5 days in Puerto Rico Itinerary

5 days in Puerto Rico Itinerary

Created using Inspirock Puerto Rico trip itinerary planner

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Route & dates

5 days in Puerto Rico Itinerary

Start: Chicago
Fly:  8​h 30​min
1
Culebra
— 1 night
Fly:  30​min
2
San Juan
— 3 nights
Fly:  7​h 45​min
End: Chicago

1
night
Culebra

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
On the 20th (Thu), visit a coastal fixture at Culebrita Lighthouse and then enjoy the sand and surf at Flamenco Beach.

To find traveler tips, reviews, and other tourist information, you can read our Culebra visit site .

Chicago, USA to Culebra is an approximately 8.5-hour flight. You can also do a combination of flight, shuttle, and ferry; or do a combination of flight and ferry. Traveling from Chicago to Culebra, you'll lose 2 hours due to the time zone difference. Plan for a bit warmer temperatures traveling from Chicago in June, with highs in Culebra at 89°F and lows at 79°F. Finish up your sightseeing early on the 20th (Thu) so you can catch the flight to San Juan.

Things to do in Culebra

Parks Beaches Outdoors
Find places to stay Jun 19 — 20:
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Flamenco Beach ©
Flamenco Beach
Culebrita Lighthouse ©
Culebrita Lighthouse

3
nights
San Juan

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Go for a jaunt from San Juan to El Yunque National Forest to see El Yunque Rain Forest about 1h 10 min away. There's lots more to do: scramble along the landscape with a canyoning and rapelling tour, contemplate the long history of San Juan National Historic Site, appreciate the extensive heritage of Old San Juan, and get engrossed in the history at Catedral Metropolitana Basilica de San Juan Bautista.

To see where to stay, more things to do, maps, and tourist information, you can read our San Juan trip planner.

San Juan is very close to Culebra. In June in San Juan, expect temperatures between 89°F during the day and 78°F at night. Finish your sightseeing early on the 23rd (Sun) to allow enough time to travel back home.

Things to do in San Juan

Tours Outdoors Historic Sites

Side Trip

El Yunque Rain Forest
Find places to stay Jun 20 — 23:
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El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

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