The lure of a Caribbean all-inclusive holiday is one many of us not only dream about, but one in which positive action can support aspiration by setting aside some travel money and planning for what you would expect to be the trip of a lifetime.

But how can you make sure that your first Caribbean experience lives up to everything you dreamt it to be?

In this article I share some of my favourite and practical tips and advice for making the most out of your first all-inclusive Caribbean experience.

Does all-inclusive really mean all-inclusive?

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All-inclusive can mean many things to many people as well as differ in application between all-inclusive providers. When finalising your first Caribbean travel arrangements it is important to fully clarify what is and is not included as part of the standard all-inclusive offering.

Tips for choosing the best all-inclusive Caribbean holiday options:

Tip 1 – Check the location of the hotel in relation to the included benefits. Many hotels may be a substantial travel to some of the included excursions as well as restaurants within the deal. Being clear about the associated distance and ease of travel between your resort and the associated inclusive offerings can make a big difference between expected value of the package and actual benefits derived.

Tip 2 – Identify who the deal caters for. In the Caribbean there are some very distinct all-inclusive audience targeting including families and adult only experiences. At the point of booking make sure that you are the intended target demographic otherwise you may find a complete disparity between what you were hoping to enjoy on your luxury getaway and what is actually available.

Tip 3 – Check out the variety of included food. Free (included) food and drink is without doubt one of the biggest lures of the all-inclusive offering however, if the inclusive food is restricted to one or two buffet locations, it is unlikely that the food enjoyment will remain throughout your two week plus stay. Consider menus, food variation and more, as eating will likely form a large part of your stay.

Tip 4 – Compare everything! The Internet is a wonderful thing, and it certainly comes to the fore when it comes to comparing product and service offerings. When you know what you want and have a refined list of sites providing it, take the extra step to use comparison sites so that you do not fell short-changed when it comes to committing to pay for your luxury holiday. Booking off peak can also provide lots of potential savings opportunities but do be aware of hurricane season!   

According to the Telegraph:

“It makes good sense to book all-inclusive hotels as part of a package: the overall cost of the holiday may well end up cheaper, and you get financial protection. Some all-inclusives are exclusive to a particular tour operator, but most can be booked by multiple operators, so shop around for the best deals.”

Why you should pre-book everything…

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The more you plan before your break, the less you need to think about while you are away.

Pre-book as much as you can as early as you can. Pre-booking can provide you with discounted costs as well as more savvy spending (the sun can have a strange impact on the wallet with last minute purchases and holiday spending).

You can often build up your all-inclusive provision to cater for more exhaustive areas like holiday trips, excursions, and even gifts!

According to Elite Island Resorts UK you can pre-book pretty much everything, including your health and fitness needs:

“You can easily maintain your fitness routine on holiday with well-equipped gyms that feature Cybex cardio and weight training machines, plus free-weight equipment. Group exercise classes are offered for everything from Caribbean dancing to beach yoga and pool water aerobics.”

Acknowledging the culture

Caribbean holidays set idyllic expectations and in order for your holiday to meet them it is useful to include in your travel planning, understanding of the country specific culture as well as more localised nuances too.

One of the things that crops up quite often as an example of this, is whether you should tip or not when you are eating and drinking all-inclusive. To answer this one, it will depend on the restaurant in question. Take a look at the eateries websites who are included in your inclusive offering prior to dining out to save any awkward moments.

Other related items to consider include:

– Don’t take for granted that all food and water and created equal. According to the State Department, diseases caused by food and water are the leading cause of illness in travellers to the Caribbean.

– Caribbean travel facilities (including items like cruises) can be seasonal. To avoid disappointment, ensure that you factor in the time of year you are traveling.

– Mobile phone signal and coverage may vary from place to place (especially if island hopping) so you may want to have back up plans in place for meeting places and times for friends and family.

– The Atlantic hurricane season tends to start in early summer (June) and can run through until the end of the year (November time).

– Specific areas and Islands can have very distinct micro cultures and tourist expectations. An area related to adult entertainment and targeting the 18-30s will have very different tourist behaviour expectations to one based on historical culture and tradition.

Caribbean Island-hopping advice

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From the Northern shores in Jamaica through to the beautiful beach destinations in Turks and Caicos, the Caribbean Islands offer beauty plus entertainment, and everything in between. Here are a few island hopping tips which can help to maximise your experience, regardless of budget.

As stated by Ordinary Traveler:

“One of the most popular ways of traveling to the Caribbean is by cruise line. Commercial cruise ships offer a way to visit multiple islands on a single trip and, with included food, lodging, and activities, can be an economical way of seeing the islands.

However, if you’re looking for a less tourist-y experience, or are hoping to spend more than a single afternoon at each port of call, don’t worry—it’s very possible to fly to most of the larger islands on American Airlines or JetBlue. If you have a group of adventurous friends, you can even rent a yacht complete with captain and cook to sail from island to island.”

One of the driving forces behind hopping between Caribbean Islands is the fact that each island brings with it something new and contrasting to your travel experiences. Some islands will be rich with history, plantations, and traditional forts, whilst others will display nautical offerings and experiences.

One thing that can be guaranteed is that the cuisine will always offer something exciting ranging from fruit wines and local beers and distilleries, to seafood, sugar cane and tropical fruits.

Here are some top island-hopping tips:

Tip 1 – Add food tours to your travel plans. This is a great way to sample lots of foody experiences and will likely make your restaurant decision making much easier.

Tip 2 – Keep an eye on local weather changes. Local climates change fast in the Caribbean so be agile with your island-hopping plans, and factor in some entertainment based contingency plans for last minute weather updates.

Tip 3 – Take local transport when you can. Budgets can easily get stretch when moving from destination to destination, so minimising travel spend can make a big difference to your holiday budgeting. Most islands have very reliable taxi services and resorts can usually provide transportation services and advice for safe, quick and lower cost travel. By saving on the journey costs between destinations you can spend more experiencing them!

What are the best islands to visit in the Caribbean?

Well based on The Cray Tourist advice the top 10 are:

  1. Jamaica
  2. Turks and Caicos
  3. Lucia
  4. Cuba
  5. Antigua and Barbuda
  6. US Virgin Islands
  7. Aruba
  8. Dominican Republic
  9. Grenada
  10. The Bahamas

Travel safety tips and advice

As with any travel abroad there are important safety considerations that are worth keeping in mind – some you might find quite surprising that are directly applicable to the Caribbean (including the fact that you cannot go topless or nude on most Caribbean Islands).

Alpha Travel Insurance state:

“Travelling to this exotic part of the world with travel insurance is essential. The Caribbean is home to some of the most expensive medical treatment facilities; should you fall ill or injure yourself whilst on holiday you could end up with a medical bill higher than the cost of your trip. With travel insurance, this can be covered.”

Some of the ‘Do-not’ advice from Active Caribbean include DO NOT:

– Stand under ‘Manchineel trees’ when it rains. Any Caribbean local will be able to tell you that the Manchineel tree is one of the most poisonous in the world. It is often located near and on coasts, and they contain strong toxins which can cause the skin to blister

– Go out wearing your swimwear in the shops or the streets, as it can often be looked down upon

– Be tempted to touch, remove, play with, or damage coral when you are snorkelling or diving. It is massively important to protect coral

– Travel wearing camouflage design and patterned clothing, it is seen as offensive on a number of the Caribbean islands

– Decide to go diving or snorkelling when you are wearing jewellery. Not only does this avoid any loss of expensive jewellery but, shiny objects look similar to silver fish. This can often attract unwanted attention from some Caribbean fish like barracudas

Final thoughts…

The all-inclusive Caribbean can mean many things to different holiday goers and providers alike, so it is important that you effectively demystify, plan and book as much as you can well in advance of your actual trip.

Some factors we discussed to consider include:

– Distinct Islands culture and offerings

– Safe travel tips

– Seasonal changes including hurricane season

Wherever you plan to go in the Caribbean, travel safe, make the most out of every experience and feel free to share your experience here!

Image credits:

Images included within this post are commercially free licenses at


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Lee Wilson – Head of Enterprise SEO, Vertical Leap.

Lee has worked with many travel industry companies spanning the past 15 years and has been leading marketing teams since the early 2000’s. He currently heads up the SEO department for a UK top 10 leading search marketing and digital agency (Vertical Leap).

Lee recently had his first solely authored industry book published ‘Tactical SEO – the theory and practice of search marketing’, and can often be found writing about digital marketing, business strategy, and other associated topics online.


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