13-Day Classic Multi-Country Caribbean Tour

About the destination: San Juan, the capital of and largest city in Puerto Rico, was officially established in 1521, making it one of the oldest cities in all of the Americas. Being a United States territory, San Juan is a pretty unique place to visit in the Caribbean; the capital city offers all the comforts and amenities of any American city, but has still managed to retain a distinct Latin atmosphere and culture. The historic part of the city, Old San Juan, is among the oldest settlements within Puerto Rico full of colourful streets that have historical and cultural significance. As you stroll down the streets of Old San Juan, you can't help but be amazed at the five centuries of history that have been so beautifully preserved. One of the most famous monuments in Puerto Rico, El Morro, is a 16th century fort list with impressive towers and tunnels. Few cemeteries are as scenic as San Juan Cemetery. Lush and diverse, El Yunque Rainforest is a natural paradise. Puerto Rico is synonymous with great beaches. You’ll find many along San Juan's coast, soft sand and palm trees await you here. San Juan is a great mix of beach, history, great culture and nightlife. So, what are you waiting for?

About the destination: is the capital and largest city of the Bahamas. Located on New Providence Island, Nassau has a blend of old world and colonial architecture, it is known for it's natural beauty but it also has tons of rich cultural history. There is so much to learn, see, and do.

About the destination: Havana is a city that seems to move to its own rhythm: the distant roar of classic cars, the echo of son, salsa, and bolero spilling from doorways, and the sea breeze rolling in from the Malecón. In Old Havana (Habana Vieja), pastel-colored facades peel gracefully, revealing courtyards shaded by palms and wrought-iron balconies lined with laundry. Plaza Vieja and Plaza de la Catedral offer a perfect introduction to the city’s colonial soul, with baroque churches, restored mansions, and lively cafés where you can sip a mojito as you watch everyday life unfold. Beyond the historic center, Havana’s neighborhoods showcase different facets of Cuban culture. In Centro Habana, streets are more chaotic and authentic, with crumbling buildings, bustling markets, and locals chatting on corners. Vedado, once the city’s glamorous residential area, mixes art deco architecture with modern hotels, leafy avenues, and the famous Coppelia ice cream parlor. Don’t miss a stroll along the Malecón at sunset, when families, fishermen, and musicians gather along the seawall, and the city glows in the soft evening light. Havana’s cultural life is intense and ever-present. Music is everywhere: from impromptu jam sessions in tiny bars to polished shows at iconic venues like the Tropicana. Visit the Museo Nacional de Bellas Artes to discover Cuban art, and explore Fábrica de Arte Cubano, a former factory turned into a cutting-edge cultural center, where galleries, live music, and performances share the same space. Classic car tours, cigar factories, and rum tastings offer a deeper look into some of Cuba’s most famous traditions. Travelers should be prepared for contrasts: beautifully restored plazas next to decaying buildings, limited internet access, and occasional shortages of everyday items. This is part of Havana’s reality and charm. Bring cash (preferably euros), expect slower service, and approach the city with patience and curiosity. If you do, Havana will reward you with genuine encounters, unforgettable sunsets, and the unique feeling of stepping into a living, breathing time capsule.

About the destination: Kingston is the capital and largest city of Jamaica. The birthplace of both reggae music and Bob Marley, Kingston is home to a lively music scene, as well as the Bob Marley Museum (bobmarley-foundation.com), one of the most visited tourist sites in the city. The city's colonial past is on display, especially in the downtown area, near the Parade, which is a British military drill field.