What to Do in the Caribbean This Winter

There are many reasons to visit the Caribbean in the winter. Hurricane season has passed, dry weather has set in, and bugs, abundant in the rainy season, are mild. The scorching afternoon sun, common in the summer, has mellowed too, leaving behind warm spring-like temperatures and calm ocean breezes. Winter is peak season in the Caribbean as travelers from Canada and the United States trade their wool scarves, parkas, and snow boots for beach bags, swimsuits, and flip-flops.

Catching Waves with Surfing Lessons

surfing in puerto rico

  • Don’t Miss:  Riding the best waves in Puerto Rico under the training of a professional surfer – perfect for beginners
  • Near:  Rincón, Puerto Rico
  • Best Time to Go:  December through April

The heart-racing thrill of watching a skilled surfer catch a big wave has always intrigued you, but the logistics just haven’t worked out. Well, there is no better time than the present, and there is no better place to learn than at Surfing Lessons Puerto Rico & Adventure Company. Their instructors are excellent at providing a successful and memorable surfing experience.

Be sure to listen closely to your patient instructor as you paddle out past the break, find your wave, and catch that first ride. Don’t leave the Caribbean without pocketing a few authentic surfing skills. To feed your new surfing addiction after the lesson, do some shopping at El Rincón Surf Shop just down the road.

Seven Mile Beach in Jamaica

seven-mile-beach in jamaica
  • Don’t Miss:  Spectacular crisp, white beaches, rich with Jamaican history and culture
  • Near: Negril, Jamaica
  • Best Time to Go: December through April

With seemingly endless miles of natural Caribbean beauty, Seven Mile Beach offers the quintessential Jamaican beach experience. Once a favorite haunting ground for pirates, today its pure white beaches and transparent turquoise waters are a sun lover’s paradise. There are restaurants, bars, and beach activities galore. Look for vacation rentals near the beach for easy access and beautiful views.

Jamaican beach vendors travel the beach selling everything from jewelry to cooked lobster tails complete with plates and silverware. Don’t miss sunset when sky fills with oranges, reds, pinks, blues, purples, and greens as the sun falls below the horizon. After the sun puts on its show, stop by Margaritaville for their blended namesake or an ice cold Red Stripe.

Samana Zipline Tour in the Dominican Republic

samana view in the dominican republic
  • Don’t miss:  Swimming in the Lulu Waterfall after enjoying the exhilarating zip line
  • Near:  Samana, Dominican Republic
  • Best Time to Go:  December through April

The Samana Zipline is the number one attraction in the Dominican Republic and offers over 7,400 feet of zip lines. From the top of a jungle mountain, the zip line starts at the plank of a pirate ship then zips from one mountain to the next, down twelve different lines, until you reach the bottom.

Slip on your safety gear, walk the plank, and start zipping. After a day above the trees, swim in Lulu Waterfall, then try a few local flavors of chocolates and fruits. Top it all off with a shot of Mama Juana, a favorite Dominican Republic drink. At the end of the day, you can take a safari truck provided by Samana Zipline back to your vacation home.

Stingray City on Grand Cayman

stingray city off of grand cayman
  • Don’t Miss:  Kissing the stingrays
  • Near:  Grand Cayman Island
  • Best Time to Go:  December through April

Book your excursion to Stingray City with Stingray Sailing, the best on the island. Their catamarans are spacious, and the staff is professional and welcoming. The first stop is the Stingray City sandbar to swim with the stingrays, then off to snorkel at the coral reef and Starfish Beach.

At Stingray City, when you hop in the clear ocean water you will feel the stingrays brush right up against you. Don’t fear, they are very friendly, like dogs excitedly welcoming you home. Hold them, feed them fish or bottled squid, and even give them a little kiss if you’d like. To capture the memories, bring an underwater camera to get the best pictures.

Royal Port Golf Club on Bermuda

bermuda golf

Set among the bright blue backdrop of the stunning Caribbean ocean, golfing at the Royal Port Golf Club is a memorable experience. This course has challenged the best, and its 18 championship holes are home to the PGA Grand Slam of Golf.

Take a swing at the famed 16th hole, and see if you can make it over the Atlantic Ocean to the green. Try not to let Bermuda’s colorful tropical vistas distract you off the tee. The course is also renowned for its challenging fairway bunkers. For a discounted rate, book an afternoon tee time.

Trikes - Aruba

aruba tour
  • Don’t Miss:  Discovering Aruba to it’s fullest on the back of an open-air Trike
  • Near:  Aruba
  • Best Time to Go:  December through April

There’s no better way to explore one of the Caribbean’s most beautiful islands than on the back of a Trike. These three-wheeled motorcycles give you unobstructed views while you motor through the fresh Caribbean air. Choose a Trike in your favorite color, slip on your sunglasses, and hit the road for an exciting guided island adventure.

Stop at the California Lighthouse for some great picture taking, and don’t forget to include your Trike in a picture or two. While on your ride, stop at Zeerovers, a local's place for great seafood and beer. Get there at the right time and you'll see the fresh fish coming in from the day’s catch. You may want to reserve your Trike at the same time you make your vacation rental reservations, as they fill up quickly.

Hunte’s Gardens in Barbados

hunte's garden in barbados
  • Don’t Miss:  The lily pond where fish nibble your fingers and toes
  • Near:  St. Joseph and Bathsheba, Barbados
  • Best Time to Go:  December through April

Nestled in the Barbados rain forest, the vibrant Hunte's Gardens offer some of the most exotic flora and fauna not just from the Caribbean, but from all over the world. The garden also attracts a variety of birds, insects, and other interesting wildlife. Enjoy a few moments of solace while sitting on one of the quirky benches they have strategically placed to soak in the scenery.

Anthony Hunte is the owner and a horticulturist with a unique vision. Meeting Mr. Hunte is a special treat, as he’s a welcoming and friendly man. His adorable dog, Flora, is a fitting companion. A few hours spent here very well could be the highlight of your Barbados vacation.

Magic Ice in St. Thomas

ice exhibit in st. thomas
  • Don’t Miss:  The story of how the Norwegian arctic ice sculptures traveled to St. Thomas
  • Near :  St. Thomas Island
  • Best Time to Go:  All year

Visiting an ice exhibit might seem like the last thing you would want to do when trying to escape the chilly conditions back home, but Magic Ice, the biggest permanent ice gallery in the world, is a must-see. A favorite St. Thomas attraction, the unbelievable Norwegian ice sculptures artistically portray the history of the Caribbean.

It’s a cold exhibit, so slip on the provided hooded coat, gloves, and leg warmers before venturing inside. If those don't provide enough warmth, swig a free shot of Cruzan rum for a little extra inner glow. The exhibit is full of sculpted mermaids and birds, kings and queens, and, of course, pirates. There’s also an ice slide that kids love to climb up and zoom back down. For adults, brightly colored lights shine on the sculptures to enhance intricate details, giving the whole exhibit a fantasy world appearance.


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