The Caribbean’s commonly known for pristine beaches, clear turquoise water and luxurious resorts, with most travelers overlooking the fascinating history behind its modern tropical glamour. Some islands are actually the sites of the oldest settlements in the Americas. Since the coastlines once served as strategic economic and military landmarks back in the Colonial Era, many of these towns are built right on the beach. A beach vacation is a perfect occasion to learn about the Caribbean’s remarkable and vibrant past while getting in some much-needed relaxation.
7 Historic Beachfront Towns to Visit on a Caribbean Beach Vacation
San Juan, Puerto Rico
Puerto Rico’s capital used to be a walled and fortified city. The western part of town is over 500 years old and its Colonial Spanish architecture mixed with Caribbean colors makes it one of the most beautiful cities in the Caribbean.
Historical Meets Modern
Pass through the city gates of Old San Juan and walk on narrow cobblestone streets lined by art galleries, shops and boutiques. The list of important colonial landmarks here is endless but you can start by exploring two perfectly preserved fortresses by the sea or checking out Puerto Rico’s best restaurants on Fortaleza Street and sipping on an original Piña Colada. There’s something for both day and night, with easy access from here to the calm waters of Playita del Condado and when night falls, the Night Tales walking tour that walks you through town when Old San Juan feels magical and haunted.
Unwind at the luxurious Condado Vanderbilt, where you can spend a relaxing day on popular Condado Beach just a 10-minute drive from Old San Juan. Puerto Rico offers non-stop flights for as low as $80 even during season in spring, depending on where you’re coming from. You can fly right into the island’s international airport, just a 30-minute drive from San Juan.
Campeche City, Mexico
Visit this 17th-century walled harbor city in the Mexican Caribbean and feel like you’re in the movie “Pirates of the Caribbean”. It was once an indigenous village named Ah Kim Pech, that was conquered by Spanish conquistadors in 1517 and became the city of San Francisco de Campeche. Now, it’s known simply known as Campeche City or Campeche.
Journey Back in Time
Baroque Spanish architecture and former pirate hang-outs line the streets along with modern shops, museums and street art. Campeche has perfectly preserved outer walls and fortifications that used to defend this port town from pirate attacks and excellent restaurants containing fusions of Mayan, Spanish and Caribbean cuisine. If you need a break from all the history, you can walk right through the city gates and meet a modern Mexican city.
The state of Campeche is also like a trip back in time. Outside of the city, ancient Mayan ruins lay hidden in the rainforest, like the 2000-year-old Mayan town of Edzna and the Riviera Maya resort strip is nearby for some amazing beach resorts to unwind at after your adventure. You can also kayak in the ancient mangroves of Los Petenes or take leisure time on beautiful Playa Bonita and Tucán Siho Beach. Music lovers will want to visit in May, during Campeche’s International Jazz Festival.
St. George's Town, Bermuda
The former capital of Bermuda was built in 1609 on the island’s East End and is the oldest English town in the Americas. Get mesmerized by St. George’s old British Colonial buildings, its wharf and narrow cobblestone streets, which are just wide enough for horse carriages to go through.
Visit Old King’s Square
King’s Square is the epicenter of this 18th-century town and many streets—like Printers Alley, Duke of York Street or Aunt Peggy’s Lane—still retain their old names. St. Peter’s Church, built in the 17th century, is among the oldest buildings still standing. From the fort, you can head out to beautiful Gates Bay and St. Catherine’s Beach for swimming and sunbathing, or divers can explore the coral reefs dotted with numerous shipwrecks. And if you’re looking for a great night out, try nearby Hamilton, for upscale bars and sports bars. Or, explore the Crystal Caves underground to see more of Bermuda’s geological history. For a place to relax, consider St. George’s Resort Club close to the historic center. Gojo’s Cafe and White Horse Restaurant are both nearby on King’s Square, so you can enjoy amazing Caribbean food while viewing the town.
The pastel-colored colonial architecture lining the Inner City and Harbor of Willemstad is an echo to the island’s Dutch colonial past. The Netherlands established a trading colony here in 1634 named Fort Amsterdam before it became Willemstad. Influences from the Netherlands, Spain, Portugal and the Caribbean have diversified this old city and made it colorful and vibrant.
Explore Colonial Buildings & a Floating Bridge
Punda is Willemstad’s oldest district, filled with old walls and ramparts. Other districts like Pietermaai and Scharloo contain 18th-century buildings built over a natural deep-water harbor overlooking Sint Anna Bay. Willemstad also offers a great art fix while you’re vacationing there, like the Museum Kura Hulanda and the Gallery Alma Blou. Walk on the floating Queen Emma Bridge or visit the limestone Hato Caves. The warm, soft sand of nearby Kenepa Beach is perfect for sunbathing and Shete Boka National Park is a great option for hiking.
Cockburn Town, Turks and Caicos
The small, quiet capital situated on Cockburn Town Beach on Grand Turk is said to be the site where Columbus first made landfall in 1492. Cockburn Town was later settled by Bermudan sea salt producers and became an important port for the sea salt industry.
Sleepy Caribbean Charm & History Through the Ages
Grand Turk is laid-back and remote from the resort strips of busier Turks and Caicos islands. Visitors can walk by the striking British-Bermudan Colonial buildings and discover shipwrecks off places like Governor’s Beach—one of the prettiest beaches on the island. Make sure to also spend a day strolling and swimming on quaint Cockburn Town Beach, where you can discover the remnants of a sea wall that still dots the coastline. Old shops like Jimmy Buffett’s Margaritaville Trading Post add to that laid-back charm and historical feel.
For history closer to our time, check out the Friendship 7 monument right in town—the space capsule that made its ocean landing here in 1962 carrying astronaut John Glenn. The luxurious Bohio Dive Resort just south of the historic lighthouse has great diving and tour packages throughout spring. For accommodations, check out the Mediterranean-style Island House on North Creek—it offers a free rental car to explore this historic island gem.
Santo Domingo, the Dominican Republic
Santo Domingo was first founded in 1496 by Spanish conquistadors and is the oldest city in the Americas. It’s also a place of firsts in the New World— the first hospital, monastery, palace, cathedral, court and university are here. Ciudad Colonial, as the old town is called, has a unique, magical charm. Cobblestone streets are set between old 16th-century buildings and the ruins of 15th-century buildings. The beachfront area of Santo Domingo was also once inhabited by the Taíno indigenous tribe and you’ll find many place names and remnants of their culture here.
Colonial-Style Restaurants & Views of the Sea
Foodies will love the numerous restaurants lining historic Plaza España. For a more enigmatic feel of the old town, check out El Conde’s Bar, which is set in a dark cobbled alley in midst of old buildings and offers Caribbean fusion cuisine. Or, visit some of Santo Domino’s museums and learn more about the city’s incredible heritage and history. You can take a historical city tour and even a shopping tour. Before heading to beaches like the quaint Playa Guaycanes or popular Playa Boca Chica, check out the fortresses on the bluff overlooking the sea. The views are incredible and reminiscent of what colonists saw 500 years ago.
Oranjestad, Sint Eustatius
Referred to by the locals as ‘Statia’, this sleepy, tiny island in the Caribbean Netherlands used to be an important, bustling epicenter for colonial trade routes. Oranjestad, its port town, drove imports and exports in the Caribbean but fell to disrepair when it sided with the United States during the Independence War.
Fort Oranje & Its Underwater Ruins
Oranjestad’s historic Fort Oranje and Lower Town are lined with well-preserved, 17th-century forts, buildings and the oldest synagogue in the Western Hemisphere. At the edge of the old town, you’ll discover a part of the city that was once a bustling merchant district and has since been reclaimed by the sea. Divers will love exploring the offshore ruins of this former district and leeward beaches like Zeelandia Bay and Corre Corre are great for sunbathing and listening to the enigmatic pounding of the surf. Or, Oranje Beach on Oranje Bay is excellent for swimming and has offshore ruins that you can wade and swim through. Plus, hikers will love the nearby volcano and its views over the Caribbean Sea. Back in Oranje Bay, consider the excellent Kings Well Resort for a place to stay and enjoy Statia’s serenity.