Caribbean Destinations Rich in History

From ancient pyramids in Mexico to imposing forts in Puerto Rico, discover time-honored sites that date back centuries.
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Caribbean colors on Dutch-gabled houses give Willemstad, Curacao’s capital, a unique Dutch-Caribbean vibe.

Credit: Royal Caribbean

One of the most popular vacation destinations, the Caribbean is a favorite place to get away for many. Beautiful beaches, warm weather, welcoming people, food full of flavors and tropical cocktails… what’s not to love? Even better, the island gems and nations are also chock-full of history.

Each of the Caribbean’s 7,000 islands has its own story, and you can discover many of them on a Royal Caribbean cruise. From the Southern Caribbean to the Eastern and Western parts, soak in the tropics’ charm and rich cultures as you sail to a new destination just about every day. Imagine taking in Mexico’s ancient Maya temples, Barbados’ UNESCO World Heritage Sites and Puerto Rico’s ancient fortress, all while enjoying the traditions, food, art and music that have taken shape throughout that time. Plus, you get to end each day on a ship that’s full of adventures and ways to relax, from skydiving on the RipCord by iFly simulator to kicking back by the resort-style pools with a drink in hand.

Wondering where to go? To start, here are five Caribbean destinations rich in history that you can explore on a cruise.

Castillo San Felipe del Morro, an ancient fortress and UNESCO World Heritage Site, was built on a scenic overlook to protect San Juan, Puerto Rico, from invasions.

Credit: Venturelli Luca/Shutterstock

San Juan, Puerto Rico

Wander down cobblestone streets and fall in love with San Juan’s candy-colored, 16th-century townhomes and charming plazas, all tucked within a 15-foot-thick wall from the same era. The second-oldest European settlement (established in 1521) in the Americas, Puerto Rico’s capital is packed with historic landmarks. One of the most famous sites is the ancient fortress and UNESCO World Heritage Site Castillo San Felipe del Morro, or El Morro, in Old San Juan. Built over the course of 251 years from 1539, the stunning structure helped to protect Puerto Rico from invasions by the British and the Dutch.

San Juan is also home to beautiful beaches, so you can take a refreshing dip at spots like Luquillo and Carolina Beach just minutes after diving into the island’s history. And when it comes to getting a taste of Puerto Rico: grab a pina colada—said to have originated here—and some mofongo, a famous local dish made with fried plantains and mashed with crispy pork.

How to get there: Five- to 11-night cruises from cities like Cape Liberty, New Jersey; Boston; and Miami, Orlando and Fort Lauderdale, Florida.

See all the cruises that visit San Juan here.


Bridgetown, Barbados, has two UNESCO World Heritage Sites that include points of interest like the 17th-century Parliament Buildings.

Credit: iStock

Bridgetown, Barbados

The 166-square-mile island nation of Barbados features an eclectic mix of welcoming Bajan culture, West African vibes, reggae and calypso sounds as well as a noticeable British influence (it gained its independence in 1966). The Historic Bridgetown area and its Garrison are UNESCO World Heritage Sites filled with points of interest, such as Bush Hill House, where a young George Washington briefly resided, and British colonial architecture like the 17th-century Parliament Buildings. The Garrison, once Great Britain’s military headquarters, still stands complete with a fort, barracks and a towering guardhouse.

After venturing out to see Barbados’ past, have your pick of 80-plus beaches—like Crane Beach and its rare pink sand. Other adventures range from polo and cricket matches to rum tastings at the Mount Gay distillery, which became the birthplace of rum when it was founded in 1703. A must, if you can time it right, is the Crop Over festival. It’s a three-month-long summer harvest celebration that’s heavy on the calypso and celebrates local music, arts, food and culture.

How to get there: Five- to 14-night cruises from cities like Miami; Baltimore, Maryland; and San Juan, Puerto Rico.

Find the cruises that will take you to Bridgetown here.


A large part of Mexico’s history is rooted in the ancient Maya civilization, which built many once-sprawling cities.

Credit: Tony Moran/Shutterstock

Costa Maya, Mexico

South of Cancun is Costa Maya, a lesser-known but equally beautiful destination in Mexico filled with lush jungles, soft sand beaches as well as pyramids and many other ruins that date back to the Maya civilization. Check out Kohunlich, built around 500 A.D. and famous for its Temple of the Masks, and the sprawling remnants of Chacchoben, a site believed to be over 3,000 years old (from 1,000 B.C.).

Costa Maya is also the place to be for outdoor adventures. For example, there’s the Sian Ka’an Biosphere Reserve, a 1.3-million-acre refuge and UNESCO World Heritage Site. It’s known as one of the most biodiverse places on Earth, with rainforests, marshes, mangroves, coral reefs, lagoons and tons of wildlife that call it home. You can also swim in Cenote Azul, a glittering blue freshwater lagoon, and snorkel at the Mesoamerican Barrier Reef, or Great Maya Reef, one of the largest reefs in the world.

How to get there: Five- to nine-night cruises from cities like New Orleans; Galveston, Texas; and Miami, Tampa, Orlando and Fort Lauderdale, Florida.

Take your pick of all the cruises that head to Costa Maya here.


The streets of the Punda neighborhood of Willemstad, Curacao, feature colorful, Dutch-gabled houses from the 17th century.

Credit: Birdiegal/Shutterstock

Willemstad, Curacao

Take one look at Willemstad, Curacao’s capital, and you’ll see a unique combination of Dutch and Caribbean influences. Vibrant Caribbean colors come alive on the city’s Dutch-gabled buildings, and there are waterways, bustling street cafes, and 17th- and 18th-century architecture that’s reminiscent of Amsterdam in The Netherlands. All this and more are why Willemstad is a UNESCO World Heritage Site.

The island’s history is everywhere, so keep your eyes and ears open. There’s music inspired by the city’s Afro-Caribbean culture, like the African-inspired, drum-based Tambu, and lively festivals such as a month-long carnival that starts in February. There are also plenty of historic sites to explore, like Fort Amsterdam, built in 1635 and now home to the government, as well as the oldest synagogue in the Americas—which is still in use to this day. A trip to the ancient Hato Caves—massive limestone caverns filled with mystical pools, waterfalls and 1,500-year-old cave paintings—is also a must.

How to get there: Six- to 14-night cruises from cities like Cape Liberty, New Jersey; Miami, Orlando and Fort Lauderdale, Florida; and Bridgetown, Barbados.

Check out cruises heading to Willemstad and other Caribbean destinations here.


The past is present in Philipsburg, St. Maarten, especially along its historic Front Street and Back Street, which have buildings like this Methodist Church from in 1851.

Credit: Lisa Strachan/Shutterstock

Philipsburg, St. Maarten 

St. Maarten and all of its 8.3 miles from end to end are home to 120 different nationalities that speak 80-plus languages. Shaped by African, British, Dutch and French influences, today, St. Maarten is governed by two countries—France and The Netherlands.

The architecture ranges in style and dates back to the 1700s, which you can see in historic sites like Fort Amsterdam and Fort Willem—built around Philipsburg for protection during a period of bustling international trade (and accompanying pirates). The old mansions along the famous Front Street and Back Street, including the courthouse built in 1793 that sits between both, will make you feel like you’ve traveled back in time.

Get the island’s Caribbean flavor by hitting a fish fry or lolo—a roadside barbecue stand—and sip on guavaberry liqueur, which is unique to St. Maarten. You can also unwind at places like Simpson Bay, the Caribbean’s largest saltwater lagoon, and at the top of Mount Concordia, which marks the border between St. Maarten’s two sides and has incredible views of both.

How to get there: Five- to 12-night cruises from cities like Cape Liberty, New Jersey; Miami, Orlando and Fort Lauderdale, Florida; and San Juan, Puerto Rico.

Find the Caribbean cruises that visit Philipsburg here


If your ideal vacation combines ice skating and playing laser tag one moment and climbing ancient pyramids and fortresses the next, check out Royal Caribbean cruises to these historic hotspots and more here.