San Juan long weekend: Old Town food tour, Escambrón beach, and El Morro — 4 days in San Juan, Puerto Rico
Photo: P. Hughes · CC BY-SA 4.0

🏝️ San Juan, Puerto Rico · 4 days

San Juan long weekend: Old Town food tour, Escambrón beach, and El Morro

Old forts, a rainforest, and a glowing bay — no passport. 4-day San Juan, Puerto Rico trip for 2 people: Dinner at a criollo spot, Old San Juan walking tour, Museum of San Juan. Stay at Hotel El Convento. About $1,285 per person, estimated, checked Oct 27, 2026.

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Costs

Restaurants$250
Relax$40
Flights$1,360
History & culture$90
Lodging$750
Nightlife$80
About $1,285 / person for 2 people (estimated, checked Oct 27, 2026)$2,570 estimated

Estimate · prices last checked 2026-10-27.

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Where you stay

Getting there

Day by day

Day 1 2026-12-27

Start with Old San Juan evening stroll. After that: Dinner at a criollo spot. The prices are estimates, not tickets in hand.

  • MorningOld San Juan evening strollPlanning estimate for Old San Juan evening stroll. It is not a live fare or a reserved ticket.Free
  • AfternoonDinner at a criollo spotPlanning estimate for Dinner at a criollo spot. It is not a live fare or a reserved ticket.$60Book on OpenTableWe may earn a commission if you book, at no extra cost to you. How we make money
  • OvernightHotel El ConventoOne standard room at Hotel El Convento. The nightly figure is an estimate, not a quote.$250Book on Booking.comWe may earn a commission if you book, at no extra cost to you. How we make money

We may earn a commission if you book, at no extra cost to you. How we make money

Day 2 2026-12-28

Start with Old San Juan walking tour. After that: Museum of San Juan; Evening food tour. The prices are estimates, not tickets in hand.

  • MorningOld San Juan walking tourPlanning estimate for Old San Juan walking tour. It is not a live fare or a reserved ticket.$60Book this on ViatorWe may earn a commission if you book, at no extra cost to you. How we make money
  • AfternoonMuseum of San JuanPlanning estimate for Museum of San Juan. It is not a live fare or a reserved ticket.FreeBooking link coming soon
  • EveningEvening food tourPlanning estimate for Evening food tour. It is not a live fare or a reserved ticket.$190Book on sanjuanfoodtours.comWe may earn a commission if you book, at no extra cost to you. How we make money
  • OvernightHotel El ConventoOne standard room at Hotel El Convento. The nightly figure is an estimate, not a quote.$250Book on Booking.comWe may earn a commission if you book, at no extra cost to you. How we make money

We may earn a commission if you book, at no extra cost to you. How we make money

Day 3 2026-12-29

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.

  • MorningPoet's Passage local art shopPlanning estimate for Poet's Passage local art shop. It is not a live fare or a reserved ticket.Free
  • AfternoonEscambrón beach (chairs)Planning estimate for Escambrón beach (chairs). It is not a live fare or a reserved ticket.$40
  • EveningOld San Juan bar hopPlanning estimate for Old San Juan bar hop. It is not a live fare or a reserved ticket.$80Book this on ViatorWe may earn a commission if you book, at no extra cost to you. How we make money
  • OvernightHotel El ConventoOne standard room at Hotel El Convento. The nightly figure is an estimate, not a quote.$250Book on Booking.comWe may earn a commission if you book, at no extra cost to you. How we make money

We may earn a commission if you book, at no extra cost to you. How we make money

Day 4 2026-12-30

Start with Casa Blanca museum and gardens. After that: Castillo San Felipe del Morro. The prices are estimates, not tickets in hand.

  • MorningCasa Blanca museum and gardensPlanning estimate for Casa Blanca museum and gardens. It is not a live fare or a reserved ticket.$10
  • AfternoonCastillo San Felipe del MorroPlanning estimate for Castillo San Felipe del Morro. It is not a live fare or a reserved ticket.$20Book on nps.govWe may earn a commission if you book, at no extra cost to you. How we make money

We may earn a commission if you book, at no extra cost to you. How we make money