Traveling to the Caribbean is bliss. It’s filled with idyllic island beaches, soaring verdant mountains, too-many-to-count shades of sea blues, warm sunshine and inviting cultures that are unique to each destination. With direct flights from many parts of the U.S., traveling to the Caribbean, or Caribbean-like destinations, can be as easy as search-book-go.
Here, we take a look at six Caribbean and Caribbean-adjacent destinations that are perfect for an exceptional weekend vacation. Don’t blame us if you find yourself wanting to stay longer!
As always, check for travel restrictions and closures before planning your trip.
Bermuda
Though technically not in the Caribbean, a quick flight from the East Coast delivers you to this British island territory, famous for its pink-sand beaches and breathtaking turquoise seas. A weekend is plenty of time to discover all of Bermuda’s 21 square miles, or focus in on one area to experience the island at a slower pace.
The recent history of Hamilton, Bermuda’s capital, dates back more than 200 years, and it’s here you can tour Fort Hamilton, built in 1870. Dive deeper into the island’s history at the National Museum of Bermuda in the Royal Navy DockYard. More history is found in the Town of St. George, which was settled in 1612, where you’ll find Fort St. Catherine, built the same year.
Outdoor enthusiasts will want to make their way to Southampton, where plenty of golf courses, boat tours and scuba diving outfitters await to delight on land or under the sea. Whichever route you choose, be sure to take time to spread out a blanket or towel on the beach at Horseshoe Bay — this is where Bermuda’s famous pink sands sparkle in the sunshine.
Aruba
The Dutch Caribbean island is part of the ABC Islands, along with Bonaire and Curaçao, but the list of things to see and do in Aruba easily spans from A to Z — and beyond.
Plenty of beaches can be found around the island, like Palm Beach, with its private cabanas and palapas (shaded huts); Hadicurari Beach; and Arashi Beach, with glassy-calm water and gentle surf.
A fun way to travel from point A to point B on the island is in an open-air Jeep. Feel the warm Caribbean breeze flow over you as you discover the island away from the beaches.
Arikok National Park on the northeastern side of the island encompasses more than 7,900 acres, or approximately 20 percent of all of Aruba. The landscape in the park ranges from rugged coastline to sand dunes, volcanic (Hooiberg Mountain) to aquatic (the Natural Pool, known as “Conchi” on-island).
Sunset is always a celebration on Aruba. Drive your Jeep to the California Lighthouse, which offers 360-degree views of the island, or opt for a sunset sail on a catamaran to be on the water when the sun disappears below the horizon.
Jamaica
You may find that you’re already familiar with a lot of what makes Jamaica, well, Jamaica, and that’s no surprise — the island’s cultural attributes like music, cuisine and drinks have been on the international scene for quite some time.
A terrific place to start a weekend vacation in Jamaica is in Kingston, the island’s capital. The Bob Marley Museum sits in the reggae musician’s former home in the heart of the capital, and one of the Caribbean’s largest art collections is at the National Gallery of Jamaica. When night falls, check out Dub Club, a popular reggae dance hall that is sure to provide an energetic good time.
Jamaica’s famous Seven Mile Beach is on the Negril side of the island and is a perfect place to soak in the Caribbean sun, swim in the warm sea and laze the day away.
Another spot to check out on Jamaica is Montego Bay, about an hour from Negril and three hours from Kingston. Spend a few hours on Doctor’s Cave Beach, another Jamaican hot spot, and visit the Montego Bay Cultural Centre that dives deep into the island’s rich culture.
Panama City, Panama
The greens and blues of the waters that lap onto the shores of Panama City give the cosmopolitan city airs of being on the Caribbean Sea. However, the city is in fact framed by the Pacific Ocean and the Canal de Panama, or the Panama Canal, which links it to the Caribbean.
Speaking of the canal, this is a terrific way to start a weekend vacation in the Central American country. Opened in 1914, the canal is integral to Panama City’s economy and industry. Spend the better part of a day passing through all six of the original locks, from the Pacific Ocean to the Caribbean, learning all about the canal’s history and impact on a global scale. If you don’t have time for an entire day on the canal, learn all about it at the Museo del Canal.
In the city itself, must-see sites include the eye-catching, Frank Gehry–designed Biomuseo; Panamá Viejo, a UNESCO World Heritage Site with maps, artifacts and more that tell the story of the city’s origins dating back to 1519; and marine life and on-land mammals like sloths at the Smithsonian Institution’s Punta Culebra Tropical Research Institute.
Meander through Casco Viejo, the city’s oldest neighborhood, which also happens to be its hippest, with plenty of boutiques, galleries and cafés that will lure you to step inside.
San Jose, Costa Rica
Another Central American city with both Caribbean and Pacific vibes blended with mountain influences and enticing cultural heritage is San José, sitting nearly smack dab in the middle of Costa Rica.
Within the heart of the city is Parque Metropolitano La Sabana, a massive amount of green space where you’re likely to see families enjoying the day together. If you’re visiting during the season, you may be able to catch a soccer match at the National Stadium, which is inside the park’s boundaries. The Costa Rican Art Museum and La Salle Natural Science Museum are located within the park.
In contrast to all of its natural green spaces is the city’s high concentration of preserved and restored colonial buildings, which you’ll find in Barrio Amón. Be sure to look up so you don’t miss any of the details!
Mexico
The varying shades of blue and green of the waters that kiss Puerto Vallarta — PV to those in the know — via Banderas Bay shores give it the feel of being on the Caribbean Sea rather than the Pacific Ocean. Adding to the ambience are bright plazas, tiled rooftops and draping bougainvillea.
A terrific way to get a feel for PV is by walking along the Malecón, a wide promenade lined with palm trees that winds alongside the beach from the downtown area to Old Vallarta. You won’t be alone on your stroll — bronze statues cast by local artists are dotted along the route, and boutiques and restaurants will draw your attention.
Carry yourself over a bridge to Isla Cuale, an island in the middle of the Cuale River with shoppings stalls and artists displaying their masterpieces. The nearby Cuale Museum offers an account of the Indigenous people who lived on this same land thousands of years ago.
Beach life is certainly a way of life in PV, and the region is flush with options. In town, there’s the sandy beach that spills off of the Malecón, and for something a little quieter, Playa Amapas is set amid a jungle and rock formations.
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