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5 Days of Exploration in San Juan

5 Days of Exploration in San Juan Itinerary

Last updated: 2024 Jun 14

Discovering Old San Juan

Morning
Start your day with a hearty breakfast at Café Manolín Old San Juan, a local favorite known for its traditional Puerto Rican fare. Afterward, head to Old San Juan and immerse yourself in the rich history and vibrant culture of this historic district. Stroll through the cobblestone streets and admire the colorful colonial buildings.
Afternoon
For lunch, enjoy a meal at El Jibarito, where you can savor authentic Puerto Rican dishes. Post-lunch, visit Castillo San Felipe del Morro, an iconic fortress offering stunning views of the Atlantic Ocean. Spend some time exploring its impressive ramparts and learning about its historical significance.
Evening
In the evening, dine at Marmalade Restaurant & Wine Bar, renowned for its innovative cuisine and extensive wine list. End your day with a leisurely walk along Paseo de la Princesa, a scenic promenade that offers beautiful views of San Juan Bay.
Bedtime
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Visit Old San Juan in San Juan, Puerto Rico
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Old San Juan

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Visit Castillo San Felipe del Morro in San Juan, Puerto Rico
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Castillo San Felipe del Morro

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Cultural Immersion in San Juan

Morning
Begin your day with breakfast at La Bombonera, a historic café famous for its mallorcas (sweet bread rolls). Then, visit San Juan Cathedral (Catedral de San Juan Bautista), one of the oldest cathedrals in the Americas. Take your time to appreciate its stunning architecture and serene atmosphere.
Afternoon
Have lunch at Jose Enrique, a highly-rated restaurant known for its contemporary take on traditional Puerto Rican cuisine. Afterward, explore Museum of Art of Puerto Rico (Museo de Arte de Puerto Rico), where you can admire an extensive collection of Puerto Rican art spanning several centuries.
Evening
For dinner, head to Santaella, which offers a delightful fusion of local flavors and modern culinary techniques. Conclude your evening with drinks at La Factoría, one of the world's best bars, known for its creative cocktails and vibrant ambiance.
Bedtime
Find amazing hotels in San Juan, Puerto Rico.
Visit San Juan Cathedral (Catedral de San Juan Bautista) in San Juan, Puerto Rico
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San Juan Cathedral (Catedral de San Juan Bautista)

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Visit Museum of Art of Puerto Rico (Museo de Arte de Puerto Rico) in San Juan, Puerto Rico
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Museum of Art of Puerto Rico (Museo de Arte de Puerto Rico)

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Nature and Adventure in San Juan

Morning
Kick off your day with breakfast at La Cueva del Mar, where you can enjoy fresh seafood dishes to start your morning right. Then embark on an exciting adventure with the From San Juan El Yunque Waterfall Hiking and Cliff Jumping. Experience the natural beauty of El Yunque National Rainforest as you hike through lush trails and take refreshing dips in waterfalls.
Afternoon
After returning from your hike, have lunch at Casita Miramar, known for its charming ambiance and delicious local cuisine. In the afternoon, relax by visiting Condado Lagoon (Laguna del Condado). You can rent paddleboards or simply enjoy the serene surroundings.
Evening
Dine at Oceano for dinner while enjoying breathtaking ocean views. Later, unwind with a romantic night experience kayaking under the stars with the unique glow from bioluminescent organisms during the San Jose Romantic Night Experience for 2 with Lights Kayak.
Bedtime
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Visit From San Juan El Yunque Waterfall Hiking and Cliff Jumping in San Juan, Puerto Rico
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From San Juan El Yunque Waterfall Hiking and Cliff Jumping

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Visit Condado Lagoon (Laguna del Condado) in San Juan, Puerto Rico
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Condado Lagoon (Laguna del Condado)

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Artistic Exploration & Local Flavors

Morning
Start your morning with breakfast at Pirilo Pizza Rustica which offers delicious pizzas even early in the day! Then head over to explore artistic endeavors by joining an engaging workshop:  Make Authentic Espadrilles in San Juan. Create your own pair of traditional espadrilles as a unique souvenir from this trip.
Afternoon
Enjoy lunch at Punto de Vista Rooftop Restaurant with panoramic views over Old San Juan before heading towards Museum of History Anthropology & Art (Museo de Historia Antropología y Arte) for an enriching cultural experience exploring various exhibits highlighting regional history anthropology & art collections spanning different eras.
Evening
Wrap up Day 4 dining al fresco style amidst lush tropical gardens while savoring delectable dishes served up by none other than acclaimed chef Wilo Benet himself inside his restaurant -{ R-Cocina Abierta}. Cap off another fantastic day sipping cocktails crafted meticulously just steps away inside trendy hotspot-{ R-La Factoría } once again given it’s vast selection ensuring no two drinks are ever alike!
Bedtime
Find amazing hotels in San Juan, Puerto Rico.
Visit Make Authentic Espadrilles in San Juan in San Juan, Puerto Rico
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Make Authentic Espadrilles in San Juan

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Visit Museum of History, Anthropology and Art (Museo de Historia, Antropología y Arte) in San Juan, Puerto Rico

Museum of History Anthropology & Art (Museo de Historia Antropología y Arte)

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Historic and Scenic Finale

Morning
Begin your final day with breakfast at La Bombonera, enjoying their famous mallorcas. Afterward, visit Castillo San Cristobal, another impressive fortress that offers panoramic views of the city and the ocean. Take your time exploring its extensive grounds and learning about its historical significance.
Afternoon
For lunch, head to 1919 Restaurant, known for its elegant setting and gourmet cuisine. Post-lunch, take a leisurely stroll through Pine Grove Beach, where you can relax on the sandy shores or take a dip in the clear waters.
Evening
Conclude your trip with dinner at Jose Enrique, savoring contemporary Puerto Rican dishes. After dinner, enjoy a sunset walk along San Juan Bay, taking in the beautiful views as you reflect on your memorable trip.
Bedtime
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Visit Castillo San Cristobal in San Juan, Puerto Rico
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Castillo San Cristobal

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Pine Grove Beach

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