Curator’s statement
Old San Juan dazzles with its vibrant hues and pastel facades, radiating an irresistible charm. The cobblestone streets, worn smooth by centuries of footsteps, come alive under the soft glow of historic lampposts, casting a warm shimmer that dances with the city’s lively music. The blend of colorful architecture, joyful street scenes and the nearby sparkling beaches create an enchanting atmosphere. Here, history is not just preserved but celebrated, offering an experience rich in both beauty and culture.
The Fora Difference
Book with Samantha to access exclusive perks and experiences on your trip.
Killer perks
Free upgrades, spa credits and more—we got you
Personalized recs
Customized travel planning for your style
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay
Unlock perks by contacting Samantha to book your trip.
Day 1: Arrival and exploration
Accommodation: Stay at El Convento Hotel, a beautifully restored 17th-century convent located on Plaza Colon, offering a central and historic base for your stay.
Start your day with a visit to Cafe Caleta, just footsteps from El Convento right across the Plaza. They serve exceptional espresso sourced from Filtrado farm in Puerto Rico — perfect for coffee enthusiasts. Afterwards, embark on a guided walking tour of Old San Juan's cobblestone streets. Learn about the city's history, architecture and culture from a knowledgeable local guide, ideal for uncovering hidden gems and orienting yourself in this vibrant city.
Take a break during the hot afternoon for a siesta to recharge. As evening approaches, experience Old San Juan's charm with an evening walk as the cobblestone streets come alive under the glow of old street lamps.
Dinner: Enjoy dinner at the food trucks on the promenade.
Day 2: Beach and local flavors
Start your day with another visit to Cafe Caleta for your morning ritual. Enjoy the city before it wakes up while taking in the beautiful Plaza Colon.
Head to Balneario El Escambron with a short Uber ride, about 20 minutes from Old San Juan. Relax on this tranquil beach, known for its clear, calm waters perfect for swimming alongside sea turtles. No snorkeling gear is necessary — just bring a good pair of goggles to enjoy observing these gentle creatures. However, snorkeling guides are available if you wish to explore in a group.
Lunch: Return to Old San Juan for a leisurely lunch at Spiga, a charming spot renowned for its fresh pastries and notable lunch menu.
Afternoon: Shopping: Explore Hand Made The Brand, a boutique in Old San Juan known for its artisanal Spanish sandals hand-painted by talented local artists. Have a pair customized to capture your personal style and receive a unique souvenir.
Evening: End your day with dinner in your hotel.
Day 3: Historic exploration and farewell
Morning: On your final day, stroll at your leisure through its historic streets, revisiting favorite spots and soaking in the UNESCO World Heritage site's unique atmosphere.
Afternoon: Delve deeper into Old San Juan's history with visits to iconic sites such as Castillo San Felipe del Morro or Casa Blanca. Appreciate the colonial architecture and breathtaking coastal views these landmarks offer, providing a fitting finale to your journey.
Farewell dinner: Conclude your adventure with a farewell dinner at El Vino Crudo, located just a 20-minute Uber ride away. El Vino Crudo is renowned for its intimate ambiance and innovative cuisine. Their menu celebrates local flavors with a contemporary twist, featuring dishes crafted from the freshest Puerto Rican ingredients. Whether you're savoring their signature ceviche or indulging in their perfectly grilled seafood, every bite at El Vino Crudo is a culinary delight.
Finish off your evening with one of their delectable desserts, all prepared in-house to ensure a sweet ending to your unforgettable journey through Old San Juan.
Travel Advisor
Samantha Platner
Get in touch with Samantha
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can normally expect a response from Samantha within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).
For more inspiration and insider recommendations, visit our San Juan page.