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15-Day Southern Caribbean In Depth

Embark on an unforgettable 15-Day Southern Caribbean In Depth journey aboard the luxurious Seabourn Ovation. This extensive voyage from Miami offers an unparalleled exploration of the region's most captivating islands and hidden gems, promising a truly immersive and indulgent escape.

Discover vibrant cultures in San Juan, Bridgetown, and Roseau, then unwind in the pristine waters of Great Harbour, Jost Van Dyke, and South Friars Bay. Explore the dramatic landscapes of Montserrat, the charming beauty of Virgin Gorda, and the lively shores of Antigua, experiencing a rich tapestry of Caribbean life and breathtaking scenery.

With Seabourns signature all-suite luxury, exceptional service, and gourmet dining, every moment is crafted for your utmost pleasure. Dive deeper into the Caribbean, experiencing its diverse beauty and charm in unparalleled comfort and style. This is more than a cruise; it is an intimate exploration of paradise.

  • Cruise Line: Seabourn
  • Ship: Seabourn Ovation
  • Duration: 15 Nights
  • Departure: November
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£5,269 pp
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15-Day Southern Caribbean In Depth Prices

Price per person
Nov 20, 2026
£5,269 pp
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15-Day Southern Caribbean In Depth 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

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 6

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 7

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.

Day 8

Port Elizabeth, Bequia

Stunningly beautiful and pleasantly laid-back, Port Elizabeth in St Vincent and the Grenadines is an unmissable Caribbean gem. This charming coastal town owes its beauty to the array of turquoise waters, golden beaches, verdant mountains, and brightly colored architecture. Nestled within the serene Bequia Island, the second-largest island in the Grenadines, it promises an enchanting experience to every discerning traveler.

As you step onto the sun-kissed shores, you're greeted with the sight of quaint waterfront eateries, local shops, and a bustling harbor filled with boats ranging from small fishing smacks to luxury yachts. The town's charm lies in its simplicity and small size; it carries an air of unspoiled authenticity which can be enjoyed leisurely on foot.

The Belmont Walkway is a beautiful seafront promenade in Port Elizabeth that stretches around much of the bay. It serves as a lovely path to explore the town at your own pace while soaking in the stunning vistas. The walkway is dotted with a medley of local restaurants and bars from where you can try out some of the best culinary delights that St Vincent and the Grenadines offers, including freshly-caught seafood paired with locally-grown vegetables and exotic fruits.

Whaleboner Bar and Restaurant, located at one end of Belmont Walkway, is worth a special mention. With its entrance fashioned from two whale jawbones and serving exceptional lobster pizza, it's certainly a unique feature of Port Elizabeth.

Beyond the limits of the town, one can enjoy spectacular views from the top of Mount Pleasant. Breathtaking scenes of beaches, reefs, and neighbouring islands like Mustique and Canouan are visible from here making it a perfect spot for photography enthusiasts.

For water-lovers, there is an array of activities to indulge in. From diving amongst vibrant coral reefs and exploring underwater caves to sailing across the sparkling blue waters and visiting nearby islands, it's a paradise for adventurers. The Princess Margaret Beach and Lower Bay Beach are among the favourites, offering warm sand, clear waters, and tranquillity.

Port Elizabeth is not just about nature and beauty; it also hosts lively local events that showcase the rich culture of the region. The Bequia Music Fest held annually in January or February is a popular attraction that fills the air with music ranging from reggae and calypso to blues and rock.

Port Elizabeth's marketplace is another place where the town's pulse can be felt. Packed with stands selling fresh produce, local spices, artisan goods, and handmade crafts, it's a vibrant spot to experience local life. 

Visiting this charming town in St Vincent and the Grenadines blends the allure of pristine beaches, turquoise seas, fascinating local culture, and flavourful cuisine into an unforgettable Caribbean experience. The friendly residents put the cherry on top of your visit, greeting you with warm smiles and helpful advice to make your stay even more enjoyable. In all its simplicity and charm, Port Elizabeth exemplifies the essence of the Caribbean in a way few places do.

Day 9

Bridgetown

Bridgetown originally called 'Indian Bridge' is the capital and commercial centre of Barbados with about 80 000 inhabitants. It is a busy port with a natural harbour inlet known as the Careenage and is well utilised by pleasure craft and fishing boats.Bridgetown has a long and colourful history as a British settlement from the 17th century. A bustling city with many attractions for travellers its mix of modern and historic buildings are interspersed with markets monuments and a number of lush gardens.The main street Broad Street is where one finds banks department stores and duty-free shops. At the top of Broad Street is the Parliament Building (the Barbados Parliament is the third oldest in the Commonwealth dating from 1639) facing National Heroes Square. Bridgetown is home to a number of historical buildings that will interest visitors including the Garrison Historic Area which is a must-visit for military history buffs.Another attraction in Bridgetown is a massive Baobab tree (said to have been brought to the island from Guinea Africa around 1738). It takes 15 adults with outstretched arms to encircle the trunk.Tourists in Bridgetown will find much to see and do: cricket games at Kensington Oval which hosted the 2007 Cricket World Cup; the Barbados Derby at the racetrack in the Garrison area; and many other events and activities. A range of duty-free shops near the harbour sell staples like Mount Gay Rum while more colourful shopping options include the Cheapside Market and the Swan Street pedestrian mall. Local restaurants in the Careenage serve up fresh lobster and fish with Caribbean flair.

Day 10

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.

Day 12

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 13

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.

Day 14

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 15

Virgin Gorda

Virgin Gorda, the third-largest of the British Virgin Islands (BVI), is a stunning tropical paradise that offers visitors an enticing combination of natural beauty, relaxation, and adventure. The island spans approximately 8.5 square miles and has a population of around 4,000 inhabitants, creating a friendly and laid-back atmosphere that makes tourists feel welcome. It is accessible by ferry, private boat, or a small airport that caters to chartered flights.

Geographically, Virgin Gorda is known for its remarkably diverse landscapes, ranging from the white sandy beaches to the rugged mountains, leaving nature enthusiasts and beachgoers equally enchanted. The island's name, which translates to "Fat Virgin," was coined by Christopher Columbus in 1493, allegedly because the island’s profile on the horizon resembles a plump woman lying on her side.

The jewel in Virgin Gorda's crown is "The Baths," a geological wonder consisting of gigantic granite boulders that form scenic grottoes and pools on the island’s southwest shore. These natural formations are believed to be the result of volcanic activity, and their incredible shapes are filled with sea water and coral sand beaches. The Baths is a national park and offers a unique experience for snorkeling, exploring through the caves, and swimming in the natural tidal pools. It's a must-visit location that attracts people from around the world for its sheer beauty and tranquil turquoise waters.

Virgin Gorda also features some of the most luxurious resorts, villas, and restaurants in the Caribbean. Its exclusive North Sound is a well-known hideaway for yachts and offers several marinas and high-end accommodations. Here, visitors can take part in sailing, fishing, and water sports in one of the BVI's most sheltered harbors. Wellness-focused travelers can also indulge in spa services that incorporate the serenity and resources of the tropical environment.

The island’s economy thrives on tourism, but there is a sense of unspoiled charm as development is kept to ecologically sensitive levels. The community is dedicated to preserving the outstanding beauty of their environment, resulting in careful management of tourism activities.

For those looking to take a step back from water-based activities, Virgin Gorda does not disappoint. The island's hilly terrain is perfect for hiking, with trails leading to the highest point, Gorda Peak, which stands at 1,370 feet. The Gorda Peak National Park provides stunning panoramic views of the surrounding islands and cays, and on a clear day, even the distant Anegada can be seen. The mountain is also home to unique flora and fauna, such as the Virgin Gorda gecko, found nowhere else in the world.

Visitors to Virgin Gorda will savor the local cuisine, which is a blend of African, European, and Caribbean influences. Seafood is, unsurprisingly, a staple, and you’ll find it prepared in myriad delicious ways, from grilled lobster to conch fritters, often served with the island's staple side dishes like rice and peas.

Yet, what truly endears visitors to Virgin Gorda is the warmth of its people. From luxury resort staff to the vendors selling crafts at the local markets, everyone seems to have a story to share about the island. The cultural events and festivals, particularly during the Easter Festival, provide a lively display of local music, dance, and traditions.

In conclusion, Virgin Gorda is a small slice of heaven offering an authentic Caribbean experience. It's a place where luxury meshes with the simplicity of island life, where natural beauty is preserved, and where every traveler finds a tranquil escape. Whether it's for a honeymoon, family vacation, or a solo retreat, this island epitomizes the Caribbean's allure.

Day 16

Sint Maarten

Tucked away in a small corner of the Caribbean lies the island of Sint Maarten and Saint Martin, the world's smallest area of land divided into two nations. The French and Dutch have shared this strip of paradise peacefully for more than 350 years, ever since a gin-drinking Dutchman and a wine-imbibing Frenchman allegedly walked around the island to see how much territory they could claim for their country in a day. The French won more land, but the Dutch lay claim to the most prized part.

The Dutch may well have a point. Sint Maarten is known for its beaches, casinos and rum-fuelled festive nightlife. Duty-free shopping is the order of the day for tourists filling the numerous condos and resorts. Those who find it overdeveloped and artificial can get a taste of a different side of the Caribbean on the quiet, picturesque beaches of Simpson Bay and Little Bay, while visitors looking for a more rugged holiday would do well to head north to the French side of the island.

Saint Martin is significantly quieter than its Dutch counterpart. The French side of the island is a lovely mix of white-sand beaches, small town centres and beautiful stretches of mountainside. Shopping is a more relaxed affair at the outdoor markets, offering up some of the finest Caribbean cuisine.

The island as a whole hosts 120 different nationalities, giving it a rich cultural heritage. Food, drink and friendly Caribbean hospitality are all on the agenda. Visitors enjoy snorkeling, diving and jet-skiing, or head inland to hike in the mountains or zip-line through the treetops.

15-Day Southern Caribbean In Depth Ships

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15 Nights

15-Day Southern Caribbean In Depth

Seabourn
Departure: November
VISITING: Miami San Juan Great Harbour, Jost Van Dyke South Friars Bay Roseau Port Elizabeth Bridgetown Rodney Bay Montserrat Antigua South Friars Bay Virgin Gorda Sint Maarten
FROM £ 5,269 pp

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