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10-Day Leeward Islands Holiday

Embark on an unforgettable 10-Day Leeward Islands Holiday with Seabourn, departing from vibrant Miami. Experience ultra-luxury cruising aboard the elegant Seabourn Quest, where personalized service and an intimate atmosphere define your journey through the sun-drenched Caribbean.

Discover a captivating string of island gems. Explore the historic charm of San Juan, the pristine beaches of Anguilla, and the dramatic volcanic landscapes of Montserrat. Unwind in the tranquil waters of St Kitts, and embrace the laid-back vibe of Jost Van Dyke. Each stop offers unique beauty and authentic island culture.

This meticulously crafted itinerary promises days filled with relaxation, adventure, and exquisite culinary delights. Indulge in Seabourns all-inclusive luxury as you explore secluded coves and vibrant towns. A Leeward Islands Holiday is your perfect escape to paradise, creating cherished memories.

  • Cruise Line: Seabourn
  • Ship: Seabourn Quest
  • Duration: 10 Nights
  • Departure: December
FROM
£5,398 pp
Enquire Now

10-Day Leeward Islands Holiday Prices

Price per person
Dec 18, 2027
£5,398 pp
Enquire
More Dates

10-Day Leeward Islands Holiday Itinerary

Day 1

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.

Day 4

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.

Day 5

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.

Day 6

Montserrat

Montserrat, often referred to as "The Emerald Isle of the Caribbean," is a British Overseas Territory located in the Leeward Islands, in the Caribbean Sea. It is a small island with a rich cultural heritage, stunning natural beauty, and a deep-rooted history that makes it a fascinating destination for travelers seeking a unique experience.

One of the most distinctive features of Montserrat is its dormant volcano, Soufrière Hills. Although the volcano erupted in 1995 and caused significant damage to the island, it has since become a major attraction for visitors. The Montserrat Volcano Observatory offers tours and educational programs, providing an opportunity to learn about the volcano's impact on the island and witness the awe-inspiring landscape it created.

Beyond its volcanic terrain, Montserrat boasts breathtaking natural scenery that spans from lush rainforests to idyllic beaches. The island is a paradise for outdoor enthusiasts, offering opportunities for hiking, birdwatching, and snorkeling or diving in its crystal-clear waters. You can explore trails like the Oriole Walkway, which takes you through the rainforest and offers a chance to spot the Montserrat Oriole, a rare bird species endemic to the island.

For history buffs, Montserrat has a fascinating past intertwined with its indigenous inhabitants, African slaves, and European colonizers. The Montserrat National Trust Visitor Centre in Salem provides insights into the island's history, culture, and traditions. You can also discover the remnants of the island's colonial heritage in Plymouth, the former capital now buried beneath volcanic ash and accessible only on guided tours.

The cultural vibrancy of Montserrat is palpable as you immerse yourself in its music, art, and festivals. The island is hailed as the birthplace of modern calypso music, and the Montserrat Cultural Centre in Little Bay hosts various cultural events, including music festivals and art exhibitions. One of the most notable celebrations is the annual St. Patrick's Festival, which showcases Montserrat's Irish heritage and features lively parades, traditional music, and dance performances.

While Montserrat offers a relaxing and serene atmosphere, it is also dotted with charming local establishments where you can savor delicious Caribbean cuisine. From roadside food stands offering mouthwatering jerk chicken to waterfront restaurants with panoramic ocean views, the island's culinary scene reflects its diverse cultural influences.

When it comes to accommodations, Montserrat offers a range of options to suit different preferences and budgets. You can choose from cozy guesthouses, boutique hotels, and luxury villas scattered around the island. Many of these accommodations provide stunning views of the Caribbean Sea and Soufrière Hills, ensuring a memorable stay in paradise.

In conclusion, Montserrat is a hidden gem in the Caribbean, offering a unique combination of natural beauty, cultural richness, and historical significance. Whether you are seeking adventure in the great outdoors, a glimpse into the island's volcanic past, or an immersive cultural experience, Montserrat has something to offer. So, pack your bags, and get ready to explore this enchanting island that will leave you spellbound with its charm and beauty.

Day 7

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.

Day 8

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.

Day 11

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.

10-Day Leeward Islands Holiday Ships

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10 Nights

10-Day Leeward Islands Holiday

Seabourn
Departure: December
VISITING: Miami San Juan Road Bay Montserrat South Friars Bay Great Harbour, Jost Van Dyke Miami
FROM £ 5,398 pp

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