Start your day wandering the blue cobblestone streets of Old San Juan with a café con leche at Café Cuidad before heading to the commanding terraces of Castillo San Cristóbal for sweeping harbor views and a primer on Spanish colonial defenses. Afterward, stroll to La Fortaleza's grounds and then explore the colorful art galleries and artisan shops along Calle del Cristo, stopping for a light snack of frituras at a nearby food stall to fuel the rest of your exploration.
After lunch, continue your discovery by wandering down to the waterfront and boarding the small ferry across to Paseo de la Princesa, where you can stroll the shaded promenade, admire the stone restored arches, and browse local craft stalls. Finish the afternoon with a visit to the nearby Museo de las Américas to see exhibits on Caribbean and Latin American art and history, then sip a cold piña colada on the terrace of Raíces Bar & Restaurant while watching the sunset over the bay.
As night falls, wander to the lively plazas near Plaza Colón and settle in for dinner at La Mallorquina Bistro, savoring fresh seafood and mofongo while live bolero fills the air. Afterward, take a moonlit stroll along the city walls toward La Perla viewpoint for dramatic coastal photos, then finish with craft cocktails at the rooftop bar of El Pretexto while soaking in the warm harbor breeze and the glow of Old San Juan's pastel facades.
Rise early and drive from Old San Juan to the foothills of El Yunque National Forest, beginning with a guided walk on the misty La Coca Trail to see the cascading waterfall and learn about native flora from a local naturalist. After the hike, continue to the nearby El Portal Visitor Center for an interpretive exhibit and then reward yourself with a fresh coconut and pincho at the roadside stands in Luquillo Kiosks before settling under the palm trees at Luquillo Beach to soak up sun and swim in calm, warm waters.
After a restful swim at the beach, head back up into the mountains for a canopy experience on the Sierra Palm Trail and the adjacent Big Tree Trail, where a short, shaded walk brings you to towering kapok and palm groves while you watch for endemic birds like the Puerto Rican tody. Follow the hike with a late-afternoon stop at La Mina Falls overlook (accessible via a brief spur) and then descend toward Kiosko El Boricua in Luquillo for coconut shrimp and a cold piña colada as the sky softens into sunset.
As night falls, return toward the coast and enjoy fresh-caught seafood at La Estación in Fajardo, then take a short drive to Balneario La Monserrate for a peaceful sunset stroll along the shoreline. Cap the night with a guided bioluminescent kayak tour from Laguna Grande-paddling through glowing waters is a magical, eco-friendly way to end a day in the rainforest and on the beach.
Start your final morning with a sunrise stroll along Ashford Avenue before grabbing a coconut pastry and strong café at Café Lareño, then rent a board for a gentle surf lesson with instructors from Paddle & Surf PR in Isla Verde Beach. After working up an appetite, refuel with a relaxed brunch of fresh ceviche and tropical fruit at Playa Papaya while enjoying ocean views, then wander the nearby boutiques of La Terraza Shops for last-minute souvenirs before checking out.
After brunch, drift into a leisurely afternoon exploring the seaside greenway: rent a cruiser and pedal the waterfront path from Condado Lagoon toward the palm-lined promenade at La Concha Resort, stopping for an iced coffee at Café Don Ruiz and people-watching on the oceanfront benches. Continue with a calm paddle in a clear kayak around the protected mangrove channels of Laguna del Condado, then freshen up for an early sunset aperitivo at Oceano Rooftop before collecting your bags and heading to the airport.
Wind down your final evening with a sunset stroll and souvenirs from the artisan stalls at Plaza Antonia Quiñones, then savor a relaxed seafood dinner at the waterfront Santaella Patio where island flavors meet elegant presentation. After dinner, enjoy a final drink toasting the trip at the low-lit tiki bar La Placita Rooftop, then take a calm moonlit walk along Balneario de Carolina to let the Atlantic breeze carry you toward tomorrow's departure.
| Place / Activity | Cost |
|---|---|
| Café Cuidad (café con leche) | $4 |
| Castillo San Cristóbal (entry) | $5 |
| La Fortaleza (grounds visit) | Free |
| Calle del Cristo (galleries & shops) | Free |
| Frituras (street snack) | $6 |
| Ferry to Paseo de la Princesa (small local ferry) | $1 |
| Paseo de la Princesa (promenade & craft stalls) | Free |
| Museo de las Américas (entry) | $6 |
| Raíces Bar & Restaurant (drink) | $10 |
| La Mallorquina Bistro (dinner per person) | $25 |
| La Perla viewpoint (moonlit stroll/photos) | Free |
| El Pretexto (craft cocktails) | $14 |
| Drive to El Yunque (transport cost per person, rental split or shuttle) | $12 |
| Guided La Coca Trail walk (local guide / small-group) | $35 |
| El Portal Visitor Center (entry/exhibits) | Free |
| Luquillo Kiosks (coconut & pincho snack) | $8 |
| Luquillo Beach (access) | Free |
| Sierra Palm Trail / Big Tree Trail (hiking) | Free |
| La Mina Falls overlook (short spur) | Free |
| Kiosko El Boricua (coconut shrimp & drink) | $18 |
| La Estación (dinner per person) | $30 |
| Balneario La Monserrate (sunset stroll) | Free |
| Bioluminescent kayak tour (Laguna Grande) | $60 |
| Café Lareño (coconut pastry & café) | $6 |
| Paddle & Surf PR (surf lesson per person) | $60 |
| Playa Papaya (brunch per person) | $20 |
| La Terraza Shops (souvenirs) | $20 |
| Cruiser rental (hourly) along Condado Lagoon (per person, 2-3 hr split) | $10 |
| Café Don Ruiz (iced coffee) | $4 |
| Clear kayak rental Laguna del Condado (per person) | $25 |
| Oceano Rooftop (aperitivo/drink) | $14 |
| Plaza Antonia Quiñones (artisan stalls) | Free |
| Santaella Patio (dinner per person) | $40 |
| La Placita Rooftop (final drink) | $12 |
| Balneario de Carolina (moonlit walk) | Free |
| Estimated Total (per person) | $624 |