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December 31, 2012updated Mar 15, 2013

Your 6-Day Cruising Itinerary for a Perfect Trip on the Leeward Islands

By Chris Boyle


Whether you’re seeking true extravagance or pure relaxation, we have chosen the perfect six-day itinerary that has it all

Cruising the Leeward Islands is exactly as stress-free and relaxing as one might imagine. Traveling no more than 25 nautical miles a day, you can islandhop your way from St. Martin to Antigua, enjoying leisurely sails and sojourns ashore to shop, sightsee and sample the local cuisine. In addition to the luxury offerings, these islands beguile visitors with their tropical climates, beautiful natural scenery, old-world colonial charm and unhurried pace of life. Between your scheduled activities, be sure to leave plenty of time to sip rum punch while you watch the sun set over crystal blue waves and familiarize yourself with the Caribbean phrase ‘liming’—a colloquial term that describes the art of relaxing and having a good time.

As the northernmost chain of islands in the West Indies, the Leewards were known for their easy sailing as they are located downwind of prevailing trade winds. For us they make for the perfect getaway, providing the elite traveler with a little bit of everything. Sunbathe on Anguilla’s world-famous beaches and dine at St. Martin’s top gourmet restaurants. Scuba-dive through beautifully protected reefs in Saba and explore nature’s wonders with a hike up the dormant volcano on Sint Eustatius—small island paradises that have remained untouched by tourists. Enjoy legendary St. Barthélemy nightlife and experience the island lifestyle at charming, little plantation inns on St. Kitts and Nevis. Whatever activities you choose, you can be sure of one thing: by the end of the cruise, you’ll have left all your worries far, far behind.

➤ Arrive in St. Martin

Day 1: St. Martin to Anguilla

Day 2: Anguilla to St. Barthélemy

Day 3: St. Barthélemy to Saba

Day 4: Saba to Sint Eustatius

Day 5: Sint Eustatius to St. Kitts to Nevis

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Day 6: Nevis to Antigua

Day of Arrival


Fly to Princess Juliana International Airport and transfer to Marina Fort Louis where your yacht awaits.

You’ll quickly discover after touching down at Princess Juliana airport that this beautiful island is actually comprised of two separate nations.

Half French and half Dutch, St. Martin/St. Maarten has two different names and two different sets of picturesque beaches, charming cottages, friendly locals and top-notch restaurants. For the full experience of both, take in the stunning views from the cute French village of Marigot and stroll through the cobblestone streets of Dutch Phillipsburg. Sip rum punch on the lively beach at Orient Bay and snorkel in its radiant blue waters, but be sure to dry off in time for your dinner reservations. Known as the ‘Gourmet Capital of the Caribbean,’ St. Martin’s concentration of gastronomic delights is not to be missed.


Crab Beignet, temptation



Cuisine: Nouvelle Carribbean

Style/Ambiance: As the ultimate place to be seen in St. Maarten, Temptation not only wows patrons with its chic atmosphere, it also happens to be the indisputable culinary jewel of the island.

Chef Dino Jagtiani—the first native St. Maartenite to have graduated from the prestigious Culinary Institute of America—curates a fabulous menu of eclectic Carribbean dishes, each with an exciting modern twist. Innovative creations such as lump crab stuffed shrimp wrapped in ‘salmon bacon’ and seared foie gras PB&J made with roasted peanut sauce and Port-fig jelly ensure that Temptation’s reservations list is the longest in town. The restaurant offers an impressive wine selection as well, with special boutique offerings from producers such as Didier Dagueneau and Philip Togni. We highly recommend the signature dessert: a green apple tempura with heavenly honey-thyme ice cream and caramel, named after Chef Dino himself and enjoyed by Temptation’s many celebrity guests, from Chris Rock to Sir Richard Branson.

 Asha Jagtiani

+599 545 2254

Atlantis Casino, Rhine Road, Cupecoy, St. Maarten


Christian Dior Spa


Treatments and facilities: After a day out on the beach or the waves, St. Maarten’s fabulous Christian Dior Spa, with its luxurious setting and white marble clad interiors, will take your relaxation and rejuvenation to an entirely new level.

Staffed by the expertly trained beauty therapists of Christian Dior Institute, this elite spa is a world leader in anti-aging therapies and microdermabrasion. Their famed ‘Youth Treatment’ comes in individually-tailored one or two hour packages and can be followed up with the spa’s vast repertoire of massages, body masks, and underwater jet baths. Offering unparalleled pampering and advanced treatment techniques, the Christian Dior Spa at The Cliff is not to be missed.

Signature treatments: The microdermabrasion technique at Christian Dior spa is performed with the most sophisticated and high-tech tools available and promises to refine, tone, stimulate and re-oxygenate the skin using the finest sapphire particles for a truly lavish and age-defying experience.

Rola Legoubey

+721 546 6620

The Cliff, Rhine Road, Cupecoy, St. Maarten

Where to shop


The savvy tax-free Caribbean shopper knows Le West Indies is the place to go for luxury purchases.

This shopping center offers twenty-three stylish boutiques to peruse and is also home to a few of the island’s top restaurants, including award-winning Le Gaïac. Overlooking the bay and quaintly tucked into the rock of scenic Fort Louis hill, Le West Indies provides a beautiful environment to do your shopping in. We recommend visiting Lacoste (+590 528 484; for sporty polos to wear on deck and snatching up the latest tote bag at Lancel (+590 519 715;, perfect for carrying your beach essentials.

Font de Mer, Marigot, St. Martin



DAY 1: St. Martin to Anguilla

10 nautical miles

This 16-mile sliver of paradise has plenty of draws, but if there’s one thing to come for, it’s most certainly the heart-stoppingly beautiful Anguillan beaches.

This low-lying coral island’s coastline is lined with them and for the devoted sun-worshipper, it can become hard to tell where one ends and another begins. If it’s dazzling white sand you’re after, lay your towel out at Rendezvous or Shoal Bay, where millions of miniscule shell particles give the beaches an iridescent shine. At Cap Jaluca, with its sparkling clear waters, you might spot a sunbathing celebrity, such as Liam Neeson. Finally, experience the sunset on Little Bay or Sandy Ground, where you can watch the sand turn from beige to pink. Between beach hopping, you may want to play a round at CuisinArt Golf Club or enjoy a fine meal at Malliouhana (+1 264 497 6111;, where gourmet French fare is served on a shaded outdoor terrace overlooking the crystal blue sea.


CuisinArt Golf club


Designed by renowned golf pro Greg Norman to showcase the island’s native fauna and a winding sand marsh, this 18-hole championship golf course boasts a 16,000-square-foot green that rests along the Anguilla channel.

Beautiful large sea grape trees and a Merrywing pond frame the especially perilous 423-yard drive on the 16th hole, which plays into the trade winds. With a range of luxurious amenities and an extensively stocked pro shop, CuisinArt is a golf-lover’s paradise. Relax with a drink in the elegant clubhouse bar after your morning round.

+264 498 2254

Rendezvous Bay, Anguilla


Shoal Bay East Beach

Without a doubt Anguilla’s best features are its thirty-some stunningly beautiful beaches, unmatched in the Leeward Islands for both quantity and quality.

From your first glimpse of its pure white sand and smooth turquoise waters, you’ll immediately see why Shoal Bay Beach is consistently rated one of the best in the world. Head to the quieter east end, known as Upper Shoal Bay, for a more secluded experience. The limestone ridge about a hundred yards offshore is a great spot for snorkeling, where you’ll be able to see hundreds of small tropical fish. Or if you prefer, just order a piña colada from Elodia’s Beach Bar (+1 264 497 3363) while you sunbathe on the incredibly fine sand. It’s not hard to see why Shoal Bay’s many devotees refer to it as heaven on earth.

Shoal Bay, Anguilla


Gustavia Harbor

DAY 2: Anguilla to St. Barthélemy

20 nautical miles

The elite traveler will need no introduction to the legend that is the St. Barths winter season.

A favorite escape for moguls, models and Hollywood A-listers, there is simply no island in the Caribbean that can compete with its signature brand of lavishness. Yet in addition to its eternally cool and chic reputation, St. Barths also manages to maintain a charming French quaintness and warmth. Sunbathe on the beautiful southern coast at Gouverneur Beach, explore the picturesque streets of Gustavia, and enjoy a long, lazy lunch at one of the island’s many gourmet restaurants. If it’s nightlife you’re after, St. Barths’s glamorous star-studded beach clubs are second to none. Book a VIP table and keep the champagne flowing at Nikki Beach in Saint-Jean. Don’t expect to go to bed before the sun comes up.


Appetizers, Le Gaïac


Cuisine: French

Style/Ambiance: Restaurant Le Gaïac is the embodiment of cool Caribbean luxury, making it a spot for the most discerning of diners.

This breezy openair venue serves up Creole-accented gourmet French cuisine by Executive Chef Stéphane Mazieres, using the freshest local ingredients, and patrons enjoy their meal while seated in an elegant pavilion overlooking the Toiny resort’s infinity pool and panoramic ocean views. Menu favorites include the parmesan spaghetti with black truffles and Le Gaïac’s specialty grilled lobster. The restaurant even operates its very own greenhouse, growing all the organic produce used in their kitchen. If you’re in town on a Sunday, be sure to drop by for Le Gaïac’s ‘Brunch du Toiny’: this scrumptiously delicious spread is an island institution.

Guy and Dagmar Lombard

+800 680 0832

Hotel le Toiny, Anse le Toiny, St. Barthélemy




Treatments and facilities: The pampering experience is nothing short of first-rate at the Guanahani Spa by Clarins.

Partners in luxury, Guanahani and Clarins offer the St. Barths traveler an eleven treatment room oasis amid the tropical garden setting of the opulent Guanahani hotel. The most state-ofthe art rejuvenating Clarins products are used in all their facials and beauty treatments, and the massage therapists are trained in various techniques from around the world. Whichever treatment you choose, enjoy it in your own private poolside cabana, followed by a steam bath or hydrojet session and lounge until dinnertime with a good book in the enclosed outdoor relaxation area. There is also a full service Frederic Fekkai salon in the spa, should you need to get your hair styled before your evening engagement.

Signature treatments: ‘Donceur du Lagon’ is the ultimate treat for the skin and consists of a Clarins facial followed by a lavish body scrub. To perfectly suit your skincare needs, choose between any of their specialty facial treatments, including Age-Defying, Hydrating, Purifying and Super-Restorative.

Annabelle Signoret

+590 590 529 036

Anse de Grand Cul de Sac, St. Barthélemy




International jetsetters, vacationing Hollywood celebs, and all manner of glitterati come to the Caribbean outpost of legendary beach club Nikki Beach to throw back some cocktails, soak up the atmosphere and party until dawn.

You can expect to rub shoulders with Jay-Z and Beyoncé, Mariah Carey, Josh Duhamel, Ashton Kutcher and Bono, who all enjoy letting loose at this glitzy club when visiting the island. So for a taste of the champagne-spraying extravagance that is St. Barths after dark, Nikki Beach is most definitely your port of call. The club offers VIP tables and bottle service so you can be sure to party it up like a true A-lister.

Patrick Ubbeda

+590 590 276 464

Plage de St. Jean, St. Barthélemy


The best introduction to the sexy vibe of St. Barths nightlife is drinks and a sunset at wonderfully chilled out Dõ Brazil.

Owned by former tennis star Yannick Noah, this daytime Brazilian bistro and nighttime hotspot perches prettily on the rocks overlooking Shell Beach and is a great place for people watching. Enjoy their selection of ceviche and sip on caipinrinhas while you show off a hard day’s work of sun tanning.

+590 290 666

Shell Beach, Gustavia, St. Barthélemy

Where to shop


Tax-free St. Barths is a playground for the luxury shopper, offering everything from liquor and perfume to crystal and watches.

For haute couture, head to Gustavia’s Rue de la République. Lined with designer boutiques including Bulgari, Cartier, Hermès and Giorgio Armani, this is the Caribbean’s answer to Rodeo Drive or Rue du Faubourg Saint-Honoré. Independent boutique Stephane & Bernard (+590 590 27 65 69; stocks an exquisite selection of designer women’s wear by the likes of Jean-Paul Gaultier, Sonia Rykiel and Christian Lacroix. For Prada and Paul Smith shoes, check out shoe store Human Steps (+ 590 590 27 60 46;

Rue de la République, Gustavia, St. Barthélemy


View of Saba

DAY 3: St. Barthélemy to Saba

25 nautical miles

Known as ‘The Unspoiled Queen’ of the Leeward Islands, the small Dutch island of Saba is only five square miles in size.

Unlike many of the others, Saba is not known for beaches or nightlife, but for its ecotourism and adventurous offerings, boasting some of the best hiking, climbing and scuba-diving spots you will ever encounter. Its lush forests and animal wildlife are preserved by the Saba Conservation Foundation, which ensures the natural beauty of the island is protected. For the traveler looking to get truly away from it all, this is the untouched Caribbean paradise you’ve been searching for. Hike the majestic 3,000-foot tall Mount Scenery, scuba-dive in the western reefs, and admire the charming local island architecture in one of Saba’s four small villages; The Bottom, Windwardside, Hell’s Gate and St. Johns.



With its spectacular underwater world, Saba lures many divers to the island.

All the coastal waters surrounding the island have been designated as an official marine park and carefully controlled operation of the scattered thirty-some dive sites have kept the reefs in pristine condition. The visibility is unbeatable and there’s something for everyone, whether its interesting coral heads near the surface for a bit of snorkeling, or ninety-foot-drop walls for the serious diver—home to sponges, corals, groupers and turtles. Most of the best dive sites are on the calmer western side of the island between Tent Bay in the south and Diamond Rock in the north. A great one is the ‘Labyrinth’, a series of 50-foot deep channels created by ancient lava flows, on which hundreds of colorful corals have formed.


The hike from Windwardside to the peak of Mount Scenery takes you up more than one thousand concrete steps through the beautiful, undisturbed forest of Mount Scenery. Blanketed in green moss and delicate ferns, the wood is known as an ‘Elfin Forest’ because of its rolling mist and whimsical mahogany trees. Look out for colorful butterflies, birds and iguanas, and bring a camera to capture the panorama from the peak. Make sure you also have bottled water and appropriate footwear. For some variation on your way down, descend via the less steep Budd’s Mountain Trail.

+599 416 2630

Saba Trail Shop, Windwardside, Saba


Fort oranje

DAY 4: Saba to Sint Eustatius

15 nautical miles

Historically a bustling trading post and one of the most important ports in the New World, Sint Eustatius, commonly called Statia, is now a small tranquil island, holding on to that leisurely Caribbean pace of life.

Make use of the toys on board and spend the day jetskiing through the calm waters of Oranjestad Bay with the magnificent Quill Volcano looming over your shoulder. Or step ashore and you will find that you’ve left the tourists behind for a beguiling island refuge with great hiking, welcoming locals, and lovely colonial buildings, some of which have been impeccably restored. Oranjestad, Statia’s main town located on the island’s west side, is pleasant and laid-back, making it great to wander around. Check out Fort Oranje—this towering fortress with cannons and original stone walls was built by the French and reclaimed by the Dutch in the 1600s.



The Quill Volcano

The Quill is the long-dormant volcano that rises two thousand feet above the Statia skyline with a crater nearly one thousand feet in diameter.

Sint Eustatius National Parks Foundation offers a choice of eight guided hikes, including ‘Round The Mountain’—a rambling, five-hour trail taking you to the best vantage points—and ‘Mazinga Peak’, a steep 60-minute ascent to the highest point on the mountain. The Botanical Garden Trail links up with the Miriam Schmidt Botanical Gardens—a good place to relax and picnic after the climb.

+599 318 2884

St. Eustatius National Parks Foundation, Gallows Bay, Sint Eustatius


Brimstone hill fortress

DAY 5: Saba to St. Kitts to Nevis

15 + 15 nautical miles

Steeped in the history of their 18th century sugar plantation economies, the sister islands of St. Kitts and Nevis offer lush landscapes, including mountains and rainforests, beautiful cultural attractions, and well-preserved colonial architecture.

No other Caribbean island has such old-world charm. St. Kitts has plenty of activities for the day-tripper, including the Scenic Railway and the Brimstone Hill Fortress, a sprawling 1700s British fort with incredible island views that is now a UNESCO World Heritage Site. Meanwhile, Nevis is a small, sleepy getaway with fantastic spas, restaurants, and charming, restored plantation estates. Together, these two make the perfect pair.



Encircling the whole island and once used to transport cane from outlying estates to the mill in Basseterre, these old sugar tracks have been transformed into today’s Scenic Railway, which takes visitors on a two-hour tour of St. Kitt’s spectacular scenery.

Known as the ‘Last Railway in the West Indies,’ the tracks pass through small villages and farms, miles of stunning coastline, deep green rainforests, rippling fields of sugar cane, and across tall steel bridges spanning low canyons. Enjoy it all from the specially designed double-decker ‘island railcars’ which feature an upper open-air deck and a lower air-conditioned parlor. Sip a rum punch while you watch the sights go past and relax to the sound of traditional folk songs and hymns sung on board by the Railway Choir.

+1 869 465 7263

Needsmust Train Station, Basseterre, St. Kitts


Jacuzzi, Four Seasons Resort Spa


Treatments and facilities: For tranquil island bliss, visit the Four Seasons Spa and enjoy its extensive list of customized facials, body scrubs, masks and ayurvedic treatments.

Among the fifteen kinds of massages offered, the specialty Nevisian massage uses the spa’s own unique blend of mineral-rich Nevisian volcanic sand and aromatherapy oils. With a beautifully appointed outdoor relaxation deck and peaceful waterfall pool, this spa reaches new heights of luxurious indulgence. They also offer a range of salon services, including custom perfume blending. Signature treatments: Stimulate your senses with The Rum Tonic. Beginning with a sugar-cane exfoliation to buff away dead skin cells, the body is then treated with a papaya-pineapple scrub followed by a luxurious skin glaze of rum, ginger and Nevis honey.

Ana Rivera

+1 869 469 6238

Pinney’s Beach, Charlestown, Nevis


Restaurant 750


Cuisine: International

Style/Ambiance: Providing the finest dining on the island, Restaurant 750 at the Montpelier Plantation Inn is an experience not to be missed.

Enjoy freshly caught lobster or seared mahimahi by candlelight on the veranda of one of the grandest old West Indian mansions, while overlooking floodlit gardens, the lights of Charlestown and the Caribbean Sea. Wine is also taken very seriously at Restaurant 750 so be sure to ask the sommelier for a pairing. After dinner, retire to the Great Room, the inn’s chic colonial parlor, to sample the collection of aged rums, or simply sip a coffee under the stars.

Tim Hoffman

+1 869 469 3462

Montpelier Plantation Inn, Montpelier, St. Kitts


hermitage plantation inn


The Hermitage is one of the most loved plantation inns on Nevis and said to be the oldest all-wood house in the Antilles. Have lunch here and admire the colonial interiors—wide-planked floors, intricate latticework and louvered windows—then head out to the stables and saddle up for a leisurely mid-day ride on one of The Hermitage’s beautiful thoroughbreds. Guided rides into the rainforest or the surrounding landscapes of Gingerland and Saddle Hill give you the chance to explore the island on horseback, in true old-world plantation fashion. The Inn also offers carriage rides in gorgeous hand-carved mahogany coaches.

Richard and Maureen Lupinacci

+1 869 469 3477

Hermitage Plantation, St. John’s Parish, Nevis



DAY 6: Nevis to Antigua

15 nautical miles

Antigua’s beaches are as famous as they are numerous (the island is said to have 365, one for every day of the year) so if it’s sun and sand you’re after, you’ll find this island hard to beat.

Some of our favorites include Dickinson Bay in the northwest, Half Moon Bay in the east and Rendezvous Beach in the south. When you’ve grown tired of beach hopping, head into town—St. John’s is relaxed and authentic, full of old streets to stroll through. Great island sights include the twin-towered cathedral and the Saturday morning market. Redcliffe Quay, one of the oldest parts of town, is now comprised of converted warehouses and home to some of Antigua’s best boutiques, bars and restaurants. For a touch of luxury to finish it all off, head down to Carlisle Bay on the southern coast for dinner at the glamorous restaurant, East.




Cuisine: Asian fusion

Style/Ambiance: This upscale Asian restaurant and celebrity hangout is one of Antigua’s hottest spots for wining and dining.

Step through the intricately carved Indonesian doors into a stylish and dramatic Oriental dining room, where you can spend the evening enjoying East’s mix of gourmet Japanese, Thai, Indian and Vietnamese flavors. We love the miso roasted sea bass, and for dessert, save enough room for green tea brûlée served with banana ice cream and white chocolate foam—a real treat.

Edwin Kramer

+1 268 484 0000

Carlisle Bay, Old Road, St. Mary’s, Antigua

WHere to shop

Antiguanite, Goldsmitty


For something truly original, visit the jewelry store and workshop of local Dutch goldsmith Hans Smit while you’re in town.

His unique eighteen and fourteen-carat gold creations are set with precious ‘Antiguanite’—twentythree million year old petrified coral which is hand-cut and polished into beautifully patterned gemstones. Some other unique stones Smit prefers to use include Imperial Topaz, Tahitian black pearl and the extremely rare pink Conch pearl, only found in the West Indies. Most of these gems are available in the workshop for bespoke commissioned pieces to ensure you go home with your very own one-of-a-kind Caribbean treasure.

Hans Smit

+1 268 462 4601

11 Redcliffe Quay, St. John’s, Antigua

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