At this time of year, Chicagoans can’t resist shopping for vacation deals to the Caribbean Islands. Who can blame us? Arctic blasts, snowzilla, and the grey-sky winter blues. The question is: “Which Caribbean island?” The answer: It depends on what you want to do.

Cane Garden Bay beach in Tortola is one of the most beautiful beaches in the Caribbean Islands. Photo by Jamie Bartosch/Suburban TravelingMom

Cane Garden Bay beach in Tortola is one of the most beautiful beaches in the Caribbean Islands. Photo by Jamie Bartosch/Suburban TravelingMom

Caribbean Islands

Which of the Caribbean Islands is best? I get asked this question a lot by traveling families. My answer is always, “it depends.” It does. Because every family likes different things. My family doesn’t like giant resorts or kids clubs, but I know families who love them.

So it’s really about what you want to do. Just rotate between the beach and pool? Or do you want to explore a culture? Do you want to be in a private place, or a party place?

There really is a lot of variety in the Caribbean. And at least one island (and probably several) will be a good fit for your family.

I haven’t been to every island, but I’ve gotten around. So I feel like I can speak with some authority. While not every Caribbean island is included in this list, I hope it will help with your decision making.

Not Too Expensive: Jamaica and Aruba

One of the best value hotels in the Caribbean is Jewel Runaway Bay Resort in Jamaica. (Read my review here.)

A mid-sized all-inclusive, it includes a new water park, no competition for pool chairs or restaurant reservations, very nice staff, and an adjacent farm with horses that the kids can brush and ride, nighttime laser tag, a teen room with Xbox, and nice pools and beach. It’s in an isolated town, and not super fancy, but it’s comfortable, clean and well worth the money.

Photo by Jamie Bartosch/Suburban TravelingMom Playing beach volleyball at Jewel Runaway Bay Resort in Jamaica.

Photo by Jamie Bartosch/Suburban TravelingMom
Playing beach volleyball at Jewel Runaway Bay Resort in Jamaica.

While parts of Aruba have a wild spring break party vibe, we found a good balance (and good value) at the Aruba Marriott (Read my story about Aruba here). It’s one of those resorts where you don’t need to leave, because everything you need is on-site. Also, I’ve been heard raves about Aruba’s new Phillips Animal Garden, a zoo that’s great for younger children.

If You Like All-Inclusives: Dominican Republic and Riviera Maya

I routinely see great deals to all-inclusives at these places at Costco Travel, TravelZoo.com, amd Booking.com. The creme de la creme of all-inclusives for families are the Beaches Resorts in Jamaica and Turks & Caicos. While on the pricey side, the family activities they offer (a DJ scratch class!) are amazing. Cosmopolitan TravelingMom gave a great rundown of what the resort offers, and what are worthwhile add-ons.

If You Don’t Like Touristy Places: St. Kitts, Tortola and St. John

When I’m on vacation, I don’t want to be with crowds. I don’t want to be near ports where massive cruise ships dock. I want to feel like I’m away. That’s one of the reasons I love these Caribbean Islands. On St. Kitts, I can’t say enough good things about Ottley’s, a property that’s not on the beach, but has a really warm, homey feel to it (plus an awesome restaurant). My review of the hotel is here, and my list of family-friendly things to do in St. Kitts is here.

Tortola and St. John are made up of small hotels and tiny restaurants, and they are that perfect balance of low-key vibe that is more friendly and low-key than touristy. We rented condos during our stays here, which I recommend for families. We’ve had good experiences finding places on vrbo.com.

Kids playing in the Caribbean in Puerto Rico.

Kids playing in the Caribbean in Puerto Rico. Photo by Jamie Bartosch/Suburban TravelingMom

For Culture, History and Food: Puerto Rico and Cuba

While Cuba is not recommended for young kids (see one TravelingMom’s opinion about it), it might be a great cultural experience for older kids.

My kids loved Puerto Rico. We went on an interesting guided hike through the rainforest, ziplined at a place especially for first-timers.

My kids also liked walking in the dungeons at Castillo San Cristobal. We didn’t even get to the Bioluminescent Kayak Tour, which I hear is super fun. But the kids practiced their Spanish and even tasted mofongo, a Puerto Rican rice dish. Here’s my rundown of family-friendly things to do in Puerto Rico. Added bonus: no passports are required for Puerto Rico.

For a Long, Beautiful Beach: Grand Cayman Island

Grand Cayman is one of my family’s favorite Caribbean Islands. Seven Mile Beach is clear blue water and white sand as far as you can see. It’s all public property, so you can walk up and down it all day and look at the resorts, pick up shells, or stop to snorkel. We stayed at the Westin Casuarina, which is a large resort with all the creature comforts we needed, and we had a nice stay.

When we needed a break, we visited Starfish Point, where you see live starfish in the water.

Don’t miss Stingray City (it’ll be your favorite photo op), and our favorite, the Turtle Farm, where we got to hold and feed turtles of all sizes. My story on Grand Cayman is here.

Another super-cool beach worth mentioning: the Baths on Virgin Gorda, in the British Virgin Islands. You can take a ferry here from Tortola. My kids loved climbing around these enormous rocks that create little grottos.

One important note about beaches in the Caribbean. There are many fabulous choices. But make sure to check that your beach is a soft sand beach and not a rock beach. If you stay on one side of Tortola, for example, the beaches are rocky and not very kid-friendly. But on the other side (on the Cane Garden Bay side), the island is gorgeous soft sand. Just make sure to check.

Photo by Jamie Bartosch/Suburban TravelingMom Watching the sunset on Grand Cayman Island.

Photo by Jamie Bartosch/Suburban TravelingMom
Watching the sunset on Grand Cayman Island.

If You Like All the Conveniences of Home: St. Thomas, St. Martin

These popular cruise ship port cities can be generic and touristy. But they have all the comforts of home – good WiFi (rare in the Caribbean), Americanized restaurant menus, 24-hour service, and a festive vibe. We’ve always stayed at large American chain hotels near the ports, and the pools and beaches are packed. What I remember the most was that everyone was on their cell phones. Not my cup of tea. But if you’re a family who likes to stay connected, this is a good choice.

If You Want to Go High-End: Nevis, Anguilla, St. Barts, Turks & Caicos, and St. Vincent and the Grenadines

Which of the Caribbean Islands is right for your family? It all depends.St. Vincent was recently described as the place billionaires go to get away from the millionaires. But if you’re more in the $800/night  range, there are a lot of really nice places in the Caribbean for you. The most kid friendly is Turks & Caicos, and many TravelingMoms have excellent suggestions for resorts and activities.

If you have any questions about any of the places, post your question via our Ask a TravelingMom feature and we will rally the Traveling Mom writers to give you our honest mom-to-mom advice.