59 days in Caribbean, United States, Mexico, Central America, South America & Africa Itinerary

59 days in Caribbean, United States, Mexico, Central America, South America & Africa Itinerary

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Route & dates

59 days in Caribbean, United States, Mexico, Central America, South America & Africa Itinerary

Start: Philadelphia, United States
Fly:  8​h 15​min
1
San Juan, Puerto Rico
— 5 nights
Fly:  4​h 15​min
2
Punta Cana, Dominican Republic
— 4 nights
+2
shuttle + taxi + Fly:  3​h
3
Port-au-Prince, Haiti
— 1 night
Fly:  7​h 45​min
4
Kingston, Jamaica
— 1 night
Fly:  21​h 15​min
5
Honolulu, United States
— 4 nights
Fly:  15​h 30​min
6
Guadalajara, Mexico
— 3 nights
Fly:  5​h 15​min
7
Puebla, Mexico
— 2 nights
8
Mexico City, Mexico
— 5 nights
Fly:  6​h 15​min
9
San Jose, Costa Rica
— 2 nights
Fly + Drive:  12​h
10
Machu Picchu, Peru
— 4 nights
+4
train + foot + bus + taxi + Fly:  14​h 15​min
11
Rio de Janeiro, Brazil
— 5 nights
Fly:  1​h 15​min
12
Sao Paulo, Brazil
— 4 nights
+2
Fly + foot + train:  14​h 15​min
13
Johannesburg, South Africa
— 3 nights
Fly:  8​h 30​min
14
Paje, Tanzania
— 1 night
Drive:  1​h 15​min
15
Zanzibar City, Tanzania
— 2 nights
Fly:  9​h
16
Cape Town, South Africa
— 7 nights
Fly + train:  22​h 45​min
End: Philadelphia, United States

5
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Deepen your sense of the past at sights like Old San Juan and San Juan National Historic Site. Museum-lovers will appreciate Museo de Arte de Ponce and Museo de Casa Blanca. Get out of town with these interesting San Juan side-trips: Puerto Rico Premium Outlets (in Barceloneta), Caribbean Trading Company Store (in Palmer) and El Yunque National Forest (Luquillo Beach & El Yunque Rain Forest). Next up on the itinerary: stroll through Condado Beach, look for gifts at Puerto Rican Art & Crafts, buy something for everyone on your list at Plaza las Americas, and kick back and relax at Carolina Beach.

For reviews, where to stay, other places to visit, and other tourist information, use the San Juan trip planner .

Philadelphia, USA to San Juan is an approximately 7-hour flight. You can also do a combination of train and flight; or do a combination of train and flight. The time zone difference when traveling from Philadelphia to San Juan is 1 hour. Traveling from Philadelphia in June, San Juan is a bit warmer at night with lows of 78°F. Finish your sightseeing early on the 17th (Mon) to allow enough time to travel to Punta Cana.

Things to do in San Juan

Parks Outdoors Beaches

Side Trips

Carolina, El Yunque National Forest, Museo de Arte de Ponce, Caribbean Trading Company Store, Puerto Rico Premium Outlets
Find places to stay Jun 12 — 17:
Highlights from your plan
Pine Grove Beach ©
Pine Grove Beach
Old San Juan ©
Old San Juan
Museo de Arte de Ponce ©
Museo de Arte de Ponce

4
nights
Punta Cana, Dominican Republic

Punta Cana ©
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Head to La Perla Dominicana and Life is goodfor some retail therapy. Your cultural itinerary includes sights like Altos de Chavon and Aromas Museum. The adventure continues: kick back and relax at Bavaro Beach, look for gifts at HARRISON'S Fine Caribbean Jewelers, don't miss a visit to Jesus Maestro Parish, and tour the pleasant surroundings at Macao Beach.

To find maps, traveler tips, photos, and tourist information, refer to the Punta Cana driving holiday app .

Getting from San Juan to Punta Cana by flight takes about 4.5 hours. Other options: do a combination of flight and shuttle; or do a combination of ferry and bus. In June in Punta Cana, expect temperatures between 87°F during the day and 76°F at night. Wrap up your sightseeing on the 21st (Fri) to allow time to travel to Port-au-Prince.

Things to do in Punta Cana

Outdoors Shopping Tours

Side Trip

Altos de Chavon
Find places to stay Jun 17 — 21:
Highlights from your plan
Bavaro Beach ©
Bavaro Beach
Altos de Chavon ©
Altos de Chavon
Macao Beach ©
Macao Beach

1
night
Port-au-Prince, Haiti

Port-au-Prince ©
Port-au-Prince, the capital of Haiti, gives most visitors their first taste of the country, along with all of its rugged and lively charm.
Start off your visit on the 21st (Fri): explore the world behind art at Village Artistique de Noailles, delve into the distant past at Papillon Enterprise, sample the tasty concoctions at Barbancourt Rum Distillery, explore and take pictures at Place Saint-Pierre, then look for gifts at Comite Artisanal Haitien, and finally make a trip to Champ de Mars.

To see ratings, traveler tips, reviews, and more tourist information, refer to the Port-au-Prince online journey maker .

You can do a combination of shuttle and flight from Punta Cana to Port-au-Prince in 3 hours. Alternatively, you can drive; or take a bus. You'll gain 1 hour traveling from Punta Cana to Port-au-Prince due to the time zone difference. Expect a bit warmer weather when traveling from Punta Cana in June: highs in Port-au-Prince hover around 93°F, while lows dip to 81°F. You will have some time to spend on the 22nd (Sat) before leaving for Kingston.

Things to do in Port-au-Prince

Shopping Parks Historic Sites

Side Trips

Village Artistique de Noailles, Place Saint-Pierre
Find places to stay Jun 21 — 22:
Highlights from your plan
Papillon Enterprise ©
Papillon Enterprise
Musee du Pantheon National Haitien ©
Village Artistique de Noailles ©
Village Artistique de Noailles

1
night
Kingston, Jamaica

Kingston ©
The country's capital, Kingston offers all the excitement of a lively and storied city, while also housing the services and facilities travelers need to get around and see the rest of the island.
Kick off your visit on the 22nd (Sat): enjoy the scholastic atmosphere at University Of The West Indies - Mona and then take an in-depth tour of Institute of Jamaica.

Start your trip to Kingston by creating a personalized itinerary on Inspirock.

Explore your travel options from Port-au-Prince to Kingston with the Route module. In June in Kingston, expect temperatures between 90°F during the day and 78°F at night. Wrap up your sightseeing on the 23rd (Sun) to allow time to travel to Honolulu.

Things to do in Kingston

Parks Historic Sites Outdoors

Side Trip

Hellshire Beach
Find places to stay Jun 22 — 23:
Highlights from your plan
Hellshire Beach ©
Hellshire Beach
Port Royal ©
Port Royal
Devon House ©
Devon House

4
nights
Honolulu, United States

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Get some historical perspective at USS Arizona Memorial and Iolani Palace. Give yourself a bit of retail therapy at Polynesian Cultural Center and Royal Hawaiian Center. Change things up with these side-trips from Honolulu: Pu’u O Mahuka Heiau State Monument (in Pupukea) and Haleiwa (Sunset Beach Park & Waimea Bay). Next up on the itinerary: kick back and relax at Waikiki Beach, identify plant and animal life at Hanauma Bay Nature Preserve, examine the collection at USS Bowfin Submarine Museum & Park, and browse the different shops at Ala Moana Center.

To find other places to visit, where to stay, photos, and more tourist information, you can read our Honolulu road trip planning tool .

Explore your travel options from Kingston to Honolulu with the Route module. You'll gain 5 hours traveling from Kingston to Honolulu due to the time zone difference. In June, daily temperatures in Honolulu can reach 86°F, while at night they dip to 74°F. On the 28th (Fri), you're off toGuadalajara.

Things to do in Honolulu

Museums Parks Outdoors

Side Trips

Haleiwa, Nuuanu Pali Lookout, Polynesian Cultural Center, Pu’u O Mahuka Heiau State Monument
Find places to stay Jun 24 — 28:
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach
Sunset Beach Park ©
Sunset Beach Park

3
nights
Guadalajara, Mexico

Guadalajara ©
One of Mexico's cultural hubs, Guadalajara represents the home of mariachi music and hosts numerous large-scale events, ranging from international film festivals to celebrated book fairs.
Museum-lovers will get to explore Instituto Cultural Cabanas and Museo Pantaleon Panduro. Popular historic sites such as Palacio de Gobierno and Expiatory Temple are in your itinerary. Explore Guadalajara's surroundings by going to Chapala Malecon (in Chapala), Guachimontones (in Teuchitlan) and Mundo Cuervo La Rojena (in Tequila). There's still lots to do: take in the spiritual surroundings of Basilica de Zapopan, pause for some serene contemplation at Guadalajara Cathedral, view the masterpieces at Tlaquepaque and Tonala Artisans Tour, and buy something for everyone on your list at Andares.

For traveler tips, more things to do, photos, and other tourist information, refer to the Guadalajara road trip app .

Traveling by flight from Honolulu to Guadalajara takes 14 hours. Alternatively, you can do a combination of flight and bus. The time zone changes from Hawaii Standard Time (HST) to Central Standard Time (CST), which is usually a 4 hour difference. Traveling from Honolulu in June, you can expect nighttime temperatures to be slightly colder in Guadalajara, with lows of 63°F. On the 2nd (Tue), wrap the sightseeing up by early afternoon so you can travel to Puebla.

Things to do in Guadalajara

Historic Sites Parks Museums

Side Trips

Tlaquepaque, Chapala Malecon, Guachimontones, Mundo Cuervo La Rojena, Ajijic Malecon
Find places to stay Jun 28 — Jul 2:
Highlights from your plan
Guachimontones ©
Guachimontones
Museo Pantaleon Panduro ©
Museo Pantaleon Panduro
Palacio de Gobierno ©
Palacio de Gobierno

2
nights
Puebla, Mexico

Puebla ©
Recognized as a World Heritage Site thanks to its photogenic colonial buildings, Puebla remains one of Mexico's top destinations for architecture enthusiasts.
On the 2nd (Tue), see the interesting displays at Museo de Arte Popular Santa Rosa de Lima and then contemplate in the serene atmosphere at Church of Santo Domingo (Iglesia de Santo Domingo). Here are some ideas for day two: take a stroll through Zocalo, see the interesting displays at Amparo Museum (Museo Amparo), pause for some serene contemplation at Catedral Basilica de Puebla, browse the collection at Biblioteca Palafoxiana, then tour the pleasant surroundings at Africam Safari, and finally shop like a local with Bazar los Sapos.

For other places to visit, reviews, where to stay, and tourist information, refer to the Puebla trip itinerary maker site .

Traveling by flight from Guadalajara to Puebla takes 3.5 hours. Alternatively, you can do a combination of flight and bus; or drive. Plan for a bit cooler nights when traveling from Guadalajara in July since evenings lows in Puebla dip to 52°F. Finish your sightseeing early on the 4th (Thu) to allow enough time to drive to Mexico City.

Things to do in Puebla

Historic Sites Parks Outdoors

Side Trips

San Pedro Cholula, Botanic Garden Comunitario Dra Helia Bravo Hollis
Find places to stay Jul 2 — 4:
Highlights from your plan
Rosary Chapel (Capilla del Rosario) ©
Church of Santa Maria Tonantzintla ©
Templo San Francisco Acatepec ©
Templo San Francisco Acatepec

5
nights
Mexico City, Mexico

Mexico City ©
Breathtakingly large, Mexico City provides a home for almost 9 million people living in nearly 1,700 distinct neighborhoods.
Your cultural itinerary includes sights like National Museum of Anthropology and Zona Arqueologica Teotihuacan. Popular historic sites such as Museo del Templo Mayor and Metropolitan Cathedral (Catedral Metropolitana) are in your itinerary. Explore the numerous day-trip ideas around Mexico City: Cuernavaca (Archaeological Zone of Xochicalco & Robert Brady Museum). There's lots more to do: admire the masterpieces at Palacio de Bellas Artes, examine the collection at Museo Dolores Olmedo Patino, contemplate the long history of Historic Center (Centro Historico), and step into the grandiose world of Chapultepec Castle.

To find photos, where to stay, other places to visit, and more tourist information, read our Mexico City trip maker tool .

You can drive from Puebla to Mexico City in 1.5 hours. Alternatively, you can take a bus; or take a shuttle. July in Mexico City sees daily highs of 74°F and lows of 56°F at night. Wrap up your sightseeing on the 9th (Tue) early enough to travel to San Jose.

Things to do in Mexico City

Historic Sites Museums Neighborhoods

Side Trips

Cuernavaca, Zona Arqueologica Teotihuacan
Find places to stay Jul 4 — 9:
Highlights from your plan
National Museum of Anthropology ©
National Museum of Anthropology
Zona Arqueologica Teotihuacan ©
Zona Arqueologica Teotihuacan
Palacio de Bellas Artes ©
Palacio de Bellas Artes

2
nights
San Jose, Costa Rica

San Jose ©
A trip to San Jose, the capital, commercial center, and cultural hub of Costa Rica, gives you a chance to experience the lively atmosphere and rich cultural past of this vibrant country.
Kick off your visit on the 9th (Tue): get engrossed in the history at Jade Museum, take an in-depth tour of National Museum (Museo Nacional), look for gifts at Chieton Moren, don't miss a visit to Mercado Nacional de Artesanias, then browse the eclectic array of goods at Central Market (Mercado Central), and finally wander the streets of Multiplaza. Get ready for a full day of sightseeing on the 10th (Wed): let the river carry you with a rafting and tubing tour, steep yourself in history at Our Lady of the Angels Basilica (Basilica de Nuestra Senora de Los Angeles), admire the masterpieces at Precolumbian Gold Museum, then admire the masterpieces at Museo de Arte Costarricense, then tour the pleasant surroundings at Parque La Sabana, and finally take in the exciting artwork at Galeria Namu.

Plan a trip to San Jose easily and quickly by telling Inspirock to suggest an itinerary.

Fly from Mexico City to San Jose in 6.5 hours. Alternatively, you can drive; or take a bus. Plan for a bit warmer temperatures traveling from Mexico City in July, with highs in San Jose at 80°F and lows at 67°F. Wrap up your sightseeing on the 11th (Thu) early enough to travel to Machu Picchu.

Things to do in San Jose

Museums Shopping Adventure

Side Trips

Our Lady of the Angels Basilica (Basilica de Nuestra Senora de Los Angeles), Multiplaza
Find places to stay Jul 9 — 11:
Highlights from your plan

4
nights
Machu Picchu, Peru

Machu Picchu ©
A symbol of the Incan civilization, the abandoned city of Machu Picchu represents a must-see on a Peru vacation.
Head to Misha Wasi and Mercado de Artesaniasfor some retail therapy. Appreciate the collections at Choco Museo and Museo de Sitio Manuel Chavez Ballon. Venture out of the city with trips to Maras (Moray & Salinas de Maras), Ollantaytambo (Naupa Iglesia, Inka Pintay, & more) and Cerveceria del Valle Sagrado (in Urubamba). Next up on the itinerary: delve into the distant past at Santuario Historico de Machu Picchu, look for gifts at Machu Picchu market adjacent to the train station, admire the natural beauty at Los Jardines de Mandor, and snap pictures at Inca Bridge.

For reviews, ratings, photos, and tourist information, you can read our Machu Picchu planning app .

You can do a combination of flight and car from San Jose to Machu Picchu in 18 hours. Due to the time zone difference, you'll lose 1 hour traveling from San Jose to Machu Picchu. On the 15th (Mon), you'll have the morning to explore before heading off to Rio de Janeiro.

Things to do in Machu Picchu

Historic Sites Parks Nature

Side Trips

Ollantaytambo, Maras, Cerveceria del Valle Sagrado
Find places to stay Jul 11 — 15:
Highlights from your plan
Santuario Historico de Machu Picchu ©
Salinas de Maras ©
Salinas de Maras
Winay Wayna ©
Winay Wayna

5
nights
Rio de Janeiro, Brazil

Rio de Janeiro ©
Bustling with samba music and all-night street parties, no city encapsulates the spirit of Brazil better than Rio de Janeiro.
Centro Cultural Municipal Parque das Ruinas and Museu Historico do Exercito e Forte de Copacabana will appeal to museum buffs. We've included these beaches for you: Copacabana Beach and Leblon Beach. Explore Rio de Janeiro's surroundings by going to Petropolis (Catedral de Sao Pedro de Alcantara & Imperial Museum) and Museum of Contemporary Art (in Niteroi). The adventure continues: enjoy the sand and surf at Praia de Ipanema, tour the pleasant surroundings at Pedra do Arpoador, take a stroll through Santa Teresa, and step into the grandiose world of Ilha Fiscal.

Inspirock's itinerary builder makes planning a Rio de Janeiro trip simple and quick.

Do a combination of train, bus, and flight from Machu Picchu to Rio de Janeiro in 17.5 hours. Alternatively, you can drive; or do a combination of train and bus. You'll lose 2 hours traveling from Machu Picchu to Rio de Janeiro due to the time zone difference. In July, daytime highs in Rio de Janeiro are 78°F, while nighttime lows are 66°F. Wrap up your sightseeing on the 21st (Sun) to allow time to travel to Sao Paulo.

Things to do in Rio de Janeiro

Parks Outdoors Beaches

Side Trips

Petropolis, Museum of Contemporary Art
Find places to stay Jul 15 — 21:
Highlights from your plan
Copacabana Beach ©
Copacabana Beach
Praia de Ipanema
Praia de Ipanema
Corcovado Christ the Redeemer ©
Corcovado Christ the Redeemer

4
nights
Sao Paulo, Brazil

Sao Paulo ©
Don't let the city's nickname--"Land of Drizzle"--dampen your spirits during a trip to Sao Paulo.
Get some cultural insight at Paulista Avenue and Football Museum. Get some historical perspective at Mosteiro De Sao Bento and Catedral da Se de Sao Paulo. You'll find plenty of places to visit near Sao Paulo: Tombo beach (in Guaruja) and Juquehy Beach (in Sao Sebastiao). And it doesn't end there: pick up some local products at Mercadao - Sao Paulo Municipal Market, take a stroll around The Julio Prestes Cultural Center - Sala Sao Paulo, admire the masterpieces at Pinacoteca do Estado de Sao Paulo, and take a stroll through Liberdade.

To see reviews, where to stay, photos, and tourist information, read our Sao Paulo online travel planner .

You can fly from Rio de Janeiro to Sao Paulo in 1.5 hours. Alternatively, you can do a combination of flight and bus; or drive. Traveling from Rio de Janeiro in July, things will get a bit cooler in Sao Paulo: highs are around 72°F and lows about 55°F. You will have some time to spend on the 25th (Thu) before leaving for Johannesburg.

Things to do in Sao Paulo

Shopping Museums Neighborhoods

Side Trips

Tombo beach, Juquehy Beach
Find places to stay Jul 21 — 25:
Highlights from your plan
Paulista Avenue ©
Paulista Avenue
Pinacoteca do Estado de Sao Paulo ©
Pinacoteca do Estado de Sao Paulo

3
nights
Johannesburg, South Africa

Johannesburg ©
Founded when gold was discovered in the area in the late 19th century, Johannesburg quickly grew into a bustling metropolis, South Africa's largest city and the region's economic hub.
Apartheid Museum and Union Buildings are good opportunities to explore the local culture. For shopping fun, head to Neighbourgoods Market or Sandton City Shopping Centre. Go for a jaunt from Johannesburg to Centurion to see Irene Village Mall about 44 minutes away. The adventure continues: ponder the world of politics at Constitution Hill, try your luck at Emperors Palace, browse the different shops at 44 Stanley, and take a stroll through Maboneng Precinct.

For more things to do, other places to visit, reviews, and other tourist information, refer to the Johannesburg trip itinerary builder tool .

You can do a combination of flight and train from Sao Paulo to Johannesburg in 14.5 hours. The time zone difference when traveling from Sao Paulo to Johannesburg is 5 hours. Prepare for slightly colder weather when traveling from Sao Paulo in July: high temperatures in Johannesburg hover around 67°F and lows are around 40°F. Wrap up your sightseeing on the 29th (Mon) early enough to travel to Paje.

Things to do in Johannesburg

Fun & Games Casinos Shopping

Side Trips

Sandton, Union Buildings, Irene Village Mall, Emperors Palace
Find places to stay Jul 25 — 29:
Highlights from your plan
Apartheid Museum ©
Apartheid Museum
Constitution Hill ©
Constitution Hill
Maboneng Precinct ©
Maboneng Precinct

1
night
Paje, Tanzania

Paje ©
Located on the island of Unguja, the quaint village of Paje lies on a shallow sandy lagoon, which attracts swarms of kitesurfing enthusiasts and marine life lovers.
Kick off your visit on the 29th (Mon): explore the wealth of natural beauty at Jozani Chwaka Bay National Park.

To see traveler tips, photos, more things to do, and tourist information, read Paje trip maker tool .

Use the Route module to find suitable travel options from Johannesburg to Paje. The time zone difference when traveling from Johannesburg to Paje is 1 hour. Expect a bit warmer weather when traveling from Johannesburg in July: highs in Paje hover around 85°F, while lows dip to 72°F. Finish up your sightseeing early on the 30th (Tue) so you can go by car to Zanzibar City.

Things to do in Paje

Parks Nature Outdoors

Side Trip

Zanzibar Island
Find places to stay Jul 29 — 30:
Highlights from your plan
Paje Beach ©
Paje Beach
Jozani Chwaka Bay National Park ©
Jozani Chwaka Bay National Park
Scuba & Snorkeling

2
nights
Zanzibar City, Tanzania

Zanzibar City
Discover a myriad of attractions in Zanzibar City, like its World Heritage-listed historic core, charming beach villages, and the modern neighborhood of Ng'ambo.
Kick off your visit on the 30th (Tue): take in the architecture and atmosphere at Old Slave Market/Anglican Cathedral and then explore the ancient world of Hamamni Persian Baths.

To see where to stay, ratings, maps, and more tourist information, read our Zanzibar City trip itinerary maker tool .

Traveling by car from Paje to Zanzibar City takes an hour. In July, daytime highs in Zanzibar City are 85°F, while nighttime lows are 72°F. On the 1st (Thu), you'll have the morning to explore before heading off to Cape Town.

Things to do in Zanzibar City

Parks Shopping Historic Sites

Side Trip

Fahari Zanzibar
Find places to stay Jul 30 — Aug 1:
Highlights from your plan
Nakupenda Beach
Nakupenda Beach
Hamamni Persian Baths ©
Hamamni Persian Baths
House of Wonders (Beit-el-Ajaib) ©
House of Wonders (Beit-el-Ajaib)

7
nights
Cape Town, South Africa

Cape Town ©
Sweeping beaches, towering hilltops, and picturesque vineyards adorn the landscape of Cape Town, dominated by the imposing Table Mountain.
Popular historic sites such as Robben Island Museum and Maclear's Beacon are in your itinerary. District Six Museum and Iziko South African National Gallery will appeal to museum buffs. Take a break from Cape Town with a short trip to Dorp Street in Stellenbosch, about 50 minutes away. The adventure continues: admire all the interesting features of Greenmarket Square, learn about winemaking at Groot Constantia, kick back and relax at Boulders Beach, and take in the waterfront activity at Victoria & Alfred Waterfront.

For reviews, where to stay, maps, and other tourist information, read our Cape Town itinerary planner.

Getting from Zanzibar City to Cape Town by flight takes about 8 hours. Other options: do a combination of ferry, car, and bus. The time zone changes from Eastern African Time to South Africa Standard Time, which is usually a -1 hour difference. Plan for cooler temperatures traveling from Zanzibar City in August, with highs in Cape Town at 65°F and lows at 47°F. Finish your sightseeing early on the 8th (Thu) to allow enough time to travel back home.

Things to do in Cape Town

Parks Shopping Historic Sites

Side Trip

Dorp Street
Find places to stay Aug 1 — 8:
Highlights from your plan
Cape of Good Hope ©
Cape of Good Hope
Boulders Beach ©
Boulders Beach
Table Mountain National Park ©
Table Mountain National Park

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