37 days in Puerto Rico Itinerary

37 days in Puerto Rico Itinerary

Created using Inspirock Puerto Rico trip maker

Make it your trip
Fly
1
Isla de Vieques
— 6 nights
Fly
2
Culebra
— 6 nights
Fly
3
El Yunque National Forest
— 5 nights
Fly
4
Isabela
— 5 nights
Drive
5
Ponce
— 6 nights
Drive
6
San Juan
— 8 nights
Fly

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Isla de Vieques

— 6 nights

Isla Nena

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.
Isla de Vieques is known for beaches, nature, and adventure. Your trip includes some of its best attractions: enjoy the sand and surf at Balneario Sun Bay, tour the pleasant surroundings at Playa Navio, step off the mainland to explore Vieques Island, and see some colorful creatures with a scuba or snorkeling tour.

To see traveler tips, photos, ratings, and more tourist information, go to the Isla de Vieques trip builder website.

Chicago, USA to Isla de Vieques is an approximately 9-hour flight. The time zone difference moving from Central Standard Time (CST) to Atlantic Standard Time (AST) is 2 hours. Expect much hotter temperatures when traveling from Chicago in October; daily highs in Isla de Vieques reach 88°F and lows reach 76°F. Finish your sightseeing early on the 12th (Tue) to allow enough time to fly to Culebra.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Wildlife
Find places to stay Oct 6 — 12:

Culebra

— 6 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Culebra is known for beaches, wildlife, and outdoors. Your trip includes some of its best attractions: enjoy the sand and surf at Flamenco Beach, stroll through Playa Tamarindo, discover the deep blue sea with a scuba or snorkeling tour, and get advice or help at Culebra Public Library.

To see photos, more things to do, reviews, and other tourist information, use the Culebra tour itinerary builder.

Traveling by flight from Isla de Vieques to Culebra takes 3.5 hours. Alternatively, you can ride a ferry. In October in Culebra, expect temperatures between 88°F during the day and 78°F at night. Wrap up your sightseeing on the 18th (Mon) early enough to fly to El Yunque National Forest.

Things to do in Culebra

Parks · Outdoors · Beaches · Wildlife
Find places to stay Oct 12 — 18:

El Yunque National Forest

— 5 nights
Change things up with these side-trips from El Yunque National Forest: Isla Palominos (in Las Croabas) and Fajardo (Laguna Grande Bioluminescent Bay, Kayaking & Canoeing, &more). Make the 20th (Wed) an awe-inspiring day at El Yunque Rain Forest.

To find photos, other places to visit, reviews, and more tourist information, refer to the El Yunque National Forest holiday planner.

Traveling by flight from Culebra to El Yunque National Forest takes 2 hours. Alternatively, you can do a combination of ferry and car. In October, daytime highs in El Yunque National Forest are 90°F, while nighttime lows are 78°F. Wrap up your sightseeing on the 23rd (Sat) early enough to fly to Isabela.

Things to do in El Yunque National Forest

Parks · Nature · Wildlife · Outdoors

Side Trip

Find places to stay Oct 18 — 23:

Isabela

— 5 nights
Isabela is a municipality of Puerto Rico (U.S.) located in the north-western region of the island, north of San Sebastián; west of Quebradillas; and east of Aguadilla and Moca. Explore the numerous day-trip ideas around Isabela: Playa Sucia (in Cabo Rojo), Porta del Sol - West (in Mayaguez) and Parque Nacional de las Cavernas del Rio Camuy (in Camuy). And it doesn't end there: enjoy the sand and surf at Jobos Beach, contemplate the waterfront views at Camuy River (Rio Camuy), explore the fascinating underground world of Aventura Cueva Ventana, and trot along with a tour on horseback.

For more things to do, ratings, reviews, and tourist information, you can read our Isabela online trip builder.

You can fly from El Yunque National Forest to Isabela in 2.5 hours. Alternatively, you can drive; or do a combination of shuttle and car. In October, daily temperatures in Isabela can reach 87°F, while at night they dip to 74°F. Cap off your sightseeing on the 28th (Thu) early enough to go by car to Ponce.

Things to do in Isabela

Parks · Outdoors · Nature · Beaches

Side Trips

Find places to stay Oct 23 — 28:

Ponce

— 6 nights
Ponce is both a city and a municipality in the southern part of Puerto Rico. Explore Ponce's surroundings by going to Macromural Brisa Tropical (in Yauco), Cana Gorda Beach (in Playa de Guanica) and Bosque Estatal de Guanica (in Guanica). There's still lots to do: explore the world behind art at Museo de Arte de Ponce, tee off at Costa Caribe Golf & Country Club, examine the collection at Parque de Bombas, and admire the sheer force of Catarata Salto de Collores.

To find other places to visit, photos, ratings, and tourist information, you can read our Ponce travel route planner.

Drive from Isabela to Ponce in 2 hours. In October, daily temperatures in Ponce can reach 85°F, while at night they dip to 75°F. Finish your sightseeing early on the 3rd (Wed) so you can drive to San Juan.

Things to do in Ponce

Outdoors · Parks · Museums · Nature

Side Trips

Find places to stay Oct 28 — Nov 3:

San Juan

— 8 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Change things up with these side-trips from San Juan: Playa Luquillo (in Luquillo) and Cayo Icacos (in Fajardo). Make the 5th (Fri) a memorable day with a climbing tour. The adventure continues: appreciate the extensive heritage of Old San Juan, scramble along the landscape with a canyoning and rapelling tour, brush up on your knowledge of spirits at Casa Bacardi Puerto Rico, and admire the masterpieces at Museo de Arte de Puerto Rico.

To find other places to visit, where to stay, ratings, and tourist information, read our San Juan online route planner.

Drive from Ponce to San Juan in 1.5 hours. Alternatively, you can fly; or take a shuttle. November in San Juan sees daily highs of 87°F and lows of 76°F at night. Finish your sightseeing early on the 11th (Thu) to allow enough time to fly back home.

Things to do in San Juan

Outdoors · Tours · Parks · Beaches

Side Trips

Find places to stay Nov 3 — 11:

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Surfing, Windsurfing & Kitesurfing
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.