San Juan, Puerto Rico – October 2026

October 16 – 19, 2026

A long weekend split between Old San Juan’s fort and cobblestones and Santurce’s markets and museum.

Day 1 – Old San Juan

• Condado Vanderbilt (Hotel) – Booked through Chase’s The Edit program, which included free breakfast and a $100 credit. The room is small but has a nice bathroom and a private little veranda with a city view.
• Landed late Friday night and the Puerto Rican mosquitoes found me immediately. Sunscreen and bug spray went on the shopping list.
• Hotel Breakfast (Breakfast) – Buffet, eaten poolside with a view of the water. Amazing.
• Columbus landed here on November 19, 1493, during his second voyage, and Ponce de León founded the first Spanish settlement in 1508. Spain ceded the island to the U.S. in 1898 after the Spanish-American War, Puerto Ricans became U.S. citizens in 1917, and the commonwealth was established in 1952. It runs much like a state: federal laws apply and the U.S. handles defense and foreign policy, but residents can’t vote for president in the general election.
• Castillo San Felipe del Morro (Fort) – Took a Lyft to the fort and made our way across Old Town. The Spanish started building it in 1539 and kept expanding it for about 250 years to guard the entrance to San Juan Bay. It’s now part of a UNESCO World Heritage Site. Entry is $20 per person, but we renewed our National Park pass instead. I have memories of visiting here with my parents as a kid.
• Don Ruiz Coffee (Coffee) – A stop for caffeine and air conditioning. The café sits inside Cuartel de Ballajá, a former Spanish military barracks from the mid-1800s that now also houses a museum. Iced matcha and a latte.
• Catedral Basílica Menor de San Juan Bautista – One of the oldest cathedrals in the Americas, dating back to the early 1500s. It’s home to Ponce de León’s tomb, which was moved here from a nearby church in the early 1900s.
• Puerta de San Juan – The original door to the city and the last of the old city gates still standing. Ships docked nearby, and arriving passengers walked through this gate and up the street to the cathedral to give thanks for a safe crossing.
• Paseo de la Princesa – A 19th-century waterfront promenade running along the old city walls, named for a former jail that still stands along it. On weekends it fills with an artist market of local vendors selling art, crafts, and food.
• La Casita de Rones (Drinks) – Creamy piña colada and a rum old fashioned. Puerto Rico is best known for the piña colada, which was invented in San Juan in the 1950s.
• Hotel Pool (Wind Down) – Relaxing evening watching the waves and reading. A future groom’s dad asked us to film the engagement at sunset. Another piña colada and plantain chips for dinner.

Day 2 – Santurce

• Hotel Breakfast (Breakfast) – Another delicious breakfast. Tried their version of a mallorca, a soft, fluffy sweet roll made with yeasted dough, traditionally enriched with lard and dusted with powdered sugar. They’re a staple in bakeries across the island.
• Ciudadela Sunday Market – Local artisans, handmade jewelry, crafts, plants, and plenty of local food. It runs the 3rd Sunday of the month on the plaza between the buildings, near the Planet Fitness entrance. We got a café frío and a matcha and strolled to the museum next door.
• Museo de Arte de Puerto Rico (Museum) – A mix of contemporary and classic art plus a tropical garden with sculptures. We lucked into free admission for “Access for All Day: Bienestar en el Museo” (Wellness at the Museum). Normally $20 per person. Very cool museum.
• My “survival Spanish” has been less helpful here. The locals speak Spanish VERY fast. We considered joining a group tour at the art museum but were hopelessly lost and explored on our own. People are friendly, and most speak flawless English too.
• We’ve spotted several sculptures around town by Fernando Botero, the Colombian artist whose signature style, Boterismo, features exaggerated, rounded figures.
• Puerto Rico Costco – It started raining as we left the museum, so we went to check out the local Costco. We always like looking for unique local items. After spending $25 on a Lyft to get there, it was pretty much just like our Costco. We picked up some local coffee but spent more getting there and back than we saved. A surprising amount of cold weather clothing for somewhere that doesn’t get cold.
• La Casita Blanca (Lunch) – A late lunch of Puerto Rican home cooking at a James Beard America’s Classics Award winner. Walk-ins only, with a short line to be seated. Complimentary pumpkin soup and codfish fritters to start.