Curator’s statement
Puerto Rico holds a special place in my heart because it’s got the perfect mix of vibrant city life, laid-back beach vibes and unforgettable cultural experiences. Whether it’s sipping coffee in Old San Juan, exploring the lush rainforest or just lounging at a dreamy hotel pool, this island knows how to make you feel at home while offering up something new at every turn. For me, it’s all about finding those hidden gems and crafting a journey that’s as unique as the traveler.
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Day 1: Arrival
Check-in at Condado Vanderbilt: Drop the bags, soak in the ocean views and get into vacation mode.
Beach & Pool Time (at the hotel): You’re here to relax, so start slow. Lounge by the pool or head straight to the private beach.
Welcome drinks at VC Lounge (at the hotel): Set the tone with a cocktail and ocean breeze.
Dinner at farm-to-table 1919 (at the hotel, reservations recommended): If you're up for an elevated first-night dinner, this is one of San Juan’s best. Think refined Puerto Rican flavors with a focus on local ingredients. Led by Michelin-starred Chef Juan José Cuevas.
Day 2: Beach & town
Breakfast at Ola Oceanfront (at the hotel): Fresh fruit, strong Puerto Rican coffee and ocean views.
Pool & beach day (at the hotel): Lounge, read, nap, repeat. Cabana service is a move.
Lunch at Tacos & Tequila (at the hotel): Keep it easy with poolside tacos and a margarita.
Afternoon in Old San Juan: Take a short Uber to explore the colorful streets and check out:
Ole in Old Town: Custom-fitted Panama hats, the perfect unique souvenir.
San Juan Handmade: Make your own espadrilles (they even have baby/toddler sizes!). Reserve this with the link if you are interested!
Castillo San Felipe del Morro: The iconic 16th-century fort with stunning views.
Drinks at La Factoría: A must-visit speakeasy with world-class cocktails.
Dinner at El Jibarito: Authentic Puerto Rican food in a lively spot locals love. Expect a wait, but it’s worth it.
Nightcap at Los 3 Cuernos: Just a few minutes away, with great music, friendly bartenders and a killer rum punch.
Day 3: Adventure & local fare
Coffee run: A couple of standout spots:
Café Comunión: Home to Puerto Rico’s National Latte Art Champion.
Finca Cialitos: Old San Juan café sourcing beans from its own estate. Worth bringing some home!
Option 1: El Yunque Rainforest: Rent a car and drive to Puerto Rico’s lush rainforest for an easy hike and waterfalls. Afterward, stop in Piñones for some roadside frituras (fried local snacks) and pinchos (grilled skewers). *I can also book you an excursion!
Option 2: Another Pool & Beach Day (at the hotel): No shame in doubling down on relaxation.
Sunset cocktails at Oceano: Swanky beachfront spot in Condado. The ceviche is excellent.
Dinner at Santaella: A guaranteed great meal with an upscale yet relaxed vibe. Think elevated Puerto Rican flavors with killer cocktails.
Day 4: Rum, markets & last beach day
Morning at Mercado Agrícola de Viejo San Juan: If it’s a Saturday, stroll through this local farmers’ market near El Morro for fresh produce, artisanal goods and Puerto Rican vanilla beans.
Last Beach & Pool Day (at the hotel): Soak it up.
Ron del Barrilito Distillery Tour: Order the coffee cocktail with your post-tour drink token — it’s unreal.
Need to know
Must-do highlights
If you do nothing else, consider these your no-regret moves:
Dinner at Santaella: A perfect mix of vibrant atmosphere, incredible cocktails and Puerto Rican flavors done right.
Custom hat at Ole in Old San Juan: A one-of-a-kind souvenir, fitted just for you.
Make your own espadrilles at Barcelona Handmade: The cutest custom footwear, and they even have baby/toddler sizes.
Ron del Barrilito Distillery Tour: The best rum tour on the island. Trust me on the coffee cocktail.
El Jibarito for dinner and drinks at Los 3 Cuernos: A combo of authentic Puerto Rican food and a lively bar with a killer rum punch.
Beach & Pool Time at Condado Vanderbilt: Because let’s be real, the goal here is maximum relaxation.
Travel Advisor
Sydney Getzin
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For more inspiration and insider recommendations, visit our Puerto Rico page.