Jamaica

With over 4,400 square miles of beaches, mountains, and vibrant culture, Jamaica stands out as one of the Caribbean's most dynamic destinations. But what really struck me during my time in Montego Bay wasn't the size or the scenery—it was the people. I've traveled to plenty of places, but Jamaica is where I felt the most welcomed. Everyone smiles, says hello, and genuinely goes out of their way to be accommodating. That authentic warmth is what sets this island apart. Jamaica pulses with a cultural energy unlike anywhere else in the Caribbean. This is where reggae was born, and you can feel that rhythm and soul the moment you step off the plane. It's not just another beach destination, it's an island with real character and depth. Whether you want pure beach relaxation or cultural immersion and adventure, Jamaica delivers. The hospitality isn't just marketing talk; it's real, and it's what will make your family vacation truly memorable.

Negril's Seven Mile Beach is perfect for families with younger children, the sand is soft, the water is calm and shallow, and the whole vibe is refreshingly laid-back. Over in Ocho Rios, you'll find GoldenEye, the estate where Ian Fleming penned the James Bond novels, now a stunning resort. The area also puts you close to natural attractions like YS Falls, where you can swim in turquoise pools and even zipline over the cascades. And don't miss the catamaran trips, sailing along Jamaica's coast with snorkeling stops and rum punch is quintessential Caribbean. Montego Bay is the place to go if you want to arrive, check into your resort, and let someone else handle the details. The all-inclusives here have kids' clubs and activities that keep children entertained while parents actually get to relax. But the best properties do more than just pamper you, they give you a real taste of Jamaican culture, not just a generic resort experience. At Round Hill, we met Straw Boss Richard, who's been handcrafting baskets for 52 years, watching him work was mesmerizing and his craft was gorgeous.

What To Do

Jamaica offers a great mix of beach relaxation and adventure that keeps the whole family engaged. Seven Mile Beach in Negril has calm, shallow water perfect for younger kids. Snorkeling around the island is excellent, with healthy reefs full of colorful fish. Catamaran trips are a must, you'll sail the coast, stop for snorkeling, and enjoy some island vibes. It's quintessential Caribbean. Dunn's River Falls is Jamaica's most famous attraction where you actually climb up the terraced waterfall with a guide, exhilarating for kids. YS Falls offers a similar experience with less crowds, plus ziplines over cascades. For something gentler, bamboo rafting down the Martha Brae River lets you drift through lush scenery. Mystic Mountain has a bobsled ride through the rainforest that's thrilling without being too intense. Visit local jerk centers to watch your food get prepared over pimento wood fires—the flavors are incredible. At Round Hill, we met Straw Boss Richard, who's been handcrafting baskets for 52 years. These authentic interactions give you a real connection to Jamaica beyond the resort experience.

When To Visit

The best time to visit Jamaica depends on what matters most to you; weather, crowds, or budget.

December to April is peak season and for good reason. The weather is perfect; dry, sunny, and consistently in the low-to-mid 80s. This is when everyone wants to be there, so expect higher prices and more crowded resorts. If you're tied to school holidays and this is your window, but book well in advance.

May and November are the sweet spots if you want good weather without the peak-season prices. You might catch some rain, but it's usually brief. The beaches are less crowded, and you'll get better deals on accommodations. These shoulder months offer excellent value.

June to October is officially hurricane season.