Yachtsman's Caribbean in Depth from San Juan, 5 December 2026 (14 nights)

Declared a UNESCO World Heritage Site, La Fortaleza was built between the 16th and 20th centuries with the aim of protecting the city of San Juan. It has been a fortress, a prison and a residence, and is open for visitors to explore during the day.

In San Juan, there is a fort called Castillo San Cristóbal. The Spanish constructed it to defend San Juan against land-based assaults. Part of the San Juan National Historic Site, it's arguably the greatest fortification erected by the Spanish in the New World.

The writings of local poet Lady Lee Andrews are shown at this store, art gallery, and cafe. A lot of aspiring poets attend the regular open-mic sessions; this is something that makes it a unique place to visit during a trip to San Juan.

Dating between the 17th and 18th century, Brimstone Hill Fortress is situated on a hill in St. Kiss. Designed by British military engineers, this historic fortress offers the perfect day out for those wanting to immerse themselves into the history of the area.

One of the top sights in Carambola, Romney Manor is a set of historic plantation estate houses. Within them, you can learn how to create tie-dye clothing. An extraordinary attraction, the picturesque Romney Manor makes for a unique day out.

Spanning 29 kilometres, the St. Kitts Scenic Railway is a popular narrow gauge railway line. Hop on this incredible railway and enjoy all of the picturesque scenery throughout St. Kitts. Completed in 1926, it the journey takes just over 3 hours.

This picturesque bay is known for its calm waters and stunning views. It's a popular spot for swimming, sunbathing, and kayaking.

This lively peninsula is a hub for water sports, shopping, and dining. Take a boat tour, try your hand at windsurfing, or simply relax on the beach and soak up the sun.

This museum is located on the former sugar plantation where Empress Joséphine grew up. Here you can explore the life and times of this fascinating woman, from her childhood in Martinique to her reign as Empress of France.

Created by a local fisherman, the Old Hegg Turtle Sanctuary strives to help with the survival of local turtles. In operation for over 12 years, they have released over 2000 turtles back into the ocean. A wonderful place to visit, you can get up close and personal with these fascinating creatures.

One of the most popular and picturesque attractions in Port Elizabeth, the Princess Margaret Beach is a beautiful beach with golden sand, lush vegetation and turquoise waters that are ideal for a relaxing afternoon swim.

Situated at the northern end of Admiralty Bay, you can visit the ruins of Fort Hamilton for free throughout the day. Originally constructed by the British military, you'll see the canon battery, lookout and other fascinating parts of the remaining fort whilst admiring views out towards the ocean.

Dive into the crystal blue waters of the Caribbean and experience one of the unique underwater sculptures on the coast of St George’s. Serving as both a base for marine life to thrive and a venue for avid watersport enthusiasts, this incredible attraction is home to over 75 sculptures stretching across 800 square metres of the seabed. Take the plunge and discover something amazing.

Dating back to the 18th century, Fort George is considered the most historic structure in St Georges. Bursting with history, it was a staple in the political and military changes that have taken place over the last 300 years. With views stretching across the harbours and the town's red-tiled roofs, Fort George offers breathtaking island scenery. A perfect stop to experience the culture of Grenada

With a 30-foot waterfall in a grotto of lush vegetation, Annandale Falls holds some of the most beautiful views and locations in Grenada. With natural pools deep enough to swim in, you can experience the beautiful nature of the Caribbean. Home to many species of animals native to the island, experience the beauty of St. George's up close and personal.

Step back in time to 1751 as you explore this fascinating attraction. Once home to the first president of the United states, it’s a dedicated World Heritage Site. Giving an insight into what life was like in the 18th century, this is a must visit for anyone who has an interest in American or Barbadian history.

In the heart of the city lies the Chamberlain Bridge. Originally a 19th century swing bridge, and now a lift bridge that was constructed in 2006, it offers picturesque views out over the waterfront and situated close to the popular Bridgetown boardwalk.

An important landmark in the city, the Parliament Buildings are built in a gothic architecture. Featuring stained glass windows, a clock tower, the National Gallery and more, it makes for a fascinating visit whilst stopping off in the capital.

Dating between the 17th and 18th century, Brimstone Hill Fortress is situated on a hill in St. Kiss. Designed by British military engineers, this historic fortress offers the perfect day out for those wanting to immerse themselves into the history of the area.

One of the top sights in Carambola, Romney Manor is a set of historic plantation estate houses. Within them, you can learn how to create tie-dye clothing. An extraordinary attraction, the picturesque Romney Manor makes for a unique day out.

Spanning 29 kilometres, the St. Kitts Scenic Railway is a popular narrow gauge railway line. Hop on this incredible railway and enjoy all of the picturesque scenery throughout St. Kitts. Completed in 1926, it the journey takes just over 3 hours.

Situated over 114 metres above the ocean, Fort Napoleon is a prominent fort that grants incredible views of the bay of Les Saintes. Not only does it house a museum, but several fortifications and an armoury.

Surrounded by lush vegetation, the Pain De Sucre Beach is one of the most picturesque beaches in Guadalupe. With crystal clear water, tropical fish and golden sands it's the perfect place to unwind after a day of exploring.

The Notre-Dame-de-l' Assomption is a church that's dedicated to the Virgin Mary. Built to honour the French victory against the English in the 17th century, it features several impressive features including stained glass, murals and statues.

Take a short walk to the top of Morne Bruce, a small Mountaintop on the outskirts of Roseau, and take in the incredible views of the island. Looking over the city and white-sand beaches with a backdrop of mountains, it's the best of both worlds.

Visit one of Dominica's oldest trading markets in Roseau. An incredibly historic place in the Caribbean that has found new life by showcasing local goods and crafts from the people native to the city. Take a step into the day-to-day life of the residents and experience Roseau like no other.

Some of Dominca's beautiful Botanical Gardens make up the vibrant capital city. Tucked beneath Morne Bruce Hill, the 40-acre botanic gardens contain Banyan trees, Century palms, and beautiful tropical flowers. This is a great place for a wander in the nature of the Caribbean.

Rodney Bay is a paradise for those wanting to enjoy an afternoon of scuba diving. With crystal-clear waters, an array of marine wildlife and beautiful corals, you'll have a fantastic time.

Alternatively, if you want to head out on a hike, head up the awe-inspiring Mt. Pimard Trail. Located near Gros Islet, this 2.6-km out-and-back trail will provide plenty of photo opportunities!

Step back in time to 1751 as you explore this fascinating attraction. Once home to the first president of the United states, it’s a dedicated World Heritage Site. Giving an insight into what life was like in the 18th century, this is a must visit for anyone who has an interest in American or Barbadian history.

In the heart of the city lies the Chamberlain Bridge. Originally a 19th century swing bridge, and now a lift bridge that was constructed in 2006, it offers picturesque views out over the waterfront and situated close to the popular Bridgetown boardwalk.

An important landmark in the city, the Parliament Buildings are built in a gothic architecture. Featuring stained glass windows, a clock tower, the National Gallery and more, it makes for a fascinating visit whilst stopping off in the capital.