8 days in Puerto Rico Itinerary

8 days in Puerto Rico Itinerary

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Route & dates

8 days in Puerto Rico Itinerary

Start: Chicago
Fly:  7 h 45 min
1
San Juan
— 2 nights
Drive:  1 h
2
Fajardo
— 3 nights
Ferry:  1 h 30 min
3
Culebra
— 2 nights
Fly:  9 h 30 min
End: Chicago

2
nights
San Juan

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Kick off your visit on the 22nd (Sat): look for gifts at Seafoam, get to know the fascinating history of Sitio Histórico de San Juan, then take in the architecture and atmosphere at Catedral Metropolitana Basilica de San Juan Bautista, and finally appreciate the extensive heritage of Old San Juan. Get ready for a full day of sightseeing on the next day: skim along the rocks with a canyoning and rapelling tour, then brush up on your knowledge of spirits at Casa Bacardi Puerto Rico, and then savor the flavors at Food & Drink.

To find other places to visit, reviews, and tourist information, read San Juan trip maker website.

Chicago, USA to San Juan is an approximately 8- hour flight. You can also do a combination of flight and car. The time zone difference when traveling from Chicago to San Juan is 2 hours. Traveling from Chicago in February, things will get warmer in San Juan: highs are around 84°F and lows about 73°F. Finish your sightseeing early on the 23rd (Sun) so you can drive to Fajardo.

Things to do in San Juan

Historic Sites Tours Neighborhoods

Side Trip

Casa Bacardi Puerto Rico
Find places to stay Feb 21 — 23:
Highlights from your plan
Old San Juan ©
Old San Juan
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan
Food Tours

3
nights
Fajardo

Fajardo ©
Fajardo is a small city and municipality in Puerto Rico (U.S.) located in the east region of the island, bordering the Atlantic Ocean, north of Ceiba and east of Luquillo. You've now added Palomino Stables to your itinerary. Step out of Fajardo with an excursion to El Yunque Rain Forest in El Yunque National Forest--about 46 minutes away. There's lots more to do: enjoy the sand and surf at Luquillo Beach, add some adventure to your tour with a kayaking and canoeing tour, examine the collection at El Portal Tropical Forest Center, and wander the wide-open spaces of Carabali Rainforest Park.

To find ratings, photos, reviews, and other tourist information, go to the Fajardo road trip tool.

Drive from San Juan to Fajardo in an hour. Alternatively, you can take a shuttle. February in Fajardo sees daily highs of 83°F and lows of 73°F at night. Finish your sightseeing early on the 26th (Wed) to allow enough time to ride a ferry to Culebra.

Things to do in Fajardo

Parks Nature Outdoors

Side Trips

El Yunque National Forest, Luquillo
Find places to stay Feb 23 — 26:
Highlights from your plan
Palomino Stables ©
Palomino Stables
El Yunque Rain Forest ©
El Yunque Rain Forest
Luquillo Beach ©
Luquillo Beach

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.
On the 27th (Thu), enjoy the sand and surf at Playa Punta Soldado Beach and then kick back and relax at Flamenco Beach. Keep things going the next day: stroll through Zoni Beach and then step off the mainland to explore Culebrita Island.

For traveler tips, where to stay, more things to do, and other tourist information, read Culebra day trip planner.

You can ride a ferry from Fajardo to Culebra in 1.5 hours. In February, plan for daily highs up to 84°F, and evening lows to 73°F. Wrap up your sightseeing on the 28th (Fri) to allow time to travel back home.

Things to do in Culebra

Parks Beaches Outdoors
Find places to stay Feb 26 — 28:
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

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