The Leeward Islands, part of the northern Lesser Antilles in the Caribbean Sea, are a captivating chain of islands renowned for their dazzling beaches, turquoise waters, and diverse cultural influences shaped by centuries of colonial history. Once contested by European powers, these islands bear the imprint of African, Indigenous, French, British, Dutch, and Danish heritage, each contributing to their unique charm.
Today, travelers are drawn to the Leeward Islands for a mix of serene relaxation, adventurous water sports, and vibrant island life. From exploring UNESCO-listed forts and sailing between cays to sampling local delicacies and enjoying lively festivals, the Leeward Islands offer a rich variety of experiences. Each island has its own personality, yet together they form an unforgettable tapestry of Caribbean beauty and culture.
- Antigua & Barbuda – Known for having 365 beaches, one for every day of the year, Antigua is perfect for sailing, snorkeling, and exploring colonial-era sites like Nelson’s Dockyard. Barbuda offers a quieter escape with pink sand beaches and a large frigate bird sanctuary.
- Saint Kitts & Nevis – These sister islands combine historic charm and natural beauty. Saint Kitts features the Brimstone Hill Fortress and scenic railway tours, while Nevis offers lush hiking trails up Nevis Peak and tranquil beaches.
- Anguilla – A laid-back island famous for its pristine beaches, luxury resorts, and vibrant dining scene featuring fresh seafood and island flavors.
- Saint Barthélemy (St. Barts) – A glamorous French Caribbean island known for its upscale boutiques, gourmet restaurants, and chic beaches, blending European sophistication with Caribbean charm.
- Saint Martin / Sint Maarten – A unique island split between French and Dutch sides, offering a blend of cultures, cuisines, and activities—from bustling nightlife in Philipsburg to relaxed café culture in Marigot.
- Montserrat – Known as the “Emerald Isle of the Caribbean,” Montserrat is famed for its lush landscapes and the dramatic Soufrière Hills volcano, which has shaped much of the island’s modern history.
The Same
Both the DINKs and the Family share an enduring love for the Caribbean, making the Leeward Islands a frequent feature in our travel plans when we crave white-sand beaches, turquoise waters, and that signature island breeze.
While our travel styles differ—one seeking more adult-centric escapes and the other focused on family fun—we often gravitate to the same Leeward Island destinations for their mix of relaxation, cultural richness, and easy access to both land and sea adventures. Antigua and Saint Kitts are two islands we’ve both explored, each offering its own blend of history, beauty, and warm hospitality.
Saint Kitts
Saint Kitts, the larger of the twin-island nation of Saint Kitts & Nevis, offers a captivating blend of lush landscapes, colonial history, and vibrant island life. Its centerpiece, the UNESCO-listed Brimstone Hill Fortress, stands as one of the best-preserved historical fortifications in the Americas, offering sweeping views of the coastline. Beyond history, visitors can ride the Scenic Railway, hike Mount Liamuiga for breathtaking vistas, or simply relax on the island’s black and golden sand beaches.
- SEE: Tour Brimstone Hill Fortress and take in panoramic views from its ramparts.
- EAT: Sample goat water stew or freshly grilled mahi-mahi.
- DRINK: Sip a Carib beer or coconut water straight from the shell.
When our Caribbean cruise docked in Saint Kitts, both the DINKs and the Family explored the island’s diverse offerings. One of us gravitated toward its historical and cultural treasures, while the other sought out scenic beaches and local flavors.
Antigua and Barbuda
Antigua & Barbuda, a twin-island nation in the heart of the Caribbean, is famed for its turquoise waters, coral reefs, and an impressive claim of 365 beaches—one for every day of the year. Antigua offers a lively mix of history and recreation, from the UNESCO-listed Nelson’s Dockyard to panoramic views at Shirley Heights and world-class sailing. Barbuda, its quieter sister island, is home to pink-sand beaches and the largest frigate bird sanctuary in the Western Hemisphere. Together, they provide the perfect balance of adventure, culture, and relaxation.
- SEE: Explore Nelson’s Dockyard and catch sunset from Shirley Heights.
- EAT: Fresh lobster or the island’s national dish, pepperpot with fungi.
- DRINK: Wadadli beer or a chilled rum punch.
During our Caribbean cruise, both the DINKs and the Family made a stop in Antigua, each crafting a day around the island’s incredible coastline and warm, welcoming vibe. While our itineraries looked different—one gravitating toward hidden beaches, the other diving into historic sites.
The Family
Before kids, we took a Caribbean cruise that made a stop in Saint Martin/Sint Maarten. The island’s split personality between the French and Dutch sides was fascinating.
Saint Martin / Sint Maarten
Saint Martin / Sint Maarten is a unique Caribbean gem split between two nations—the French collectivity of Saint Martin and the Dutch constituent country of Sint Maarten. This dual identity gives visitors the best of both worlds: refined French charm with open-air cafés and boutique shopping in Marigot, and lively Dutch energy with casinos, nightlife, and bustling beaches in Philipsburg. Island highlights range from Maho Beach—famous for planes soaring just overhead—to tranquil coves perfect for snorkeling and sailing.
SEE: Watch low-flying planes at Maho Beach and wander the streets of Marigot.
EAT: Freshly baked croissants on the French side or hearty barbecue from a Dutch beachside stand.
DRINK: A ti’ punch in Marigot or a cold Heineken in Philipsburg.
Summary
The Leeward Islands charm visitors with their diversity—each island offering its own mix of history, natural beauty, and culture. Whether you’re sailing around Antigua, hiking volcanic trails in Montserrat, lounging on Anguilla’s untouched beaches, or enjoying the cosmopolitan vibe of Saint Martin/Sint Maarten, there’s a Leeward Island to match every traveler’s dream.
For both the DINKs and the Family, these islands offer timeless appeal. While our approaches to travel may differ—one savoring quiet coves and romantic dinners, the other chasing kid-friendly adventures—we share a love for the region’s vibrant cultures and breathtaking scenery.
Whether your perfect Caribbean getaway involves luxury resorts, barefoot beach bars, or thrilling outdoor adventures, the Leeward Islands promise experiences that linger long after your tan fades and the sound of steel drums becomes a memory.
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