Looking for a Valentine’s escape that skips cliché chocolates for something more memorable?
San Juan brings romance with a twist — think cobblestone streets, historic charm, and just enough beachfront cocktails to make you wonder if you should stay permanently.
In just 72 hours, you can fall in love with San Juan, Puerto Rico’s capital—and each other all over again!
Day 1: Arrival Night – February 13, 2025
Touch down at Luis Muñoz Marín International Airport (SJU) and check into your Marco Polo Collection property in San Juan neighborhoods of Condado, Ocean Park, or Isla Verde. After settling in, start with a sunset stroll along Condado Beach and adjacent La Ventana al Mar (1054 Ashford Ave). The ocean breeze alone will make you forget about work emails. Then, head to Cocina Abierta (58 Caribe St) for dinner that’s as creative as your Valentine’s plans.
End the evening at La Factoría (148 San Sebastián St), where each room offers a different vibe — from salsa dancing to secret speakeasies. It’s a choose-your-own-adventure, and every choice is worth it.
DAy 2: February 14, 2025 – Valentine’s Day in San Juan
Morning
Start your Valentine’s Day with breakfast at Caficultura (401 San Francisco St), an elegant café known for its beautifully plated dishes and artisanal coffee — a perfect way to kick off a romantic morning before taking a romantic stroll through Old San Juan. Explore colorful streets, historic forts, and hidden plazas. Pause at Parque de las Palomas (Calle Tetuan) for bay views, then cool off with gelato at Anita La Mamma del Gelato (150 Cristo St).
Afternoon
Indulge in a rejuvenating couples’ session at Cloud Spa (103 Ave. de Diego), where blissful treatments will leave you feeling refreshed and relaxed. Post-spa, enjoy a late lunch at El Comedor (609 Ave. Miramar). Known for its refined Puerto Rican cuisine, it’s a spot where lingering feels mandatory. After all, why rush?
Evening
For dinner, book a table at Santaella (219 Canals St), where Chef José Santaella blends Puerto Rican tradition with modern flair. The lush setting and expertly crafted dishes make romance feel effortless. If you’re up for an after-dinner drink, head to JungleBird (254 Canals St), a trendy bar in Santurce known for its creative cocktails and vibrant tiki-inspired atmosphere.
Day 3: February 15, 2025 – Relax & Explore
Morning
Kick off the morning with a coffee at über-hip Café Regina (58 McLeary St), where the lattes are as smooth as the Ocean Park breeze. Afterward, hit Ocean Park Beach for a refreshing swim or take a kite surfing lesson — because why not make a splash?
Afternoon
For lunch, choose between La Casita Blanca (351 Tapia St) or Casita Miramar (605 Ave. Miramar). Both offer a traditional Puerto Rican dining experience with home-style dishes served in charming, rustic settings. Expect generous portions of island favorites like mofongo, asopao, and pastelón, all made with fresh, local ingredients. After lunch, take a leisurely stroll through Santurce’s street art district, where vibrant murals narrate the island’s culture. If you’re in the mood for more art, visit Museo de Arte Contemporáneo (229 Ponce de León Ave) for thought-provoking modern pieces, or head to Museo de Arte de Puerto Rico (299 Ave. de Diego) to admire a mix of classical and contemporary works in a stunning building.
Evening
Cap off the day with dinner at Cocina al Fondo (658 Calle San Juan), where James Beard Award-winning Chef Natalia Vallejo brings Puerto Rican flavors to life with a modern twist. It’s the perfect spot to savor your last night in San Juan. For those wanting a lively end to their trip, head to La Placita de Santurce (Plaza del Mercado) for live music and dancing.
Day 4: February 16 – Departure Morning
With most flights departing early, grab a quick but memorable breakfast at Kasalta Bakery (58 McLeary St) or España Bakery (1206 Marginal Villamar). One last café con leche to go, and you’re off — until next time!
Ready to Book Your Winter Getaway?
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Discover Old San Juan this Valentine’s Day.
Image courtesy of Discover Puerto Rico