14 days in Puerto Rico Itinerary

14 days in Puerto Rico Itinerary

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Route & dates

14 days in Puerto Rico Itinerary

Start: Chicago
Fly:  8​h
1
San Juan
— 3 nights
Drive:  45​min
2
Luquillo
— 2 nights
Drive:  15​min
3
Fajardo
— Few hours
Drive:  15​min
4
Ceiba
— 1 night
ferry:  1​h 45​min
5
Culebra
— 3 nights
ferry:  2​h 30​min
6
Isla de Vieques
— 3 nights
ferry + Drive:  2​h
7
San Juan
— 1 night
Fly:  7​h 45​min
End: Chicago

3
nights
San Juan

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
You've added Paseo de la Princesa, San Juan Cemetery, La Fortaleza - Palacio de Santa Catalina, and other attractions to your itinerary. Keep things going the next day: admire the masterpieces at Fundacion Casa Cortes, brush up on your knowledge of spirits at Casa BACARDI Puerto Rico, then get to know the fascinating history of San Juan National Historic Site, then steep yourself in history at La Fortaleza - Palacio de Santa Catalina, and finally stroll the grounds of San Juan Cemetery.

For where to stay, traveler tips, photos, and other tourist information, use the San Juan road trip planning tool .

Chicago, USA to San Juan is an approximately 8-hour flight. You can also do a combination of flight and car. You'll lose 2 hours traveling from Chicago to San Juan due to the time zone difference. Expect somewhat warmer weather when traveling from Chicago in May: highs in San Juan hover around 88°F, while lows dip to 76°F. You will leave for Luquillo on the 4th (Sat).

Things to do in San Juan

Historic Sites Neighborhoods Breweries & Distilleries

Side Trip

Casa Bacardi
Highlights from your plan
Old San Juan ©
Old San Juan
Paseo de la Princesa ©
Paseo de la Princesa

2
nights
Luquillo

Luquillo ©
Luquillo is a municipality of Puerto Rico (U.S.) located in the northeast coast, northwest of Fajardo; and east of Rio Grande. Your day-by-day itinerary now includes Cascada La Mina (La Mina Falls), Mt. Britton Lookout Tower, Juan Diego Falls, and other attractions you added. Kick off your visit on the 4th (Sat): trek along with Las Cabezas de San Juan Nature Reserve. On the 5th (Sun), you'll have a packed day of sightseeing: identify plant and animal life at El Yunque Rain Forest, admire the sheer force of La Coca Falls, look for all kinds of wild species at Angelito Trail, admire the sheer force of Las Paylas, then trek along Big Tree Trail, and finally take in the dramatic scenery at Juan Diego Falls.

To find where to stay, photos, traveler tips, and tourist information, you can read our Luquillo vacation planner.

You can drive from San Juan to Luquillo in an hour. Alternatively, you can take a shuttle. In May in Luquillo, expect temperatures between 85°F during the day and 76°F at night. Cap off your sightseeing on the 6th (Mon) early enough to go by car to Fajardo.

Things to do in Luquillo

Parks Wildlife Outdoors

Side Trips

El Yunque National Forest, Mt. Britton Lookout Tower, Las Cabezas de San Juan Nature Reserve
Highlights from your plan
El Yunque Rain Forest ©
El Yunque Rain Forest
El Yunque ©
El Yunque
Big Tree Trail ©
Big Tree Trail

few
hours
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. To find maps, ratings, other places to visit, and more tourist information, refer to the Fajardo trip itinerary planning website .

Fajardo is very close to Luquillo. In May, daily temperatures in Fajardo can reach 85°F, while at night they dip to 76°F. You'll set off for Ceiba on the 6th (Mon).

Things to do in Fajardo

Outdoors Tours Parks

1
night
Ceiba

Ceiba
Ceiba is a small municipality in northeast Puerto Rico (U.S.). On the 8th (Wed), head outdoors with Bellaventuras.

For photos, ratings, reviews, and tourist information, read Ceiba online trip itinerary maker .

Ceiba is just a short distance from Fajardo. In May, daytime highs in Ceiba are 85°F, while nighttime lows are 76°F. Wrap up your sightseeing by early afternoon on the 8th (Wed) to allow time for travel to Culebra.

Things to do in Ceiba

Outdoors Tours Parks

3
nights
Culebra

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Your day-by-day itinerary now includes Culebrita Island as well as Culebra National Wildlife Refuge. Your itinerary includes some good beach time at Zoni Beach and Playa Punta Soldado Beach. Step out of the city life by going to Tamarindo Beach and Flamenco Beach.

To see more things to do, reviews, and other tourist information, you can read our Culebra day trip planning tool .

Traveling by ferry from Ceiba to Culebra takes 2 hours. In May, daily temperatures in Culebra can reach 87°F, while at night they dip to 77°F. Finish your sightseeing early on the 16th (Thu) so you can travel to Isla de Vieques.

Things to do in Culebra

Parks Outdoors Beaches
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Tamarindo Beach ©
Tamarindo Beach
Zoni Beach ©
Zoni Beach

3
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.
Get in touch with nature at La Chiva and Kayaking & Canoeing. Explore hidden gems such as Sun Bay and Caracas Beach. There's more to do: take in the exciting artwork at Siddhia Hutchinson Fine Art Gallery and shop like a local with Gallery Galleon.

For traveler tips, photos, reviews, and more tourist information, use the Isla de Vieques tour builder .

Do a combination of flight and car from Culebra to Isla de Vieques in 2.5 hours. Alternatively, you can ride a ferry. Expect a daytime high around 85°F in May, and nighttime lows around 76°F. Finish your sightseeing early on the 19th (Sun) so you can travel to San Juan.

Things to do in Isla de Vieques

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

1
night
San Juan

San Juan
For reviews, other places to visit, traveler tips, and other tourist information, you can read our San Juan visit website .

Traveling by flight from Isla de Vieques to San Juan takes 2 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and shuttle. On the 20th (Mon), you're off tohome.

Things to do in San Juan

Outdoors Tours Parks

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