The Leeward Islands
The lush storybook shores of the Leeward Islands have long been a natural playground for pirates, explorers, and sailors seeking rum, sun, and silver crescents of sand. This stunning string of islands includes some of the most popular Caribbean destinations. From honeymoon Antigua to sublime St. Kitts, you can spend weeks chartering around these super chic islands. Caught between the rolling surf of the Atlantic and the blue hues of the Caribbean, you can take your pick between hammock-swaying harmony, historic expeditions, or glorious adventures in the great outdoors.Download The Leeward Islands Guide
DAY 1: Antigua
Welcome to Antigua - your jumping off point for becoming one of the yachting crowd. Colorful architecture, the historic weight of the UNESCO Nelson's Dockyard, and the fabulous fortifications standing proud against a backdrop of hazy blue; this is the Caribbean at her most quintessential.
Stash your bags aboard your yacht before taking a whirlwind tour of Antigua's finest historical sights. Start with the iconic Nelson's Dockyard before taking a short climb up Shirley Heights for panoramic drama and a keen view of your sailing path. Explore the sugar plantations at Betty's Hope and hit up one of the plentiful island bars to sample a local rum cocktail. Back on board and it's time for your first yacht dinner beneath the moonlight.
DAY 2: Barbuda
After a breakfast on deck soaking up the bustling nautical atmosphere of Antigua's harbor scene in the bright mornings, it's time to pull up anchor and set sail for the bliss of Barbuda. A seventeen-mile slip of pink sands, wild birds, and off the beaten track vibes are a warm welcome.
Enjoy lunch on the yacht before heading to the famed Frigate Bird Sanctuary located in a gentle lagoon in the Wa-Omoni Beach Park. Here, thousands of Frigate birds can be found during mating season, giving you the chance to get up close and personal to these magnificent man-o'-war birds. Back in Barbuda and it's the Pink Sands Beach that whispers with a thousand grains of magic. True to its name, it's a truly memorable moment to step out of the turquoise hued waters and onto sands the color of blushing wine. Drop anchor for the night - perhaps enjoy a picnic supper on the sands or uncork a bottle of wine back on your yacht for a contemplative eve beneath the stars.
DAY 3: St Kitts
Leave behind the crushed pink sands of Barbuda as you journey on to joyous St Kitts. A relative newcomer on the yachting itinerary, St Kitts may be less polished than her sisters, but she retains a wild side of her spirit that will tempt even the most discerning sailors to step ashore. Black sand beaches, breathtaking views at every angle, and exceptional snorkeling and diving around the surrounding reefs is more than enough to keep you anchored for the day.
Spend the afternoon at leisure; choose to ride the sugar train (considered one of the most scenic railways in the Caribbean), play a round of golf at the Royal St Kitts, or ask the captain to tender you out to snorkel around the glimmering waters of White House Bay with its impressive collection of shallow water wrecks. Before the sunset sets the sky on fire, there's just enough time to 'lime' with the locals. Grab a chilled beer and converse with the residents at one of the island's smattering of rum shack bars.
DAY 4: Nevis
This morning let the sunlight rouse you, there isn't far to go. In fact you are merely skipping across to St Kitts' sister island of Nevis. Nevis is the pint-sized island sibling - offering near horizontal vibes and a glut of glorious outdoor activity. Kickstart your day in the capital of Charlestown, strolling around the 19th century churches and watching the road for goats and monkeys who tend to tumble around this tiny island.
Take a big lunch and if you are feeling spritely, lace up your hiking boots and tackle the imposing 3200m summit of Nevis Peak for astonishing views out over the verdant rainforests, St Kitts, and the blue kiss of the Caribbean sea. Sip a cocktail at the Sunshine Bar and enjoy a glorious night at anchor at pretty Pinney's Beach.
DAY 5: St Barts
After a morning dip at Pinney's, climb back onboard as you cruise towards the star of the show - St Barts. Needing little introduction, St Barts is the epitome of glam. A superyacht playground for the rich and famous; there's an endless array of beautiful boutiques, postcard beaches, and decadent dining experiences to be had.
Hit the hip and happening shops of Gustavia and splurge on some one of a kind fashion wares and hand-rolled Cuban cigars. Grab a glitzy spot of lunch at La Langouste if in the mood for lobster or head over to the hottest dining spot of L'Espirit Saline. The latter is right on Saline Beach, meaning after polishing off stunning plates you can soak up the sun on a gorgeous strip of sand and cool off in coral-rich waters. Another beach that should certainly be on your calling card for St Barts is the beautiful Baie de St Jean. Popular with the celebrity crowd, its pristine sand melding with sea style makes it a glorious spot to kick back and people watch.
Take a later afternoon massage at the Eden Rock Hotel and perhaps stay for supper - just to see the magic of its On the Rocks restaurant where gourmet classics are served with simply marvelous ocean views
DAY 6: Anguilla
Take breakfast on deck as you admire the way the sunlight glimmers off St Barts' red rooftops before setting sail for the splendor of Anguilla. Boasting no less than 33 majestic beaches, you could spend your whole time on Anguilla cruising from sand to sand. For those who prefer to blend their beach time with some cultural charm, there's an Anguilla Heritage Trail.
Back to the beaches. Shoal Bay beach is considered one of the most beautiful in the whole of the Caribbean thanks to its gleaming white sands, untouched vibes, and radiant coral gardens. Spend the afternoon hitting up the finest diving sites in Anguilla with a visit to Dog Island, Prickly Pear, and Stoney Bay Marine Park where you can explore the sunken Spanish galleon.
Salty, sun drenched and satiated, why not take the tender over to Sandy Cay for local crayfish served on a shimmering slip of sand. Barefoot suppers don't get better than this.
DAY 7: St Martin
Your final full day of sailing takes you to sassy St Martin. Half French, half Dutch and fully Caribbean - there's so much to explore. On the French side you will find a glut of gorgeous restaurants, chic spots to shop, and an air of European sophistication. The Dutch side of St Martin is a little livelier with lots of energetic bars, casinos for rolling the dice, and charming Dutch architecture painted in the bright pastels of the Caribbean.
Spend the day exploring the French side and then perhaps hit the rum bars in St Martin for a taste of its nightlife scene. Escape the bustle of town to soak up the natural grace of Loterie Farm where hiking trails and ziplines invite you deeper into the canopy. Head to the Tijon Parfumerie to learn how to make your own French scent to take home and wander the pretty streets of Marigot.
Take dinner back on the yacht or save yourself for French specialties at the Caribbean's gourmet capital. Blvd de Grand Case is where the islands most lauded restaurants sit. For more laid-back huge helpings of heartwarming fare you could duck over to Philipsburg - the capital of the Dutch side. If you are seeking raucous energy, this is definitely the place to stay out late soaking up the action.