Beaches - Isla Verde, where the Courtyard Marriott is located and adjacent to the airport, has the most iconic stretch of wide beaches in San Juan. Post up here for hours sipping on a cold Medalla (local beer, pronounced: meh-dai-yuh); great people watching. Fairmont "El San Juan" Hotel - Walkable (10 min) from the Courtyard Marriott, the El San Juan Hotel has one of the most iconic and happening hotel lobby scenes you'll ever see. Grab a drink at the bar, try your luck at the casino, and listen to a live salsa band. Ocean Lab Brewing Co - At the opposite end of Isla Verde Beach from the Courtyard Marriott, Ocean Lab is a craft brewery right on the beach with music, pool, and a beach club.
Take an hour or so to walk the perimeter and take in the charm of the old walled city from La Princesa promenade on the south side to El Castillo San Felipe fort on the north side. Then stroll through some of the old cobblestone streets - San Sebastian, Calle Sol, and Calle Luna are some of the prettiest. Restaurants: Cafe Mallorca - A truly authentic Puerto Rican diner. Simple, bustling, great food. Bodega Chic - Excellent food. St. Germain Bistro & Cafe - Small venue, great to grab a sandwich and coffee for lunch. The Mezzanine - Upstairs from St. Germain this is another small venue with great cocktails and appetizers on a terrace above the old city. Marmalade - A fancier option for dinner - food and cocktails that won't disappoint. Lupulo - A trendy, laid back atmosphere with a great craft beer selection and bar food. La Factoria - Hands down one of the coolest bars in the world. It gets crowded so best to get there early. Excellent craft cocktails.
Running from Old San Juan to Ocean Park/Calle Loiza, Condado has a Miami vibe with lots of hotels, high rise apartments, restaurants and shops. Take a stroll down Ashford Ave, check out the beaches, and try a mofongo (mashed plantain) at one of the many local restaurants on the strip. Restaurants: Cocina Abierta - Creative menu, excellent food.
Santurce is the neighborhood just south of Condado. While not far from other areas, it is best to arrive by taxi/Uber. La Placita - Market by day and street party by night, La Placita is a favorite local happy hour spot, with a vibrant atmosphere and dancing that spills out into the streets at night. Get there around sundown on a Thursday or Friday night and have a mojito (or three!). Restaurants: Mai Pen Rai - Excellent Thai food.
Bordering the Ocean Park neighborhood between Isla Verde and Condado, Calle Loiza is an up and coming street full of nice bars and restaurants. Recommendations: Acapulco - Excellent, authentic mexican tacos.
El Yunque Rainforest: For those looking to explore a bit, El Yunque is located about 30-45 minutes southeast of San Juan and features miles of hiking trails, waterfalls, and breathtaking views of the island from above. Rincon: For those of you coming for more time and are up for a road trip (3 - 4 hours from San Juan), Rincon is a small but growing surf community on the west end of the island. Popular with both locals and tourists alike, it is a great place to get some more beach time, take a surf lesson, and experience a more laid back side of the island.