The Caribbean is a paradise of sun-drenched beaches, vibrant cultures, and rich histories. This region, known for its diverse islands, offers a unique blend of Spanish, African, and indigenous influences. From the cobblestone streets of San Juan to the colonial charm of Santo Domingo, the Caribbean promises an unforgettable journey.

San Juan, the capital of Puerto Rico, is a city where history meets modernity. Its colorful streets are lined with colonial architecture, while its beaches offer a perfect escape. Meanwhile, Santo Domingo, the capital of the Dominican Republic, is the oldest continuously inhabited European settlement in the Americas, boasting a UNESCO World Heritage-listed Colonial Zone.

Travelers should be aware of the tropical climate, which means packing light, breathable clothing and plenty of sunscreen. The local cuisine is a delightful mix of flavors, with dishes like mofongo in Puerto Rico and sancocho in the Dominican Republic. Be sure to try the local rum and coffee, both of which are world-renowned.

San Juan

San Juan is a vibrant city that perfectly blends the old with the new. Its historic Old San Juan district is a must-visit, with its cobblestone streets, colorful buildings, and impressive forts like El Morro and San Cristóbal. The city is also known for its lively nightlife, beautiful beaches, and delicious cuisine.

For accommodations, consider staying at a charming VRBO in Old San Juan or a luxurious hotel in Condado. Check out options on VRBO or Hotels.com.

Day 1: Arrival in San Juan

Afternoon: Arrive in San Juan and check into your accommodation. Take a leisurely stroll through Old San Juan, exploring its vibrant streets and historic sites.

Evening: Enjoy dinner at Marmalade Restaurant & Wine Bar, known for its innovative dishes and extensive wine list. Afterward, sip on a cocktail at La Factoría, a popular bar with a speakeasy vibe.

Day 2: Exploring Old San Juan

Morning: Start your day with a coffee at Café Cuatro Sombras, a local favorite. Then, visit the impressive Castillo San Felipe del Morro, a 16th-century fortress with stunning ocean views.

Afternoon: Head to the Museo de las Américas to learn about the region's cultural history. For lunch, try the mofongo at Raíces, a traditional Puerto Rican dish made with mashed plantains.

Evening: Dine at Santaella, where you can savor modern Puerto Rican cuisine. End your night with a walk along the Paseo de la Princesa, a scenic promenade with beautiful views.

Day 3: Beach Day in San Juan

Morning: Spend the morning relaxing on the sandy shores of Condado Beach. Grab a breakfast sandwich from Kasalta Bakery before heading to the beach.

Afternoon: Continue your beach day at Isla Verde, known for its clear waters and lively atmosphere. Enjoy a beachfront lunch at El Alambique Beach Lounge.

Evening: Have dinner at Oceano, a chic oceanfront restaurant offering fresh seafood and stunning views. Afterward, explore the nightlife in the Condado district.

Santo Domingo

Santo Domingo is a city steeped in history, with its Colonial Zone offering a glimpse into the past. The city is also a hub of culture and cuisine, with vibrant markets, lively music, and delicious food.

For accommodations, consider a cozy VRBO in the Colonial Zone or a modern hotel in the city center. Explore options on VRBO or Hotels.com.

Day 4: Travel to Santo Domingo

Morning: Depart San Juan for Santo Domingo. Flights are available via Kiwi.com, with a flight time of approximately 1.5 hours.

Afternoon: Arrive in Santo Domingo and check into your accommodation. Begin exploring the Colonial Zone, starting with the Catedral Primada de América, the oldest cathedral in the Americas.

Evening: Enjoy dinner at Pat'e Palo, a historic tavern offering a mix of international and Dominican dishes. Afterward, enjoy a drink at Onno's Bar, a lively spot with great music.

Day 5: Discovering Santo Domingo's History

Morning: Start your day with a visit to the Alcázar de Colón, the former residence of Diego Columbus. Enjoy breakfast at La Cafetera, a charming café nearby.

Afternoon: Explore the Museo de las Casas Reales, which offers insights into the colonial history of the Dominican Republic. For lunch, try the sancocho at Adrian Tropical, a hearty Dominican stew.

Evening: Dine at El Mesón de la Cava, a unique restaurant set in a natural cave. After dinner, take a stroll along the Malecón, a scenic waterfront promenade.

Day 6: Nature and Relaxation

Morning: Take a day trip to Los Tres Ojos, a series of stunning limestone caves and lakes. Enjoy a picnic breakfast surrounded by nature.

Afternoon: Head to Boca Chica Beach for a relaxing afternoon by the sea. Enjoy fresh seafood at Neptuno's Club, a popular beachfront restaurant.

Evening: Return to Santo Domingo and have dinner at La Cassina, known for its elegant atmosphere and delicious Italian cuisine.

Day 7: Departure

Morning: Spend your final morning exploring the Mercado Modelo, a bustling market where you can shop for souvenirs and local crafts. Enjoy a farewell breakfast at Café Santo Domingo.

Afternoon: Depart Santo Domingo for your journey home, taking with you unforgettable memories of your Caribbean adventure.

This 7-day itinerary offers a perfect blend of history, culture, and relaxation in the Caribbean. From the vibrant streets of San Juan to the historic charm of Santo Domingo, you'll experience the best of what this region has to offer.