If you’re anything like us, you tolerate winter with muffled grumbles, counting down the days until summer begins. Instead, get out of dodge with a tropical winter vacation. These warm-weather destinations offer families plenty of beaches, resorts with swimming pools, and outdoor activities to entertain the entire family, free from winter hibernation.
Did you know the Bahamas consists of 30 inhabited islands? In the duty-free hub of Nassau, as well as neighboring Paradise Island, the beach life includes the high life—giant casinos, glitzy restaurants, and duty-free shops. Nassau and Paradise Island also did not see damage from Hurricane Dorian. Another side of the Bahamas includes the Out Islands, where you can relax in quiet settings, unscathed by the hand of modernity and Hurricane Dorian. The one commonality that binds all of these diverse islands together is the surrounding ocean. Azure waters, whose temperatures range from 75 to 84 degrees Fahrenheit, are fringed by pearly white or pink beaches. Pick an island, any island, and you can’t help but find an excellent beach and warm waters.
Then there are the Exumas, even less developed than Harbour Island. With crystal-clear water, uninhabited islands to picnic, and soft, rolling hills, this is the place to go if you and the kids want a tropical winter vacation. The Tropic of Cancer runs directly through George Town, the capital and principal settlement of the Exumas. Whether it’s the action on Paradise Islands or the quiet solitude of the Out Islands, families will love the Bahamas. Note: Grand Bahama Island and The Abacos were greatly affected by Hurricane Dorian in August 2019 and continue to be in the rebuilding process.
Recommended Hotel: Atlantis Resort
2. Cancun, Mexico
In Cancun, the shores bloom with high-rise hotels, creating a bustle that teens and 20-somethings find especially exciting. Except for March and April, when Cancun fills with partying undergraduates on spring break, the area has much to offer families, from all-inclusive hotels to a variety of restaurants. Snorkeling, diving and shopping are also available, as well as easy access to the Yucatan’s attractions. The city is found in Riviera Maya, which offers much that makes Mexico’s Caribbean so special. You and your family can swim and snorkel in cenotes, sinkholes formed by underground rivers; splash at eco-adventure parks; explore magnificent Mayan ruins and sun on white-sand beaches. The Riviera Maya, less densely developed than Cancun’s Hotel Zone (30 minutes to the north) also offers a range of resorts, from moderately priced lodging to luxury properties, plus a range of all-inclusive family-friendly resorts.
Most of Cancun’s guestrooms crowd together in the densely developed 15-mile Hotel Zone, whereas the Riviera Maya’s accommodations are spread over 86 miles, allowing for more greenery. Officially, the Riviera Maya stretches along Mexico’s Caribbean coast for 86 miles, from just south of Puerto Morelos to Punta Allen. However, some maps include Puerto Morelos as part of the Riviera Maya.
Recommended Hotel: Moon Palace Golf & Spa Resort
3. Costa Rica
Costa Rica continually amazes us. In the rain forests, parakeets twitter, howler monkeys scamper from branch to branch, sloths hide in the crooks of trees and scarlet macaws take flight. You can float along mangrove-lined canals, view active and dormant volcanoes, lounge on beaches and, in season, watch turtles nest. An ecologically aware country, Costa Rica protects much of its land as parks, refuges or reserves. Costa Rica is also eminently family-friendly. It’s safe (the “ticos” like Americans) and affordable, with hotel rooms and restaurants costing less than those in many U.S. cities and Caribbean islands. The only “problem” for visitors is the temptation to try to do it all in one vacation. Our advice? Don’t. Avoid spending too much time on the road. Instead, pick a few regions to visit during your warm-weather winter vacation with the kids, and select one hotel in each area to use as a base for day trips.
Recommended Hotel: Si Como No
4. Dominican Republic
The Dominican Republic features both the tallest point in the Caribbean — Pico Duarte, which rises more than 10,100 feet—and the lowest point—Lake Enriquillo, which falls 131 feet below sea level. Add rainforest, cacti-studded desert, 16 national parks and nearly 1,000 miles of coastline lacing the Caribbean Sea and the Atlantic Ocean, and you have one of the best tropical winter vacations for families. When you have a spare moment, layer on the sunscreen and go play. Punta Cana, on the eastern tip of the island, is one of the most popular destinations in the entire Caribbean. In the winter months, several hundred flights a week arrive at the Punta Cana International Airport to whisk the European and American crowd over to the growing legion of all-inclusive resorts.
Recommended Hotel: Dreams La Romana Resort & Spa
In Florida, head south and you’ll find the vibrant cities of Fort Lauderdale and Miami on the east coast; on the west coast, it’s Sanibel and Capitva Islands and Tampa. Further south and across the Seven Mile Bridge and you’re in the Florida Keys, worlds away from the rest of the state and Florida’s own Caribbean islands. And, of course, smack dab in the center is the home of the mouse: Walt Disney World. You can’t go wrong with a warm-weather winter vacation in Florida!
Recommended Hotel: Southernmost on the Beach
Brimming with posh resorts and hotels (including all-inclusive Hawaii resorts), incredible dining and exciting family activities, it almost seems impossible that Hawaii could hold any more beauty and pleasure. Ah, but we didn’t mention the beaches. Like beauty queens who rack up titles, Hawaii’s white-, red- and black-sand beaches are consistently ranked among the best. Maui is the second-largest of the eight Hawaiian islands and is basically a chain of small towns and hip beach havens. Sprawling luxury resorts thrive in Maui, thanks to the millions of visitors who flock to paradise each year, but Maui also has condos and value accommodations for those willing to do the research.
Recommended Hotel: Four Seasons Resort Maui at Wailea
Families underestimate the size of Jamaica. Driving from one end to the other can take close to six hours. Yet, within its confines are some of the finest stretches of coastline in the Caribbean, offering the lush Blue Mountains that rise from its core. In Montego Bay and Negril, ladies with baskets of tropical fruit perched on their heads stroll the beaches, slicing and dicing sugary pineapples or butter-soft papayas faster than a chef at a Japanese steakhouse. The all-inclusive resorts just outside of Ocho Rios continue to make the town a top family destination, especially when you want to escape the snow. Hang at the beach to swim and sail, or head outside the resort to climb Dunn’s River Falls. Guides escort families up through the cascading water as they climb the 600-foot-high waterfall. Other nearby excursions include taking a tube down a clear stream in the mountains above the city, horseback riding along a quiet stretch of the coast and taking a drive to the birthplace of reggae legend, Bob Marley.
Recommended Hotel: IBEROSTAR Rose Hall Suites
8. Puerto Rico
More than one warm weather getaway is required to explore all that Puerto Rico offers with your family. With seven square blocks of cobbled streets, Old San Juan delights families with centuries-old forts, as well as art galleries, cafes and boutiques. The forts, the oldest European constructions in the National Park Service, along with the ancient city walls and the governor’s mansion, have been designated a World Heritage Site. Beyond San Juan, there’s much to see and do. On the “mainland,” hike the rain forest, explore caves, and snorkel through schools of rainbow-colored fish. On Vieques and Culebra, Puerto Rico’s offshore islands, enjoy a laid-back, uncrowded Caribbean idyll. A bonus for U.S. citizens traveling to Puerto Rico is that no passport is needed for this warm weather winter destination!
Recommended Hotel: El Conquistador Resort
9. Southern California
Southern California is a region brimming with adventure and wonder galore. The upside to the region is that there are attractions, incredible restaurants, museums and memorable hotels sprinkled liberally throughout the many neighborhoods and communities that make the San Diego region, well, San Diego. And all this is under the most sublime weather (with the exception of May Gray and June Gloom). The downside is that choosing how to spend your time in the area is no small feat. Coronado or LEGOLAND? La Jolla or the Gaslamp Quarter? A Padres game or SeaWorld? You see the dilemma…
Recommended Hotel: Hotel del Coronado
10. U.S. Virgin Islands
Long with beautiful beaches, first-rate snorkeling, Caribbean culture and easy accessibility from the states, the U.S. Virgin Islands come with a reassuring sense of familiarity; after all, English is the primary language, the U.S. dollar is the currency and U.S. citizens don’t need passports.
St. Thomas, home to the busy port and USVI capital Charlotte Amalie, bustles with cruise passengers and other vacationers drawn as much to the island’s beaches as they are to its abundant shops.
St. Croix, the largest of the USVI in land mass, remains less developed than St. Thomas. On St. Croix, you can drive through 15 acres of dense vegetation dubbed a “rain forest” by islanders and spot the stone ruins of more than 100 once-thriving sugar plantations in the countryside.
St. John is our favorite of the islands. Two-thirds of the 28-square-mile island — 9,500 acres of land plus surrounding reefs—are protected as the Virgin Islands National Park, part of the U.S. National Park Service. The park is not only St. John’s main attraction, but it’s also the jewel of the USVI for its snorkeling, beaches and natural scenery. Trails wind up and over hills, through tall, tropical trees and some end at the island’s white sand beaches. At Trunk Bay, a popular snorkeling site, you can follow an underwater trail through the reef.
Recommended Hotel: Caneel Bay Resort
What to Pack for Your Next Trip
Women’s/Mom’s Cool Overwater Bungalow Swimsuit for Summer
Mom’s/Women’s Summersalt Swimwear for a Cheap Vacation
Swimwear for Women/Mom in Summer
Our team of parents and travel experts chooses each product and service we recommend. Anything you purchase through links on our site may earn us a commission.