New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Travel AI

Caribbean Adventure: 8-Day Trip to Puerto Rico, Dominican Republic, and the Philippines

Caribbean Adventure: 8-Day Trip to Puerto Rico, Dominican Republic, and the Philippines Itinerary

Last updated: 2024 Jun 14

Historic San Juan and Culinary Delights

Morning
Begin your Caribbean adventure with a delightful breakfast at Barrachina, the birthplace of the piña colada. Afterward, take a morning stroll through the charming streets of Old San Juan Walking Tour, visiting historic sites like El Morro and La Fortaleza.
Afternoon
For lunch, savor the flavors of Puerto Rican cuisine at El Varadero Bar y Restaurante, known for its fresh seafood. Spend your afternoon at the Casa Bacardi Distillery Tour with Cocktail Class, learning about the island's famous rum and enjoying a mixology session.
Evening
Dine at Platos, a local favorite for its fusion cuisine. After dinner, experience the vibrant nightlife of San Juan at La Placita de Santurce, where live music and dancing fill the streets.
Bedtime
Find amazing hotels in San Juan, Puerto Rico.
Visit Old Town Artisans in San Juan, Puerto Rico

Old San Juan Walking Tour

Book Now
next arrow

Thrills and Ziplines at Toro Verde Adventure Park

Morning
Fuel up with breakfast at Metropol Restaurant - Isla Verde, offering a mix of Puerto Rican and international dishes. Then, embark on an adrenaline-pumping morning at Puerto Rico The Beast Zipline at Toro Verde Adventure Park, one of the longest ziplines in the world.
Afternoon
Enjoy a hearty lunch at Encanto Beach Club Bar & Grill, located in a beautiful beachfront setting. Afterward, continue your ziplining adventure with Puerto Rico The Monster Zip Line Toro Verde Adventure Park, another exhilarating ride.
Evening
Unwind with a relaxed dinner at El Guacamayo Pool Bar & Grill, where you can enjoy the poolside ambiance and a variety of tropical drinks.
Bedtime
Find amazing hotels in San Juan, Puerto Rico.
Visit Puerto Rico The Beast Zipline at Toro Verde Adventure Park in San Juan, Puerto Rico
star4.53

Puerto Rico The Beast Zipline at Toro Verde Adventure Park

Book Now
Visit Puerto Rico The Monster Zip Line Toro Verde Adventure Park in San Juan, Puerto Rico
star4.96

Puerto Rico The Monster Zip Line Toro Verde Adventure Park

Book Now

Day Trip to Ponce and Historical Sites

Morning
Take a morning drive to the city of Ponce and enjoy breakfast at A Pedir de Boca, known for its local specialties. Explore the city on a Ponce Guided City Walking Tour, visiting landmarks like Parque de Bombas and Museo de la Historia de Ponce.
Afternoon
Have a leisurely lunch at Las Palmas Bar and Rest., offering a mix of international and Caribbean dishes. Afterward, visit the Museo de Arte de Ponce, home to an impressive collection of European and Latin American art.
Evening
Return to San Juan and dine at The Beach House, enjoying a beachfront dinner with a romantic atmosphere.
Bedtime
Find amazing hotels in San Juan, Puerto Rico.
Visit Ponce Guided City Walking Tour in San Juan, Puerto Rico
star4.82

Ponce Guided City Walking Tour

Book Now
next arrow

Island Hopping to Sosua, Dominican Republic

Morning
Catch an early flight to the Dominican Republic and enjoy breakfast at Sereno Beach Bar & Grill in Sosua. Spend the morning relaxing at Sosua Beach (Playa Sosua), known for its clear waters and vibrant marine life.
Afternoon
Have a beachside lunch at Our House Rest & Bar, where you can taste local Dominican flavors. Afterward, explore the nearby Encuentro Beach (Playa Encuentro), a popular spot for surfing.
Evening
Return to Sosua and dine at Mahi Mahi Bar and Grill, savoring fresh seafood and a laid-back Caribbean atmosphere.
Bedtime
Find amazing hotels in San Juan, Puerto Rico.
Visit Sosua Beach (Playa Sosua) in San Juan, Puerto Rico
star4.65

Sosua Beach (Playa Sosua)

Book Now
Visit Encuentro Beach (Playa Encuentro) in San Juan, Puerto Rico
star5.00

Encuentro Beach (Playa Encuentro)

Book Now

Cultural Immersion and Evening Entertainment

Morning
Start your day with breakfast at Pira Rum, where you can enjoy a variety of rum-infused dishes. Then, visit the Casa Blanca, the former residence of the Ponce de Leon family, to learn about the island's history.
Afternoon
For lunch, head to Tasty Bar Lounge and indulge in their gourmet burgers and craft cocktails. Afterward, spend a relaxing afternoon at Condado Beach, soaking up the sun and the vibrant atmosphere.
Evening
Dine at Señor Frog's, a fun and lively restaurant with a menu of Mexican and international dishes. After dinner, enjoy a comedy show or live music at the El San Juan Live Music and Entertainment Pass.
Bedtime
Find amazing hotels in San Juan, Puerto Rico.

Nature and Wildlife Exploration

Morning
Have breakfast at El Bohio Sport & Pool Bar and then head to the El Yunque Rainforest Half-Day Trip. Explore the lush rainforest, hike to waterfalls, and learn about the unique flora and fauna of Puerto Rico.
Afternoon
After the rainforest, enjoy a traditional Puerto Rican lunch at Barrachina, the birthplace of the piña colada. Then, visit the Bioluminescent Bay (Mosquito Bay) on the island of Vieques for a magical evening kayak tour through the glowing waters.
Evening
Return to San Juan and have a relaxed dinner at Lupi's Mexican Grill And Sports Cantina, where you can enjoy a variety of Mexican dishes and watch the game.
Bedtime
Find amazing hotels in San Juan, Puerto Rico.
Visit Chios Sailing Boat Cruise to Oinouses with Meal & Drinks in San Juan, Puerto Rico
star5.00

El Yunque Rainforest Half-Day Trip

Book Now
next arrow

Historical Sites and Cultural Delights

Morning
Begin your day with a hearty breakfast at Broncos Cowboy Bar & Restaurant. Then, take a morning stroll through the Zona Colonial, the oldest permanent European settlement in the Americas, and visit historical sites like the Alcázar de Colón and the Catedral Primada de América.
Afternoon
For lunch, head to Don Tito Restaurant & Music Hall and enjoy their live music along with a variety of Dominican dishes. Afterward, visit the National Pantheon (Pantheon Nacional) and the Museo de las Casas Reales to learn about the history and culture of the Dominican Republic.
Evening
Dine at El Varadero Bar y Restaurante, a popular spot for both locals and tourists, and enjoy the beachfront ambiance. End your evening with a visit to Golden Zone, where you can explore the vibrant nightlife of Santo Domingo.
Bedtime
Find amazing hotels in Santo Domingo, Dominican Republic.
Visit Mykonos Delos and Rhenia Islands Cruise with BBQ Meal in Santo Domingo, Dominican Republic
star4.80

National Pantheon (Pantheon Nacional)

Book Now
next arrow

Day Trip to Boca Chica and Relaxation

Morning
Enjoy breakfast at Platos, a restaurant known for its fusion cuisine. Then, take a morning trip to Boca Chica, a popular beach destination near Santo Domingo. Relax on the sandy shores, swim in the clear waters, and soak up the sun.
Afternoon
Have a beachside lunch at Metropol Restaurant - Isla Verde, offering a mix of international and Caribbean dishes. Afterward, indulge in some water sports or simply continue to unwind on the beach.
Evening
Return to Santo Domingo and dine at El Varadero Bar y Restaurante, where you can enjoy a delicious meal with a view of the ocean. Reflect on your Caribbean journey and enjoy the last evening of your trip.
Bedtime
Find amazing hotels in Santo Domingo, Dominican Republic.

Adjacent Cities

kayakFind the right stay during your trip.
Got a question about your trip?