Antigua offers a beach for every day of the year, and its capital, St. Johns, is the ideal base for exploring them. This small but lively town is the island's hub for culture, dining, and shopping, with colourful streets, farmers markets, local handicrafts, and historic sites like St. Johns Cathedral and Fort James. Nearby favourites include picturesque Dickinson Bay and secluded Runaway Beach.

Located on a quiet peninsula along the southwestern coast of Tortola, Soper's Hole has been catering to savvy sun-seekers for years. It's been dubbed one of the most picturesque marinas in the British Virgin Islands, with access to spectacular beaches that range from lively to remote and tranquil. The yachting lifestyle comes to life along the waterfront, where fine restaurants, chic cafes, and fun-loving bars beckon with refreshing cocktails and delicious Caribbean cuisine.

Set along Guadeloupe's quieter coast, Deshaies captures the appeal of a barefoot French Caribbean escape. Defined by sea, greenery, and island life, a walkable waterfront village, understated cafés, and nearby beaches set the tone, while botanical gardens and forested hills add perspective beyond the coastline. Time passes between gentle strolls, shaded terraces, and time in the water, creating an unhurried experience that encourages rest, renewal, and simple pleasures.

Martinique is one of France's smallest overseas territories, yet one of its most enchanting, with lush rainforests, volcanic mountains, and sugar-white beaches. Begin in Saint Pierre, once the "Paris of the Caribbean," a charming west-coast colonial town with fine restaurants, elegant architecture, and calm beaches. Visit a heritage rum distillery, hike wild jungle trails, or dive reefs and shipwrecks. Between adventures, enjoy its French, Creole, and African flavors.

Charlotteville, Tobago, is one of the island's most private, sought-after escapes. Its white-sand beaches, clear waters, lush greenery, and sleepy waterfront feel far from Scarborough's bustle. Visitors come for peace, scenic hiking and walking trails with sweeping ocean views, and nearby reefs and dive sites beneath calm turquoise seas.

Discover Barbados' quieter northside. Speightstown offers private access to the best the island has to offer, including beaches, signature golf courses, wondrous Harrison's Cave, and Farley National Park. Immerse yourself in history and culture at the Arlington House Museum in Speightstown or stroll through UNESCO-recognized Bridgetown, where you can savour Barbados' national dish, cou-cou and flying fish, paired with a local rum.

Dive into Sint Maarten's rich Dutch heritage and easygoing Caribbean atmosphere during your journey. Home to a world-renowned regatta boat race, a fabulous shopping scene, and countless beautiful beaches and bays, it's the perfect place to linger a few days after your yachting escape. If you're craving a taste of world-class Gallic cuisine and even more retail therapy, head over to the island's picturesque French side.