🏝️ San Juan, Puerto Rico · printable plan
San Juan long weekend: Old Town food tour, Escambrón beach, and El Morro
By TopVacay @topvacay. Inspired by Anna Unpacked. Prices last checked 2026-10-27. Totals are estimates: $2,570 for 2 travelers.
Recomputed from the price lines stored on each trip. No live hotel, ticket, or airfare feed is connected.
Day by day
Day 1
Start with Old San Juan evening stroll. After that: Dinner at a criollo spot. The prices are estimates, not tickets in hand.
- Morning · Old San Juan evening stroll
- Afternoon · Dinner at a criollo spot
- Overnight · Hotel El Convento
Day 2
Start with Old San Juan walking tour. After that: Museum of San Juan; Evening food tour. The prices are estimates, not tickets in hand.
- Morning · Old San Juan walking tour
- Afternoon · Museum of San Juan
- Evening · Evening food tour
- Overnight · Hotel El Convento
Day 3
Start with Poet's Passage local art shop. After that: Escambrón beach (chairs); Old San Juan bar hop. The prices are estimates, not tickets in hand.
- Morning · Poet's Passage local art shop
- Afternoon · Escambrón beach (chairs)
- Evening · Old San Juan bar hop
- Overnight · Hotel El Convento
Day 4
Start with Casa Blanca museum and gardens. After that: Castillo San Felipe del Morro. The prices are estimates, not tickets in hand.
- Morning · Casa Blanca museum and gardens
- Afternoon · Castillo San Felipe del Morro
Packing
- Comfortable walking shoesThe plan is on foot more than in a car.
- Day bagA small bag holds the water, the layer, and the tickets.
- Light layerMuseums and evenings run cooler than the street.
- Compact umbrellaA short rain should not cancel the afternoon.
Reserve ahead
- American 1402day 1 once you set dates · Hold the seats before the fare you estimated moves.
- Delta 1636day 4 once you set dates · Hold the seats before the fare you estimated moves.
- Dinner at a criollo spotday 1 once you set dates · Popular tables go early. Book the seating, then build the rest of the day around it.
- Hotel El Conventoday 1 once you set dates · This is the room for that night. Reserve it before you count on the rate.
- Hotel El Conventoday 2 once you set dates · This is the room for that night. Reserve it before you count on the rate.
- Hotel El Conventoday 3 once you set dates · This is the room for that night. Reserve it before you count on the rate.