advantages are meeting and spending time with fellow cruisers and enjoying inclusions such as transfers to and from the shore excursion.

However, if you prefer to explore different places at your own pace, then booking a shore excursion may not be for you. You might prefer to go it alone and benefit from the freedom to do and see what you want and go where you want without being hindered by a group.

– READ MORE: Could this be the most affordable way to cruise the Caribbean? –

Dos and don’ts for a Caribbean cruise and stay holiday

Do use a travel agent to help you pick the cruise line which meets your preferences. Everyone is different and, with so many different cruise lines sailing in the Caribbean, there will always be a line which works best for you.

Don’t rush. Take the time to think about what you want from your cruise, and the team at Paramount Cruises will be more than happy to help match you with the perfect cruise line.

Do book early, for the best choice of cabins, flights and hotels – especially if travelling around Christmas time or the school holidays.

Do balance your trip. If your cruise is port-intensive, consider a relaxing beach hotel stay. If your cruise has more sea days, pick a land stay packed with sightseeing.

Don’t hold back! Make sure you try out some local delicacies, visit a range of restaurants, cafes and bars, and fully experience the culture of the place that you are staying in.

Do create a list before your stay of everywhere you want to see and the places you want to go, so that you can make the most of your stay in the amount of time that you have.

– READ MORE: What’s actually included on Royal Caribbean? –