Southern & Eastern Caribbean from Boston with Stays, 16 October 2025 (26 nights)

Boston’s legendary baseball ground and home of the world-famous Boston Red Sox since 1912, making it the oldest stadium in US baseball. If you’re a sports fan, a tour of the proud history at the stadium is a must, or even catch a game and soak up the legendary atmosphere.

Freedom trail is the best way to learn about how the start of the American war of independence and the revolution affected the history and outlook of Boston and wider America. With sixteen historical sites and over two and a half miles of scenic walking, this is a must-visit for all ages.

The city’s historic market place boasting interior and exterior stalls and stores, with plenty of places to grab a bite to eat, as well as three old market buildings ideal for a flavour and feel of Boston life.

Established in 1870, Boston’s art museum boasts being the fifth largest in overall size in the USA and one of the most extensive collections of artworks with around 450,000 individual pieces to view, from ancient Egypt to French impressionist and Dutch golden age exhibitions.

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; making it a unique place to visit during a trip to San Juan.

This cool cable car takes you all the way up from the bottom of the cruise terminal harbour area to Paradise Point for stunning views all the way up. At the top is a great restaurant and bar too to take in the sights in true paradise.

Originally called Skytsborg and constructed by Danish colonists for defence and a vantage point, this modern-day hotel also has entertaining guided tours to learn all about the history of Edward and his infamous band of marauding pirates.

A short drive away from the port, the Charlotte Amalie Overlook grants extraordinary views out towards the ocean. Although this isn’t within walking distance, the views that you get across the city is well worth the effort.

This unexpected treasure in the Caribbean is an absolute must for movie fanatics and science-fiction enthusiasts. Showcasing the history of Nick Malley, who created Yoda from Star Wars, this museum boasts memorabilia from the franchise, such as scripts, storyboards and props.

Enjoy a relaxing walk along Great Bay Beach - a popular attraction within the town, with beautiful white sand, a vibrant boardwalk and an array of ships, restaurants and more on its shore.

Feel transported back in time, to the time of the pirates at this fun attraction. From hearing true stories of pirates’ escapades to state-of-the-art multimedia displays, this family-friendly attraction is a unique experience in Phillipsburg.

The largest open air market in the city, the Castries Central Market has over 300 different stalls, selling everything from trinkets to fresh fruit. Set up in 1891, this vibrant market is a wonderful place to grab a bite to eat or something to take home.

Alternatively, head to the picturesque Rodney Bay. Located in the Gros Islet District, this pretty bay is a wonderful place to unwind whilst sipping a cocktail or enjoying a swim in the nearby turquoise waters.

A popular beach in the southwest of the capital, Marigot Bay is a picture-perfect beach that’s often voted as the best in the capital. From its surrounding restaurants and bars to the beautiful water and golden sand, Marigot Bay should be on your list of things to do whilst in the capital.

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.

Within easy reach of the capital lies the breathtaking Hato Caves. A popular tourist attraction on the island, the Hato Caves is known for its marine limestone walls. Accessible via several local tours, they have been accessible since the early 1990s.

Popular with families, the Curacao Sea Aquarium offers an array of exhibits, live shows and more. Home to dolphins, sharks, stingrays, sea lions and other marine creatures, the Sea Aquarium is a fun way to spend an afternoon on the island.

If you’re looking to relax and unwind during your time in Willemstad, head to Mambo Beach. Aligned with restaurants, beach bars, shops and more, this beach is a vibrant attraction perfect for those wanting to discover all that this charming city has to offer.

Whilst on Half Moon Cay, enjoy a paddle across the picturesque crystal lagoon. Surrounded by breathtaking mangroves and local wildlife, this activity is a peaceful way of exploring all that the island has to offer.

Whilst on the island, head to Stingray Cove, where you’ll have the opportunity to feed and touch the beautiful and gentle stingrays. Perfect for any nature lover, this activity is popular with those of all ages.

Experience Half Moon Cay in a one-of-a-kind way, by horseback! Ride a trained quarter horse along a winding trail, soaking in the sensational views, and then enjoy the unique experience of riding a horse swimming along the shoreline. This is an unmissable opportunity to explore the island!

With over 1.5 million acres of wetland, Everglades National Park is the third largest national park in the US. There’s plenty to explore in this stunning landscape, and visitors can take a tour with a guide, hop on a tram or simply hike one of the many trails.

With no shortage of vibrant, lively attractions, Miami Beach is the place to be for sunshine, sand and the beautiful sea. Visitors enjoy a plethora of bars and eateries in the surrounding area, hit the art deco district or simply relax on a lounger on the beach.

Whether you love art or you’re looking for an attraction in Miami, the Wynwood Walls are extraordinary. A unique outdoor gallery, you can spend your time admiring all of the huge, colouful murals that have been created by international artists.

This museum holds exhibitions telling the story of the island from the historic Lucayan Culture up to the present day. A highlight has to be the Molasses Reef shipwreck from 1505, the oldest recorded shipwreck in the New World.

Enjoy a relaxing swim or snorkelling experience at the picturesque Pillory Beach. Aligned with picturesque resorts and casuarina trees, this glistening beach is a wonderful place to kick back and unwind during your day in Grand Turk.

Standing at an impressive 60 feet tall, Grand Turk Lighthouse overlooks the beautiful North Creek. Built by Alexander Gordon, a prominent British architect in 1852, this historic lighthouse has been a significant attraction since its construction in the 19th century.

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; making it a unique place to visit during a trip to San Juan.

This cool cable car takes you all the way up from the bottom of the cruise terminal harbour area to Paradise Point for stunning views all the way up. At the top is a great restaurant and bar too to take in the sights in true paradise.

Originally called Skytsborg and constructed by Danish colonists for defence and a vantage point, this modern-day hotel also has entertaining guided tours to learn all about the history of Edward and his infamous band of marauding pirates.

A short drive away from the port, the Charlotte Amalie Overlook grants extraordinary views out towards the ocean. Although this isn’t within walking distance, the views that you get across the city is well worth the effort.

Whilst on Half Moon Cay, enjoy a paddle across the picturesque crystal lagoon. Surrounded by breathtaking mangroves and local wildlife, this activity is a peaceful way of exploring all that the island has to offer.

Whilst on the island, head to Stingray Cove, where you’ll have the opportunity to feed and touch the beautiful and gentle stingrays. Perfect for any nature lover, this activity is popular with those of all ages.

Experience Half Moon Cay in a one-of-a-kind way, by horseback! Ride a trained quarter horse along a winding trail, soaking in the sensational views, and then enjoy the unique experience of riding a horse swimming along the shoreline. This is an unmissable opportunity to explore the island!

With over 1.5 million acres of wetland, Everglades National Park is the third largest national park in the US. There’s plenty to explore in this stunning landscape, and visitors can take a tour with a guide, hop on a tram or simply hike one of the many trails.

With no shortage of vibrant, lively attractions, Miami Beach is the place to be for sunshine, sand and the beautiful sea. Visitors enjoy a plethora of bars and eateries in the surrounding area, hit the art deco district or simply relax on a lounger on the beach.

Whether you love art or you’re looking for an attraction in Miami, the Wynwood Walls are extraordinary. A unique outdoor gallery, you can spend your time admiring all of the huge, colouful murals that have been created by international artists.