The Caribbean islands…to hear it conjures visions of endless tropical beaches, the smell of exotic spices, the rhythmic beating of reggae music and fruity-flavored cocktails with little umbrellas in them…There are a few things you should know before you go, so here’s a guide filled with helpful tips for your next winter Caribbean escape!

A woman researches her winter Caribbean escape on a laptop while holding a cappuccino.

Research Before You Go

Absolutely every island is different. The Caribbean is a polyglot of over 700 independent island nations and territories and each one is different, from the culture to the terrain to the language – even within the same country or territory. They’re wonderfully individualistic. Many even have their own special cocktail.

Even if you’ve been to another island before, or maybe you’ve seen your destination in a movie. Don’t assume it will all be the same – research the island you’re visiting before you make your winter Caribbean escape.

Check the language – do not assume the locals will speak English. The Caribbean islands have been colonized by numerous large nations over time, so you could encounter any number of different languages from island to island – English, French, Dutch, Spanish and more.

Go to your country’s official State Department website and check the entry requirements. For some countries, a valid passport will do the job for a short visit. For others you may need to bring proof of a departing flight and more.

Check the local currency. Each island you visit may have a different currency. Find out which currency to bring and have a small amount of it in hand when you arrive.

Packing a carry on for a winter Caribbean escape!

What to Pack

Bring sunblock! It may be winter at home, but on your Caribbean escape you’ll be near the equator, surrounded by water reflecting the sun’s rays all around you. It’s expensive to buy on the islands and the selection may be limited. So, pack enough for both face and body, and make sure it’s reef safe physical (mineral) sunblock (not chemical sunscreen).

And don’t let your scalp burn and your hair fry! Pack a small spray bottle for this DIY scalp-protecting hack: Mix about 1/2 cup water and about 1 tbsp sunscreen. Shake it up and spritz it on your scalp. And put a small bottle of detangler in your day bag to keep locks silky at the beach or pool – spray ’em every time you come back from the water.

Power up correctly. Check to determine whether you’ll need an electrical outlet adapter for your destination.

Travel green – bring your reusable straws. Lots of the resorts are jumping on the #strawssuck train now. They’re eliminating straws and that’s awesome, but if you like to cool down with smoothies and icy libations you still might need one. Bring some stainless-steel reusable straws so you don’t have to wait for that frozen drink to melt to enjoy it. Get a set with cleaning brushes so you can take the straw back to your room later and clean it for the next day.

Look out for tummy trouble. Between the tap water, the foods you’re not used to having at home and the bacteria in the sand, it’s always wise to have a little Pepto on hand.

And here are a few things NOT to pack for your winter Caribbean escape: heels (strappy sandals will do!), perfume (attracts bugs) and lotions (makes you sweat more!).

A woman on her winter escape walking along a Caribbean seaside in a flowy dress, carrying a woven handbag.

Exploring the Island

Leave the resort! There is so much to see and experience on each island. From lush jungles to incredible beaches…amazing food…a vibrant culture…there’s so much to see. Sure, the pool’s nice, but there’s a whole world for you to experience out there.

Cover up around town. Many of the local cultures are somewhat conservative. Swimsuits are appropriate for the beach and the pool, but locals don’t appreciate seeing you walk around town that way. A sundress or a cover-up will do the job and show them you respect their country and their customs.

Don’t flaunt weed openly. It’s essentially accepted, super easy to get and completely prevalent, but it is still frowned upon, if not actually illegal in public. So, keep it on the down low when you’re not in your hotel room.

A woman holding the steering wheel, driving on a Caribbean island at sunset.

Driving Around the Islands

Booking a rental car? Don’t assume driving will be easy here. Some islands drive on the left side and some on the right, and often there may be few or no stoplights or lines on the road, many unpaved roads, and often single lane roads along steep cliffs. Research driving conditions before you go and prepare accordingly.

Getting directions – it’s different here. At home, someone might say something like this: “Take 405 South. Exit on Beach Blvd. and go left…” On a Caribbean island it might sound more like this: “Go to the end of the paved road and make a right. Turn left after the third curve. Make a right by the big grey rock with a lot of iguanas on it. Follow that road until you see a goat chained to a post and then turn right again. Keep going until you get to the old sailboat…” They’ll be good directions, just not exactly what you’re probably used to.

The view from a very small airplane, showing part of the wing and an island coast and the sea beneath it.

Flying Island to Island

The regional inter-island airlines are much cheaper. But, be warned – their flight schedules change often, and luggage guidelines may be very specific and strict. The planes are typically tiny and ocean winds are strong, so there may be incredibly strict weight guidelines. Carry on a toothbrush, a change of clothes and a swimsuit in case your luggage is moved to a lighter flight and doesn’t arrive with you.

A glowing pink neon sign pointing the way to the washroom.

Taking Care of “Business”

Many islands, in the Caribbean and around the world, lack the kind of robust sewage system we’re used to in places like the United States and the UK. So, flushing toilet paper is often prohibited. Look around when you get there – check for signs in the washroom warning you not to flush paper, and a pedal garbage bin next to the toilet for you to throw it away instead.

A young boy wearing a snorkel mask, standing in the Caribbean sea holding a starfish.


Be patient while you’re out mingling. Life may be fast-paced and always busy at home. On the island though, everything will move slower. Time sort of becomes irrelevant. Nothing seems to happen on time, and nobody seems too concerned about it, except maybe you…just relax. You are on vacation after all, right?

Chat with the locals! The Caribbean people are incredibly friendly and inviting. Be friendly. Ask questions. Smile and say hello when you enter a shop – don’t let “How much is this?” be the first words they hear you speak – that is seen as rude and disrespectful here.

Keep cash on hand – many shops and restaurants prefer it, and some will not accept credit cards at all. And don’t forget to tip!

Prepare yourself mentally for the catcalling. It will happen here. A lot. It is sort of a virtually unavoidable cultural norm on many of the islands.

And on that note, take some protection with you. Sure, it may not be your plan to hook up. But the hot weather, the cheap alcohol, the party in the bar…sometimes plans change. Protect yourself.

Rise & Rove is a modern group travel company with curated, led trips across the globe for like-minded, rad women. Small group size, unique activities, boutique accommodations, experiences with locals. Come solo, leave with new friends!

Check out our upcoming destinations! We will be rolling out new trips regularly and have some exciting things in the works!

Rise & Rove: How Rad Women do R&R

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