Going Island-Hopping in the Caribbean? Here’s What You Need to Know

What could possibly be more relaxing and romantic than visiting one sun-soaked Caribbean island? Experiencing several of them all on one trip—your honeymoon! This excerpt from Lonely Planet’s new guidebook The Honeymoon Handbook tells you exactly how to plan the perfect Caribbean island-hopping itinerary.

Caribbean Island-Hopping

Gone are the days when the Caribbean was merely honeymoon 101: a beach and beverage. Today, the popular Leeward Islands—many of them overseas territories of European countries—offer a profound sense of place that mixes local culture with the qualities of their parent countries with the easiness of the breeze. And this collection of islands is more accessible than ever thanks to improving inter-island boat and air transfers, meaning you can easily string together a few stops in one trip.

Consider starting in multicultural Saint Martin/St. Maarten, an island so beloved that France and the Netherlands agreed to share it. Bright foodie-friendly flavors await on the French half, and the Dutch side is your springboard to Anguilla—a scrubby limestone outcrop that has, hands down, the best beaches in the Caribbean that shimmer with an indescribable turquoise tint.

Barthelemy is the patron saint of chicness and his island spins its own brand of Antillean savoir faire—well, it is French after all. The lifestyle of the rich and famous is always on tap for those who seek it, but the quaint down-to-earth side of St. Bart’s lurks just beneath the flashy veneer.

The Dutch emerald islet of Saba lacks beaches but promises a rain-forest-cloaked volcano and world-renowned dive sites in their stead. The jungles that wind between settlements host incredible wildlife long forgotten on the more developed islands nearby.


Pack: Make sure you have all of your sun-related toiletries before you hit the ground, as island prices are inflated. 

Fly: Saint Martin/St. Maarten’s Princess Juliana International Airport (SXM); Puerto Rico’s San Juan Luis Munoz Marin International Airport (SJU) 

When: January to April is dry with low humidity; September and October are best avoided as hurricanes can sometimes blow through.


Fly into Saint Martin/St. Maarten and pop over to the French side for Creole-fusion fare near Grand Case and trendy beaches, such as Baie Orientale with its Euro club vibe and water sports.

Cruise down to Saba (90-minute boat ride or 10-minute flight) for diving in the national marine reserve and hiking the Santa Cruz trail.

Try the effortlessly stylish St. Barts, which promises hidden coves and a surprisingly provincial charm around small-town Lorient and Corossol.

If you have time, puddle-jump (roughly a one-hour flight) up to Puerto Rico for the Antillean version of big-city living in historic San Juan, then skip to Vieques next door where the bays glow with bioluminescence at night.

Diamond Tip: Wait until you’re on the ground to suss out the best spots for local fare—they’re often barbecue tents or roadside offerings that don’t have websites.

Dream Digs: There’s something undeniably aspirational about St. Barts, and the best part is discovering that a surprisingly mellow destination. It’s prime villa country too, with private digs inhabiting the bays and soaring peaks—all offering sweeping views of the sea and private pools.

Choose one of the island’s rental agencies instead of an online community marketplace to hook you up with a full-service abode. If you want the trappings of a hotel, go for Le Guanahani, which embraces every inch of Caribbean charm from the bright colors that bathe the wooden slatting to the gingerbread trim and profusion of shady palms.

…And Two If By Sea: Island-hopping in the Caribbean is the wave of the future, so to speak, now that the influx of tourists to the region is steadily on the upturn. Burgeoning island tourism has allowed for an increase in inter-island infrastructure with smaller airlines adding regular flights and ferries beefing up their service.

Another well-connected constellation of islands is St Lucia, Martinique and Dominica, which are linked by public boat and really play up their cultural heritage and natural assets. Or, hit up the Virgin Islands (British and American) where private schooner rentals and one-resort islets are plentiful, and staunch preservation has kept much of the area’s natural assets in tact: The national park on St John occupies 60 percent of the island.

Essential Honeymoon Experiences: Charter a private boat tour to one of the smaller sandbars or empty islets orbiting any of the developed islands in the region for a romantic day trip complete with endless rum punches, fresh seafood and miles of turquoise and blue in every direction.

Check out the commodity that put the Caribbean on the map: sugar-cane rum. Tastings are a fun way to get acquainted with the local culture. Some of the islands—especially the French ones—take their cocktails very seriously, with flavors heavily influenced by the terroir and briny winds.

Reproduced with permission from The Honeymoon Handbook, © 2017 Lonely Planet. For more honeymoon tips, buy Lonely Planet’s essential honeymoon planning tool here.

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