How to Plan Family Caribbean Vacations That Create Lasting Memories

How to Plan Family Caribbean Vacations That Create Lasting Memories

Family Caribbean Vacations, WIMCO Villas, Beaches, Barbados
The best family Caribbean vacations include sights, adventures, beaches and perhaps a few rounds of golf – here are some picks from our favorite family-friendly islands.

Most people plan vacations because they need to get away, unplug, and relax. However, when you travel with your family, you’re also seizing an opportunity for true quality time and the chance to create amazing memories. The trick is to visit an island that offers something fun for everyone, while still providing the quality accommodations and dining to which you are accustomed.

The Caribbean islands of Barbados, Nevis, and Anguilla all offer unique, family-friendly experiences that your loved ones will be raving about for years to come. And don’t worry, we’ll be sure to share the best places to escape for a bit of golf and tennis as well.

Family Caribbean Vacations in: Barbados

Family Caribbean Vacations in Barbados, WIMCO Villas, Rental Car

Barbados is the most easterly of the Caribbean islands and its people, the Barbadians, are known for being extremely friendly. Even better? Most villas in Barbados come with their own staff, making total relaxation inevitable.


Harrison’s Cave – This underground cave of crystallized limestone is a popular attraction on Barbados. There are streams and pools of crystal clear water, column-like rock formations, and lovely waterfalls.

Island Safari Jeep Tours – There’s nothing like a guided tour that goes both on-road and off-road to give you a picture of the island’s landscape. Island Safari offers a few different 4×4 Jeep tours, including private tours if you want to make it an extra special activity for your family.

Folkestone Marine Park & Museum – If your family has experience with scuba diving, Folkestone Marine Park has a reef that was formed by the sinking of a ship (which rests in 120 feet of water less than half a mile from shore). There is also a museum that has a great aquarium with many different marine species, which would be delightful for smaller children.


Barbados is home to countless outstanding beaches, however, families may enjoy certain parts of the island more than others. Beaches on the west and south coasts tend to be more family-friendly, as they see less wind and waves. Both are great for relaxing and watersports, like jet skiing, kayaking, and snorkeling, but the the south beaches are a little better for sports that require a slightly livelier surf — for example, windsurfing and boogie boarding.

Golf & Tennis

Barbados is a golf lover’s paradise. Sandy Lane offers three different courses — two of which were designed by Tom Fazio. Royal Westmoreland, recently ranked in Golf Digest’s Top 100 Golf Courses outside of the U.S., has a world-class 18-hole championship golf course. Other golfing options include Barbados Golf Club, Rockley Club, Apes Hill Club, and Almond Beach Village. You’ll find tennis courts in various locations around Barbados, but Sandy Lane is a wonderful place to play. Sandy Lane offers nine floodlit tennis courts and a resident tennis professional to help with your backhand.

Family Caribbean Vacations in: Nevis

Family Caribbean Vacations in Nevis, WIMCO Villas, Horseback Riding on the Beach

If you are looking for a slower, more authentic Caribbean experience, Nevis has a unique, unspoiled beauty that you shouldn’t miss. This exclusive island is only 36 square miles and you will never see a casino in town or a huge cruise ship in port. Nevis is an island where you turn off your iPhone, unwind, and reconnect with your family in a tranquil setting.


Horseback Riding – Nevis Equestrian Centre offers rides on the beaches, historic trails, and through Nevisian villages. These rides are for all skill levels, and anyone age 6 or older can enjoy.

The Botanical Gardens of Nevis – The Botanical Gardens, found on the land where the Montpelier Estates once stood, feature breathtaking views and an impressive collection of tropical plants and flowering trees from around the world. Keep an eye out for the Poinciana or Flamboyant, the national flower of St. Kitts and Nevis. Then, when you’re tired, visit the on-site restaurant and enjoy herbs picked right from the garden.

Hamilton Estate – Bring the kids to explore the fascinating ruins of the Hamilton Estate, which was a sugar plantation until the 1950s. Among the ruins, you’ll find foundations of the Great House, volcanic stone windmill tower, cistern, chimney, boiling house, and steam engine. The panoramic views of Charlestown and St. Kitts are quite impressive as well.


Nevis has several different beaches, with most people favoring those on the northern and western shores. Pinney’s Beach, a three-mile paradise on the outskirts of Charlestown, is the most famous beach on the island. While the powdery sand and beautiful blue water are unmatched, many visitors come to love the fact that the beaches are never crowded.

Golf & Tennis

Golfers can’t leave Nevis without playing on the par 70 course at Four Seasons Nevis, designed by the legendary Robert Trent Jones. The Four Seasons Nevis is also home to fantastic tennis facilities. They offer ten courts, night play, and professional instruction.

Family Caribbean Vacations in: Anguilla

Family Caribbean Vacations in Anguilla, WIMCO Villas, Sailing in AnguillaWhile Barbados can be a bit more bustling, and Nevis is extremely tranquil, Anguilla seems strike a nice balance between the two. When your family is looking for a little more action, they’ll find it in town. However, there are plenty of places for peace and quiet when everyone needs a few moments (or more) to relax.


Heritage Collection – This well-done museum will give your family an excellent look at Anguilla and its interesting history. You’ll enjoy viewing artifacts, photographs, and records — and the curator is often there to answer questions and tell stories.

Pelican Trail & Water Sports at Little Bay – A visit to Pelican Trail & Water Sports is an all-day adventure the whole family will love. An entry fee allows unlimited use of snorkel equipment and the water trampoline, and guided two hour tours in glass kayaks are available for an additional fee. Of course, you can also just lounge, snorkel, or swim as well. Keep an eye out for the iguanas!

Tradition Sailing Cruise – This sail charter company offers five-star service and unforgettable adventures. You can choose from their lunch, sunset, snorkeling, and other cruises, and craft an experience that will be perfect for your family.


Anguilla is known for having some of the most outstanding beaches in all of the Caribbean. Of the 33 beaches, Shoal Bay East is probably the most famous. It offers beach bars, restaurants, and has an offshore reef that is great for snorkeling and diving. Another beach, Rendezvous Bay, is a beautiful location for walking and swimming.

Golf & Tennis

CuisinArt Resort & Spa is home to Anguilla’s first and only golf course — but it’s definitely one to remember. The $50 million, 18-hole champion course was designed by Greg Norman and provides breathtaking views of the island.

Anguilla Tennis Academy offers instruction for both children and adults, however, if you’d rather just get in there and play, that is an option too!

Planning a Family Caribbean Vacation Doesn’t Have to Be Hard

The most important thing to remember when organizing your family vacation in the Caribbean is that you can’t really go wrong. You are going to be with people you love on a beautiful island — everything else will just be icing on the cake.

And, as always, WIMCO will book your villa or hotel, arrange air travel, and organize rental cars. We can even take care of first-day provisioning so that when you arrive on-island, your fridge is already stocked with snacks and Champagne. If you have any questions, or would like to book your family’s next vacation, call us at 1-888-997-4326.

Leave a comment: Do you have any favorite family-friendly Caribbean vacation destinations? Share your memories with us and our readers!