58 days in Puerto Rico Itinerary

58 days in Puerto Rico Itinerary

Created using Inspirock Puerto Rico Trip Planner

Make it your trip
Fly
1
Culebra
— 10 nights
Ferry to Ceiba, Puerto Rico, Drive to Ponce
2
Ponce
— 11 nights
Drive
3
Aguadilla
— 10 nights
Drive to Ceiba, Puerto Rico, Ferry to Isla de Vieques
4
Isla de Vieques
— 11 nights
Fly
5
San Juan
— 14 nights
Fly

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Culebra

— 10 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Get outdoors at Flamenco Beach and Playa Tamarindo. Culebrita Lighthouse and Museo Historico de Culebra are good opportunities to explore the local culture. There's still lots to do: kick back and relax at Playa Zoni, tour the pleasant surroundings at Brava Beach, look for all kinds of wild species at Wildlife Areas, and get advice or help at Culebra Public Library.

To find traveler tips, ratings, other places to visit, and tourist information, read our Culebra sightseeing planner.

San Francisco, USA to Culebra is an approximately 14-hour flight. The time zone difference moving from Pacific Standard Time (PST) to Atlantic Standard Time (AST) is 4 hours. Expect a bit warmer weather when traveling from San Francisco in October: highs in Culebra hover around 88°F, while lows dip to 78°F. On the 15th (Sun), you're off to Ponce.

Things to do in Culebra

Parks · Outdoors · Beaches · Wildlife
Find places to stay Oct 4 — 15:

Ponce

— 11 nights
Ponce is both a city and a municipality in the southern part of Puerto Rico. Relax by the water at Playa Sucia and Atolladora Beach (Ballena Bay). Museo de Arte de Ponce and Hacienda Buena Vista are good opportunities to explore the local culture. You'll find plenty of places to visit near Ponce: Volkylandia Volkswagen Museum (in Yauco), Bosque Estatal de Guanica (in Guanica) and La Parguera (Playa Rosada & Isla Mata La Gata). Next up on the itinerary: examine the collection at Parque de Bombas, tour the pleasant surroundings at La Guancha de Ponce, contemplate in the serene atmosphere at Cathedral of our Lady of Guadaloupe, and get engrossed in the history at Casa Museo Federico Degetau.

For maps, photos, traveler tips, and more tourist information, read Ponce trip itinerary maker site.

Getting from Culebra to Ponce by combination of ferry and car takes about 4 hours. Other options: do a combination of flight and shuttle; or do a combination of ferry, taxi, bus, and car. October in Ponce sees daily highs of 85°F and lows of 75°F at night. Finish up your sightseeing early on the 26th (Thu) so you can go by car to Aguadilla.

Things to do in Ponce

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Oct 15 — 26:

Aguadilla

— 10 nights

Garden of the Atlantic

Destroyed over the centuries by earthquakes and hurricanes, resilient Aguadilla now serves as one of Puerto Rico's top surfing destinations.
Take a break from the city and head to Jobos Beach and Parque Nacional de las Cavernas del Rio Camuy. Do some cultural sightseeing at Palacete Los Moreau and Arecibo Lighthouse & Historical Park. You'll find plenty of places to visit near Aguadilla: Penon Amador Beach (in Camuy), Cabo Rojo (Isla de Ratones & Playa Buye) and Rincon (Sandy Beach, Tres Palmas Marine Reserve, &more). And it doesn't end there: kick back and relax at Playa Crashboat, tee off at Bahia Beach Plantation, head outdoors with Pozo de Jacinto, and get your game on at Ice Skating.

Inspirock's itinerary builder makes planning a Aguadilla trip simple and quick.

Drive from Ponce to Aguadilla in 2 hours. In October, daytime highs in Aguadilla are 87°F, while nighttime lows are 74°F. Wrap up your sightseeing on the 5th (Sun) early enough to travel to Isla de Vieques.

Things to do in Aguadilla

Parks · Outdoors · Nature · Beaches

Side Trips

Find places to stay Oct 26 — Nov 5:

Isla de Vieques

— 11 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.
You'll get in some beach time at Balneario Sun Bay and Playa La Chiva. Your cultural itinerary includes sights like Puerto Ferro Lighthouse and Siddhia Hutchinson Fine Art Gallery. The adventure continues: head outdoors with Outdoor Activities, tour the pleasant surroundings at Playa Media Luna, take a pleasant ride with a tour on horseback, and kick back and relax at Playa Navio.

To see where to stay, maps, other places to visit, and tourist information, go to the Isla de Vieques trip itinerary planner.

You can do a combination of car and ferry from Aguadilla to Isla de Vieques in 4.5 hours. Other options are to fly; or do a combination of car, shuttle, taxi, and ferry. Expect a daytime high around 86°F in November, and nighttime lows around 75°F. Wrap up your sightseeing on the 16th (Thu) early enough to fly to San Juan.

Things to do in Isla de Vieques

Outdoors · Parks · Beaches · Tours
Find places to stay Nov 5 — 16:

San Juan

— 14 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.
Your itinerary includes some good beach time at Playa Luquillo and Carolina Beach. Step out of the city life by going to El Yunque Rain Forest and Climbing Tours. Explore San Juan's surroundings by going to Dorado (Dorado Beach East & Dorado del Mar Golf Club), Scuba & Snorkeling (in Fajardo) and Carabali Rainforest Park (in Luquillo). There's still lots to do: appreciate the extensive heritage of Old San Juan, enjoy the sand and surf at Condado Beach, contemplate the long history of La Fortaleza - Palacio de Santa Catalina, and don't miss a visit to Paseo de la Princesa.

To find photos, traveler tips, reviews, and other tourist information, refer to the San Juan trip planner.

You can fly from Isla de Vieques to San Juan in 2 hours. Other options are to do a combination of ferry and car; or do a combination of ferry, taxi, and shuttle. November in San Juan sees daily highs of 87°F and lows of 76°F at night. On the 30th (Thu), wrap the sightseeing up by early afternoon so you can fly back home.

Things to do in San Juan

Outdoors · Parks · Beaches · Tours

Side Trips

Find places to stay Nov 16 — 30:

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.