After arrival, ease into San Juan with a leisurely breakfast at Café Cuatro Sombras sampling strong Puerto Rican coffee and mallorca pastries, then wander the colorful streets to admire the blue tiles of Paseo de la Princesa and browse artisan stalls at the nearby Raíces Fountain. Pause for a mid-morning tasting of local rum at Casa Bacardí's urban shop or grab hand-pressed juices at La Bombonera before continuing your stroll toward the fort for the afternoon's sunset plans.
Head deeper into Old San Juan for a relaxed lunch and people-watching on the shaded plaza at Plaza Colón, then sample fresh ceviche and ropa vieja at the nearby seafood-focused La Mallorquina or the vibrant José Enrique (counter dining, local flavors). Afterward, wander up to the leafy courtyard of Casa Blanca to explore its historic gardens and panoramic harbor views before making your way toward Castillo San Felipe del Morro in time for its famous sunset breezes and kite-flying local scene.
As twilight deepens, wander to La Placita de Santurce for a lively evening scene where you can sip a handcrafted piña colada at El Batey and sample small plates like tostones and alcapurrias from nearby stalls. Later, enjoy live salsa or acoustic sets at the intimate Nuyorican Café-perfect for soaking in local music before a relaxed nightcap at the rooftop bar O:live with sweeping views of the city lights.
Start your day with a beachfront breakfast at Café del Sol overlooking the gentle waves, then stroll the palm-lined boardwalk toward Playa Condado for sunbathing and a quick surf lesson with instructors from Kite & Surf Puerto Rico. Mid-morning, swap boards for a guided stand-up paddle tour through the calm lagoon at Laguna del Condado to spot mangrove birds and enjoy sheltered water views before a fresh seafood brunch at the casual, oceanfront Oceano Beach Club.
After a morning on Condado's sand, head east to Isla Verde Beach for an afternoon of higher-energy water sports-book a guided jet-ski tour with Caribbean Watersports PR or ride a banana boat for laughs and coastal views. Pause mid-afternoon for a chilled cocktail and small plates at the beachfront Piu Bello Rooftop Bar before a sunset paddleboarding session in the sheltered stretch near Piñones boardwalk, where mangrove-lined waterways add a quieter, nature-focused contrast to your day.
Wind down after a high-energy day with sunset cocktails and small plates at Oceana Rooftop Bar, where floor-to-ceiling windows frame the harbor and live acoustic sets often accompany the view. Later, take a short taxi to La Factoría de Isla Verde for inventive craft cocktails and a vibrant bar-hop scene-try their signature twists on classic rum drinks and linger for salsa beats or a DJ set to close the night.
Rise early and drive east to El Yunque for a refreshing half-day hike-start at La Mina Trailhead for a verdant walk past towering ceiba trees, then cool off with a swim beneath the cascades at La Mina Falls. After the hike, detour to the scenic overlook at La Coca Falls for panoramic rainforest views and stop by El Yunque Visitor Center to grab bottled coffee and local fruit before returning to San Juan to pack and check out with energy for your afternoon departure.
Return to San Juan mid-afternoon and unwind with a leisurely lunch at La Estación in Fajardo for grilled Caribbean flavors and fresh ceviche before heading into a relaxed harbor-side experience. After lunch, stroll the scenic Old Harbor Paseo or book a short bioluminescent-kayak preview with Kayaking Puerto Rico to learn safety basics and packing tips, then return to your accommodations to finish packing and enjoy a final cocktail at Nivel Rooftop with harbor views before your evening departure.
After returning to San Juan and finishing packing, savor a relaxed dinner at Santaella where elevated Puerto Rican plates and a lush patio set the tone for a final evening. Follow dinner with a gentle paseo along the waterfront at La Puntilla, pausing for a rum-forward digestif at Barrachina to toast the trip before a calm return to your hotel to collect luggage and head to the airport.