Island hopping through the Caribbean sounds like a dream—and for the most part, it was. But after visiting 20 different islands, I realized not all of them left the same impression. Some were so unforgettable, I’m already planning my return. Others looked great in photos but didn’t quite live up to the hype once I got there. Here’s what stood out (and what I’d pass on next time).
St. Lucia
The dramatic Piton mountains of St. Lucia rise majestically, enveloped by lush rainforests that seem to whisper tales of adventure. This island is a hiker’s paradise, offering trails that lead to breathtaking vistas. Couples seeking romance find solace in the luxurious resorts that dot the landscape, where every sunset feels like a painted masterpiece. Whether it’s the thrill of climbing a peak or the tranquility of a spa, St. Lucia offers a splendid blend of excitement and relaxation. It’s an island where adventure and luxury coexist seamlessly, making it a must-return destination.
Grenada
Grenada, affectionately known as the ‘Spice Island,’ enchants with its fragrant air and warm-hearted locals. The uncrowded Grand Anse Beach is a haven for those seeking tranquility, where waves gently kiss the shore. Beyond the beaches, Grenada boasts cascading waterfalls and verdant spice plantations that invite exploration. The island’s genuine charm lies in its authentic vibe, a refreshing escape from commercial tourism. Whether lounging on the beach or wandering through spice-scented pathways, Grenada’s simplicity and beauty beckon for a return visit. It’s a place where nature and hospitality embrace visitors warmly.
Curaçao
Curaçao captivates with its colorful Dutch architecture and lively atmosphere. Strolling through Willemstad feels like walking through an artist’s palette, where each building boasts its own hue. Beneath the azure waves, vibrant coral reefs await divers and snorkelers, offering an underwater spectacle. The island’s culinary scene adds to its charm, with local flavors that tantalize the palate. Less touristy than neighboring Aruba, Curaçao offers a refreshing change of pace. It’s a place where culture, nature, and cuisine blend harmoniously, creating a unique island experience that’s hard to resist revisiting.
Anguilla
In Anguilla, the world slows down, inviting you to savor every moment on its pristine white sand beaches. Without the presence of cruise ships or bustling casinos, tranquility reigns supreme. The island’s turquoise waters sparkle under the sun, offering a peaceful retreat for the soul. Seafood lovers delight in the local cuisine, where fresh catches transform into delectable dishes. Anguilla’s charm lies in its simplicity and elegance, a place where relaxation finds its true meaning. It’s an island escape that remains untouched by time, making it a perfect haven to revisit time and again.
Dominica
Dominica is a rugged gem, an island for the wild at heart. With its dense rainforests and cascading waterfalls, it offers a playground for nature enthusiasts. Hiking through the Morne Trois Pitons National Park reveals untouched beauty, where every path leads to a new discovery. This isn’t a typical beach destination; instead, it’s a sanctuary for those seeking solitude and connection with nature. Dominica’s unspoiled landscapes speak to the adventurer in us all, providing a unique escape from the ordinary. It’s a place where the wilderness calls, and the spirit of exploration thrives.
Nassau, Bahamas
In Nassau, the beauty of the beaches is often overshadowed by the hustle and bustle of cruise ship crowds. Vendors line the shores, eager to sell their wares, making relaxation a challenge. High prices and a sense of commercialization pervade the atmosphere, detracting from the island’s natural allure. While the azure waters are undeniably inviting, the stress of navigating tourist traps diminishes the experience. Nassau’s charm seems lost amidst the chaos, leaving visitors yearning for a more serene escape. It’s a reminder that not all paradises are created equal, and some require more than just scenic views.
St. Thomas (U.S. Virgin Islands)
St. Thomas, a convenient stop for travelers, struggles with overdevelopment and traffic woes. The island’s natural beauty feels dulled by the perpetual congestion and commercial sprawl. While it’s perfect for a quick layover, the charm wanes during an extended stay. Navigating the bustling streets can feel overwhelming, overshadowing the picturesque vistas. St. Thomas is a reminder that convenience doesn’t always equate to relaxation. The island’s potential is undeniable, but the execution leaves much to be desired. For those seeking a tranquil retreat, other islands might offer a more fulfilling experience, free from the hustle.
Martinique
Martinique, with its French-Caribbean flair, offers a taste of Europe in the tropics. Yet, the island’s allure is tempered by high prices and a less-than-hospitable atmosphere. While its beaches are lovely, the warmth often associated with island hospitality feels lacking. The juxtaposition of luxury and unwelcoming vibes creates a perplexing experience for visitors. Despite its scenic beauty, Martinique struggles to capture the heart as easily as its neighbors. It’s an island that leaves one pondering the balance between charm and cost, and whether the experience justifies the expense. A more inviting ambiance might change the narrative.
Jamaica (Montego Bay area)
Montego Bay in Jamaica pulsates with energy, yet the constant buzz of tourists and vendors can feel overwhelming. The persistent selling interrupts moments of relaxation, casting a shadow on the island’s natural beauty. Safety concerns linger, prompting visitors to stay cautious rather than carefree. While Jamaica’s picturesque landscapes are undeniable, Montego Bay’s atmosphere shifts the focus from exploration to navigation. The allure of the island is overshadowed by the commercial hustle, leaving some to seek serenity elsewhere. For those desiring peace, quieter locales might better capture the essence of a true Caribbean escape.
St. Maarten (Dutch side)
St. Maarten’s Dutch side brims with activity, a lively hub for shoppers and sightseers. Yet, the island’s commercial focus and bustling traffic near Maho Beach often eclipse its natural allure. While the thrill of planes overhead excites some, others find the crowds and congestion taxing. The island offers a vibrant scene but lacks the tranquility sought by many Caribbean travelers. For those seeking a brief adventure, St. Maarten delivers, but for extended relaxation, other destinations may prove more rewarding. It’s a vibrant stop on the journey, yet not one that beckons for a prolonged stay.