After arriving and dropping bags at your accommodation, start with a leisurely breakfast at Cafetería Mallorca sampling warm mallorcas and café con leche before wandering the colorful streets. Then take a gentle, accessible stroll along the city walls to Plaza de Armas and down to Paseo de la Princesa, where you can enjoy street musicians, local artisans, and views over the harbor-perfect for easing into the day without rushing or needing a car.
Head to Castillo San Cristóbal for a relaxed, wheelchair-friendly wander through vaulted tunnels and wide ramped battlements, where panoramic views of the ocean set a dramatic tone without strenuous walking. After the fort, enjoy a casual late lunch and people-watching on the shaded terrace at Café El Punto, then stroll over to the historic Casa Blanca garden to soak up fragrant tropical plants and quiet courtyards as the afternoon light softens into early evening.
After check-in, wander a short distance to La Factoria in Old San Juan for inventive tapas-style plates and crafted cocktails in a relaxed courtyard setting where you can sit and reconnect after travel. If you prefer a quieter seaside vibe, head to The Condado Vanderbilt Hotel's Sea Glass Restaurant for poolside or ocean-view dining and an easy-paced menu; follow dinner with a gentle, well-lit promenade along Ashford Avenue to enjoy the night breeze without any swimming required.
Begin with a rooftop breakfast at Café Puerto Rico sampling traditional huevos rancheros and fresh tropical juice, then stroll toward San Juan Gate to admire the old city entrance and watch ferries glide into the bay. From there, join a guided, small-group tour of Casa del Obispo to learn about colonial life and art, finishing at Plaza San José where you can enjoy morning coffee and watch artisans set up their stalls-an unhurried continuation from yesterday's gentle exploration that keeps the pace relaxed for non-swimmers and the group without a car.
Wander uphill to San Juan Cathedral to admire centuries-old stone floors and the peaceful cloister (easy pace, benches for rests), then cross toward Casa Blanca Museum & Gardens for a complementary look at colonial domestic life amid shaded paths and fragrant blooms. After soaking in history, take a short taxi or bus ride to La Placita de Santurce for a lively late-afternoon food crawl-sample bite-sized frituras at Lote 23 or cozy up at Santaella for refined local flavors, while the non-swimmers in your group can enjoy shaded outdoor seating and live-music previews as evening approaches.
As the sun dips, take a short taxi to the lively neighborhood of La Perla for a guided, community-led street art walk that highlights colorful murals and local stories (choose a small, reputable group for safety and context). Follow with dinner at La Estación in nearby Santurce for hearty Puerto Rican barbecue and inventive cocktails, then finish the night with live bolero or salsa at Nuyorican Café, where seated areas and mellow music make it easy for non-swimmers to join the fun without long walks.
Start your day with a relaxed seaside breakfast at Caficultura Condado, enjoying fresh fruit plates and strong Puerto Rican coffee while watching the calm morning surf. Afterward, stroll over to Parque del Indio for shaded benches and shoreline views, then book a gentle glass-bottom boat tour from Escambrón Marina (short transfer by taxi) so non-swimmers can admire coral and tropical fish without getting wet, or opt for a wheelchair-accessible beachfront promenade along Ashford Avenue to soak up ocean breeze and pastel villas.
After a gentle morning, take a short taxi to Parque del Tercer Milenio for shady lawns and beachfront views where the group can relax on benches or have a picnic while watching paddleboarders; the two non-swimmers can stay comfortable on shore with life-jacket-friendly float rings available nearby from Condado Surf Shop. Later, hop a quick ride to Playa Ocean Park to rent a covered cabana and enjoy seated beachfront service and fresh ceviche at La Placita del Mar-perfect for cooling off, people-watching, and sampling local bites without venturing into deep water.
As the sun softens, take a short taxi to Piñones Boardwalk for a breezy seaside stroll among palms and kiosks selling alcapurrias and empanadillas-grab a couple of snacks to share while you explore the public art and mangrove-lined paths. Afterward, settle into a relaxed dinner with ocean views at Pina Colada Restaurant & Bar, where non-swimmers can enjoy shaded patio seating, mocktails, and live guitar while watching the night-lit coastline before returning to Condado or Isla Verde for a quiet evening.
Catch a private shuttle or taxi from San Juan to El Yunque Visitor Center for an accessible introduction to the forest with interpretive exhibits and shaded rest areas, then join a short, guided boardwalk walk along the wheelchair-friendly El Yunque Trail to hear coquí calls and feel the mist without steep climbs. After the walk, relax at the picnic tables near La Coca Falls overlook, where the group can enjoy packed tropical snacks and photos while a guide points out native plants and safe, shallow streams ideal for those who prefer to stay onshore.
After a relaxed morning at the visitor center, take a short, guided shuttle to Baño Grande, where the group can enjoy shaded picnic tables and shallow, roped-off pools ideal for non-swimmers to cool their feet while others wade cautiously. Next, join an easy interpretive walk along the accessible portion of the Big Tree Trail (choose the shorter loop) to spot giant ferns and endemic orchids with frequent bench stops, then pause at the scenic Yokahu Tower overlook for panoramic forest views and group photos before a gentle return to the shuttle for a calm drive back toward San Juan.
As twilight settles over the canopy, enjoy a relaxed, accessible dinner at La Estación de Montaña, a nearby family-run spot where you can savor roasted plantain bowls and grilled fish on a covered patio while listening to nighttime forest sounds. After dinner, join a short, guided night-walk from El Verde Visitor Trailhead (small-group, flashlight-friendly) to hear coquí frogs and spot nocturnal insects from the boardwalk-an easy-paced, memorable close to the day before a calm shuttle ride back to San Juan.
Ease into your final morning with a leisurely breakfast at Panadería España, sampling freshly baked pan sobao and strong Puerto Rican coffee while watching locals start their day. Afterward, stroll through the nearby Mercado de Santurce to browse colorful produce, artisanal cheeses, and handmade souvenirs-perfect for last-minute gifts-then settle on a shaded bench at Parque de las Palomas to enjoy your purchases and soak up one last neighborhood atmosphere before checking out.
Head to Barrio Tablado for a relaxed late-morning-to-afternoon stroll along the waterfront promenade, where you can sit at shaded benches, watch local fishermen, and pick up last-minute artisan jewelry from pop-up stalls. Then take a short taxi to Plaza del Mercado de Río Piedras to sample small bites-try a mofongo sampler or fresh coconut agua-and browse handcrafted pottery before returning to your lodging for an easy check-out and a calm transfer to the airport.
For a low-key final evening, enjoy a sunset drink on the covered terrace at La Terraza de San Juan, where the group can sip tropical mocktails and small plates while watching harbor lights come alive; it's an easy, seated way to savor the last ocean views without long walks. Afterward, take a short taxi to El Local de Arte for a relaxed browse of contemporary Puerto Rican art and crafts-staff can recommend compact pieces for carry-on-then end the night with a cozy farewell dessert at Dulcería Colonial, sampling house-made flan or cocadas before returning to your lodging for an easy airport transfer.