8 days in Puerto Rico Itinerary

8 days in Puerto Rico Itinerary

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Route & dates

8 days in Puerto Rico Itinerary

Chicago
Fly:  13​h 15​min
Culebra
— 3 nights
Fly + taxi:  30​min
Isla de Vieques
— 3 nights
taxi + Fly:  30​min
San Juan
— 1 night
Fly:  11​h 45​min
Chicago

2
days
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 18th (Tue), enjoy the sea views from Culebrita Lighthouse and then enjoy the sand and surf at Flamenco Beach. Get ready for a full day of sightseeing on the 19th (Wed): stroll through Tamarindo Beach, kick back and relax at Zoni Beach, and then tour the pleasant surroundings at Playa Punta Soldado Beach.

To see traveler tips, maps, other places to visit, and more tourist information, go to the Culebra trip itinerary planner.

Chicago, USA to Culebra is an approximately 13.5-hour flight. The time zone difference when traveling from Chicago to Culebra is 2 hours. Traveling from Chicago in July, plan for a bit warmer nights in Culebra, with lows around 79°F. Finish your sightseeing early on the 20th (Thu) to allow enough time to travel to Isla de Vieques.

Things to do in Culebra

Beaches Outdoors Parks
Accommodations
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Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach
Tamarindo Beach ©
Tamarindo Beach

3
days
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.
Visit Sun Bay and Media Luna Beach for some beach relaxation. There's much more to do: enjoy the sand and surf at Blue Beach, take in the waterfront at Malecon, stroll through Caracas Beach, and steep yourself in history at Puerto Ferro Lighthouse.

For where to stay, reviews, maps, and tourist information, use the Isla de Vieques trip itinerary planner.

Isla de Vieques is very close to Culebra. In July, daytime highs in Isla de Vieques are 88°F, while nighttime lows are 78°F. Finish your sightseeing early on the 23rd (Sun) to allow enough time to travel to San Juan.

Things to do in Isla de Vieques

Beaches Outdoors Parks
Accommodations
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Sun Bay ©
Sun Bay
Blue Beach ©
Blue Beach
Media Luna Beach ©
Media Luna Beach

1
day
San Juan

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Start off your visit on the 23rd (Sun): take a peaceful walk through The El Yunque Rain Forest.

To see reviews, more things to do, maps, and tourist information, go to the San Juan travel planner.

San Juan is very close to Isla de Vieques. July in San Juan sees daily highs of 89°F and lows of 78°F at night. Wrap up your sightseeing by early afternoon on the 24th (Mon) to allow enough time to travel back home.

Things to do in San Juan

Wildlife Nature Parks

Side Trip

El Yunque Rain Forest
Accommodations
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El Yunque Rain Forest ©
El Yunque Rain Forest
San Juan National Historic Site ©
San Juan National Historic Site
The Capitol of Puerto Rico ©
The Capitol of Puerto Rico

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