Fall may just be getting started, but there’s no time to waste when it comes to planning sunny holidays to provide respite from the cold winter ahead. And nothing quite lifts the gloomy mood that comes with a wintry mix than the sandy isles of the Caribbean. And while you can easily access many of them by flying, why not discover more than one by boat? Sure, you’ve seen the Bahamas and Turks & Caicos, but it’s time you saw the Grenadines, Anguilla, and Mustique, too. Sounds good, right? Why don’t you go pick an itinerary, we’ve done the packing for you.
Take advantage of cruising by booking a route with stops in exotic locations like the Leeward Islands. While on board, these bronze rubber studded thong sandals ($28) are comfy for leisurely strolls on deck and cute enough to toss into any poolside tote.
You’re sailing to the Caribbean. So take advantage of gorgeous sun-drenched days with little to do but lazing poolside in this pink-red bikini set ($289).
Come cocktail hour, or to dip inside for lunch, slip on this French terry tee with raw edging ($26.95)
The tee and a few extra tank tops will pair well with a denim skater skirt ($59.90).
Or go for a zesty Caribbean vibe with a pair of neon pink shorts ($29.50).
The cruise lines can differ quite a bit when it comes to dining, but some like Azamara offer more sophisticated choices than the rest. Dress for dinner in a nude silk printed jumpsuit ($365) for an easy all-in-one option that screams island getaway.
Add color with your accessories, like this green resin stone cuff ($60).
A deep jade-colored leather foldover clutch also makes for a bold accent, while the flat shape makes for easy packing ($180).
Adding smart separates will boost your wardrobe’s versatility. For longer itineraries, throw in this black and white short-sleeved sweater ($59.50).
Wear it with this elegant yet relaxed green skirt with punched out hem ($59).
At ports of call, disembark in this blue t-shirt with a stylized wave print ($59).
Add these colorblock board shorts in light and dark blue ($75) to capture the cool and casual island feel.
Protect your eyes from the strong Caribbean sunshine with these wire-rim gold aviators by Ray Ban ($160).
For air conditioned interiors or just for covering up after a swim in the sea, bring this long sleeved tee by Tommy Bahama. It is especially travel-friendly and comes in cheerful hues ($88).
Lastly, rubber boat shoes ($150) give you the versatility of a flip flop but the polish of a classic deck style.
Dancing Into the Wee Hours
Feeling fancy? Book passage on Cunard lines, particularly if you have the time for a longer itinerary. You’ll want to bring a suit for the ship’s formal nights, but for more casual dinners throw on this bright blue cotton sweater ($140).
Add a touch of color and drama with these chinos in a bordeaux red ($59).
Or for warmer nights go for crisp shorts in a stone beige ($54.50).
On top, this amped up polo shirt by British classic Fred Perry ($110) takes any other basic piece to the next level.
Finally, play up your 007 style with a fine watch. Perhaps choose one with a rubber strap, which will suit the glamorous atmosphere ($225).
Photo Credits: Women Day: Courtesy of J. CREW; ZARA; LES NOUVELLES; BOP LLC; Gap Inc. Women Night: Courtesy of Gap Inc.; Club Monaco Corp.; STYLEBOP.com; BOP LLC; PLANET BLUE. Men Day: Courtesy of Gap Inc.; Mr Porter; Nordstrom, Inc.; SATURDAYS SURF NYC LLC.; Nordstrom, Inc. Men Night: Courtesy of Gap Inc.; Fred Perry; SATURDAYS SURF NYC LLC.; macys.com; macys.com.