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

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

4
days
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: 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, kick back and relax at Carolina Beach, buy something for everyone on your list at Plaza las Americas, 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 8.5-hour flight. You can also do a combination of train and flight; or do a combination of train, flight, and car. 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

El Yunque National Forest, Museo de Arte de Ponce, Pine Grove Beach, Puerto Rico Premium Outlets, Carolina Beach
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Pine Grove Beach ©
Pine Grove Beach
Museo de Arte de Ponce ©
Museo de Arte de Ponce
Old San Juan ©
Old San Juan

4
days
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. Your cultural itinerary includes sights like Altos de Chavon and Aromas Museum. The adventure continues: enjoy the sand and surf at Bavaro Beach, get a new perspective on things with Boat Tours & Water Sports, look for gifts at Life is good, 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 88°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
Accommodations
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Bavaro Beach ©
Bavaro Beach
Altos de Chavon ©
Altos de Chavon
Macao Beach ©
Macao Beach

1
day
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, tour the pleasant surroundings 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. In June in Port-au-Prince, expect temperatures between 93°F during the day and 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
Accommodations
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Papillon Enterprise ©
Papillon Enterprise
Marche de Fer ©
Marche de Fer
Place Saint-Pierre ©
Place Saint-Pierre

1
day
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
Accommodations
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Hellshire Beach ©
Hellshire Beach
Port Royal ©
Port Royal
Devon House ©
Devon House

4
days
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 Shangri La. 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, tour the pleasant surroundings at Kapiolani Regional Park, let your taste buds guide you at a local gastronomic tour, and go for a walk through Diamond Head State Monument.

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, Pu’u O Mahuka Heiau State Monument, Polynesian Cultural Center
Accommodations
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Iolani Palace ©
Iolani Palace
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach

3
days
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 Palacio de Gobierno. Popular historic sites such as Expiatory Temple and Guachimontones are in your itinerary. Explore Guadalajara's surroundings by going to La Rojena (in Tequila), Ajijic Malecon (in Ajijic) and Chapala Malecon (in Chapala). There's lots more to do: pause for some serene contemplation at Guadalajara Cathedral, admire the masterpieces at Museo Pantaleon Panduro, pause for some photo ops at Minerva (La), and admire nature's wide array of creatures at Zoologico Guadalajara.

Plan my trip to Guadalajara with suggested itineraries provided by Inspirock.

Traveling by flight from Honolulu to Guadalajara takes 15.5 hours. You'll lose 4 hours traveling from Honolulu to Guadalajara due to the time zone difference. Plan for little chillier nights when traveling from Honolulu in June since evenings lows in Guadalajara dip to 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, Guachimontones, La Rojena, Ajijic Malecon, Chapala Malecon
Accommodations
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Guachimontones ©
Guachimontones
Instituto Cultural Cabanas ©
Instituto Cultural Cabanas
Expiatory Temple ©
Expiatory Temple

2
days
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). Keep things going the next day: take a stroll through Zocalo, see the interesting displays at Amparo Museum (Museo Amparo), take in the architecture and atmosphere at Catedral Basilica de Puebla, then get lost in a book at Biblioteca Palafoxiana, then stroll through Africam Safari, and finally pick up a one of a kind souvenir at Bazar los Sapos.

You can plan Puebla trip in no time by asking Inspirock to help create your itinerary.

Traveling by flight from Guadalajara to Puebla takes 5.5 hours. Alternatively, you can do a combination of flight and bus; or drive. Traveling from Guadalajara in July, plan for little chillier nights in Puebla, with lows around 52°F. Finish your sightseeing early on the 4th (Thu) so you can drive to Mexico City.

Things to do in Puebla

#Historic Sites, #Parks, #Zoos & Aquariums

Side Trip

San Pedro Cholula
Accommodations
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Catedral Basilica de Puebla ©
Catedral Basilica de Puebla
Iglesia de Tonantzintla ©
Iglesia de Tonantzintla
Rosary Chapel (Capilla del Rosario) ©

4
days
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 (Museo Nacional de Antropologia) and Metropolitan Cathedral (Catedral Metropolitana). Popular historic sites such as Museo del Templo Mayor and Zona Arqueologica Teotihuacan are in your itinerary. Explore the numerous day-trip ideas around Mexico City: Cuernavaca (Archaeological Zone of Xochicalco & Robert Brady Museum). Next up on the itinerary: explore the world behind art at Palacio de Bellas Artes, see the interesting displays at Museo Dolores Olmedo Patino, steep yourself in history at Chapultepec Castle, and appreciate the extensive heritage of Historic Center (Centro Historico).

For traveler tips, ratings, photos, and other tourist information, refer to the Mexico City road trip planner .

Drive from Puebla to Mexico City in 1.5 hours. Alternatively, you can take a bus; or take a shuttle. In July in Mexico City, expect temperatures between 74°F during the day and 56°F at night. Finish your sightseeing early on the 9th (Tue) to allow enough time to travel to San Jose.

Things to do in Mexico City

#Historic Sites, #Neighborhoods, #Museums

Side Trips

Cuernavaca, Zona Arqueologica Teotihuacan
Accommodations
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2
days
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 do a combination of bus and flight; or drive. 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

Multiplaza, Our Lady of the Angels Basilica (Basilica de Nuestra Senora de Los Angeles)
Accommodations
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3
days
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 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 Ollantaytambo (Naupa Iglesia, Inka Pintay, & more), Cerveceria del Valle Sagrado (in Urubamba) and Maras (Moray & Salinas de Maras). 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 take in nature's colorful creations at Los Jardines de Mandor.

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

You can do a combination of flight and train from San Jose to Machu Picchu in 12 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
Accommodations
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Santuario Historico de Machu Picchu ©
Winay Wayna ©
Winay Wayna
Archaeological Park Ollantaytambo ©
Archaeological Park Ollantaytambo

6
days
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 Imperial Museum will appeal to museum buffs. We've included these beaches for you: Copacabana Beach and Pedra do Arpoador. Explore Rio de Janeiro's surroundings by going to Museum of Contemporary Art (in Niteroi) and Catedral de Sao Pedro de Alcantara (in Petropolis). And it doesn't end there: kick back and relax at Praia de Ipanema, explore and take pictures at Maracanã, tour the pleasant surroundings at Mirante da Prainha, and look for gifts at Shopping Leblon.

For photos, more things to do, where to stay, and tourist information, you can read our Rio de Janeiro road trip planning tool .

Getting from Machu Picchu to Rio de Janeiro by combination of train, bus, and flight takes about 14.5 hours. Other options: do a combination of car and flight; or drive. The time zone difference when traveling from Machu Picchu to Rio de Janeiro is 2 hours. July in Rio de Janeiro sees daily highs of 78°F and lows of 66°F at night. Cap off your sightseeing on the 21st (Sun) early enough to travel to Sao Paulo.

Things to do in Rio de Janeiro

#Parks, #Outdoors, #Beaches

Side Trips

Petropolis, Museum of Contemporary Art
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Copacabana Beach ©
Copacabana Beach
Praia de Ipanema
Praia de Ipanema
Corcovado Christ the Redeemer ©
Corcovado Christ the Redeemer

3
days
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 Museu de Arte de Sao Paulo Assis Chateaubriand - MASP. 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, pause for some serene contemplation at Catedral da Se de Sao Paulo, explore the world behind art at Pinacoteca do Estado de Sao Paulo, and get into the urban bustle at The Julio Prestes Cultural Center - Sala Sao Paulo.

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

Tombo beach, Juquehy Beach
Accommodations
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Pinacoteca do Estado de Sao Paulo ©
Pinacoteca do Estado de Sao Paulo
Paulista Avenue ©
Paulista Avenue

3
days
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. Constitution Hill and South Western Townships will appeal to history buffs. Explore Johannesburg's surroundings by going to Irene Village Mall (in Centurion) and Montecasino (in Sandton). There's much more to do: get in on the family fun at Gold Reef City, try to win big at Emperors Palace, hunt for treasures at Market on Main, and stop by Sandton City Shopping Centre.

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

Traveling by flight from Sao Paulo to Johannesburg takes 14.5 hours. Alternatively, you can do a combination of bus and flight. 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

#Fun & Games, #Casinos, #Shopping

Side Trips

Union Buildings, Irene Village Mall, Montecasino, Emperors Palace
Accommodations
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Montecasino ©
Montecasino
Apartheid Museum ©
Apartheid Museum
Constitution Hill ©
Constitution Hill

1
day
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
Accommodations
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Paje Beach ©
Paje Beach
Zanzibar Butterfly Centre ©
Zanzibar Butterfly Centre
Jozani Chwaka Bay National Park ©
Jozani Chwaka Bay National Park

1
day
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 1.5 hours. 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
Accommodations
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Hamamni Persian Baths ©
Hamamni Persian Baths
House of Wonders (Beit-el-Ajaib) ©
House of Wonders (Beit-el-Ajaib)

7
days
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 and Groot Constantia are in your itinerary. District Six Museum and Cape Town Holocaust Centre will appeal to museum buffs. Next up on the itinerary: enjoy the sand and surf at Boulders Beach, take in nature's colorful creations at Kirstenbosch National Botanical Garden, admire all the interesting features of Cape of Good Hope, and hunt for treasures at Greenmarket Square.

To see maps, more things to do, where to stay, and other tourist information, refer to the Cape Town itinerary planner.

You can fly from Zanzibar City to Cape Town in 9 hours. Another option is to do a combination of ferry, train, and bus. Due to the time zone difference, you'll gain 1 hour traveling from Zanzibar City to Cape Town. In August, Cape Town is much colder than Zanzibar City - with highs of 65°F and lows of 47°F. Finish up your sightseeing early on the 8th (Thu) so you can travel back home.

Things to do in Cape Town

#Parks, #Shopping, #Historic Sites

Side Trip

Dorp Street
Accommodations
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Boulders Beach ©
Boulders Beach
Table Mountain National Park ©
Table Mountain National Park
Victoria & Alfred Waterfront ©
Victoria & Alfred Waterfront

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