A Journey of Caribbean Celebrations & Island Wonders

From spectacular beaches, to impressive monuments, to electrifying nightlife, San Juan, Puerto Rico is bursting with historical and cultural attractions that are sure to inspire and exhilarate.

A former Spanish colony established by explorer Ponce de León, San Juan is replete with monuments dating back to the sixteenth century. Originally built to fortify the Spanish military against attacks from native Taíno peoples and rival European colonial powers, both the Castillo San Cristóbal and Castillo San Felipe del Morro fortresses are popular sites for educational tours detailing the island’s extensive colonial history. These expansive bastions sit on San Juan’s rocky seaside cliffs and offer spectacular views of the Atlantic Ocean.

San Juan’s many beaches beckon you! Relax with warm sands, snorkel in glittering turquoise waters, and marvel at vast lines of palm trees on Condado Beach, Ocean Park Beach, Carolina Beach, and a host of other coastal havens. Better yet, go for a nighttime boat ride in one of Puerto Rico’s three bio-luminescent bays, Laguna Grande, where dinoflagellates illuminate the water in hues of neon aqua. The city’s nearby natural parks and ecological wonders are equally worth a visit, including the limestone caves of Cueva Ventana and the lush tropical ecosystem of El Yunque National Rainforest.

Your stay in San Juan won’t be complete without experiencing the city’s thrilling nightlife scene. San Juan boasts a number of bars, breweries, and dance clubs with delicious cocktails and mouthwatering (and authentically Puerto Rican!) culinary creations. Sip on the sweet coconut flavor of a classic piña colada, a Puerto Rico original, or sample some mofongo, a staple dish made of chicharrón and fried plantain.

Unwind in this vibrant Caribbean capital and let San Juan regale you with its many charms!

Nestled under the imposing view of volcanic Mount Liamuiga, charming Basseterre is the best place to begin your next Caribbean adventure to St. Kitts. From the island’s untouched natural beauty, best seen by boarding the famous St. Kitts Scenic Railway, to the glittering beaches of Frigate Bay, perfect for snorkeling and jet skiing, there are plenty of excursions guaranteed to thrill you in Basseterre. Be sure to stop by the city center to visit Independence Square or venture thirty minutes outside of Basseterre to scenic Brimstone Hill Fortress; both sites will give you a glimpse into the area’s French colonial past. Set sail for this Caribbean capital and soak up the tropical sun!

Road Town, the vibrant capital of Tortola in the British Virgin Islands (BVI), offers a charming blend of Caribbean culture, history, and natural beauty. Nestled around a horseshoe-shaped harbor and fringed by lush green hills, Road Town is the bustling heart of the BVI, where visitors can explore colorful markets, historical landmarks, and an inviting waterfront. The city's scenic Main Street is lined with colonial-style buildings, some dating back to the 18th century, now housing boutiques, art galleries, and local eateries. A stroll through this historic area reveals the character and charm of Tortola, with each turn offering a glimpse into its storied past.

For those who love sailing, Road Town is a gateway to some of the most beautiful waters in the Caribbean. The city’s marinas, such as the popular Nanny Cay Marina, are buzzing with yachts and catamarans ready to embark on island-hopping adventures to nearby gems like Jost Van Dyke, Virgin Gorda, and Anegada. The BVI is renowned as the "Sailing Capital of the World," making it a paradise for both seasoned sailors and beginners looking to learn. Visitors can set sail for the famous Baths on Virgin Gorda, known for their unique rock formations and crystal-clear waters, or experience the vibrant nightlife on Jost Van Dyke, home to the iconic Soggy Dollar Bar.

In Road Town, the botanical wonder of JR O'Neal Botanic Gardens offers a peaceful retreat from the lively streets. This four-acre garden showcases the island’s diverse flora, from fragrant frangipanis to towering palm trees. For a deeper dive into the island's culture and history, visit the 1780 Lower Estate Sugar Works Museum, a former sugar plantation turned museum that provides insight into the island’s colonial past and the history of sugar production in the Caribbean. Visitors can also explore the Virgin Islands Folk Museum, which houses artifacts that tell the story of the BVI, from its indigenous Arawak roots to its maritime heritage.

Fun fact: The name "Road Town" derives from the nautical term "the roads," which refers to a place less sheltered than a harbor but where ships can anchor. This name reflects Road Town’s historical role as a vital trading port in the Caribbean, which today remains a lively and essential hub for visitors exploring the British Virgin Islands.

The capital of picturesque St. Barthélemy, Gustavia is a veritable island paradise in the Caribbean. A former French colony, this small city on St. Barths’s west coast offers a variety of fine dining, designer shopping, and spectacular beachside activities to ensure a relaxing tropical getaway. Be sure to visit the historic site of Fort Karl for a panoramic view of Gustavia’s glittering harbor, then walk to Shell Beach to take a dip in warm, turquoise waters.

Nestled between Biscayne Bay to the east and Everglades National Park to the west, Miami, Florida is one of the Sunshine State's most vibrant, culturally diverse, and dynamic cities. Neon pink lights and tropical nights beckon you to this popular tourist destination, a favorite port for travelers on Caribbean and Trans-Atlantic cruises.

Miami’s expansive stretch of sand and sun is a beach-lover’s paradise. Lined with palm trees, Miami Beach and South Beach are excellent sites to soak up some Vitamin C, take a plunge in warm cerulean waters, and traverse the bay by boat. South Beach boasts amazing nightlife, including stunning rooftop bars with ocean views and vivid nightclubs. The LGBTQ community has contributed immensely to the city’s nightlife – several gay bars and drag clubs are some of Miami’s most sought-after spots for dancing. You’ll find the famous Art Deco district, with a delightful collection of vintage architectural masterpieces, mere steps from the sandy coastline.

A veritable melting-pot, Miami has been heavily influenced by Latin American culture. Visit the city’s Little Haiti and Little Havana neighborhoods to discover authentic Cuban and Haitian cuisine, colorful art museums, jazz bars, and robust brewed coffee. Revel in a savory bite of the classic Cubano sandwich, a staple in Miami.

Whether golfing, fishing, partying, or sun-bathing, sunny Miami, Florida has something for everyone!