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 + Drive:  13​h 15​min
1
Ponce
— 1 night
Drive + Ferry:  2​h
2
Isla de Vieques
— 4 nights
Fly:  30​min
3
San Juan
— 1 night
Fly:  11​h 45​min
End: Chicago

1
night
Ponce

Ponce ©
Ponce is both a city and a municipality in the southern part of Puerto Rico. Start off your visit on the 14th (Sun): take in the spiritual surroundings of Cathedral of our Lady of Guadaloupe, don't miss a visit to Plaza of Delights (Plaza de las Delicias), then see the interesting displays at El Museo Castillo Serralles, and finally get to know the fascinating history of La Guancha. Here are some ideas for day two: examine the collection at Parque de Bombas, explore the world behind art at Museo de Arte de Ponce, and then enjoy the sea views from Cardona Island Light.

For where to stay, maps, more things to do, and more tourist information, use the Ponce vacation trip planner.

Chicago, USA to Ponce is an approximately 13.5-hour flight. The time zone difference when traveling from Chicago to Ponce is 2 hours. Prepare for much warmer weather when traveling from Chicago in January: high temperatures in Ponce hover around 84°F and lows are around 69°F. Finish your sightseeing early on the 15th (Mon) to allow enough time to travel to Isla de Vieques.

Things to do in Ponce

Museums Historic Sites Outdoors
Highlights from your plan
Museo de Arte de Ponce ©
Museo de Arte de Ponce
El Museo Castillo Serralles ©
El Museo Castillo Serralles
Cathedral of our Lady of Guadaloupe ©

4
nights
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.
Relax by the water at Blue Beach and Green Beach. You'll explore the less-touristy side of things at Sun Bay and Secret Beach. There's lots more to do: enjoy the sand and surf at Caracas Beach, enjoy the sea views from Puerto Ferro Lighthouse, and get engrossed in the history at Fortin Conde de Mirasol Museum.

For traveler tips, more things to do, other places to visit, and more tourist information, read our Isla de Vieques trip builder.

Do a combination of car, flight, and taxi from Ponce to Isla de Vieques in 2 hours. Alternatively, you can do a combination of taxi and flight. In January in Isla de Vieques, expect temperatures between 82°F during the day and 72°F at night. Wrap up your sightseeing on the 19th (Fri) early enough to travel to San Juan.

Things to do in Isla de Vieques

Outdoors Beaches Parks
Highlights from your plan
Secret Beach ©
Secret Beach
La Chiva ©
La Chiva
Caracas Beach ©
Caracas Beach

1
night
San Juan

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
On the 19th (Fri), appreciate the extensive heritage of San Juan National Historic Site, then stroll the grounds of San Juan Cemetery, and then appreciate the extensive heritage of Old San Juan.

For traveler tips, reviews, and more tourist information, read San Juan tour planner.

San Juan is just a short distance from Isla de Vieques. In January, daily temperatures in San Juan can reach 84°F, while at night they dip to 73°F. On the 20th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in San Juan

Historic Sites Neighborhoods
Highlights from your plan
Paseo de la Princesa ©
Paseo de la Princesa
Old San Juan ©
Old San Juan

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