20 days in San Francisco, Puerto Rico & Chicago Itinerary

20 days in San Francisco, Puerto Rico & Chicago Itinerary

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20 days in San Francisco, Puerto Rico & Chicago Itinerary

Melbourne, Australia
Fly:  20​h 15​min
San Francisco, United States
— 3 nights
Fly + Drive:  13​h 45​min
San Juan, Puerto Rico
— 4 nights
Fly + taxi:  30​min
Isla de Vieques, Puerto Rico
— 2 nights
taxi + Fly + Drive:  2​h
Ponce, Puerto Rico
— 3 nights
Drive + Fly:  1​h 45​min
Culebra, Puerto Rico
— 2 nights
Fly:  9​h
Chicago, United States
— 3 nights
Fly:  22​h 45​min
Melbourne, Australia

3
days
San Francisco, United States

San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Let the collections at Exploratorium and Asian Art Museum capture your imagination. Your inner history buff will appreciate Alcatraz Island and Filbert Steps. There's still lots to do: snap pictures at Golden Gate Bridge, engage your brain at California Academy of Sciences, see the interesting displays at Cable Car Museum, and take in the spiritual surroundings of Grace Cathedral.

For where to stay, traveler tips, reviews, and other tourist information, read our San Francisco travel planner.

Melbourne, Australia to San Francisco is an approximately 20.5-hour flight. You'll gain 18 hours traveling from Melbourne to San Francisco due to the time zone difference. Expect much colder weather when traveling from Melbourne in January: highs in San Francisco hover around 17°C, while lows dip to 8°C. Wrap up your sightseeing on the 4th (Thu) early enough to travel to San Juan.

Things to do in San Francisco

Museums Childrens Museums Historic Sites
Highlights from your plan
Exploratorium
Alcatraz Island
SS Jeremiah O'Brien

3
days
San Juan, Puerto Rico

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
You'll explore the less-touristy side of things at Estudio de Arte Samuel Lind and Cathedral of San Juan Bautista. Popular historic sites such as Old San Juan and Paseo de la Princesa are in your itinerary. Next up on the itinerary: explore the world behind art at Museo De Arte De Puerto Rico, appreciate the extensive heritage of San Juan National Historic Site, get interesting insight from Tours, and look for gifts at Ole Curiosidades.

For photos, ratings, and other tourist information, read San Juan itinerary builder.

Do a combination of flight and car from San Francisco to San Juan in 14 hours. The time zone difference when traveling from San Francisco to San Juan is 4 hours. Expect much hotter temperatures when traveling from San Francisco in January; daily highs in San Juan reach 34°C and lows reach 26°C. Finish your sightseeing early on the 8th (Mon) so you can travel to Isla de Vieques.

Things to do in San Juan

Historic Sites Tours Museums

Side Trip

Estudio de Arte Samuel Lind
Highlights from your plan
Old San Juan
Estudio de Arte Samuel Lind
Paseo de la Princesa

3
days
Isla de Vieques, Puerto Rico

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 explore and learn at Siddhia Hutchinson Fine Art Gallery and Fortin Conde de Mirasol Museum. Discover out-of-the-way places like Gallery Galleon and Caracas Beach. There's much more to do: explore the activities along Sun Bay, get great views at Puerto Ferro Lighthouse, and tour the pleasant surroundings at Blue Beach.

To find maps, more things to do, reviews, and tourist information, read our Isla de Vieques travel itinerary planner.

Isla de Vieques is very close to San Juan. In January, daytime highs in Isla de Vieques are 32°C, while nighttime lows are 26°C. Finish your sightseeing early on the 10th (Wed) to allow enough time to travel to Ponce.

Things to do in Isla de Vieques

Outdoors Beaches Parks
Highlights from your plan
Caracas Beach
Blue Beach
Sun Bay

2
days
Ponce, Puerto Rico

Ponce is both a city and a municipality in the southern part of Puerto Rico. Start off your visit on the 11th (Thu): explore the world behind art at Casa Museo Federico Degetau, take an in-depth tour of Ponce History Museum, and then get engrossed in the history at Museo de Arte de Ponce. Here are some ideas for day two: enjoy the sea views from Cardona Island Light, then examine the collection at El Museo Castillo Serralles, then examine the collection at Parque de Bombas, and finally take in the spiritual surroundings of Cathedral of our Lady of Guadaloupe.

For photos, where to stay, other places to visit, and more tourist information, read Ponce travel planner.

Traveling by combination of taxi, flight, and car from Isla de Vieques to Ponce takes 2 hours. Alternatively, you can do a combination of taxi and flight. In January, plan for daily highs up to 34°C, and evening lows to 24°C. Finish your sightseeing early on the 13th (Sat) so you can travel to Culebra.

Things to do in Ponce

Museums Historic Sites

Side Trip

Casa Museo Federico Degetau
Highlights from your plan
Museo de Arte de Ponce
Casa Museo Federico Degetau
Cardona Island Light

2
days
Culebra, Puerto Rico

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
On the 13th (Sat), kick back and relax at Flamenco Beach. Get ready for a full day of sightseeing on the 14th (Sun): kick back and relax at Carlos Rosario Beach, then enjoy the sand and surf at Tamarindo Beach, and then examine the collection at Museo Histotico de Culebra.

For where to stay, more things to do, maps, and tourist information, refer to the Culebra itinerary builder.

Do a combination of car and flight from Ponce to Culebra in 2 hours. Alternatively, you can do a combination of taxi and flight. In January, daytime highs in Culebra are 33°C, while nighttime lows are 26°C. Wrap up your sightseeing on the 15th (Mon) to allow time to travel to Chicago.

Things to do in Culebra

Outdoors Beaches Parks
Highlights from your plan
Flamenco Beach
Tamarindo Beach

3
days
Chicago, United States

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Eschew the tourist crowds and head to International Walldog Mural & Sign Art Museum and Pontiac-Oakland Automobile Museum. Let the collections at The Art Institute of Chicago and Museum of Science and Industry, Chicago capture your imagination. You'll find plenty of places to visit near Chicago: La Porte County Historical Society (in LaPorte) and Livingston County War Museum (in Pontiac). There's still lots to do: examine the collection at The Field Museum, make a trip to Millennium Park, and explore the galleries of Chicago Cultural Center.

To see more things to do, reviews, and tourist information, refer to the Chicago itinerary builder.

Traveling by flight from Culebra to Chicago takes 9 hours. Traveling from Culebra to Chicago, you'll gain 2 hours due to the time zone difference. Plan for colder temperatures traveling from Culebra in January, with highs in Chicago at 0°C and lows at -8°C. Wrap up your sightseeing on the 18th (Thu) to allow time to travel back home.

Things to do in Chicago

Museums Childrens Museums Parks

Side Trips

Pontiac, La Porte County Historical Society
Highlights from your plan
The Art Institute of Chicago
Pontiac-Oakland Automobile Museum
Millennium Park

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