Visiting The Caribbean? Here’s How To Plan An Epic Trip

It’s finally happening – the vacation of a lifetime. You’ve wanted to hit up the Caribbean ever since you saw the photos on TV as a kid. Ever since you’ve been scrimping and saving to get there one day, and it’s about the happen. Gosh, you must be speechless right now?!

Sadly, there isn’t time to reflect on the personal journey because there’s an actual one you need to plan. Turning up on an island in the middle of the sea sounds cool, yet it’s a risk. Considering you only have a few weeks and have spent a lot of money, it’s essential that the vacation lives up to the pipedream.

To do that, you need proper, thorough planning. Why risk the holiday going belly-up when you can account for every little detail? Don’t worry because it isn’t as stressful or energy-sapping as it seems. All you need to do is consider a couple of things beforehand. Here are the questions to ask well in advance.

Who’s Going?

The first thing to do is to figure out who is coming along for the trip. Do you want to do a couples thing, or are you more bothered about bringing the family? Perhaps you want to do it alone and experience some quality “me” time? Whatever you choose, make sure you know the numbers before you book.

Firstly, not having a handle on the people who are coming is dangerous from a budget point of view. You might have been saving for a while, but the Caribbean has a way of soaking up cash in the blink of an eye. Also, the clientele will decide where you stay, what you do, and what happens on vacation in general. There’s no reason to stay in a family-friendly hotel if the kids aren’t allowed.

What you have to do is decide what you want from the holiday. If it’s a family thing, are you inviting the whole clan or keeping it small? Do friends count? Or, would you prefer to keep it to you and the hubby? If it’s the latter, then don’t bother opening up the invite to anyone but you and your beau.

What’s The Destination?

Everyone has a single destination in mind when they think of the islands in the Caribbean Sea. For some, it’s Barbados and Jamaica whereas other prefer Cuba and the Dominican Republic. The key is to choose one and fly there directly and set up shop for a few days. That way, you can take in one place and not feel too overawed about seeing the area as a whole.

However, don’t dismiss moving around out of hand. Trinidad and Tobago might be paradise on earth, but that’s no excuse to avoid St Kitts and Nevis and the Virgin Islands. Let’s face it – it’s not as if it takes ages to go from one place to another. Thanks to ferries and tour operators, you can island hop in a matter of hours. Some fisherman will even take you across if you pay them the right price.

An excellent tip is to research the destinations and attractions that you want to see. Then, go on Google Maps and see if it’s possible to sail or fly to all of them in a couple of weeks. If it isn’t, you can pick the ones nearby and treat it as a mini-traveling holiday. Use to check out the cheap flights on the dates you need.

How Much Do You Want To Spend?

Your budget is something which is going to make or break the vacation. Plenty of people are happy just being in the general vicinity enjoying the culture. So, they don’t mind being thrifty and cutting back. After all, life at home doesn’t stop because you went away for three weeks.

But, considering this is a vacation of a lifetime, you might want to let loose a little. That’s fine as long as you budget for it before boarding the plane. Go to and rent luxury accommodation. Check out to see find out the best restaurants and make a booking. Enjoy the experience, but plan to spend a small fortune.

The only thing worse than spending money you don’t have is getting home and realizing you’re in trouble. It happens more often than you think, which is why you don’t want to get burned.

What Do You Want To Do?

Sunbathing and drinking cocktails aren’t the only choices. On pretty much every island, there are a plethora of things to do on a daily basis. For instance, the adrenaline junkies love to paraglide or hire jet skis. The animal-lovers strap on an oxygen tank and hit the local dive sites. The foodies walk from restaurant to shack and sample the delicacies.

The reason you should think about it beforehand is that it will impact your destination. Although the islands offer all of the above, some are better than others for certain activities. has the Cayman Islands as the best place for diving thanks to the visibility and wrecks. So, if you’re PADI-certified, then CI is the place to spend most of your time.

Anyone looking to sit back and relax for a few days can turn up to any spot because the beaches are amazing throughout the region.

When Are You Going?

The dates are important because they affect the holiday as a whole. The first thing to note is the prices. During the fall and winter months, they tend to drop a little and make everything cheaper. So, if you’re cutting back, then this is a perfect time to jet away.

Also, consider the weather. If sunbathing is a big deal for you, then you don’t want it to rain for days on end. The hurricane season formally ends at the beginning of November according to, so you might want to fly in early December.

Don’t forget about the events that are planned too.

Are you starting to realize what it takes to plan an epic vacation?

See you next time!

All-inclusive resorts

Beaches Friends Forever Getaway

Say Goodbye to Summer, Say Hello to Savings! Save up to $27 off flight & hotels with promo code HOT27. Book Now!


Fashion, Lifestyle, and Travel blogger, based in NC.


  1. Your tips are spot on amber. I think the most important one is having a budget though because often are times when people go on vacation and end up spending way more than they expected.

  2. These are some really good tips. People think the Caribbean is just beaches but there’s really so many different things to do so you totally have to consider who you’re going with. What I’m looking for in a family vacation is certainly not the same thing I’m looking for if I’m getting away with my gal pals.
    Megan recently posted…Best Tanning Oil for The Beach of 2018: Complete Reviews With ComparisonMy Profile

  3. Your method of tellіng all inn this paragraph is really pleasant, every one be capable of effortleѕsly be aware
    of it, Thanks a lot.
    alox foldekniv recently posted…alox foldeknivMy Profile

Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.