You and your family have decided that you want to go on vacation. This time, you think you want to go to a tropical place, where the sky and the sea are practically the same color. The Caribbean seems to tickle your fancy.

A place like St. John can create a lot of memories – but it is up to you to determine if you make those memories be positive or negative. There are some great times to go and some decidedly not-so-great ones. It just takes a bit of research ahead of time – and part of that is finding accommodations.

If you are thinking of making that trip a reality, before you put “luxury villa St. John” in a search engine, you want to have an idea of when you should go. You don’t want to pay more than you have to and you also might want to go when there are not going to be a lot of other people around you making things more chaotic than you would like. Read on to learn the best time to visit the Caribbean.

The Best Time to Visit the Caribbean

Usually, people tend to go between the months of December and April. The biggest reason for the draw here is that

  • This is the time of year when things tend to be the coldest in many parts of the United States, Canada, and certain areas of Europe. People are going to get away from that cold and enjoy themselves for a little bit sitting out on the beach enjoying cold beverages and going swimming. They can then go back to the colder weather refreshed.
  • These months are usually outside the hurricane season. The chances of a hurricane hitting the Caribbean during this time frame are remote. So there is very little worry about having to do things like a shelter in place.

Try To Avoid the Rainy Season 

Much like the weather in other tropical or humid climates – think Florida – there are times in the year when the chances for rain are roughly 100% for some days. This is known as the rainy season. While it can be annoying to have to hide under umbrellas for a while, it is also quite helpful in terms of keeping the trees and vegetation there in a lush state.

If you go to a place like St. John any time between May and October, it might be a good idea to pack some rain gear. While the temperatures will still mostly be pleasant, getting soaked can still be an annoyance. You don’t want to while away much of your time in your luxury villa watching the rain … you could have done that at home. 

Avoid Hurricane Season

While this may also sound like the Rainy Season, those rainstorms, while sometimes heavy, still pale in comparison to hurricanes. You would be inconvenienced having to stay inside your villa on those rainy days – but if a hurricane came, depending on the strength, you could go anywhere from being without power for a while to possibly having the roof ripped off …. or worse.

Typically, the hurricane season is from July through November. The peak time in St. John is usually in September and October. The climate may be shifting, though, so you might have to be on the lookout for hurricanes later in the year – December still seems pretty safe for now.

Planning Your Trip to the Caribbean

Now that you know the best time to come, it’s all about making sure that you properly map out your plans so that you can get the most out of your stay. If you don’t, then you risk having travel problems and being bored during your stay there.

  • Figure Out Who Is Going – This is critical since you can plan your accommodations around the people going. A family trip would require different lodgings than a couple going together or a group of friends. Look at the various options and then make your choice.
  • Figure Out Your Travel – You will likely have to fly there, but there is another option, a cruise ship – also, make sure that you have the right documents if you are going to a different country. The second option allows you to pack in more fun while you are on your way there rather than having to race around for a flight – though you might have to fly to the destination where the cruise ship is docked. Either way, try to allow enough time to get to the plane or the ship.
  • Figure Out Your Activities- Much like the lodging situation, you want to ensure that you pick out the right activities, like scuba diving, boat riding, or even going on tours, based on what the people on the trip taste are. Otherwise, you risk a lot of bored eyerolls. Have discussions about these activities before you make any reservations.
  • Figure Out The Right Place – There are a lot of places in the Caribbean. Some of them offer a lot of activities and nightlife, while others may be more sedate. Make sure that you match the right place with the type of people going – college students wouldn’t likely want to go to a place where things close at 8 p.m..
  • Figure Out What Events Are Going On When You Plan to Go – You may combine this with the above planning trip. See if there is anything going on at your Caribbean destination that the locals like to do. There may also be some migrations of sea turtles or other local wildlife.
  • Figure Out The Length of Your Visit – This would be a situation where you want to leave yourself wanting more when it is time to get on the plane rather than find yourself counting the hours until you leave. It’s better to only stay for a few days, especially your first trip – that way you can decide if you like it and intend to make regular visits a thing. Also, you need to factor in travel time, since a lot of traveling will cut into your actual stay time.
  • Figure Out Your Budget – You want to have a good time while you are on your trip, but you also want to stay within your means. Otherwise you face the possibility of not having enough money to do the things you want while you are there .. or running up some credit card bills that you will want to take a vacation from when you get back home.

Don’t Make These Mistakes

These are things that can make your trip go much smoother. There are also things that can make your trip a living nightmare. Don’t make these mistakes that can make you wish you were already back home.

  • You Forget to Bring Enough Cash – The stores that you shop at in your home county might all be set to take chip cards. That is not the case on these islands, and you could miss out on some cool souvenirs if you don’t have cash. Always have some on you – most places take American dollars.
  • You Only Come Via Cruise – Yes, we did recommend this as an option, but you also have to consider this – you will be constrained by the schedule of the cruise. You won’t be able to truly explore the island you are visiting. Instead, you will get a brief synopsis.
  • You Only Stay at a Resort – There is nothing wrong with a resort – they have great accommodations and food. You could have a great time at the pool or the beach. There are still a lot of things to go out and see – which will not be at a resort.
  • You Don’t Make Your Trip Long Enough – While you only might want to stay at the resort for a few days, you also need to plan for travel time. Otherwise, you might find yourself staying there longer than you would like, especially if there is bad weather where you are coming back to.
  • You Think All The Islands Are Alike – This is not true at all. Each island has its own activities and customs. Some like to have a party all the time while others are much more sedate.
  • You Think All the Water is Drinkable – Do not ignore this one – it can save you a lot of time and possible intestinal discomfort. There are some islands where the water can create havoc on your insides … do not even use the tap water to brush your teeth. Do some research and bring bottled water for those islands.
  • You Are Always in a Rush – If you are a high-strung person who likes to go from Point A to Point B as fast as you can, you are going to be aggravated here. Caribbean people move at their own pace and you are just going to have to relax and adapt to their time. You can resume rushing around when you get back home.
  • You Don’t Explore – There are a lot of hidden wonders around these islands. You can go explore and see them for yourselves. Make sure that you don’t go into any areas that are marked unsafe, though.
  • You Don’t Account For Possible Lack of Cell Service – You could spend to get an international calling plan, but your better bet would be to just leave the phone for emergencies at the hotel. Work can wait – that is why you went on vacation in the first place, and you don’t want to be one of those people typing away while at the pool and their spouse/partner glares at them.
  • You Avoid Taxis – There are times that this might be advisable in certain cities. This is not one of those times – the locals know where they are going. Otherwise, you might be trying to navigate some VERY confusing directions.

How to Pack for a Caribbean Vacation

You want to be sure to pack things that will both keep you comfortable and also keep you occupied during certain lulls during your trip. It’s a good idea to have a waterproof suitcase that you can wheel or carry around. Here are things that you should pack for certain parts of your trip:

  • Your Trip to and From the Caribbean – You want to bring things that will occupy you on your plane ride. They include noise-cancelling headphones, a tablet for reading, and a water bottle that can be collapsible. The last part is important since you might have to pour water that you buy from a newsstand once you get past security.
  • While Walking Around the Caribbean – It’s important that you bring several shoes for your trip. They can include sneakers, water shoes, flip-flops, and nicer shoes for an evening out. The sneakers will be vital if you happen to go out for extended walks.
  • While Relaxing at the Caribbean – You also need to have clothes – though there are some clothing-optional places. Pack dresses, shorts, t-shirts, shawl, a nicer collared shirt and socks for your trip, and you can wear any hats on your flight . Do some research ahead if there are certain places that you have a dress code.
  • Other Things to Pack – These include any OTC medications like antihistamines, your toothbrush, toothpaste, and any prescription medication that you need. Pack sunscreen, lip balm, and other things to protect yourself from the sun.

These are just some of the things that you need to consider when it comes to planning your trip. It is only the tip of the iceberg, though, since entire books have been written traveling to the Caribbean. If you follow the above tips, though, you can assure yourself of a good time throughout.

A trip to the Caribbean can be a life highlight, and if you like the place that you stay and find it within your budget, you could make it a yearly trip. Once you get the hang of things after the first trip, these things should be like second nature for you. Then you can just enjoy yourself the entire time.

Author Bio

James Sullivan has been helping with travel tourism for the past 12 years. He now wants to share his knowledge and expertise with others.


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