San Juan is the Caribbean at full volume: pastel Spanish fortresses guarding sapphire seas, rum cocktails under rustling palms, and music that spills into the streets. Founded in 1521, it’s the second-oldest European-founded city in the Americas, and its walled Old San Juan remains a UNESCO-listed jewel of cobbles, plazas, and centuries-old forts.

Beyond the history, you’ll find urban beaches for paddleboarding, a reef-filled marine park for easy snorkeling, and street art corridors that rival open-air museums. An hour east, El Yunque—the only tropical rainforest in the U.S. National Forest System—offers fern-framed trails and waterfalls. After dark, kayaks thread glowing channels on the bioluminescent bay at Fajardo, where every paddle stroke sparks blue-green light.

Practical notes: U.S. citizens don’t need a passport to visit Puerto Rico; the dollar is the currency and English is widely understood. Expect mid-80s °F (high 20s °C) most of the year; hurricane season runs June–November. Pack reef-safe sunscreen, a light rain jacket for the rainforest, and comfortable shoes for cobblestones.

San Juan

San Juan rewards curiosity. Spend a morning tracing bastions and cannon-lined walls at Castillo San Felipe del Morro and Castillo San Cristóbal, then drift down Paseo de la Princesa to the harbor. In the afternoon, switch gears in Santurce, a creative district where murals stretch down Calle Cerra and Lote 23 dishes out chef-driven street food.

For couples, the city balances downtime and adrenaline: paddleboard the glassy Condado Lagoon, snorkel the shallow reef at Escambrón Marine Park, then slip into salsa at La Placita de Santurce. Dinner ranges from refined tasting menus in Old San Juan to mofongo joints that taste like home cooking.

• Top sights: El Morro, San Cristóbal, Paseo de la Princesa, Museo de las Américas, La Perla viewpoint, Distrito T-Mobile (nightlife and zip-line), Condado and Ocean Park beaches.
• Active fun: Snorkeling at Escambrón, SUP on Condado Lagoon, surf lessons at Aviones/Isla Verde (if swell), El Yunque hiking, Fajardo bio bay kayaking.
• Essential eats: Marmalade (inventive tasting menus), Santaella (garden setting, contemporary Puerto Rican), José Enrique (beloved chef’s spot), Deaverdura (comfort Puerto Rican), El Jibarito (classic Criollo).
• Cocktails & nightlife: La Factoría (World’s 50 Best Bars alum), La Placita (Salsa till late), La Casita de Rones (rum terrace), La Vergüenza (Old San Juan rooftop with bay views).
• Fun fact: Two places claim the Piña Colada’s invention: Barrachina in Old San Juan and the Caribe Hilton—try both versions and decide your favorite.

Where to stay (neighborhoods): Old San Juan for history and walkability; Condado for beachfront, dining, and easy nightlife; Ocean Park for a quieter, local beach feel; Isla Verde for wide beaches and resort amenities near the airport.

Search stays: Browse apartments and beach condos on VRBO San Juan or compare hotels and resorts on Hotels.com San Juan. For couples, look for balconies or rooftop terraces; in Old San Juan, historic casonas often hide leafy courtyards perfect for a nightcap.

Getting there: Fly into SJU (Luis Muñoz Marín International). From the U.S. East Coast, flights are ~3.5–4.5 hours; typical roundtrips range $180–$450 depending on season. Compare fares on Trip.com Flights or Kiwi.com. Taxis/Uber to Condado are ~15 minutes ($15–$25), to Old San Juan ~20 minutes ($20–$30).

Day 1: Arrival, Old San Juan’s Golden Hour, and Cocktails

Morning: Travel day.

Afternoon: Check in and shake off the flight with a leisurely wander through Old San Juan. Start at Paseo de la Princesa, then curve along the seaside promenade to the massive lawn of El Morro—locals fly kites here at sunset with Atlantic views. Duck into Café Don Ruiz (inside the historic Cuartel de Ballajá) for single-origin Puerto Rican coffee and a cortadito pick-me-up.

Evening: Dinner at Marmalade—opt for the tasting menu with the famed “white bean soup” and creative Caribbean-inspired courses, paired with a deep wine list. Post-dinner, order a Lavender Mule or Caribella at La Factoría, a speakeasy-style labyrinth ranked among the world’s best bars; step through hidden doorways to find salsa in one room and craft cocktails in another. Nightcap options: Barrachina’s classic piña colada in a leafy patio or La Vergüenza’s rooftop for breezy harbor views.

Day 2: Beaches, Santurce Street Art, and Salsa at La Placita

Morning: Breakfast near the sand: try Café Regina (Ocean Park) for avocado toast and iced coffee or Pinky’s in Condado for hearty egg wraps. Paddleboard the calm Condado Lagoon—manatees occasionally surface—and then snorkel at Escambrón Marine Park’s easy-entry reef where parrotfish and sergeant majors cruise among coral heads. Bring a rash guard and reef-safe sunscreen.

Afternoon: Refuel at Lote 23, a vibrant food park: snag crispy chicharrón de pollo from El Cocinero, fresh poke from El Jangueo, or an arepa reina pepiada from Arepa Republic; grab a passionfruit juice or a local Medalla. Walk Santurce’s Calle Cerra to admire large-scale murals that rotate with festivals—look for pieces by Bik Ismo and Alexis Díaz. Coffee break at Café Comunión for meticulous pour-overs and seasonal pastries.

Evening: Book dinner at Santaella, a lush, garden-lit spot near La Placita where tuna tartare meets yuca fries and cocktails spotlight local fruits. Or choose José Enrique for bold Puerto Rican flavors—think whole fried snapper, asopao, and hearty mofongo with a refined touch. After dinner, join a short beginner-friendly salsa lesson at Piso Viejo or simply dive into the scene around La Placita de Santurce where music spills into the square; bars like Tasca El Pescador and JungleBird keep things lively past midnight.

Day 3: El Yunque Rainforest Hike and Bioluminescent Bay Kayaking

Morning: Pick up a rental car or join a guided tour east to El Yunque (about 60–75 minutes from San Juan). If self-driving, secure a timed-entry pass for PR-191’s main corridor in advance; parking is limited. Hike a classic combo such as the La Mina and Big Tree trails (check day-of trail status), where waterfalls thread through bamboo and giant tree ferns; expect 2–3 hours with photo stops and a refreshing dip.

Afternoon: Head to the Kioskos de Luquillo for a casual beachfront lunch—La Parrilla serves fresh grilled lobster and mofongo, Terruño plates Puerto Rican staples, and La Ostra Cosa shucks oysters with ocean views. Relax on Luquillo Beach or, time permitting, stroll the Fajardo waterfront. If you prefer boats over hikes, swap the morning for a catamaran to Cayo Icacos for snorkeling in aquamarine water (typically ~$120–$160 per person, 4–5 hours).

Evening: Early dinner at La Estación in Fajardo, a beloved smokehouse-meets-seafood spot set in a converted gas station; order the smoky ribs with guava BBQ or the whole lionfish when available. Then join a guided nighttime kayak tour on Laguna Grande’s bioluminescent bay (common start times 6:30–8:30 pm; ~$65–$90 per person). Each paddle stroke ignites dinoflagellates like underwater stars—go on a moonless night for peak glow. Drive back to San Juan (~1 hour).

Day 4: Forts, Last Bites, and Departure

Morning: Brunch at Chocobar Cortés in Old San Juan—try the grilled cheese with chocolate or the plantain omelet, then a spicy Mayan hot chocolate. Explore Castillo San Cristóbal’s tunnels and ramparts, or visit Museo de las Américas in the Ballajá barracks for Taino artifacts, Caribbean art, and rotating exhibits.

Afternoon: Squeeze in souvenir shopping along Calle Fortaleza and Calle del Cristo—look for hand-carved santos, vejigante masks, and local coffee beans. Lunch at El Jibarito for homestyle rice and beans, stewed beef, and tostones, or at Deaverdura for a “sampler” plate that lets you taste a spectrum of Puerto Rican classics. Head to SJU for your afternoon flight; the airport is 15–25 minutes away depending on traffic.

Estimated costs & tips: El Yunque guided tours run ~$85–$120 per person and include transport; bio bay tours ~$65–$90. Ubers are plentiful in metro areas; for day trips beyond San Juan, a rental car is convenient. Dress smart-casual for nicer restaurants, and book prime tables 1–2 weeks ahead, especially on weekends.

Book your stay: Find a romantic apartment in Old San Juan or a beachfront condo in Condado on VRBO San Juan, or compare boutique hotels and resorts on Hotels.com San Juan. For flights, check Trip.com and Kiwi.com for the best schedules.

In four days, this San Juan itinerary blends beach time, colonial history, rainforest adventure, and after-dark energy—a couples trip that feels both easy and unforgettable. With thoughtful pacing and standout dining, you’ll fly home sun-warmed, well-fed, and already plotting a return for more Puerto Rico magic.