Cruising the Leeward Islands

French and Dutch have lived side by side on St. Maarten/St. Martin for hundreds of years—with no border patrols or customs between them. The French side has a more genteel ambience, more fashionable shopping, and a Continental flair. The Dutch tends to be less expensive, has casino hotels, and more nightlife. Water sports abound all over—diving, snorkeling, sailing, and windsurfing are all top draws. And it's easy to while away the day relaxing on one of the 37 beaches, strolling the boardwalk of Dutch-side Philipsburg, and exploring the very French town of Marigot. Although luck is an important commodity at St. Maarten's 13 casinos, chance plays no part in finding a good meal at the island’s excellent eateries. The best way to explore St. Maarten/St. Martin is by car. Though often congested, especially around Philipsburg and Marigot, the roads are fairly good, though narrow and winding, with some speed bumps, potholes, roundabouts, and an occasional wandering goat herd. Few roads are marked with their names, but destination signs are common. Besides, the island is so small that it's hard to get really lost—at least that is what locals tell you. If you’re spending a few days, get to know the area with a scenic "loop" around the island. Be sure to pack a towel and some water shoes, a hat, sunglasses, and sunblock. Head up the east shoreline from Philipsburg, and follow the signs to Dawn Beach and Oyster Pond. The road winds past soaring hills, turquoise waters, quaint West Indian houses, and wonderful views of St. Barth. As you cross over to the French side, turn into Le Galion for a stop at the calm sheltered beach, the stables, the butterflies, or the windsurfing school, then keep following the road toward Orient Bay, the St-Tropez of the Caribbean. Continue to Anse Marcel, Grand Case, Marigot, and Sandy Ground. From Marigot, the flat island of Anguilla is visible. Completing the loop brings you past Cupecoy Beach, through Maho and Simpson Bay, where Saba looms in the horizon, and back over the mountain road into Philipsburg.

French and Dutch have lived side by side on St. Maarten/St. Martin for hundreds of years—with no border patrols or customs between them. The French side has a more genteel ambience, more fashionable shopping, and a Continental flair. The Dutch tends to be less expensive, has casino hotels, and more nightlife. Water sports abound all over—diving, snorkeling, sailing, and windsurfing are all top draws. And it's easy to while away the day relaxing on one of the 37 beaches, strolling the boardwalk of Dutch-side Philipsburg, and exploring the very French town of Marigot. Although luck is an important commodity at St. Maarten's 13 casinos, chance plays no part in finding a good meal at the island’s excellent eateries. The best way to explore St. Maarten/St. Martin is by car. Though often congested, especially around Philipsburg and Marigot, the roads are fairly good, though narrow and winding, with some speed bumps, potholes, roundabouts, and an occasional wandering goat herd. Few roads are marked with their names, but destination signs are common. Besides, the island is so small that it's hard to get really lost—at least that is what locals tell you. If you’re spending a few days, get to know the area with a scenic "loop" around the island. Be sure to pack a towel and some water shoes, a hat, sunglasses, and sunblock. Head up the east shoreline from Philipsburg, and follow the signs to Dawn Beach and Oyster Pond. The road winds past soaring hills, turquoise waters, quaint West Indian houses, and wonderful views of St. Barth. As you cross over to the French side, turn into Le Galion for a stop at the calm sheltered beach, the stables, the butterflies, or the windsurfing school, then keep following the road toward Orient Bay, the St-Tropez of the Caribbean. Continue to Anse Marcel, Grand Case, Marigot, and Sandy Ground. From Marigot, the flat island of Anguilla is visible. Completing the loop brings you past Cupecoy Beach, through Maho and Simpson Bay, where Saba looms in the horizon, and back over the mountain road into Philipsburg.

Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for yachts and is celebrated for its casual lifestyle, protected anchorages, fine beaches and beachfront restaurants and bars. The island has fewer than 200 inhabitants and they are widely known as a welcoming people. The island's name conjures up its rich, colorful past. Jost Van Dyke is said to have been named for an early Dutch settler, a former pirate. At Great Harbour, Little Harbour, and White Bay there are safe, protected bays and pristine beaches shaded with coconut palms and seagrape trees. Discover inviting shops selling local treasures, restaurants, and bars. 'The Painkiller', one of the Caribbean’s most popular drinks, originated at the Soggy Dollar Bar. Foxy’s and Gertrude's in White Bay are renowned for drinks made with the island's famous rum, frosty beers, and tales of pirates and sunken treasure. Explore Jost Van Dyke's history in the vegetation-covered ruins of centuries-old sugar mills, or on the old trails that crisscross the island. Revel in the natural beauty of the pristine, untouched beaches. Hike up to the highest spot on the island, Majohnny Point, and take in a stunning 360 degree view of the Caribbean. Relax in the natural 'bubble pool', a popular tourist attraction. Jost Van Dyke conjures up images of what the British Virgin Islands may have looked like many years ago.

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.

The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the village's dozens of shops and restaurants are on Front Street, narrow and cobblestone, closest to Great Bay. It's generally congested when cruise ships are in port, because of its many duty-free shops and several casinos. Little lanes called steegjes connect Front Street with Back Street, which has fewer shops and considerably less congestion. Along the beach is a ½-mile-long (1-km-long) boardwalk with restaurants and several Wi-Fi hot spots.Wathey Square (pronounced watty) is in the heart of the village. Directly across from the square are the town hall and the courthouse, in a striking white building with cupola. The structure was built in 1793 and has served as the commander's home, a fire station, a jail, and a post office. The streets surrounding the square are lined with hotels, duty-free shops, restaurants, and cafés. The Captain Hodge Pier, just off the square, is a good spot to view Great Bay and the beach that stretches alongside.