The Caribbean has long lured travelers with its blend of sun, spice, and sea. Puerto Rico—where Spanish colonial ramparts guard turquoise water—offers an easy gateway: no passport required for U.S. citizens, excellent food, and a rhythm that hums from cobblestone streets to beachfront kiosks.

On this 5-day itinerary, you’ll split your time between San Juan (for history, art, and nightlife) and Vieques (for unspoiled beaches and the planet’s brightest bioluminescent bay). Expect morning coffee at cafés roasting Puerto Rican beans, afternoons snorkeling with sea turtles, and evenings awash in salsa and Caribbean flavors.

Practical notes: Hurricane season runs June–November; plan flexible days and consider travel insurance. Reserve El Yunque rainforest entry if you add that side trip. Bring reef-safe sunscreen, light cash for kiosks, and book Mosquito Bay tours near a new moon for maximum glow.

San Juan

Old San Juan is a jewel-box of pastel façades, blue-cobbled streets, and twin UNESCO-listed fortresses—El Morro and San Cristóbal—overlooking the Atlantic. Beyond the walls, Condado and Ocean Park deliver breezy beaches, while Santurce splashes murals and nightlife across its streets.

Food is a headline act: think fragrant mofongo, crispy alcapurrias, and just-caught red snapper. Coffee culture is serious here; many cafés roast local beans from the island’s central mountains. When the sun dips, salsa spills out of bars and plazas.

• Top sights: Castillo San Felipe del Morro, Castillo San Cristóbal, Paseo de la Princesa, La Perla overlook, Santurce street art at Calle Cerra.
• Great eats: La Bombonera (since 1902; mallorcas), Marmalade (creative tasting menu; famed white bean truffle soup), Santaella (garden dining; modern criollo), Jose Enrique (iconic Puerto Rican flavors), La Placita for lively nights.
• Cocktails: La Factoría (multiroom speakeasy; World’s 50 Best Bars alumnus), Junglebird (tropical classics), La Casita de Rones (rum-forward by the harbor).

Stay: Browse stays near Old San Juan and Condado on VRBO and Hotels.com for everything from colonial lofts to oceanfront towers.

Getting there: Fly into San Juan (SJU). Compare fares on Trip.com flights or Kiwi.com. From the airport, rideshare to Old San Juan (~20–30 min, $18–30) or Condado (~15–20 min, $12–22).

Vieques

Vieques is San Juan’s wild, low-key sister—an island of free-roaming horses, deserted crescents of sand, and stargazing nights. The crown jewel is Mosquito Bay, the brightest bioluminescent lagoon on Earth, where every paddle stroke ignites neon-blue sparks.

Days here are delightfully uncomplicated: beach-hop through the Vieques National Wildlife Refuge, snorkel off Mosquito Pier with turtles, then tuck into a seaside dinner along Esperanza’s Malecon. The vibe is easygoing island life—no high-rises, no need to rush.

• Top beaches: Playa La Chiva (Blue Beach), Playa Caracas (Red Beach), Sun Bay for easy facilities, and Playa Negra for black volcanic sand.
• Food finds: El Quenepo (elegant Caribbean plates), Coqui Fire Café (small, spicy Tex-Mex with house hot sauces), Tin Box (farm-to-table smokehouse and pizza), Duffy’s and Bananas (laid-back bites with sea views).

Stay: Look for seaside apartments in Esperanza or tranquil hideaways in the hills on VRBO or boutique hotels and guesthouses via Hotels.com.

Getting there from San Juan: Drive or transfer to Ceiba ferry terminal (~1–1.25 hrs), then ferry to Vieques (~45–60 min; ~$5–15 pp each way). Alternatively, fly SJU–VQS (~25 min; ~$70–120 one-way) and compare options on Trip.com flights or Kiwi.com. Plan morning departures.

Day 1: Arrive in San Juan, Old San Juan Stroll, Sunset Ramparts

Morning: Fly into SJU. If you haven’t booked yet, compare fares on Trip.com or Kiwi.com. Aim for an early afternoon arrival.

Afternoon: Check in near Old San Juan or Condado via VRBO or Hotels.com. Shake off jet lag with coffee at Café Cuatro Sombras (house-roasted Puerto Rican beans and pan de mallorca sandwiches) and walk Paseo de la Princesa to the Raíces Fountain.

Evening: Time your golden hour at El Morro; locals fly kites on the lawn as cruise ships slip by. Dinner at Marmalade for a seasonal tasting menu (reserve; the white bean soup is a signature) or Deaverdura for homestyle platters (asopao, bacalaítos). Nightcap at La Factoría—find the unmarked doors leading to multiple bars with distinct menus.

Day 2: Beach, Forts, and Santurce Nightlife

Morning: Breakfast at historic La Bombonera—griddled mallorcas dusted with sugar and café con leche. Explore Castillo San Cristóbal (the largest Spanish fort in the Americas) and meander through the Calle de la Fortaleza umbrellas toward Plaza de Armas.

Afternoon: Taxi to Ocean Park Beach for a swim and kite-surfing spectating. Lunch at Lote 23 (food park; try El Jibarito de Lote for mini mofongo and Hen House for hot chicken) or head to Piñones (10–15 min east of Isla Verde) for beachfront kiosks—El Boricua and Mi Casita serve alcapurrias, bacalaítos, and cold Medallas.

Evening: Dress for a lively night in Santurce. Start with cocktails at Junglebird, dinner at Santaella (octopus “al caldero,” pork belly with guava), then circle La Placita—the plaza becomes an outdoor dance floor with salsa beats after 9 pm.

Day 3: Travel to Vieques, Esperanza Promenade, Bioluminescent Bay

Morning: Depart San Juan early. Drive or transfer to Ceiba (~1–1.25 hrs) for the ferry to Vieques (~45–60 min; ~$5–15). Prefer to fly? SJU–VQS is ~25 minutes; compare on Trip.com or Kiwi.com. Check into your lodging via VRBO or Hotels.com.

Afternoon: Settle in around Esperanza. Lunch at Duffy’s (fish tacos, cold beers) or Bananas (jerk chicken, rum punches). Walk the Malecon and scan for wild horses ambling down the street.

Evening: Your Mosquito Bay bioluminescent kayak tour is the showstopper. Choose clear-bottom kayaks if available; avoid lotions/repellent before the tour to keep the dinoflagellates healthy. Have dinner after at Coqui Fire Café (small, popular; house hot sauces) or late-night arepas and empanadillas from local kiosks.

Day 4: Refuge Beaches and Snorkeling Day

Morning: Coffee and breakfast burritos at Rising Roost. Head into the Vieques National Wildlife Refuge—start at Playa La Chiva (Blue Beach) for calm, glassy water and gentle snorkeling over seagrass beds where turtles graze.

Afternoon: Picnic at Playa Caracas (Red Beach); its arched bay offers soft sand and photogenic rock outcrops. Alternatively, snorkel off Mosquito Pier (Punta Arenas) where tarpon, rays, and turtles cruise the pylons. Grab a late lunch at Tin Box (smoked wings, wood-fired pies, and local greens).

Evening: Clean up for a seaside dinner at El Quenepo—order the lionfish when on the menu (a tasty way to support reef health) and a rum-forward dessert. Cap the night with stargazing from Sun Bay; light pollution is minimal, and on clear nights the Milky Way arcs overhead.

Day 5: Black Sand Walk, Return to San Juan, Departure

Morning: Early walk to Playa Negra for its striking black sands (arrive at low tide for broader shore). Quick breakfast at Buen Provecho (sandwiches, smoothies) in Esperanza.

Afternoon: Ferry or fly back toward San Juan (aim for late morning/early afternoon). If time allows before your flight, swing by Piñones for a last feast—alcapurrias at El Boricua and coco-fríos from a roadside stand—then head to SJU. For flight options, check Trip.com or Kiwi.com.

Evening: Fly home, sand still between your toes.

In five days, you’ll have tasted Puerto Rico’s past and present—from Spanish fortresses and salsa nights to untamed beaches and a living galaxy of glowing plankton. This Caribbean getaway balances city energy with island calm, leaving you with stories that sparkle long after sunset.