Old San Juan in 48 Hours

Make the most of a weekend in Puerto Rico's historic heart with this walkable itinerary that hits the essential sights, local coffee spots, and sunset views.

Day 1: Forts and Foundations

Morning (9 AM - 12 PM) Start at Castillo San Felipe del Morro before the heat sets in. Book your timed entry in advance and explore the tunnels, ramparts, and commanding views of the Atlantic. The fort's history spans 500 years of Spanish colonial defense.

Insider tip: Enter through the main gate for the full ceremonial approach, but if you're short on time, the side entrance near the lighthouse gets you to the best views faster.

Lunch (12 PM - 1 PM) Walk to Cuatro Sombras for locally roasted coffee and a light lunch. Their cortado and avocado toast fuel the afternoon perfectly. The roastery overlooks the bay with outdoor seating.

Afternoon (1 PM - 5 PM) Explore the cobblestone streets between Fortaleza and San José Church. Duck into Casa Blanca for a quieter historical experience and gardens with city views.

Browse local artisan shops along Calle del Cristo—look for handmade jewelry at Boveda and locally-made soaps at Spice Islands.

Evening (5 PM - sunset) End at Paseo del Morro for golden hour photos and sunset over the Atlantic. The grassy field fills with families flying kites as the light fades.

Day 2: Culture and Coast

Morning (8 AM - 11 AM) Beat the crowds at Castillo San Cristóbal, the larger fortress that protected against land attacks. The underground tunnels and multiple levels offer cooler exploration on hot days.

Late Morning (11 AM - 1 PM) Walk the city walls from San Cristóbal toward the Governor's mansion. Stop at La Fortaleza for exterior photos (tours require advance booking).

Browse the Paseo de la Princesa promenade and its weekend artisan market (Saturdays and Sundays).

Lunch (1 PM - 2 PM) Try Café Mallorca for traditional mallorca sweet bread and café con leche—a local breakfast that works perfectly for lunch.

Afternoon (2 PM - 6 PM) Cool off at Museo de Arte de Puerto Rico or explore the Instituto de Cultura galleries. If it's too hot for more walking, this is your air-conditioned cultural time.

Alternatively, take a short Uber to Condado Beach for swimming and people-watching (15-minute ride from Old San Juan).

Evening (6 PM - late) Return for dinner at Marmalade (upscale) or El Jibarito (local favorite). Both require reservations on weekends.

End with drinks at La Placita in nearby Santurce or rooftop bars back in Old San Juan like Nuyorican Café for live music.

Getting Around

• Walking: Everything in Old San Juan is walkable, but bring comfortable shoes for cobblestones
• Parking: Street parking is limited; use the Covadonga parking garage near the cruise ship terminal
• Uber/Taxi: Easy connections to beaches, airports, and other neighborhoods
• Free Trolley: The Trolley Turístico connects major sites, though walking is often faster

Where to Stay

• Hotel El Convento: Historic luxury in a former convent
• Serafina Beach Hotel: Boutique option near Condado Beach
• Sheraton Old San Juan: Modern amenities with bay views
• Casablanca Hotel: Mid-range option with colonial charm

Weather Tips

• Best months: December-April (dry season, 75-85°F)
• Hurricane season: June-November (bring rain gear)
• Daily pattern: Mornings are cooler; afternoons can be hot and humid
• What to pack: Sunscreen, hat, comfortable walking shoes, light layers for air conditioning