34 days in South America & Caribbean Itinerary

34 days in South America & Caribbean Itinerary

Created using Inspirock trip maker

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1
Cartagena, Colombia
— 2 nights
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2
San Andres Island, Colombia
— 2 nights
Fly
3
Villa de Leyva, Colombia
— 2 nights
Drive
4
Bogota, Colombia
— 2 nights
Fly
5
Medellin, Colombia
— 2 nights
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6
Oranjestad, Aruba
— 7 nights
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7
San Juan, Puerto Rico
— 7 nights
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8
Havana, Cuba
— 7 nights
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Cartagena, Colombia

— 2 nights

City of Heroes

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.
Spend the 28th (Mon) among aquatic life with a scuba or snorkeling tour. And it doesn't end there: explore the historical opulence of Castillo de San Felipe de Barajas, make a trip to Las Bovedas, contemplate the long history of Walled City of Cartagena, and contemplate in the serene atmosphere at Convent of Santa Cruz de la Popa.

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

Newcastle upon Tyne, UK to Cartagena is an approximately 16.5-hour flight. Due to the time zone difference, you'll gain 5 hours traveling from Newcastle upon Tyne to Cartagena. Prepare for much warmer weather when traveling from Newcastle upon Tyne in June: high temperatures in Cartagena hover around 38°C and lows are around 30°C. Cap off your sightseeing on the 29th (Tue) early enough to travel to San Andres Island.

Things to do in Cartagena

Historic Sites · Outdoors · Tours · Wildlife
Find places to stay Jun 27 — 29:

San Andres Island, Colombia

— 2 nights
The coral San Andres Island boasts a rich colonial history, exotic beaches, and a laidback, tropical lifestyle.
On the 30th (Wed), head off the coast to Cayo El Acuario, explore the striking landscape at Hoyo Soplador, then Head underground at Morgan's Cave, and finally kick back and relax at Playa Charquitos. Get ready for a full day of sightseeing on the next day: see some colorful creatures with Aquanautas, look for all kinds of wild species at La Piscinita, and then step off the mainland to explore Johnny Cay.

To find reviews, traveler tips, and more tourist information, you can read our San Andres Island trip itinerary planning website.

Traveling by flight from Cartagena to San Andres Island takes 3.5 hours. Expect a daytime high around 36°C in June, and nighttime lows around 30°C. Finish your sightseeing early on the 1st (Thu) so you can travel to Villa de Leyva.

Things to do in San Andres Island

Parks · Nature · Wildlife · Outdoors
Find places to stay Jun 29 — Jul 1:

Villa de Leyva, Colombia

— 2 nights
Positioned away from major trade routes and exploitable resources, the colonial town of Villa de Leyva has been largely left alone--leaving a window into the 16th century that has become one of Colombia's most popular attractions.
On the 2nd (Fri), make a trip to Hotel Plaza Mayor Villa de Leyva, then admire the landmark architecture of Casa Terracota, and then explore the activities along Pozos Azules. Here are some ideas for day two: get curious at Centro de Investigaciones Paleontologicas - CIP, then see the interesting displays at Museo El Fosil, and then hit the best photo ops around with Xplora Villa de Leyva.

To see traveler tips, photos, more things to do, and tourist information, read Villa de Leyva journey planner.

You can fly from San Andres Island to Villa de Leyva in 7 hours. Another option is to do a combination of flight and bus. Wrap up your sightseeing on the 3rd (Sat) early enough to drive to Bogota.

Things to do in Villa de Leyva

Outdoors · Tours · Museums · Childrens Museums
Find places to stay Jul 1 — 3:

Bogota, Colombia

— 2 nights

Athens of South America

Colombia's heart and soul, Bogota has earned the nickname "Athens of South America" thanks to its abundance of universities, libraries, and lower-level schools.
Start off your visit on the 4th (Sun): contemplate the long history of Bolivar Square, then examine the collection at Gold Museum (Museo del Oro), and then take your sightseeing to a higher altitude at Monserrate. On your second day here, indulge in some culinary diversions at a local gastronomic tour, then admire the masterpieces at Museo Botero del Banco de la Republica, and then stop by Vitrina Guayca.

For where to stay and tourist information, you can read our Bogota road trip tool.

You can drive from Villa de Leyva to Bogota in 2.5 hours. Alternatively, you can take a bus. Expect a daytime high around 21°C in July, and nighttime lows around 10°C. Finish your sightseeing early on the 5th (Mon) to allow enough time to travel to Medellin.

Things to do in Bogota

Museums · Tours · Nature · Parks
Find places to stay Jul 3 — 5:

Medellin, Colombia

— 2 nights

City of the Eternal Spring

Nestled between rising hills in a narrow valley, Medellin serves as an energetic melting pot of people from all socio-economic classes.
Start off your visit on the 6th (Tue): contemplate the long history of Pueblito Paisa and then get the lay of the land with Walking tours. Keep things going the next day: get up close and personal with brilliant marine life at Parque Explora and then make a trip to Plaza Botero.

Make your Medellin itinerary with Inspirock to find out what to see and where to go.

Traveling by flight from Bogota to Medellin takes 3.5 hours. Alternatively, you can drive; or take a bus. Prepare for a bit warmer weather when traveling from Bogota in July: high temperatures in Medellin hover around 34°C and lows are around 20°C. Wrap up your sightseeing on the 7th (Wed) to allow time to travel to Oranjestad.

Things to do in Medellin

Tours · Zoos & Aquariums · Parks · Historic Sites
Find places to stay Jul 5 — 7:

Oranjestad, Aruba

— 7 nights
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Explore Oranjestad's surroundings by going to San Nicolas (Baby Beach & Cosecha in San Nicolas). There's still lots to do: kick back and relax at Eagle Beach, take a memorable tour with Tours, tour the pleasant surroundings at Hadicurari Beach, and explore the striking landscape of Arikok National Park.

To find traveler tips, reviews, ratings, and tourist information, read Oranjestad online route planner.

Getting from Medellin to Oranjestad by flight takes about 5 hours. Traveling from Medellin to Oranjestad, you'll lose 1 hour due to the time zone difference. In July, Oranjestad is a bit warmer than Medellin - with highs of 38°C and lows of 31°C. Finish your sightseeing early on the 14th (Wed) to allow enough time to travel to San Juan.

Things to do in Oranjestad

Parks · Outdoors · Beaches · Nature

Side Trips

Find places to stay Jul 7 — 14:

San Juan, Puerto Rico

— 7 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Explore San Juan's surroundings by going to Luquillo Beach (in Luquillo) and El Yunque Rain Forest (in El Yunque National Forest). Make the 19th (Mon) a memorable day with a climbing tour. There's lots more to do: steep yourself in history at Old San Juan, appreciate the extensive heritage of Sitio Histórico de San Juan, admire the masterpieces at Museo de Las Americas, and skim along the rocks with a canyoning and rapelling tour.

For other places to visit, traveler tips, ratings, and tourist information, use the San Juan trip planner.

You can fly from Oranjestad to San Juan in 7 hours. Expect a daytime high around 37°C in July, and nighttime lows around 30°C. Wrap up your sightseeing on the 21st (Wed) early enough to travel to Havana.

Things to do in San Juan

Outdoors · Parks · Tours · Beaches

Side Trips

Find places to stay Jul 14 — 21:

Havana, Cuba

— 7 nights

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: appreciate the extensive heritage of Malecón of Havana, look for all kinds of wild species at Wildlife Areas, don't miss a visit to Old Havana, and steep yourself in history at El Morro.

To see more things to do, traveler tips, maps, and other tourist information, read our Havana road trip site.

You can fly from San Juan to Havana in 8 hours. Traveling from San Juan to Havana, you'll gain 1 hour due to the time zone difference. Traveling from San Juan in July, expect slightly colder with lows of 26°C in Havana. Finish up your sightseeing early on the 29th (Thu) so you can travel back home.

Things to do in Havana

Historic Sites · Tours · Museums · Outdoors

Side Trip

Find places to stay Jul 21 — 29:

Colombia travel guide

4
Historic Sites · Landmarks · Specialty Museums
Diverse in terms of landscapes, climates, and cultures, Colombia remains one of South America's least explored tourist destinations, overshadowed by its more popular southern neighbors. Combining the best of what the continent has to offer, a vacation in Colombia allows you to blend outdoor adventures with tours of picture-perfect cobblestoned towns dating back to the colonial era. Tourists on a Colombia holiday can easily hop from sun-kissed coastal spots to the hilly coffee-growing region, where thriving plantations quickly give way to a landscape of snow-covered volcanic peaks and the paramo--alpine ecosystems sheltering some of the rarest plants growing above the continuous forest line.

Aruba travel guide

4.2
Beaches · Scuba & Snorkeling · Gift & Specialty Shops
Happy Island
A Dutch outpost in the Caribbean, sun-drenched Aruba provides a mix of modern seaside resorts and quiet coastal areas ideal for those wishing to escape the crowds. Vacations in Aruba, known affectionately as the "Happy Island," generally combine water-based activities with tours of the untamed backcountry, where you can discover unusual rock formations, historic churches, ostrich farms, and animal sanctuaries. Island capital Oranjestad offers some of the finest shopping and cultural sightseeing in Aruba, with an eco-friendly electric streetcar providing quick access to all of the city's major attractions, including numerous shops, restaurants, and hotels.

Puerto Rico travel guide

4.5
Historic Walking Areas · Beaches · Forests
A U.S. territory encompassing one big island and several smaller ones, Puerto Rico appeals to visitors from around the globe with its rich history, pleasant climate, natural beauty, and renowned local cuisine. Most tourists take a vacation in Puerto Rico for that classic seaside experience, though the island offers much more than just sun and sand. Tours of Puerto Rico usually start in the city of San Juan, which boasts a trendy bar scene and plenty of art museums for visitors looking to add a bit of culture to their vacation. A short drive from the island's urban centers, pristine rainforests serve as peaceful retreats from the city bustle and ensure plenty of chances to spot wildlife and take exhilarating nature walks.

Cuba travel guide

4.4
Beaches · Historic Walking Areas · Landmarks
The largest island in the Caribbean, Cuba lies just 140 km (90 mi) south of Florida and captivates a growing number of Western visitors with its tropical landscapes and cultural attractions. Sightseeing in Cuba inevitably begins in Havana, a city of photogenic architecture, lively nightlife, and a passion for baseball. The country's smaller colonial towns usually feature central squares, ideal places to meet the locals under wrought-iron street lamps. Savvy visitors escape the cities during their Cuba holidays, devoting plenty of time to the country's charming countryside, where you can get the feel for this diverse land by conversing with friendly tobacco farmers and small-scale fruit producers.