Caribbean Island Travel Planner

I first went to the Caribbean with Matt in the late ‘90s, when he was on assignment for Departures to shoot an all-Caribbean edition, which was so big they ran it over two consecutive issues. He was gone for weeks zigzagging all over, but I got to join for part of one trip. My favorite memories were of the Meridian Club in Turks and Caicos, which had the most beautiful water, and the K Club in Barbuda, which was best known because Princess Diana had vacationed there. I remember how complicated it was to get from one island group to another—lots of connecting through Puerto Rico and overnighting in some places because there just weren’t easy connections. It didn’t really matter, though—we really fell in love with the islands, and the journey to get to wherever we were going was just a part of it. 

Since I was an early convert, I was always surprised when I’d tell friends how much I loved it there—really, everywhere—and they’d shrug and say that if they wanted a warm-weather vacation in the winter, they’d rather go to Mexico. The most common complaint was that there wasn’t good food there, it was too expensive, too complicated, etc. I just couldn’t understand how an entire group of islands could be written off like that, but then again, I’d heard people say that about Greece. They assumed the Greek island experience was Mykonos or Santorini, and couldn’t imagine that there was a completely different experience beyond that. Last year, we tackled the expensive question in our Costa Meno Caribbean edition, where we shared our favorite inexpensive places to stay, and the year before we did a deep dive on the Bahamas in this Black Book. But for this winter season, we wanted to tackle your questions, and the ones we hear the most frequently from our friends. We’re pretty sure you’ll find your place in the sun somewhere in this incredibly extensive list. —Yolanda

OUR CONTRIBUTORS

Alban Roger is a New York-based, French-born creative director. He has been going to the Dominican Republic regularly for a decade, and was one of the curators of Design Week Dominican Republic alongside his partner, the Dominican designer Jorge Brown. 

Alberto Petochi is a fifth-generation jeweler and brand consultant based in NYC.

Alexandra Dib is a NYC-based consultant in the Italian food industry, who’s been going to Puerto Rico every year for nearly two decades.    

Alex Chantecaille ran sales for her family’s eponymous cosmetics brand for 20 years. Based in London, she now works as a director of her family’s charity, Chantecaille Conservation Foundation, and spends time each year at their home on St Barth.

Alina Gonzalez was born in Havana and immigrated to NYC with her Cuban grandparents and mother. She spent the last 35 years developing award-winning beauty products for both global beauty brands and startups.

Ben Simmons is the third-generation owner of the Ocean View Club, and the founder of Little Island Design and Little Island Hotels—a collection of small, stylishly casual hotels that includes The Other Side, its new sister property The Farm, plus a new project The Current—with his wife, Charlotte. 

Brendan Monaghan is the former publisher of Condé Nast Traveler, Tatler Asia and T Magazine, and is the founder of boutique travel agency, Coolidge & Co.

Christelle Hilpron is the general manager of Cheval Blanc St Barth. She got her start on the island more than 20 years ago, working as the assistant maitre d’. Over the years, she has worked almost every job at the hotel and knows the place deeply. 

Christina Ohly Evans is the US correspondent for the Financial Times’ HTSI section.

David Coggins is the author of The Believer: A Year in the Fly-Fishing Life, as well as The Optimist and Men of Manners, and has written pretty extensively about his trips to The Bahamas and Cuba on his Substack, The Contender. 

David Jefferys has been a contributing editor for Condé Nast Traveler’s annual Readers’ Choice Awards survey for the past 20 years. Raised in New Delhi and London and now living in Atlanta, he is passionate about travel in the Caribbean. 

Francesca Squillacciotti is the co-founder of Bond Global, a new public relations agency, along with her sister Ariana. The Australian sisters have been visiting St Barth for years.

Jen Rosa Lopez worked in comms for MAC Cosmetics in LATAM and the US Hispanic market, and moved to Puerto Rico to lead strategic comms for the island’s first destination marketing organization. Today, she splits her time between NY and San Juan working as a consultant and occasionally she pens a Spanish travel substack titled @LeRolodex. 

Jonathan Petrino is a travel writer and photographer, published by ASSOULINE and Reader’s Digest, and featured in Photo Festival St Barth. When not traveling, he is a tech executive with a severe case of wanderlust, always in search of a great martini at a hotel bar.

Juella Gumbs is the marketing communications manager at Park Hyatt St. Kitts—born and raised on St. Kitts, she is a true expert on the island. Her personal connection to the destination and local’s touch shines through in all aspects of her work.

Lauren Atchison is a US-based luxury travel advisor, the founder of Found Luxury Travel, who loves planning vacations to her favorite islands.

Larissa Thomson is the founder of  ONDA Beauty and our resident clean beauty expert. She’s logged plenty of time in the Caribbean, testing out the best mineral sunscreens along the way.

Lucinda Scala Quinn is the author of eight cookbooks, including the bestselling Mad Hungry trilogy, and founder of the Mad Hungry kitchenware brand. Her new book, Mother Sauce: Italian American Family Recipes and the Story of the Women Who Created Them, will be published by Artisan in March 2025 (available for preorder). She has been visiting Jamaica for decades.

Matt Hranek is the author of A Man & His Watch, A Man & His Car, A Man & His Kitchen, The Negroni: A Love Affair with a Classic Cocktail, The Martini: Perfection in a Glass, and founder of Wm Brown Magazine. 

Melinda Hughes is an opera singer and comedian from London and the artistic director of the Allstars Festival Barbados, which fosters the careers of young Bajan musicians and runs from 5-15 March 2025.

Michael King-Hew is a serial entrepreneur, hotelier and adventurer. He and his husband David own Kamalame Cay on Andros, where they live with their three young boys and three Portuguese water dogs.

Peter Jon Lindberg was our colleague at Condé Nast Traveler back in the day; before that, he was Travel + Leisure’s longtime editor-at-large. This fall he and his wife, Nilou Motamed, launched a new digital travel magazine called Further.

Ruaridh Nicoll travels the world for a living, a privilege he atones for by offering advice to people visiting Cuba, the place he chooses to live, so feel free to contact him through instagram @ruaridhnicoll for more information.

Sam Godsal is the creative director of the beloved great-house hotel, Cobblers Cove, on Barbados’ west coast. She helps to oversee every detail of the hotel that has been in the Godsal family since the 1960s. 

Tegan Maxey grew up on Eleuthera in the Bahamas, where she developed a deep appreciation for responsible travel and its potential to support local economies. Inspired by her own adventures, she co-founded Wanderers Club, a community of travelers dedicated to immersive, impactful travel experiences. 

Valón Thorpe is the founder and CEO of Mystique Integrated Services Limited, one of the Caribbean’s leading award-winning 360 degree creative agencies.

Vasco Borges is the founder and CEO of Beach Enclave Turks & Caicos, a collection of exclusive-use beach houses and villas across North Shore, Long Bay, and Grace Bay. He initially came to the Turks & Caicos for three months, and has now been there for over 20 years.