8 days in Puerto Rico Itinerary

8 days in Puerto Rico Itinerary

Created using Inspirock Puerto Rico trip planner

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Route & dates

8 days in Puerto Rico Itinerary

Start: Chicago
Fly:  9​h 30​min
1
Isla de Vieques
— 1 day
Drive + Fly:  2​h 15​min
2
Culebra
— 2 nights
Fly:  30​min
3
San Juan
— 4 nights
Fly:  7​h 45​min
End: Chicago

1
day
Isla de Vieques

Isla de Vieques ©
For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Kick off your visit on the 18th (Thu): take a leisurely stroll along Malecon and then contemplate the waterfront views at Sun Bay.

For maps, more things to do, and tourist information, read our Isla de Vieques visit planning app .

Chicago, USA to Isla de Vieques is an approximately 9.5-hour flight. You can also do a combination of flight, shuttle, and ferry. You'll lose 2 hours traveling from Chicago to Isla de Vieques due to the time zone difference. Plan for somewhat warmer nights when traveling from Chicago in July since evenings lows in Isla de Vieques dip to 79°F. Wrap up your sightseeing on the 18th (Thu) early enough to travel to Culebra.

Things to do in Isla de Vieques

Nature Outdoors Beaches
Find places to stay Jul 18 — 19:
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Sun Bay ©
Sun Bay
Malecon ©
Malecon

2
nights
Culebra

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Start off your visit on the 19th (Fri): enjoy the sea views from Culebrita Lighthouse, head off the coast to Culebrita Island, and then kick back and relax at Zoni Beach. On the 20th (Sat), you'll have a packed day of sightseeing: get lost in a book at Culebra Public Library and then kick back and relax at Flamenco Beach.

To find reviews, photos, more things to do, and other tourist information, refer to the Culebra attractions planner .

Do a combination of car and flight from Isla de Vieques to Culebra in 2.5 hours. Alternatively, you can ride a ferry. In July, daytime highs in Culebra are 90°F, while nighttime lows are 80°F. Finish your sightseeing early on the 20th (Sat) so you can fly to San Juan.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Jul 18 — 20:
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Flamenco Beach ©
Flamenco Beach
Culebrita Island ©
Culebrita Island
Zoni Beach ©
Zoni Beach

4
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. And it doesn't end there: take a memorable tour with Tours, get engrossed in the history at Catedral Metropolitana Basilica de San Juan Bautista, enjoy the sand and surf at Condado Beach, and appreciate the extensive heritage of Paseo de la Princesa.

To find other places to visit, traveler tips, more things to do, and tourist information, use the San Juan trip planner.

San Juan is just a stone's throw from Culebra. July in San Juan sees daily highs of 89°F and lows of 78°F at night. Wrap up your sightseeing on the 24th (Wed) early enough to travel back home.

Things to do in San Juan

Outdoors Parks Historic Sites

Side Trips

El Yunque Rain Forest, Casa BACARDI Puerto Rico
Find places to stay Jul 20 — 24:
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El Yunque Rain Forest ©
El Yunque Rain Forest
Canyoning & Rappelling Tours
Climbing Tours

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