HiGame

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.



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.

Itinerary
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.

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.

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.