Curator’s statement
The Caribbean holds a very special place in my heart, not just as a travel advisor, but also as a traveler who has spent countless days exploring its islands, beaches, and hidden corners. I’ve celebrated milestones here with my own family, discovered local traditions that made me feel instantly at home, and built lasting partnerships with resorts that take such pride in making every guest feel cared for. What I love most about the Caribbean is its diversity—each island has its own story, personality, and rhythm, yet all share the same warmth and joy. Helping couples, families, and groups find the perfect island for their moment is more than a job for me—it’s personal, and I take great pride in matching people with the destination that will become a part of their life story.
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January: St. Barths & Anguilla
January is peak season with warm, breezy days and little rainfall. St. Barths thrives with chic beach clubs, luxury shopping, and lively post-holiday festivities, while Anguilla offers a more laid-back luxury vibe with pristine, uncrowded beaches. Travelers can enjoy the best of both worlds—glamorous parties and quiet, romantic hideaways—making this a perfect time for honeymooners or winter getaways.
February: St. Lucia
With its lush rainforest, volcanic peaks, and romantic vibe, St. Lucia is ideal for couples in February, especially around Valentine’s Day. The weather is warm and dry, perfect for catamaran sails around the Pitons or soaking in natural hot springs. This is one of the most popular honeymoon destinations in the Caribbean.
March: Aruba
Known as the “One Happy Island,” Aruba sits outside the hurricane belt, guaranteeing sunny skies and cooling trade winds in March. It’s a perfect spring break destination for families or groups because of its consistent weather and wide range of activities—from snorkeling and shipwreck dives to desert exploration in Arikok National Park.
April: The Bahamas
April offers clear skies and calm seas before hurricane season begins. The Bahamas’ close proximity to the US makes it a great option for quick getaways. Island hopping between Nassau and the Exumas is at its best, and travelers can experience everything from luxury resorts to swimming with the famous pigs.
May: Grenada
Known as the “Spice Island,” Grenada in May is warm, less crowded, and still in the dry season. The island’s spice plantations are lush and fragrant, while Grand Anse Beach shines as one of the Caribbean’s best. May is perfect for travelers looking for culture, authenticity, and fewer tourists.
June: Barbados
June begins the shoulder season, meaning travelers benefit from fewer crowds and better rates while still enjoying plenty of sunshine. Crop Over Festival rehearsals and early celebrations begin this month, offering a taste of Barbados’ vibrant culture and carnival spirit without peak-season chaos.
July: Jamaica
July brings festival energy and school holidays, making it great for families and music lovers. Reggae Sumfest, one of the Caribbean’s largest music festivals, takes place in Montego Bay. With its mix of culture, cuisine, and family-friendly resorts, Jamaica in July balances relaxation with lively celebration.
August: Antigua
Famous for its 365 beaches, Antigua is buzzing in August with Carnival celebrations that showcase colorful parades, music, and dance. While it is technically hurricane season, Antigua’s charm and festival atmosphere make this an ideal destination for travelers who want vibrant energy and cultural immersion.
September: Curaçao
Curaçao sits outside the hurricane belt, making it one of the safest bets in September when other islands face storm risks. Its Dutch-Caribbean architecture adds European charm, while snorkeling and diving in clear waters remain excellent. September is ideal for adventurous travelers seeking culture, cuisine, and fewer crowds.
October: Dominica
After the rainy season, Dominica’s rainforests are at their most vibrant. Waterfalls surge with power, and hiking trails like the Boiling Lake trek are in prime condition. October is best for eco-travelers and adventure seekers who want a lush, off-the-beaten-path experience.
November: Turks & Caicos
November marks the start of the dry season, offering warm, clear days and calm seas. Grace Bay Beach is at its best, with turquoise waters perfect for diving, snorkeling, or boating. This is one of the most luxurious times to experience Turks & Caicos, right before peak holiday season crowds.
December: Puerto Rico
Puerto Rico comes alive in December with one of the longest and most festive Christmas seasons in the world. Old San Juan’s streets sparkle with holiday lights, while cultural events and parrandas (musical parades) fill the air with music. Beyond the festivities, Puerto Rico offers surfing in Rincon and kayaking in bioluminescent bays—ideal for travelers seeking both holiday spirit and adventure.
Need to know
Planning a Caribbean trip is about more than picking an island—it’s about knowing the rhythm of the season, the quirks of each destination, and how to make the most of your time. Here are my most personal and practical tips, gathered from years of helping clients and traveling these islands myself.
Festivals create memories: I’ll never forget dancing shoulder-to-shoulder with locals during Antigua’s Carnival or hearing live reggae in Jamaica while the sun set over Montego Bay. These aren’t just events—they’re cultural heartbeats you carry home with you.
Hurricane season know-how: From personal experience, I know how nerve-wracking it can be to plan a summer Caribbean trip. I’ve guided clients to Aruba and Curaçao in March and September specifically because they’re outside the hurricane belt, and that insider tip saved their vacations.
Balance rest and adventure: On my own trips, I’ve learned that as tempting as it is to stay on the beach all week, the magic often happens when you venture out. A spice tour in Grenada, a rainforest hike in Dominica, or kayaking under the stars in Puerto Rico adds layers to your trip.
Packing hacks from experience: I always bring a light sweater or wrap—yes, even in the Caribbean. On one of my first trips, I was surprised by how cool the evenings got in St. Barths with the ocean breeze.
Dining like a local: Some of my favorite travel memories come from tucked-away beach shacks with fresh-caught fish and no reservations required. While I help my clients secure the best tables at five-star restaurants, I also point them to the hole-in-the-wall spots where the food is unforgettable.
Group and wedding travel insights: Having planned my own destination wedding in the Caribbean, I know firsthand how overwhelming it can feel to coordinate everyone. That’s why I create centralized hubs for guests, manage transfers, and even suggest group excursions so everyone feels taken care of and included.
Island-hopping gems: Personally, I love pairing islands for a richer trip. One of my favorite combinations was St. Martin with a side trip to Anguilla—you get vibrant nightlife on one island and serene beaches on the other.
Peace of mind through preparation: I’ve experienced delayed flights and sudden storms myself, and I never travel without insurance. It’s not glamorous, but it’s the reason I can relax fully once I’m on the island.
Ultimately, what I want travelers to know is this: the Caribbean is more than a collection of islands—it’s a living, breathing experience filled with warmth, joy, and surprises. My role is to share not just logistics, but my personal lessons, stories, and insider access so your trip feels effortless and unforgettable.
For more inspiration and insider recommendations, visit our tropical vacations page.
Travel Advisor
Amanda Schneider
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