59 days in United States, South America & Caribbean Itinerary

59 days in United States, South America & Caribbean Itinerary

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Route & dates

59 days in United States, South America & Caribbean Itinerary

Start: Wroclaw, Poland
Fly:  14 h
1
New York City, United States
— 4 nights
Train:  1 h 45 min
2
Philadelphia, United States
— 3 nights
Fly:  4 h
3
Chicago, United States
— 4 nights
Fly:  6 h 15 min
4
San Francisco, United States
— 2 nights
Fly:  7 h 30 min
5
Honolulu, United States
— 14 nights
Fly:  7 h 30 min
6
San Diego, United States
— 3 nights
Drive:  2 h 15 min
7
Los Angeles, United States
— 1 night
Fly:  10 h
8
Lima, Peru
— 13 nights
Fly:  4 h 15 min
9
Cartagena, Colombia
— 3 nights
Fly:  5 h 30 min
10
Havana, Cuba
— 5 nights
Fly:  4 h
11
Miami, United States
— 2 nights
Fly:  15 h 30 min
End: Wroclaw, Poland

4
nights
New York City, United States

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for museums, nightlife, and shopping. Your plan includes some of its best attractions: take in the pleasant sights at Central Park, browse the exhibits of 9/11 Memorial, make a trip to Rockefeller Center, and admire the striking features of Grand Central Terminal.

To see reviews, other places to visit, photos, and other tourist information, you can read our New York City holiday planner.

Wroclaw, Poland to New York City is an approximately 14-hour flight. You can also do a combination of flight and bus; or do a combination of train and flight. Traveling from Wroclaw to New York City, you'll gain 6 hours due to the time zone difference. Prepare for somewhat warmer weather when traveling from Wroclaw in October: high temperatures in New York City hover around 24°C and lows are around 16°C. Wrap up your sightseeing on the 5th (Mon) early enough to take a train to Philadelphia.

Things to do in New York City

Parks Museums Historic Sites
Find places to stay Oct 1 — 5:
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

3
nights
Philadelphia, United States

Philadelphia ©
Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
You'll find plenty of places to visit near Philadelphia: Longwood Gardens (in Kennett Square) and Brandywine Battlefield (in Chadds Ford). There's lots more to do: ponder the world of politics at Independence Hall, trek along Kelly Drive, browse the eclectic array of goods at Reading Terminal Market, and admire the masterpieces at Barnes Foundation.

To see topicsMoreInfo.option.ratings, traveler tips, photos, and more tourist information, use the Philadelphia route maker website .

Traveling by train from New York City to Philadelphia takes 2 hours. Alternatively, you can drive; or take a bus. In October, daytime highs in Philadelphia are 24°C, while nighttime lows are 13°C. Finish your sightseeing early on the 8th (Thu) so you can travel to Chicago.

Things to do in Philadelphia

Museums Parks Historic Sites

Side Trips

Brandywine Battlefield, Longwood Gardens, Harrah's Philadelphia
Find places to stay Oct 5 — 8:
Highlights from your plan
Eastern State Penitentiary ©
Eastern State Penitentiary
Longwood Gardens ©
Longwood Gardens
Independence Hall ©
Independence Hall

4
nights
Chicago, United States

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, take in the waterfront at Navy Pier, stroll around Millennium Park, and enjoy breathtaking views from 360 Chicago Observation Deck.

To find traveler tips, topicsMoreInfo.option.ratings, other places to visit, and tourist information, you can read our Chicago online vacation planner .

Traveling by flight from Philadelphia to Chicago takes 4 hours. Alternatively, you can do a combination of train and flight; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Philadelphia to Chicago. In October in Chicago, expect temperatures between 21°C during the day and 11°C at night. Wrap up your sightseeing on the 12th (Mon) to allow time to travel to San Francisco.

Things to do in Chicago

Museums Parks Childrens Museums
Find places to stay Oct 8 — 12:
Highlights from your plan
Ragnarok Axe Throwing ©
Ragnarok Axe Throwing
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

2
nights
San Francisco, United States

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Kick off your visit on the 13th (Tue): explore the wealth of natural beauty at Alcatraz Island, take in the waterfront at Fisherman's Wharf, and then contemplate the long history of Golden Gate Bridge. On the 14th (Wed), you'll have a packed day of sightseeing: see the interesting displays at Exploratorium and then stroll around Golden Gate Park.

To see where to stay, reviews, traveler tips, and tourist information, go to the San Francisco trip builder app .

Traveling by flight from Chicago to San Francisco takes 6.5 hours. Alternatively, you can do a combination of flight and train; or drive. The time zone difference when traveling from Chicago to San Francisco is minus 2 hours. Traveling from Chicago in October, things will get a bit warmer in San Francisco: highs are around 26°C and lows about 15°C. Wrap up your sightseeing on the 15th (Thu) early enough to travel to Honolulu.

Things to do in San Francisco

Parks Historic Sites Museums
Find places to stay Oct 12 — 15:
Highlights from your plan
Alcatraz Island ©
Alcatraz Island
Golden Gate Bridge ©
Golden Gate Bridge
Fisherman's Wharf ©
Fisherman's Wharf

14
nights
Honolulu, United States

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Get out of town with these interesting Honolulu side-trips: Pu’u O Mahuka Heiau State Monument (in Pupukea), Kailua (Kailua Beach Park & Lanikai Beach) and Haleiwa (Sunset Beach Park, Waimea Bay, &more). The adventure continues: explore the different monuments and memorials at USS Arizona Memorial, find your balance on the water with categoryPhrases.alias.some_of_the_best_stand_up_paddleboarding_in_the_area, buy something for everyone on your list at Ala Moana Center, and identify plant and animal life at Hanauma Bay Nature Preserve.

To see where to stay, topicsMoreInfo.option.ratings, reviews, and other tourist information, read Honolulu trip itinerary planner.

You can fly from San Francisco to Honolulu in 7.5 hours. Alternatively, you can do a combination of train and flight. The time zone changes from Pacific Standard Time to Hawaii Standard Time, which is usually a -2 hour difference. In October, Honolulu is somewhat warmer than San Francisco - with highs of 36°C and lows of 27°C. Cap off your sightseeing on the 29th (Thu) early enough to travel to San Diego.

Things to do in Honolulu

Outdoors Parks Beaches

Side Trips

Haleiwa, Kailua, Oahu, Laie, Mermaid Caves
Find places to stay Oct 15 — 29:
Highlights from your plan
Stand-Up Paddleboarding
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach

3
nights
San Diego, United States

San Diego ©
Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.
San Diego is known for zoos & aquariums, museums, and beaches. Your plan includes some of its best attractions: learn about wildlife with up-close encounters at San Diego Zoo, let the kids burn off some steam at Balboa Park, meet the residents at SeaWorld San Diego, and explore the galleries of Maritime Museum of San Diego.

Plan my San Diego trip by asking Inpirock to come up with tips and suggestions.

You can fly from Honolulu to San Diego in 7.5 hours. The time zone difference moving from Hawaii Standard Time to Pacific Standard Time is 2 hours. In October, San Diego is slightly colder than Honolulu - with highs of 30°C and lows of 20°C. Finish up your sightseeing early on the 2nd (Mon) so you can go by car to Los Angeles.

Things to do in San Diego

Parks Zoos & Aquariums Museums
Find places to stay Oct 29 — Nov 2:
Highlights from your plan
San Diego Zoo ©
San Diego Zoo
USS Midway Museum ©
USS Midway Museum
Balboa Park ©
Balboa Park

1
night
Los Angeles, United States

Los Angeles ©
Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Start off your visit on the 2nd (Mon): make a trip to Santa Monica Pier and then make an unforgettable trip to Disneyland Park.

To find other places to visit, maps, traveler tips, and other tourist information, you can read our Los Angeles trip itinerary maker app .

Traveling by car from San Diego to Los Angeles takes 2.5 hours. Alternatively, you can take a bus; or fly. In November in Los Angeles, expect temperatures between 28°C during the day and 15°C at night. You will have some time to spend on the 3rd (Tue) before leaving for Lima.

Things to do in Los Angeles

Theme Parks Historic Sites

Side Trips

Santa Monica Pier, Disneyland Park
Find places to stay Nov 2 — 3:
Highlights from your plan
Disneyland Park ©
Disneyland Park
Santa Monica Pier ©
Santa Monica Pier
Hollywood Walk of Fame ©
Hollywood Walk of Fame

13
nights
Lima, Peru

Founded in 1535 by Spanish explorer Francisco Pizarro, Lima represents an interesting blend of modern attractions and preserved colonial architecture, much of it clustered in the World Heritage-listed city center.
Change things up with a short trip to El Canon de Austisha in Huarochiri (about 2 hours away). Next up on the itinerary: admire the local landmark of Plaza de Armas (Plaza Mayor), indulge your taste buds at Food & Drink, get engrossed in the history at Museo Larco, and visit Miraflores.

To find where to stay, topicsMoreInfo.option.ratings, photos, and other tourist information, read our Lima online tour planner .

Getting from Los Angeles to Lima by flight takes about 10 hours. Other options: do a combination of bus and flight. The time zone difference moving from Pacific Standard Time (PST) to Peru Time (PET) is 3 hours. Plan for somewhat warmer nights when traveling from Los Angeles in November since evenings lows in Lima dip to 20°C. Finish up your sightseeing early on the 17th (Tue) so you can travel to Cartagena.

Things to do in Lima

Outdoors Tours Historic Sites

Side Trip

El Canon de Austisha
Find places to stay Nov 3 — 17:
Highlights from your plan
Nature & Wildlife Tours
Plaza de Armas (Plaza Mayor) ©
Plaza de Armas (Plaza Mayor)
Museo Larco ©
Museo Larco

3
nights
Cartagena, Colombia

Cartagena ©
The site of the continent's first Spanish colony, Cartagena retains much of its colonial flavor thanks to a World Heritage-listed old town, encircled by old walls and protected by imposing fortresses.
Cartagena is known for historic sites, museums, and nightlife. Your plan includes some of its best attractions: contemplate the long history of Walled City of Cartagena, gain insight at Plaza Santo Domingo, step into the grandiose world of Castillo de San Felipe de Barajas, and don't miss a visit to Plaza Bolivar.

For more things to do, where to stay, maps, and tourist information, go to the Cartagena road trip site .

You can fly from Lima to Cartagena in 4.5 hours. Alternatively, you can drive; or do a combination of bus and taxi. In November, Cartagena is somewhat warmer than Lima - with highs of 37°C and lows of 30°C. Wrap up your sightseeing on the 20th (Fri) early enough to travel to Havana.

Things to do in Cartagena

Historic Sites Tours Outdoors
Find places to stay Nov 17 — 20:
Highlights from your plan
Castillo de San Felipe de Barajas ©
Castillo de San Felipe de Barajas
Walled City of Cartagena ©
Walled City of Cartagena
Speed Boats Tours

5
nights
Havana, Cuba

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Take a break from Havana with a short trip to Sirena Beach in Cayo Largo, about 2 hours away. Next up on the itinerary: don't miss a visit to Malecón of Havana, contemplate the long history of Fortaleza de San Carlos de la Cabana, take an in-depth tour of Museum of the Revolution (Museo de la Revolucion), and take in the local highlights with Walking tours.

To find other places to visit, traveler tips, more things to do, and more tourist information, go to the Havana trip itinerary maker website .

Fly from Cartagena to Havana in 5.5 hours. Expect little chillier temperatures when traveling from Cartagena in November; daily highs in Havana reach 33°C and lows reach 21°C. Wrap up your sightseeing on the 25th (Wed) early enough to travel to Miami.

Things to do in Havana

Historic Sites Tours Museums

Side Trip

Sirena Beach
Find places to stay Nov 20 — 25:
Highlights from your plan
Walking tours
Malecón of Havana ©
Malecón of Havana
Fortaleza de San Carlos de la Cabana ©
Fortaleza de San Carlos de la Cabana

2
nights
Miami, United States

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Start off your visit on the 26th (Thu): examine the collection at Vizcaya Museum and Gardens, then have fun at Lock & Load Miami, then see the interesting displays at Lock & Load Museum, and finally buy something for everyone on your list at Bayside Marketplace. Keep things going the next day: get some thrills out on the water with a waterskiing or jet-skiing adventure, then kick back and relax at South Beach, and then buy something for everyone on your list at Dolphin Mall.

To find topicsMoreInfo.option.ratings, other places to visit, and more tourist information, read Miami online travel route planner .

You can fly from Havana to Miami in 4 hours. Another option is to do a combination of flight and train. In November in Miami, expect temperatures between 32°C during the day and 24°C at night. Finish up your sightseeing early on the 27th (Fri) so you can travel back home.

Things to do in Miami

Shopping Museums Outdoors

Side Trip

South Beach
Find places to stay Nov 25 — 27:
Highlights from your plan
Lock & Load Museum ©
Lock & Load Museum
South Beach ©
South Beach
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens

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