16-Day Leeward Island Holiday

Miami, Florida

The party and cruise capital of the word, Miami is a bright,
brash, playground city that 15.5 million tourists flock to every
year. The Roaring Twenties saw this town bloom into a seaside
capital, blessed with a legacy of Art Deco architecture, diverse
cultures, and natural wonders enough to satisfy any
holiday-goer.

Being the gateway to the Caribbean and Latin America, Miami has
a large Cuban presence, evident in the vibrant neighbourhood of
. Art lovers can meander around the art districts like
Wynwood and the Coconut Grove, while others can lounge on the miles
of sandy beaches. For families there are kid-friendly attractions
like the
and Metrozoo. The nightlife is sophisticated and
varied. The city also gives easy access to Florida's popular Gold
Coast resorts and attractions, as well as the natural wonder of the

.

It is no wonder Miami is America's favourite holiday destination
and the hub of a vibrant cruise ship industry, its port constantly
jammed with sleek passenger liners. North of the city, the miles of
beautiful beaches on the Gold Coast are hemmed in by southeast
Florida's major tourist towns: Fort Lauderdale, Hollywood, Pompano
Beach, and Palm Beach.

San Juan (Puerto Rico)

The capital city of Puerto Rico, San Juan
is one of the busiest ports in the Caribbean and home to a third of
all Puerto Ricans. Nearly every visitor to the island arrives at
San Juan, many on cruise liners. It's one of the largest home-based
cruise ports in the world, hosting many vessels with more being
added each year.

San Juan is divided into three distinct
districts: Old San Juan, the historic walled city; the beach and
resort area; and the outlying suburbs. Tourists mainly visit Old
San Juan, the site of most restaurants, shops, entertainment venues
and some exquisite beaches.

The old city is linked to the new by the
largely residential barrio of Puerta de Tierra and a series of
modern highways leading to the Condado beachfront, which is
reminiscent of Florida's Miami Beach with its high-rise hotels and
apartment blocks.

It is not only tourism that keeps the
financial mills grinding in San Juan. The city is an important
centre for petroleum and sugar refining, brewing and distilling,
and the manufacturing of cement, pharmaceuticals, metal products
and tobacco products.

In the midst of all the hustle and bustle,
there are numerous attractions in San Juan to amuse, entertain and
interest many tourists, and the city is a perfect base for
exploring the rest of what this small Caribbean island has to
offer.

Road Bay

Road Bay is a charming and bustling coastal settlement located on the northern shore of the island of Anguilla, a British Overseas Territory in the Caribbean. Known for its stunning beaches, turquoise waters, and serene atmosphere, Road Bay serves as the main port of entry for sea vessels and plays a vital role in the island's economy. As a hub for both commercial activity and tourism, it's a location where visitors can experience the harmonious blend of local island life and the hospitality that Anguilla is famous for.

The bay is surrounded by powdery white sand beaches that are perfect for sunbathing and relaxing. These beaches are often less crowded than those on more well-known Caribbean islands, offering a more private and tranquil beach-going experience. The calm, clear waters of Road Bay are also ideal for swimming, snorkeling, and water sports such as kayaking and paddleboarding. Snorkelers and divers are particularly fond of the area due to the abundant marine life and coral reefs that are situated nearby.

For those interested in sailing and boating, Road Bay provides a picturesque anchorage. The natural harbor is a safe haven for yachts and sailboats, making it a popular stop for boaters exploring the Caribbean Sea. The annual Anguilla Regatta, which hosts a series of boat races and sailing events, attracts sailors and spectators from around the world and is one of the highlights of the local calendar.

The waterfront along Road Bay is lined with a variety of dining options where visitors can enjoy fresh seafood and traditional Caribbean cuisine. Several beach bars and casual eateries offer the opportunity to sample local flavors and refreshments while taking in beautiful ocean views. Dining by the seaside, visitors can often enjoy the sounds of live music and the laid-back rhythm of island life.

The area behind the beachfront is the commercial heart of Road Bay and Sandy Ground, the neighborhood which serves as its backdrop. This district is filled with a mix of businesses including duty-free shops, small boutiques, and convenience stores, where both visitors and locals can find a wide array of goods and services.

One of the distinctive features of Road Bay is its deep cultural heritage. The Old Salt Factory and Pumphouse are historical landmarks located in the vicinity, a reminder of Anguilla's salt industry past. These preserved sites offer a glimpse into the island's history and the importance of the salt trade in its development.

Road Bay is not just a daytime destination. As the sun sets, the nightlife begins to flourish with bars and clubs opening their doors and welcoming patrons with a mix of Caribbean rhythms and international tunes. The area becomes a festive scene where locals and tourists mingle, creating a warm and vibrant nighttime atmosphere.

Accessibility to Road Bay is straightforward, with the Clayton J. Lloyd International Airport situated only a few miles away. The proximity of the airport to the bay area allows for easy transitions from air travel to enjoying the sandy beaches.

As a key component of Anguilla's maritime tradition, Road Bay encapsulates the island's blend of natural beauty, cultural heritage, and friendly community spirit. It remains a jewel in the crown of Anguilla, bringing together sailors, vacationers, and locals in a picturesque and lively setting that epitomizes the best of Caribbean charm.

South Friars Bay

South Friar's Bay is a bay in Saint George Basseterre Parish, Saint Kitts and Nevis. It is one of the two bays that stretch along the coast of the isthmus connecting the Southeast Peninsula, with the rest of the island of Saint Kitts. It is longer than its northern neighbour (North Friar's Bay). At their closest, the two coasts are less than one kilometre apart.

Marigot

A delightful mixture of France and the Caribbean, Saint Martin's capital city of Marigot is cluttered with shops and houses serving a permanent population of about 6,000. The town stretches along Marigot Bay, its main focus being the harbour at the bottom of Rue de la Republique from where ferries depart to surrounding islands and fishing boats come and go.

Originally a tiny fishing village, Marigot became the capital of Saint Martin during the sugar boom and quickly grew. Marigot's buildings are largely colonial in style, sprinkled with several smart cafes, bistros, pastry shops and luxury boutiques reminiscent of mainland French market towns. There are also several colonial landmarks, including Fort St Louis.

The main shopping centre in Marigot is at the southern end of the town near the harbour, which is a paradise for shopaholics, with boutiques stocking the latest designer fashions and jewellery, all tax-free. More adventurous shoppers will enjoy browsing the Wednesday and Saturday morning markets, located in a kiosk area near the port.

Terre-de-Haut

On visiting Terre-de-Haut, an island commune part of the French overseas collectivity of Guadeloupe, you can expect a true Caribbean paradise. The island is only two square kilometers, but it boasts a population of 2,000 people who are passionate about their island home.

From the moment your boat or plane arrives, you’ll be welcomed by the vibrant natural beauty of the island. With its rolling hills, lush tropical vegetation, and sparkling turquoise waters, Terre-de-Haut is an inspiring and energizing place to be. Sunsets here are gorgeous and the night sky glitters with stars in every direction.

The main village, also called Terre-de-Haut (after the island itself), rests on a high hill in the center of the island. Here you’ll find quaint little cafes, local eateries and stores, plus some of the best views of the harbor around. Additionally, the village offers several historic sites worth visiting, including Pigeon Island – a little hill in the center of town said to have been an important strategic point during the various wars that have taken place in this area.

But it’s what lies beyond the village that makes Terre-de-Haut truly special. The surrounding waters are a dream come true for snorkelers and divers. You can expect to find stunning coral reefs, vibrant fish of all colors, and even occasional sightings of dolphins and whales. If you’re feeling adventurous, take a guided tour of the mangroves on the east side of the island – you won’t regret it!

Everywhere you go on the island, you’ll find friendly locals eager to share their stories and offer insight into their culture and way of life. There’s even an annual Terre-de-Haut music festival filled with locals and visitors alike who come together to celebrate music and dance.

Terre-de-Haut is a perfect spot for those seeking adventure, rest and relaxation, and cultural experiences. From its unique cuisine to its stunning landscapes, this little island has something for everyone – even if only for a few days.

Fort-de-France

The largest of the Windward Islands, Martinique is 4,261 mi (6,817 km) from Paris, but its spirit and language are decidedly French, with more than a soupçon of West Indian spice. Tangible, edible evidence of the fact is the island's cuisine, a superb blend of French and creole. Martinique is lushly landscaped with tropical flowers. Trees bend under the weight of fruits such as mangoes, papayas, lemons, limes, and bright-red West Indian cherries. Acres of banana plantations, pineapple fields, and waving sugarcane stretch to the horizon. The towering mountains and verdant rain forest in the north lure hikers, while underwater sights and sunken treasures attract snorkelers and scuba divers. Martinique is also wonderful if your idea of exercise is turning over every 10 minutes to get an even tan and your taste in adventure runs to duty-free shopping. A popular cruise-ship excursion goes to St-Pierre, which was buried by ash when Mont Pelée erupted in 1902.

Rodney Bay

Rodney Bay in St Lucia is horseshoe-shaped and features one of the islands premier beaches with white sand and clear water. It is also known as St.Lucia’s entertainment and recreation centre.

Roseau

Roseau lies in a small area on Dominica's west coast, where
rugged green hills meet a deep blue sea. A mix of French and
British colonial structures run along its narrow streets,
punctuating the modern concrete buildings and recalling the
capital's history.

Most visitors gather along the Bayfront before browsing through
the Old Market. Historically speaking, the area hosted the slave
trade. These days, its craft and souvenir stalls are popular among
cruise-ship passengers. Tourists should also explore the compact
museum in the Old Post Office if time allows. Otherwise, seeing the
island's natural beauty should be the priority. The botanical
gardens are certainly a worthwhile stop in this regard. A hillside
enclave called Morne Bruce lies above them and offers a
breathtaking view of Roseau.

All in all, the destination appeals to travellers who want a
friendly, relaxed atmosphere, though the local hotel bars and clubs
can be lively. The World Creole Music Festival makes visiting in
late October a special treat.

Montserrat

Antigua

St. John’s is the vibrant capital of Antigua and Barbuda, and one of the most alluring cities in the Caribbean. Situated on the island of Antigua, St. John’s is a bustling city that is both exciting and picturesque. From the Caribbean-infused cuisine, to the historical landmarks and lively attractions, St. John’s is a place that should be at the top of your travel itinerary.

The city is alive with activity, including plenty of colorful markets and shopping areas, and is known for its diverse population. As you explore, you’ll find yourself surrounded by music, art and culture. Strolling through St. John's Old Town will give you a delightful glimpse into the past, as local craftsmen display their wares in British colonial-style buildings. From there, head to the lively Independence Square and take in the sights and sounds.

Catch a glimpse of local wildlife at the nearby Antigua Recreation Ground, or head to deep sea fishing for fun and adventure. St. John’s also plays host to a few annual festivals, like the April Carnival which features a mix of costume parades, stilt walkers, drum circles, floats and masquerade performers.

For those looking to relax in the sun, the city’s numerous beaches are ideal. The pristine sand and crystal-clear waters make them a prime destination for swimming, snorkeling, and more. If you’re looking for a peaceful time with friends and family, why not have a picnic on an isolated beach? Or try an island tour and explore the waters on a guided boat cruise.

With its combination of sun-soaked beaches, expansive parks and traditional buildings, St. John’s is a place that everyone can enjoy. Its friendly locals will welcome you with open arms, and its diverse selection of restaurants will satisfy any taste buds. Whether you’re seeking relaxation or adventure, St. John’s has it all waiting for you in Antigua.

Great Harbour, Jost Van Dyke

Great Harbour is a stunning and tranquil bay located on Jost Van Dyke, the smallest of the four main islands of the British Virgin Islands (BVI). Known for its picturesque scenery, crystal clear turquoise waters, and soft white sandy beaches, Great Harbour is an oasis for beach-goers, sailors, and adventure enthusiasts alike. Spanning just about three square miles, Jost Van Dyke hosts a small population, but it boasts an outsized reputation for its vibrant nightlife and welcoming community.

One of the most notable features of Great Harbour is its well-protected anchorage, which makes it a haven for yachts and boats throughout the year, especially during the peak sailing season. The harbour's natural geography provides shelter from the prevailing winds, creating a perfect natural marina. This has led to Great Harbour becoming a key stop on the Caribbean sailing circuit, with many sailors choosing to drop anchor and enjoy what the bay and its surroundings have to offer.

Upon arriving at Great Harbour, visitors are greeted with a laid-back vibe that is quintessential to the Caribbean way of life. The beachfront is lined with a selection of casual bars and restaurants that become hubs of activity as the sun sets. Among the most famous establishments is Foxy's Tamarind Bar & Restaurant, known for its beach barbecues, live music, and the legendary Old Year's Night (New Year's Eve) party that attracts party-goers from around the globe.

The village surrounding Great Harbour is charming and small-scale, allowing for an authentic island experience. The streets are often quiet, save for the bustle around the local businesses, which include quaint shops selling handcrafted goods, island apparel, and essential supplies for those continuing their sea voyage. The locals, known for their friendliness, are happy to share stories and offer recommendations to visitors, contributing to the harbour's reputation for warm hospitality.

For those looking to engage in watersports, Great Harbour does not disappoint. The clear waters are ideal for snorkeling and scuba diving, with vibrant coral reefs just a short swim away from the beach. Additionally, paddle-boarding, kayaking, and sailing are popular activities that allow visitors to explore the area at a leisurely pace. The nearby Sandy Cay and Sandy Spit offer additional opportunities for exploration and are excellent spots for a beach picnic or a day of seclusion and sunbathing.

The island's lush, volcanic terrain provides opportunities beyond the beach as well. Hiking trails wind through the hills, offering breathtaking panoramic views of the surrounding islands and the expanse of the Caribbean Sea. Naturalists and bird watchers will delight in the diversity of flora and fauna found on the trails.

Great Harbour's appeal is not only in its natural beauty but also in its cultural events. Beyond Foxy's famous New Year's bash, the harbour hosts celebrations like the Jost Van Dyke Music Festival and the Halloween Party, which showcase local music talent and bring the community together in a lively and joyous atmosphere.

While Great Harbour has gained popularity as a tourist destination, it remains unspoiled and continues to offer an authentic island experience. The mix of relaxing beach life, friendly locals, delicious cuisine, and year-round sailing opportunities make Great Harbour a cherished spot in the British Virgin Islands, appealing to travelers of all stripes — from those seeking serenity to those eager for the next great beach party under the Caribbean stars.

Miami, Florida

The party and cruise capital of the word, Miami is a bright,
brash, playground city that 15.5 million tourists flock to every
year. The Roaring Twenties saw this town bloom into a seaside
capital, blessed with a legacy of Art Deco architecture, diverse
cultures, and natural wonders enough to satisfy any
holiday-goer.

Being the gateway to the Caribbean and Latin America, Miami has
a large Cuban presence, evident in the vibrant neighbourhood of
. Art lovers can meander around the art districts like
Wynwood and the Coconut Grove, while others can lounge on the miles
of sandy beaches. For families there are kid-friendly attractions
like the
and Metrozoo. The nightlife is sophisticated and
varied. The city also gives easy access to Florida's popular Gold
Coast resorts and attractions, as well as the natural wonder of the

.

It is no wonder Miami is America's favourite holiday destination
and the hub of a vibrant cruise ship industry, its port constantly
jammed with sleek passenger liners. North of the city, the miles of
beautiful beaches on the Gold Coast are hemmed in by southeast
Florida's major tourist towns: Fort Lauderdale, Hollywood, Pompano
Beach, and Palm Beach.