3 days you’ll remember in San Juan, Puerto Rico.
Old World charm meets island ease in Puerto Rico’s colorful capital. With cobblestone streets, vibrant colonial facades, and breezy oceanfront views, San Juan wraps centuries of culture into a tropical coastal rhythm.
This Foresyte itinerary brings you three unforgettable days of historic exploration, Caribbean cuisine, salsa-filled nights, and sun-soaked serenity—your gateway to a perfect weekend in San Juan.
Let’s take it from the top.
Itinerary inspired by the Foresyte community.
📍 Feelin Bright Again
Day 1: Old San Juan
“Wander Old San Juan like you’ve time-traveled, cobblestones, pastel facades, sea breeze in your hair.”
Day 1: Dinner @ 1919
“1919 is upscale done right. Ocean views, thoughtful courses, and not a drop of pretense.”
Day 2: Lunch @ Paulina Escanes
“Paulina Escanes serves up breezy charm and island flavors in a space that hums with warmth.”
Day 2: Horseback Riding
“Horseback riding through the countryside brings a stillness you didn’t know you were craving.”
Day 2: Dinner @ Casa Emilio
“Casa Emilio is where locals linger. Comfort food, cold drinks, good stories.”
Day 3: Brunch @ Ola
“Ola Ocean Front keeps it crisp and coastal, sunlight on the water, ceviche on your plate.”
Day 3: Scuba Diving
“Scuba diving here is a plunge into another world. Coral walls, drifting schools, silent awe.”
Day 3: Dinner @ Marmalade
“Marmalade is the final chapter, inventive, intimate, and full of surprise.”
Day 3: LED Kayaks
“LED kayak tours light up the lagoon. Paddle slow. Let the glow carry you.”
San Juan Itinerary FAQ.
What are the top things to do in San Juan over a weekend?
Wander the pastel streets of Old San Juan, explore El Morro Fortress, relax on Condado Beach, and dance the night away in La Placita.
When is the best time to plan a weekend in San Juan?
The best time to visit San Juan is from December to April when the weather is warm, sunny, and dry—perfect for beach days and outdoor adventures.
Where should I stay in San Juan for a weekend getaway?
Stay in Old San Juan for walkable charm and history, or opt for Condado or Isla Verde for beachside hotels and nightlife.
What is San Juan best known for on a weekend visit?
San Juan is known for its colonial architecture, vibrant street life, local rum, and a fusion of Spanish, African, and Caribbean cultures.
How do I get around San Juan during a weekend trip?
Walking is ideal in Old San Juan; for beach areas and neighborhoods, rideshares and taxis are widely available and affordable.
What unique experiences should I add to my San Juan itinerary?
Sip piña coladas where they were invented, kayak the bioluminescent bay in nearby Fajardo, and catch a sunset from the El Morro ramparts.
Where meaningful travel begins.
Start your journey with Foresyte, where the planning is part of the magic.
Discover the experiences that matter most.
