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What to Pack for Jamaica


Packing for a trip can be difficult, especially if you have never been where you’re traveling before. If you’re visiting us at Anticipation for the first time, we’re sure you will have many questions. What clothing is appropriate in Jamaica? What will the weather be like? How much stuff is too much?

In this post, we’ll discuss these questions and offer some packing tips so that your packing experience will be a breeze. As always, if you have any questions at all, you can always contact us.

Now let’s get started!

To Check a Bag or Not Check a Bag?

Many travelers wonder whether they should try to squeeze all their belongings into one carry-on bag or whether they should check a bag. Travelers have many concerns to consider when making this decision. These concerns may include:

  • Does your airline charge a fee for checking a bag?

  • Does your airline allow carry-on bags and, if so, of what size?

  • Are you comfortable restricting yourself to a small bag?

  • Do you mind waiting at baggage claim for your checked bag? Or do you want to save time and avoid the wait?

  • Are you worried that your checked bags may get lost in transit?

You will need to weigh all of these concerns for yourself when you decide to whether to check a bag. Remember, there is no right answer, so try not to stress about whether you’re making the wrong choice!

Hot Tip: If you are staying with us at Anticipation, one important thing to remember when making this decision is that we employ a full-time laundress who will wash and press your dirty clothes each day. You will never have to re-wear dirty clothes if you opt to bring a carry-on and have to pack fewer clothes.

Once you have chosen what size bag you want to bring, you can start thinking about the clothing you want to pack. You'll want to consider the weather and what activities you plan to do during your stay with us when you choose your clothes.

Dressing for the Weather

The weather in Jamaica is mostly sunny and warm all year round. The sea temperature remains quite warm year-round, usually between 81° F and 86° F (27° C and 29° C), but there is some variation in climate which you should keep in mind while packing. Let’s discuss the changes in the seasons in Jamaica and what you should bring to be prepared.

Summer - Jamaican summers are known for the heat. July is the hottest month of the year with an average temperature of 83° F (29° C). It is quite unusual for any rain to fall during the summer – perfect weather for beach lovers! If you stay at Anticipation during the summer you will likely be able to get away with bringing mostly light, cool clothing. Make sure you pack sunscreen and wide brimmed hats to protect yourself from the sun. We also recommend bringing at least two swimsuits so that our laundress can wash one while you wear the other.

Winter - Although the winter in Jamaica is warmer than many northern countries, you will still likely need a jacket during the cool evenings and nights. January is the coldest month of the year, with an average temperature of 76° F (26° C). It can sometimes get as cold as 53° F (11° C) at night! If you’re planning to stay at Anticipation during the winter, you may want to pack a jacket and a few sweaters in preparation for a chilly evening. The sun is still strong in winter, so don’t forget your sunscreen.

Fall and Winter Rainy Season - It rains more in the fall and winter than in the spring or summer. October tends to be the wettest month, with an average of 5.12 in (130 mm) of rain. If you plan to stay with us during the fall or winter, we recommend packing a rain jacket, umbrella, and closed toe shoes so you can stay dry and comfortable.

Appropriate Attire

Most Jamaican vacations include days spent lounging by the pool or on the beach, adventure tours including hiking, biking or sightseeing, and formal dinners and outings in the evening. You will need to pack accordingly depending on what you plan to do during your stay with us at Anticipation.

Guests who plan to spend most of their time relaxing by our private pool or at the Tryall Club beach should bring a few choice swimsuits, light cover ups, and sandals. We recommend bringing two or three of your favorite swimsuits. This way, you can wash and dry previously worn swimsuits and you have a backup if you break a strap. Packing a fashionable cover up or sundress makes it easy to go from sunbathing on the beach to lunch without needing to stop to change. While lounging in your bikini may be appropriate on the beach, you’ll find that its more appropriate to cover up off the beach.

While you’re staying with us at Anticipation, you will have the opportunity to play sports on the Tryall Club estate. We also recommend that guests who plan to participate in sports bring moisture-wicking athletic clothes. Guests who plan to play golf should note that there is dress code on the course. All golfers must wear Bermuda shorts and a collared shirt. Guests who plan to play tennis should note that the tennis courts at the Tryall Club have an all-white dress code. Don’t worry if you forget - there is an onsite tennis pro-shop which sells the necessary tennis attire.

Additionally, you may elect to participate in complementary onsite walking tours or offsite tours, at an additional cost. Please see our blog posts on Montego Bay and the Tryall Club to learn more about these activities. If you plan to participate in a walking tour, make sure to pack breathable cotton t-shirts and shorts or capris. Comfortable walking shoes are a must.

Many formal Jamaican restaurants have a dress code. The restaurant at the Great House at the Tryall Club, for example, prohibits jeans and requires that men wear collared shirts. We recommend that women pack a cocktail dress and a few light scarves or other accessories, and that men pack collared shirts and light, cotton dress pants for formal dinners. Men typically do not wear neckties in Jamaica, so it is not necessary that men pack a tie unless they are traveling to Jamaica for a very formal event.

There is no dress code at Anticipation itself. If you plan to enjoy all your meals at the villa, you don’t have to worry about bringing appropriate dinning attire – unless you and your guests want to plan your own private, formal evening!

How Much Is Too Much?

Many travelers struggle with over packing. Bringing too much stuff can cause a lot of unnecessary hassle and will turn your dream getaway into a nightmare. Besides being cumbersome overweight checked bags may incur hefty fees from airlines. We found a bunch of great tips to help you minimize how much you bring and prevent you from unnecessarily complicating your trip.

One thing you can do to minimize how much clothing you pack is to pack three tops for every bottom. We recommend packing items that can be mixed and matched, so you can make several outfits but bring less clothes. Complete each look by bringing accessories such as necklaces, light scarves, and light jackets. Women may choose to pack a pair of shorts, a dress, a skirt, a pair of lightweight suit pants and a variety of tops. Men may choose to bring a variety of collared shirts, shorts, lightweight dress pants, and a light jacket. Make sure to pack a mix of formal and casual wear.

Remember, you will never need to worry dirty laundry during your stay at Anticipation. Our laundress will wash and press your clothes daily. This means that you can bring fewer clothes and still have access to clean laundry!

Tips to Save Space in Your Suitcase

If you want to use a carry-on bag, you may struggle to fit in all your belonging. We found a few tips to help you use every inch of space in your carry-on one.

First, wear your bulky items in the airport. This will save room in your bag and will keep you warm, as airports and airplanes are often very well air conditioned. Pants and sweaters and comfortable walking shoes are examples of bulky items you may wish to wear instead of pack.

Second, think about all the unused spaces in your bag, such as the insides of shoes. Stuff your socks, underwear, and other small items into empty cavities to make use of the space.

Third, we recommend investing in packing cubes. These cubes allow you to neatly and tightly roll or fold your clothing by holding your clothing in place. You can neatly stack these cubes in your bag and keep all your clothes organized. Rolling clothes tends to save more space than folding clothes, but you may wrinkle your clothes if you don’t roll them carefully. Remember, our laundress at Anticipation will happily rewash and press any clothes which wrinkle in your suitcase during transit. We really like the brand Eagle Creek – check them out!

Other Packing Tips and Tricks

Saving space is a priority for many travelers. Here are some other tips and tricks that may help you while you pack.

  • If you are packing any collared shirts, put your belt inside the collar to prevent it from being squashed.

  • You can put your shoes inside a shower cap to keep your clothes clean.

  • Dryer sheets can help keep your shoes from smelling, so stuff a sheet inside your shoe before packing it.

  • If you decide to check a bag, remember to never pack essential items in your checked bag in case your bag gets lost. This includes medications, identification, or anything you will not be able to go more than a few days without. It also may be wise to pack a change of clothes and some basic toiletries in whatever bag you decide to carry with you. This way you will be comfortable until your lost bag is returned.

  • You can pack an empty water bottle in your carry-on bag and fill it up at a water fountain when you get through security. This will save your money and reduce single-use plastic!

  • You can also pack trail mix or other dry, packaged snacks in your carry-on to enjoy while you travel. This way you will save money by not buying expensive airport food and won’t have to worry if you have a quick lay-over and won’t have time to buy food.

  • Whether in your checked bag or your carry-on, put any liquids in a zip lock bag. This way, if the bottle leaks, it won’t ruin your clothes.

  • Try rolling up your clothes in tissue paper to prevent them from wrinkling.

Airport Security

When packing, remember that you must comply with airport regulations, both at your home airport and at the Montego Bay airport where you will depart. These regulations can sometimes be confusing, especially for first time travelers or for people who have not traveled in a while.

Remember the 3-1-1 rule if you plan to bring liquids in your carry-on. This rule requires that you can only bring three-ounce bottles of liquids inside one quart-sized plastic bag. The amount of liquids you bring cannot exceed the one quart-sized bag, and you are only allowed one quart-sized bag per person. You may back more liquids in a checked bag, but make sure your bag doesn’t exceed your airline’s weight restrictions, or you will need to pay a fee.

We recommend that you read our blog post on airport security in the U.S., Canada, and Jamaica while you pack your bags to make sure you comply with airport regulations. Again, if you have any questions, you can always contact us for help.

The Bottom Line

All of these tips aside, we have complied a simple, customizable packing list to help you choose what clothing to bring.

Your simple packing list:

  • Three simple tops

  • One pair of shorts

  • One pair of capris

  • Two swim suits

  • Flip flops for the beach

  • Formal shoes/sandals for evenings

  • Neck ties, scarves, necklaces, or other accessories

  • A dress or collared shirt for evenings

  • Sweater, pants, and comfortable walking shoes to wear in the airport

Happy Packing!

Packing can be stressful, but it doesn’t have to be! As you prepare for your unforgettable stay with us at Anticipation, keep in mind what the weather will be like, what activities you plan to do, and what size bag you want to bring. Our laundress will clean and press your clothing daily, so you won’t have to worry about not having enough to wear. If you have any questions, please contact us.

Looking for your own escape in paradise? Contact us today and make your dream vacation a reality!

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