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

Created using Inspirock itinerary planner

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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
Drive:  1​h 30​min
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 La Fortaleza - Palacio de Santa Catalina. 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: El Yunque National Forest (Luquillo Beach & El Yunque Rain Forest), Puerto Rico Premium Outlets (in Barceloneta) and Caribbean Trading Company Store (in Palmer). Next up on the itinerary: stroll through Pine Grove Beach, buy something for everyone on your list at Plaza las Americas, kick back and relax at Condado Beach, and look for gifts at Puerto Rican Art & Crafts.

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, #Beaches, #Outdoors

Side Trips

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

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 Palma Real Shopping Village and La Perla Dominicanafor some retail therapy. We've included these beaches for you: Bavaro Beach and Macao Beach. Change things up with a short trip to Altos de Chavon in La Romana (about 1h 25 min away). The adventure continues: stop by Museo del Artesano, try your luck at Avalon Casino Punta Cana, Head underground at Cave Oleg Bat House, and don't miss a visit to Jesus Maestro Parish.

For where to stay, more things to do, traveler tips, and more tourist information, read our Punta Cana driving holiday planner.

Fly from San Juan to Punta Cana in 4.5 hours. Alternatively, you can do a combination of flight and shuttle; or do a combination of ferry and bus. June in Punta Cana sees daily highs of 87°F and lows of 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 plan Port-au-Prince vacation without wasting time, ask Inspirock to design an itinerary.

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. Traveling from Punta Cana to Port-au-Prince, you'll gain 1 hour due to the time zone difference. When traveling from Punta Cana in June, plan for a bit warmer days and about the same nights in Port-au-Prince: temperatures range from 93°F by day to 81°F at night. You'll have a few hours on the 22nd (Sat) to wrap things up before traveling to 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
Village Artistique de Noailles ©
Village Artistique de Noailles
Marche de Fer ©
Marche de Fer

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, #Beaches

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 Ala Moana Center. Change things up with these side-trips from Honolulu: Haleiwa (Sunset Beach Park & Waimea Bay) and Pu’u O Mahuka Heiau State Monument (in Pupukea). Next up on the itinerary: kick back and relax at Waikiki Beach, examine the collection at Bishop Museum, let your taste buds guide you at a local gastronomic tour, and steep yourself in history at Battleship Missouri Memorial.

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, Polynesian Cultural Center, Pu’u O Mahuka Heiau State Monument, Nuuanu Pali Lookout
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 Museo Pantaleon Panduro and Palacio de Gobierno. Popular historic sites such as Expiatory Temple and Guachimontones are in your itinerary. Explore Guadalajara's surroundings by going to Chapala Malecon (in Chapala), Mundo Cuervo La Rojena (in Tequila) and Ajijic Malecon (in Ajijic). And it doesn't end there: see the interesting displays at Instituto Cultural Cabanas, pause for some photo ops at Minerva (La), admire all the interesting features of Estadio Jalisco, and pause for some serene contemplation at Guadalajara Cathedral.

To see photos, reviews, more things to do, and other tourist information, read Guadalajara attractions planning app .

Traveling by flight from Honolulu to Guadalajara takes 15.5 hours. Traveling from Honolulu to Guadalajara, you'll lose 4 hours due to the time zone difference. Traveling from Honolulu in June, Guadalajara is slightly colder at night 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, Mundo Cuervo La Rojena, Ajijic Malecon, Andares
Find places to stay Jun 28 — Jul 2:
Highlights from your plan
Guachimontones ©
Guachimontones
Expiatory Temple ©
Expiatory Temple
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 5.5 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 ©
Catedral Basilica de Puebla ©
Catedral Basilica de Puebla

5
nights
Mexico City, Mexico

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 (Museo Nacional de Antropologia) and Palacio de Bellas Artes. Popular historic sites such as Zona Arqueologica Teotihuacan and Museo del Templo Mayor 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: examine the collection at Frida Kahlo Museum, take a stroll through Polanco, step into the grandiose world of Chapultepec Castle, and shop like a local with Coyoacan.

For photos, traveler tips, ratings, and more tourist information, go to the Mexico City tour itinerary builder tool .

You can drive from Puebla to Mexico City in 1.5 hours. Other options are to take a bus; or take a shuttle. In July, daytime highs in Mexico City are 74°F, while nighttime lows are 56°F. Wrap up your sightseeing on the 9th (Tue) early enough to travel to San Jose.

Things to do in Mexico City

#Historic Sites, #Neighborhoods, #Museums

Side Trips

Cuernavaca, Zona Arqueologica Teotihuacan
Find places to stay Jul 4 — 9:
Highlights from your plan
Food Tours
Zona Arqueologica Teotihuacan ©
Zona Arqueologica Teotihuacan

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. Here are some ideas for day two: let the river carry you with a rafting and tubing tour, contemplate the long history of Our Lady of the Angels Basilica (Basilica de Nuestra Senora de Los Angeles), explore the world behind art at Precolumbian Gold Museum, then admire the masterpieces at Museo de Arte Costarricense, then stroll through Parque La Sabana, and finally take in the exciting artwork at Galeria Namu.

To see more things to do, photos, where to stay, and tourist information, you can read our San Jose day trip planning tool .

You can fly from Mexico City to San Jose in 6.5 hours. Alternatively, you can drive; or take a bus. Prepare for somewhat warmer weather when traveling from Mexico City in July: high temperatures in San Jose hover around 80°F and lows are around 67°F. Finish up your sightseeing early on the 11th (Thu) so you can travel to Machu Picchu.

Things to do in San Jose

#Museums, #Shopping, #Parks

Side Trips

Multiplaza, Our Lady of the Angels Basilica (Basilica de Nuestra Senora de Los Angeles)
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 Artesanias and Misha Wasifor some retail therapy. Appreciate the collections at Choco Museo and Museo de Sitio Manuel Chavez Ballon. Venture out of the city with trips to Cerveceria del Valle Sagrado (in Urubamba), Maras (Moray & Salinas de Maras) and Ollantaytambo (Naupa Iglesia, Inka Pintay, & more). 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, take your sightseeing to a higher altitude at Phutuq K'usi, and hunt for treasures at Mercado de Artesanias.

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 ©
Winay Wayna ©
Winay Wayna
Archaeological Park Ollantaytambo ©
Archaeological Park Ollantaytambo

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 Banco do Brasil - CCBB Rio de Janeiro and Museu da Republica 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). And it doesn't end there: enjoy the sand and surf at Praia de Ipanema, explore the striking landscape of Parque Nacional Tijuca, tour the pleasant surroundings at Pedra do Arpoador, and stop by Feira da Praca XV.

To see more things to do, where to stay, photos, and other tourist information, read Rio de Janeiro trip maker app .

Do a combination of train, bus, and flight from Machu Picchu to Rio de Janeiro in 14.5 hours. Alternatively, you can do a combination of car and flight; or drive. Due to the time zone difference, you'll lose 2 hours traveling from Machu Picchu to Rio de Janeiro. In July, plan for daily highs up to 78°F, and evening lows to 66°F. Finish up your sightseeing early on the 21st (Sun) so you can 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
Corcovado Christ the Redeemer ©
Corcovado Christ the Redeemer
Copacabana Beach ©
Copacabana Beach
Praia de Ipanema
Praia de Ipanema

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 Catedral da Se de Sao Paulo. You'll get in some beach time at Juquehy Beach and Tombo beach. Next up on the itinerary: browse the fresh offerings at Mercadao - Sao Paulo Municipal Market, look for gifts at Livraria Cultura, explore the world behind art at Pinacoteca do Estado de Sao Paulo, and stroll through Ibirapuera Park.

To find more things to do, where to stay, traveler tips, and tourist information, go to the Sao Paulo trip planner .

Getting from Rio de Janeiro to Sao Paulo by flight takes about 1.5 hours. Other options: do a combination of flight and bus; or drive. Plan for slightly colder temperatures traveling from Rio de Janeiro in July, with highs in Sao Paulo at 72°F and lows at 55°F. You'll have a few hours on the 25th (Thu) to wrap things up before traveling to Johannesburg.

Things to do in Sao Paulo

#Museums, #Shopping, #Neighborhoods

Side Trips

Juquehy Beach, Tombo 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 Constitution Hill are good opportunities to explore the local culture. Union Buildings and South Western Townships will appeal to history buffs. Explore Johannesburg's surroundings by going to Montecasino (in Sandton) and Irene Village Mall (in Centurion). There's much more to do: get in on the family fun at Gold Reef City, hunt for treasures at Market on Main, wander the streets of Maboneng Precinct, and browse the different shops at Eastgate Shopping Mall.

To find where to stay, more things to do, ratings, and tourist information, read Johannesburg online day trip planner .

Traveling by combination of flight and train from Sao Paulo to Johannesburg takes 14.5 hours. Traveling from Sao Paulo to Johannesburg, you'll lose 5 hours due to the time zone difference. In July, Johannesburg is slightly colder than Sao Paulo - with highs of 67°F and lows of 40°F. Wrap up your sightseeing on the 29th (Mon) to allow time to travel to Paje.

Things to do in Johannesburg

#Casinos, #Fun & Games, #Shopping

Side Trips

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

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.

For traveler tips, more things to do, other places to visit, and other tourist information, refer to the Paje trip builder website .

Explore your travel options from Johannesburg to Paje with the Route module. The time zone difference moving from South Africa Standard Time to Eastern African Time is 1 hour. Traveling from Johannesburg in July, expect nights in Paje to be much warmer, around 72°F, while days are somewhat warmer, around 85°F. Wrap up your sightseeing on the 30th (Tue) early enough to drive 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
Zanzibar Butterfly Centre ©
Zanzibar Butterfly Centre
Jozani Chwaka Bay National Park ©
Jozani Chwaka Bay National Park

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, Stonetown 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 Trips

Fahari Zanzibar, Old Slave Market/Anglican Cathedral, Stonetown
Find places to stay Jul 30 — Aug 1:
Highlights from your plan
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 Maclear's Beacon and Robben Island are in your itinerary. District Six Museum and Cape Town Holocaust Centre will appeal to museum buffs. Take a break from Cape Town with a short trip to Dorp Street in Stellenbosch, about 50 minutes away. Next up on the itinerary: explore and take pictures at Victoria & Alfred Waterfront, kick back and relax at Clifton Beaches, hunt for treasures at Greenmarket Square, and take your sightseeing to a higher altitude at Table Mountain National Park.

To see reviews, more things to do, maps, and more tourist information, use the Cape Town travel route planner.

You can fly from Zanzibar City to Cape Town in 8 hours. Another option is to do a combination of ferry, car, and bus. The time zone difference when traveling from Zanzibar City to Cape Town is minus 1 hour. Prepare for colder weather when traveling from Zanzibar City in August: high temperatures in Cape Town hover around 65°F and lows are around 47°F. Cap off your sightseeing on the 8th (Thu) early enough 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
Boulders Beach ©
Boulders Beach
Table Mountain National Park ©
Table Mountain National Park
Clifton Beaches ©
Clifton Beaches

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