Jamaica is alive with energy, and nowhere is that more evident than in our year-round calendar of events. From music festivals to cultural celebrations, each event tells a story about the island’s passion, rhythm, and vibrant community spirit. At Bailey’s Tours, we make it easy for you to experience the very best of Jamaican festivities, up close and personal.
Held every July in Montego Bay, Reggae Sumfest is the largest music festival in the Caribbean. Featuring top reggae, dancehall, and international acts, this week-long celebration draws music lovers from around the world. Bailey’s Tours offers exclusive packages that include event access, accommodation, and VIP transportation – so you can enjoy the show stress-free.
Every spring, the streets of Kingston come alive with feathers, beads, and nonstop music during Jamaica Carnival. It’s a stunning celebration of Caribbean culture, complete with vibrant costumes, dancing, and soca energy. Join one of the local bands, or let Bailey’s Tours take you to the best vantage points to enjoy the festivities without missing a beat.
Held in January in Accompong, the Maroon Festival is a powerful celebration of resistance and heritage. This annual event honors the Maroons – descendants of enslaved Africans who escaped and formed free communities. Through music, rituals, and storytelling, visitors gain a deeper understanding of Jamaica’s complex past and enduring pride. Bailey’s Tours ensures your visit is respectful, informative, and unforgettable.
If you love Jamaican food, don’t miss the Portland Jerk Festival, usually held in July. This family-friendly event is dedicated to the island’s famous jerk cuisine. With live music, dance competitions, and endless food stalls, it’s the perfect blend of flavor and festivity. Our guided day trips include transport, entry, and a curated tasting experience you’ll savor long after it ends.
Beyond the big festivals, Bailey’s Tours also connects you with smaller, local events that are rich with authentic Jamaican life. From Sunday beach parties in Negril to Friday fish fries in Hellshire, we’ll help you tap into real Jamaican vibes. These experiences are often unlisted and spontaneous – which is why having a local guide makes all the difference.
Whether you’re planning your trip around a major festival or hoping to stumble into an unforgettable block party, Bailey’s Tours is here to guide you. We know when and where it’s all happening, and we’ll make sure you’re in the right place at the right time – with the right company.
