2020 Travel Guide to the Caribbean

Beautiful white-sand beach in Saint Lucia (Photo via IngaL / iStock / Getty Images Plus)
Patrick Clarke
by Patrick Clarke
Last updated: 9:00 AM ET, Wed January 15, 2020

Escape to Paradise

If there's such thing as paradise on earth, it probably looks a lot like the Caribbean. Renowned for its balmy temperatures, plentiful sunshine and picturesque beaches, the region is arguably the world's most sought-after vacation destination. Whether staying in a boutique hotel, an all-inclusive resort or a luxury villa, the Caribbean is remarkably tourist-friendly and is easily accessed from elsewhere in North America. If you haven't already, make 2020 the year you get tropical and finally experience the best that the Caribbean has to offer.

3 Best Caribbean Destinations for 2020

There's a strong case to be made that Saint Lucia is the Caribbean's best island in large part due to the diversity of experiences available here, whether you're into adventure, history, culture or simply stretching out on inviting golden-sand beaches. A stay at the five-star Marigot Bay Resort & Marina is a surefire way to make the most of your Saint Lucia vacation.

Antigua is another excellent destination for 2020 as it offers visitors an authentic Caribbean experience with fewer crowds compared to some of the region's most accessible islands. If visiting during the Atlantic hurricane season (June-November), consider a trip to Curacao. Located outside of the hurricane belt, this Dutch Caribbean island features hidden beaches, world-class snorkeling and scuba diving and loads of colonial charm in the capital city of Willemstad.

5 Best Attractions in the Caribbean

The Bob Marley Museum in Kingston, Jamaica preserves the reggae icon's legacy with fascinating tours and insights into Marley's life. Elsewhere in Jamaica, Dunn's River Falls in Ocho Rios is a popular tourist attraction and one of the world's most unique waterfalls.

Nelson's Dockyard in Antigua boasts the distinction of being the world's only continuously working Georgian dockyard and features plenty of modern amenities, sites and hiking trails to make your visit worthwhile. If hiking is your passion, then you also won't want to miss the Waitukubuli National Trail in Dominica, which is the longest in the Caribbean at well over 100 miles.

Finally, travelers will want to add the Bahamas' exotic Exumas to their Caribbean itinerary. This archipelago consists of more than 360 cays and islands and is home to the region's beloved swimming pigs.

Must-See 2020 Events

From vibrant Carnival celebrations to art, music and food festivals, you can bet the Caribbean will be rocking all year long as it plays host to a plethora of not-to-be-missed events. Barbados will be the site of April's Vujaday Music Festival while Reggae Sumfest will return to Montego Bay, Jamaica for its fourth decade in July.

There's also nothing quite like experiencing Carnival in some of the Caribbean's most passionate destinations, including Trinidad, St. Vincent and the Grenadines, Saint Lucia and Martinique, among others.

Sports fans should once again set their sights on the Bahamas in 2020, with the country set to host a slew of notable events, including the annual Battle 4 Atlantis college basketball tournament in Nassau. What's more, the Cayman Islands' annual Pirates Week festivities will return just ahead of the holidays in November with parades, fireworks, street performances, costume contests and much more.

Best Places to Stay for Families

Families have plenty of superb options when seeking out the perfect resort in the Caribbean. Kid-friendly properties like Nickelodeon Hotels & Resorts Punta Cana in the Dominican Republic and Atlantis Paradise Island in the Bahamas will ensure every member of your tribe is entertained, even the littlest ones. Jamaica's Jewel Runaway Bay and Beaches Turks & Caicos-which boasts a 45,000 square-foot waterpark-are also sure to impress the whole family.

Visiting families will absolutely love Stingray City in Grand Cayman, a popular tourist attraction where guests can get up close and personal with friendly southern Atlantic stingrays. Families can also experience the Caribbean on a Disney Cruise Line voyage to a number of standout ports of call, including Disney's private island paradise at Disney Castaway Cay in the Bahamas.

Best Places to Stay for Couples

The Caribbean is often at the top of the list for couples planning a romantic vacation and there's certainly no shortage of phenomenal options when it comes to both destinations and resorts. Barbados, St. Barths and Negril, Jamaica are among the places that stand out for honeymooners and lovebirds celebrating special occasions but the list goes on.

In many cases, all you need is a stellar all-inclusive, adults-only resort to achieve total bliss with your significant other. Sanctuary Cap Cana in the Dominican Republic recently relaunched following a multimillion-dollar renovation and even offers guests castle suites with ocean views. Couples will also be blown away by Sandals Resorts properties here, including Sandals Grenada on the Island of Spice's exclusive Pink Gin Beach.

Best Places for Group Travel

There are lots of awesome destinations for groups to explore in the Caribbean, including places like Turks and Caicos, Nevis and Punta Cana, Dominican Republic. The latter is also home to one of the region's top resorts for vacationing groups in Club Med Punta Cana. Providenciales or Provo in Turks and Caicos features an abundance of beautiful beaches like Grace Bay Beach as well as the lovely Chalk Sound National Park in addition to shops and restaurants that you'll want to check out with your travel companions.

If your group is large enough, you might consider renting out a spacious luxury villa in a more secluded locale farther away from the tourist traps in places like St. Martin or St. Barths with the help of Villas of Distinction or WIMCO Villas.

Best Places for Solo Travel

The prospect of traveling alone can be awfully intimidating. Fortunately, the Caribbean features several enticing options guaranteed to put your mind at ease and ensure a memorable trip for all of the right reasons. Turks and Caicos is a no-brainer as it's not only safe but home to some of the region's friendliest locals and also English-speaking.

San Juan, Puerto Rico is another fine destination for solo travelers who should have little trouble making new friends with locals and fellow visitors while touring historic Old San Juan during the day and bouncing from bar to club at night.

Best Foodie Destinations

Gourmet food connoisseurs can't go wrong in the Caribbean but there are some places foodies simply can't afford to miss out on in 2020, including Anguilla and the Cayman Islands. Both are home to hundreds of fantastic restaurants and are hotbeds for talented chefs. Visitors to George Town in the Cayman Islands should be sure to check out Le Vele, a highly-rated Italian restaurant featuring gorgeous waterfront views. For a meal with an unbeatable view in Anguilla, head to Straw Hat Restaurant in Meads Bay.

Best Places for Adventure Travel

It's not all about relaxation in the Caribbean. Countless outdoor enthusiasts, nature lovers and thrill-seekers are drawn here every year, especially to places like Dominica, also known as The Nature Island for its incredible hiking and diving opportunities.

Other popular adventure destinations include Puerto Rico and St. Kitts. Puerto Rico or the Island of Enchantment is an eco-adventurer's dream as the destination's rainforest-covered mountains and miles of reefs give travelers plenty of options whether hiking, scuba diving, surfing, kayaking, horseback riding or ziplining. Meanwhile, St. Kitts offers an array of pulse-pounding experiences, including ziplining with Sky Safari, scenic sailing adventures and even dune buggy beach tours.

Best Places for Sports Enthusiasts

Soccer, rugby, sailing, cricket and golf are among the most popular sports in the Caribbean and that's unlikely to change in 2020. The region is also an elite destination for water sports with many visitors renting jet skis and participating in exciting activities like kayaking, kitesurfing and more.

As previously mentioned, spectators will be drawn to Nassau in the Bahamas, site of annual college basketball tournaments (Battle 4 Atlantis), college football bowl games, marathons, tennis tournaments, cycling events and a whole lot more.

The U.S. Virgin Islands is also a top spot for sports enthusiasts who will want to plan their trip around marquee events such as the St. Thomas International Regatta-the crown jewel of Caribbean racing-in late March and November's St. Croix Triathlon.

Golfers have no shortage of stellar courses too choose from throughout the Caribbean, including a trio of excellent courses located just minutes from the Iberostar Grand Hotel Rose Hall in Montego Bay, Jamaica.

Unique to the Caribbean

The Caribbean might be the only region of the world that qualifies as its own state of mind. It's what many think of when they imagine paradise and who can blame them? Gorgeous white-sand beaches, inviting turquoise waters and seemingly endless sunshine set the Caribbean apart from nearly every other vacation destination on earth. Plus, the people of the Caribbean embody that bliss, only adding to the region's appeal.

Top Places to Avoid

Travelers will want to be cognizant of the Atlantic hurricane season (June-November) when planning their Caribbean getaway in 2020 but otherwise, it's hard to rule out any particular destination based on risk alone. Regardless of where you go, tourist-friendly areas and resort properties are generally safe. As is the case anywhere, travelers are far more likely to be the victims of crime or get into trouble when they venture outside of their comfort zones into areas they're unfamiliar with.

Make the most of your escape to paradise in the new year.

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Helping leisure selling travel agents successfully manage their at-home business.

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Agent Specialization: Group Travel

Laurence Pinckney

Laurence Pinckney

CEO of Zenbiz Travel, LLC

About Me