Exotic enough to feel novel, familiar enough to feel comfortable, the Caribbean islands are paradise for beach-loving families. Many people question whether it’s worth a long trip down there if you can just go to the ocean closer to home. My answer: Absolutely yes. Each island’s culture and beauty are totally unique, and each casts its own lazy, hazy spell.
Virtually every Caribbean island is family-friendly, albeit in different ways. Some have lots of all-inclusive resorts that cater to kids; the draw for others lies in calm, shallow water and ultrasoft sand. The tricky part is sorting through all the options and deciding which one suits you best.
As a lifelong beach fanatic and seasoned Caribbean traveler, here’s my need-to-know advice about choosing the right island … and understanding what to expect when you get there.
Top Caribbean Vacation Tips for Families
Decide whether nonstop flights are a must. This is the first question I ask Caribbean-bound Ciao Bambino clients. I adore tiny, remote islands such as St. Vincent and the Grenadines, but getting to them can involve a ferry and/or puddle jumper after a connecting flight to the region — not fun with tired kids. The tradeoff is that farther-removed islands tend to be peaceful and pristine.
If you want to fly nonstop, check airline schedules up front to narrow down your options. Jamaica, Aruba, St. Lucia, St. Thomas, Grand Cayman, the Dominican Republic, and Puerto Rico are typically among the best bets.
Even with direct/nonstop flights, you’ll often have a long transfer from the airport to your accommodations. I enjoy this, as you get an up-close peek at the island’s landscape and character, but don’t forget to factor it into the total travel time.
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Picture your ideal beachscape. When my husband and I honeymooned on St. Lucia, he was startled by the brownish gray beaches and deep blue sea. Like a lot of people, he assumed that everywhere in the Caribbean has sugar-white sand lapped by crystalline water. False!
As a rule of thumb, volcanic islands (such as St. Lucia, the U.S./British Virgin Islands, Jamaica, St. Kitts and Nevis) have dramatic peaks and valleys quilted with greenery, fringed by coarse, deeply colored sand. They also tend to be rainier — hence why all that foliage stays so lush. Coral islands (including Anguilla, Barbados, Turks & Caicos, Aruba and the Caymans) have pale, powdery beaches and calm turquoise water. They’re usually flat and scrubby. Both types are appealing; it comes down to personal preference.
Consider how much activity you want. Are your kids happy playing in the sand and surf all day, or do they need more action? If they’ll get bored hanging out on the beach, pick a property with lots going on or an island that has plenty to do. Aruba, Jamaica, Grand Cayman, the Dominican Republic, and parts of the Bahamas offer a huge variety of resorts with kids’ clubs and family programming, plus offsite excursions galore. Along with Puerto Rico and St. Thomas, however, these islands are also some of the most developed, with shopping centers, nightclubs, restaurants and in some cases casinos.
If you’re seeking something more idyllic, opt for the sleepy Grenadines, Anguilla, Vieques (Puerto Rico), Nevis, the Bahamas’ Out Islands, or the BVIs. Private islands, e.g. Parrot Cay in Turks & Caicos, offer the ultimate in seclusion. Just bear in mind that you’ll also be farther from medical services and other infrastructure.
For hiking and nature touring, I’d shortlist St. Lucia, St. John and Dominica (note, that’s not the same as the Dominican Republic). Barbados, Puerto Rico, the DR, St. Kitts and Nevis, Antigua and Grenada are standouts for historical sightseeing. Want to dive or snorkel? Try the Caymans, Virgin Islands, and Turks & Caicos.
Know that beaches on many islands are public, even in front of the resorts. You’ll rub elbows with locals (a plus!) and you may encounter vendors offering hair braiding, watersports and more. Just say a polite “No, thank you” and move on if you’re not interested.
Note that public doesn’t always mean jam-packed. I recently spent a few days at a large resort on Turks & Caicos’ beautiful Grace Bay, and even with island residents plus guests, the crowds were manageable. Even so, concierges and drivers can point you to safe, under-the-radar beaches that you may have almost to yourself.
Consider renting a villa. The Caribbean is expensive. Sticker shock at resorts is as common as sunburn, and sometimes just as painful. I’m a big fan of villa rentals to keep costs in line. Not only will you have more space and privacy, but the rates on some islands, such as Jamaica and St. Lucia, typically include a housekeeper and/or chef.
What you won’t always find: air conditioning, reliable WIFI, kid-safe swimming pools. Go through a reputable agency and ask detailed questions before you book or use Ciao Bambino’s vacation planning service to help book a fantastic option through our preferred villa agency list.
TIP: Many people request a villa right on the water, but I think it’s ideal to stay higher up if you don’t mind a short trek to the beach. The views are prettier, and you’ll catch cooling breezes that can offset the lack of A/C.
Determine whether a rental car makes sense. Unless you’re renting a villa, you probably won’t need a car. Excursions booked through your resort virtually always include transportation. If you’re staying at a private home and prefer not to drive, hiring a taxi or driver for the day can be surprisingly affordable. It’s also a great way to get insight into the local culture — drivers are usually knowledgeable, well connected and full of anecdotes and inside tips. If you have car seats, let the driver know in advance (I’ve run across more than one cab that’s missing seat belts).
Want your own wheels? Be prepared: Between rudimentary roadways, steep hills and speed demons, driving on the more rugged islands can be hair-raising. Also, remember that if you’re in a British-influenced destination such as Barbados, driving is on the left side of the road.
Embrace the local food scene. Food in the Caribbean is pricey because much of it has to be shipped in – this is one reason why all-inclusives are so popular in this part of the world. I’ve found the quality of imported items to be hit or miss, even at five-star properties. Become a vacation locavore and explore the region’s vibrant, nuanced cuisine. Many of the islands these days are growing and raising more of their own foods, with delicious results.
Anguilla, St. Maarten/St. Martin, Guadeloupe and über-chic St. Bart’s are foodie magnets, but for some of the tastiest and cheapest fare, seek out roadside stands and holes-in-the-wall on your island of choice. Just ask around to discern which spots to hit and which ones to avoid.
Accept climate-related flaws as part of the package. In tropical climates, creepy-crawlies and moisture damage are a given. I’ve seen people complain to the resort staff about finding a beetle in the bedroom or peeling paint on a balcony rail. The fact is, even at the highest of the high-end properties, there’s simply no escaping an occasional bug or blemish. Don’t take it as a knock on quality.
Set your internal clock on island time. Forget rigid schedules — you’re at the beach! Life in the Caribbean is relaxed and fluid, exactly as it should be. Does it mean 20 minutes might pass before you see the rum punch you ordered? Yes, but don’t let it throw a wrench in your day. If there’s one perfect place to master the art of going with the flow, this is it.
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Editor’s Note: Photos courtesy of the individual properties pictured, except where noted.