Island Hopping in the Caribbean

Island Hopping in the Caribbean

The Caribbean is a popular vacation destination year-round. As the rainiest months are July to November, many tourists prefer to visit between February and May. No matter when you visit, it’s a good idea to pack your luggage appropriately for hot, sunny days.

There’s plenty to do in the Caribbean. Island hopping is a common activity due to the proximity of the islands. If this is on your to-do, check out our fashion guide. We’ve put together some outfit ideas to help you stay cool and stylish on your tropical explorations:

Breezy Boat Clothes

The Caribbean islands are accessible by boat. Many visitors to the islands take a ferry between each one. Travel agencies abound with island-hopping packages, which take the hassle out of planning your itinerary. Stay cool and comfortable as you travel from island to island with stylish outfits for boat travel.

Men’s polo shirts and cargo shorts with deck shoes are a casual yet polished look for Caribbean travel. Women can wear capri pants and a sleeveless or short-sleeve blouse with slip-resistant sandals or boat shoes. Bring along a lightweight, water-resistant jacket for breezy conditions. There are packable rain jackets that fit in most carry-on bags so you’ll have one just in case.

Outfits for Sightseeing

Sightseeing often involves a lot of walking, so we’ll start our fashion discussion from the bottom up. Pack supportive walking sandals for shopping and exploring tropical destinations, as they’re made for foot travel. This type of footwear has an open design for ample airflow and a cushioned footbed and slip-resistant sole.

Women’s dresses in a light, floaty fabric are comfortable for sightseeing. If you prefer shorts, a knee-length style such as Bermuda shorts or chino shorts are a stylish option. Women’s polo shirts come in just as many colors and fabrics as men’s polos, and they’re always resort-appropriate. For casual outings, women’s and men’s linen shirts with comfortable shorts are another fashion idea to consider. Linen is lighter and even more breathable than cotton, making it an excellent fabric for tropical climates.

Men’s and Women’s Swimwear

Swimsuits are a must for island hopping. Whether hitting a swim-up bar at a resort pool or splashing in the ocean, chlorine-resistant swimwear is always a good bet. It’s made with Lycra® XtraLife™ for ten times the wear of traditional spandex, so it’s colorfast and holds its shape. There are chlorine-resistant swimsuits in one-piece styles for women, including the ultra-comfortable Tugless Tank style. Tankinis are another option if you want the look of a one-piece with expanded fashion possibilities. With multiple tankini tops and bottoms, it’s possible to create many swimwear looks.

For men, classic volley shorts are appropriate for any Caribbean destination. They’re usually made from light, fast-drying polyester or nylon, and most pairs have pockets. Another feature of most men’s swim trunks in this style share is the full elastic waist with drawcord for a custom fit. Board shorts are sportier and come in shorter lengths, making them a must-have for surfing and other water sports. Both trunk styles come in solid colors and various prints that can be matched to a swim tee in a complementary hue.

What to Wear to a Beach Party

If you’re headed to an evening beach party, you can wear your swimwear under a beach cover-up. Men’s and women’s beach cover-ups come in many styles, providing UPF 50+ for covered areas. Rash guard shorts and tops are one outfit idea. There are mid-length and long cover-up dresses that look stylish with sandals for any Caribbean celebration at the beach or pool.

Another idea is to pack beach bags with clothing changes. Undergarments, your beach party outfit, and whatever shoes you want can go in your tote. Zippered waterproof pouches can hold swimwear until you get back to your accommodations. If you want cosmetics or other toiletries to freshen up after swimming, toss them in a cosmetic case and put them in your cooler to prevent product meltdown in hot temperatures.

Dressy Date Night Looks

A little black dress works for any occasion, including a date to an upscale Caribbean restaurant. Heeled sandals can be paired with any summer dress for a vacation-worthy look that’s still dressy enough for a high-end date destination. If you’re the billowy maxi-dress type, it’s easy to dress up the look with stacks of gold-tone bangles or statement earrings.

Date night is another occasion where men’s linen shirts come in handy. They can be paired with dress pants for a formal resort-wear look. Guys can also wear button-downs in lightweight cotton with any type of formal pant. Some high-end establishments with dress codes permit men’s shorts because of the tropical locale.

Pajamas for Island Nights

Stay cool overnight in men’s and women’s cotton PJs. Cotton sleep shirts in a short length are great for Caribbean nights, or you can wear shorts and a tank top. Cotton poplin and muslin are two gauzy weaves with subtle textures allowing plenty of airflow. Guys can wear cotton boxers or lounge pants with a tank or tee.

Loungewear for the Trip Home

It’s also important to be comfortable when you’re headed home from your island-hopping experience. Men’s and women’s sweatshirts and sweatpants are always a comfortable option; keep the pieces monochromatic to stay on-trend. Any athleisure type—from women’s yoga pants to men’s joggers—can keep you in comfort and style as you travel home.

Use the fashion ideas in this article as a springboard for creating your own Caribbean vacation style. The most important factors are to choose pieces that fit well and are designed for hot-weather wear. From there, it’s a matter of choosing the vacation apparel that suits your style.


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