60 days in Caribbean, South America, Central America & Mexico Itinerary

60 days in Caribbean, South America, Central America & Mexico Itinerary

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Route & dates

60 days in Caribbean, South America, Central America & Mexico Itinerary

Start: Kosice, Slovakia
Fly:  24​h
1
San Juan, Puerto Rico
— 4 nights
Fly:  30​min
2
Culebra, Puerto Rico
— 5 nights
Fly + Drive:  2​h 15​min
3
Isla de Vieques, Puerto Rico
— 5 nights
Fly:  8​h
4
Montego Bay, Jamaica
— 4 nights
Fly:  8​h 15​min
5
Lima, Peru
— 2 nights
Fly:  8​h 30​min
6
Montevideo, Uruguay
— 4 nights
7
Buenos Aires, Argentina
— 5 nights
8
Santiago, Chile
— 5 nights
Fly + taxi:  11​h 45​min
9
Uyuni, Bolivia
— 1 day
taxi + Fly:  3​h 45​min
10
La Paz, Bolivia
— 3 nights
Fly:  4​h 45​min
11
Bogota, Colombia
— 3 nights
Fly:  2​h 15​min
12
Panama City, Panama
— 3 nights
Fly:  6​h
13
Cancun, Mexico
— 4 nights
Fly:  4​h
14
Havana, Cuba
— 5 nights
Fly:  21​h 15​min
End: Kosice, Slovakia

4
nights
San Juan, Puerto Rico

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Explore San Juan's surroundings by going to El Yunque Rain Forest (in El Yunque National Forest), Museo de Arte de Ponce (in Ponce) and Luquillo Beach (in Luquillo). There's much more to do: wander the streets of Old San Juan, shake up your sightseeing with a climbing tour, enjoy the sand and surf at Condado Beach, and indulge in some culinary diversions at a local gastronomic tour.

For maps, ratings, where to stay, and tourist information, read our San Juan trip itinerary builder website .

Kosice, Slovakia to San Juan is an approximately 24-hour flight. The time zone difference when traveling from Kosice to San Juan is minus 5 hours. In October, San Juan is warmer than Kosice - with highs of 38°C and lows of 30°C. Finish your sightseeing early on the 6th (Sun) so you can fly to Culebra.

Things to do in San Juan

Outdoors Parks Tours

Side Trips

El Yunque Rain Forest, Museo de Arte de Ponce, Luquillo Beach
Find places to stay Oct 2 — 6:
Highlights from your plan
Canyoning & Rappelling Tours
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan

5
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Culebra is known for beaches, wildlife, nature, outdoors, and adventure. Your plan includes some of its best attractions: kick back and relax at Flamenco Beach, identify plant and animal life at Culebra National Wildlife Refuge, find your balance on the water with some of the best stand-up paddleboarding in the area, and step off the mainland to explore Culebrita Island.

To find traveler tips, other places to visit, ratings, and more tourist information, read our Culebra route builder .

Culebra is just a short distance from San Juan. In October in Culebra, expect temperatures between 36°C during the day and 30°C at night. Finish up your sightseeing early on the 11th (Fri) so you can travel to Isla de Vieques.

Things to do in Culebra

Outdoors Parks Beaches
Find places to stay Oct 6 — 11:
Highlights from your plan
Culebrita Island ©
Culebrita Island
Flamenco Beach ©
Flamenco Beach
Zoni Beach ©
Zoni Beach

5
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©
For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Isla de Vieques is known for nature, beaches, wildlife, adventure, and nightlife. Your plan includes some of its best attractions: explore the activities along Sun Bay, enjoy the sand and surf at La Chiva, enjoy some diversion at Vieques Gun Club & Sporting Clays, and look for all kinds of wild species at Vieques National Wildlife Refuge.

To find reviews, ratings, photos, and tourist information, refer to the Isla de Vieques online vacation builder .

Getting from Culebra to Isla de Vieques by combination of flight and car takes about 2.5 hours. Other options: ride a ferry. In October, daytime highs in Isla de Vieques are 36°C, while nighttime lows are 28°C. Finish up your sightseeing early on the 16th (Wed) so you can travel to Montego Bay.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay Oct 11 — 16:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Vieques National Wildlife Refuge ©
Vieques National Wildlife Refuge
Media Luna Beach ©
Media Luna Beach

4
nights
Montego Bay, Jamaica

The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
Venture out of the city with trips to Seven Mile Beach (in Negril), Tryall Golf Course (in Sandy Bay) and Original Mayfield Falls Jamaica (in Pennycooke). Spend the 20th (Sun) wandering through the wild on a nature and wildlife tour. The adventure continues: take in the dramatic scenery at YS Falls, kick back and relax at Doctor's Cave Beach, get engrossed in the history at Greenwood Great House, and play a few rounds at White Witch Golf Course.

To see traveler tips, ratings, where to stay, and more tourist information, refer to the Montego Bay trip itinerary planner.

Getting from Isla de Vieques to Montego Bay by flight takes about 8 hours. Other options: do a combination of flight and bus. The time zone difference when traveling from Isla de Vieques to Montego Bay is minus 1 hour. Expect a daytime high around 38°C in October, and nighttime lows around 28°C. Wrap up your sightseeing on the 21st (Mon) early enough to travel to Lima.

Things to do in Montego Bay

Outdoors Parks Wildlife

Side Trips

Original Mayfield Falls Jamaica, YS Falls, Seven Mile Beach, Tryall Golf Course
Find places to stay Oct 16 — 21:
Highlights from your plan
Nature & Wildlife Tours
Seven Mile Beach ©
Seven Mile Beach
YS Falls ©
YS Falls

2
nights
Lima, Peru

Lima ©
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.
Lima is known for parks, historic sites, museums, shopping, and nightlife. Your plan includes some of its best attractions: don't miss a visit to Plaza de Armas (Plaza Mayor), take an in-depth tour of Museo Larco, explore the ancient world of Huaca Pucllana, and take in the spiritual surroundings of San Pedro Church (Iglesia de San Pedro).

For ratings, more things to do, photos, and other tourist information, read our Lima trip planning site .

Traveling by flight from Montego Bay to Lima takes 8.5 hours. While traveling from Montego Bay, expect cooler days and slightly colder nights in Lima, ranging from highs of 24°C to lows of 19°C. Wrap up your sightseeing on the 24th (Thu) early enough to travel to Montevideo.

Things to do in Lima

Historic Sites Tours Neighborhoods
Find places to stay Oct 21 — 24:
Highlights from your plan
Huaca Pucllana ©
Huaca Pucllana
Museo Larco ©
Museo Larco
Plaza de Armas (Plaza Mayor) ©
Plaza de Armas (Plaza Mayor)

4
nights
Montevideo, Uruguay

Montevideo ©
With a rich cultural scene and plenty of developed beaches, Montevideo vacations appeal to a growing number of visitors from around the world.
Explore the numerous day-trip ideas around Montevideo: Museo Taller de Casapueblo (in Punta Ballena), Museo – Taller de Casapueblo (in Punta del Este) and Pizzorno Family Estates (in Canelones). Next up on the itinerary: make a trip to Plaza Independencia, take in the waterfront at Rambla de Montevideo, admire the striking features of Palacio Salvo, and browse the eclectic array of goods at Mercado del Puerto.

For maps, ratings, traveler tips, and more tourist information, use the Montevideo travel itinerary planner.

You can fly from Lima to Montevideo in 8.5 hours. Alternatively, you can do a combination of bus and ferry; or drive. You'll lose 2 hours traveling from Lima to Montevideo due to the time zone difference. Traveling from Lima in October, Montevideo is slightly colder at night with lows of 13°C. Wrap up your sightseeing on the 29th (Tue) to allow time to ride a ferry to Buenos Aires.

Things to do in Montevideo

Shopping Museums Neighborhoods

Side Trips

Pizzorno Family Estates, Museo – Taller de Casapueblo, Museo Taller de Casapueblo
Find places to stay Oct 24 — 29:
Highlights from your plan
Mercado del Puerto ©
Mercado del Puerto
Plaza Independencia ©
Plaza Independencia
Rambla de Montevideo ©
Rambla de Montevideo

5
nights
Buenos Aires, Argentina

Buenos Aires ©
Cultural capital of South America, Buenos Aires remains one of the largest cities on the continent, serving as a point of departure for exploring the rest of the country.
Buenos Aires is known for nightlife, museums, parks, historic sites, and shopping. Your plan includes some of its best attractions: make a trip to Recoleta Cemetery, take in the history at Plaza de Mayo, shop like a local with Puerto Madero, and explore the world behind art at Museo Nacional de Bellas Artes.

Plan a trip to Buenos Aires easily and quickly by telling Inspirock to suggest an itinerary.

You can ride a ferry from Montevideo to Buenos Aires in 2.5 hours. Other options are to fly; or take a bus. In October, plan for daily highs up to 24°C, and evening lows to 17°C. Wrap up your sightseeing on the 3rd (Sun) early enough to travel to Santiago.

Things to do in Buenos Aires

Neighborhoods Historic Sites Shopping
Find places to stay Oct 29 — Nov 3:
Highlights from your plan
Puerto Madero ©
Puerto Madero
Cemiterio de Recoleta ©
Cemiterio de Recoleta
Parque 3 de Febrero ©
Parque 3 de Febrero

5
nights
Santiago, Chile

Santiago ©
Santiago tourism thrives largely thanks to the city's big selection of cultural and entertainment options, including museums, theaters, restaurants, bars, and giant malls.
Change things up with a short trip to Ski Portillo in Portillo (about 1h 55 min away). There's lots more to do: take in the awesome beauty at San Cristóbal Hill, don't miss a visit to Plaza de Armas, browse the eclectic array of goods at Central Market (Mercado Central), and admire the masterpieces at Museo Chileno de Arte Precolombino.

To find other places to visit, photos, ratings, and tourist information, read our Santiago trip planner .

Getting from Buenos Aires to Santiago by flight takes about 5 hours. Other options: drive; or take a bus. Traveling from Buenos Aires to Santiago, you'll gain 1 hour due to the time zone difference. Finish up your sightseeing early on the 8th (Fri) so you can travel to Uyuni.

Things to do in Santiago

Parks Winter Sports Outdoors

Side Trips

Valle Nevado - Ski Resort Chile, Ski Portillo
Find places to stay Nov 3 — 8:
Highlights from your plan
San Cristóbal Hill ©
San Cristóbal Hill
Santa Lucia Hill ©
Santa Lucia Hill
Patio Bellavista ©
Patio Bellavista

1
day
Uyuni, Bolivia

Uyuni ©
Emptiness surrounds the desert outpost of Uyuni, the gateway to the world's largest salt flats.
Start off your visit on the 9th (Sat): step off the mainland to explore Isla Incahuasi and then explore the striking landscape at Salar de Uyuni.

To see maps, reviews, ratings, and more tourist information, read our Uyuni trip maker website .

Do a combination of flight and taxi from Santiago to Uyuni in 12 hours. Alternatively, you can drive; or do a combination of bus and taxi. In November, daily temperatures in Uyuni can reach 12°C, while at night they dip to 11°C. Wrap up your sightseeing on the 9th (Sat) to allow time to travel to La Paz.

Things to do in Uyuni

Nature Parks
Find places to stay Nov 8 — 9:
Highlights from your plan
Salar de Uyuni ©
Salar de Uyuni
Isla Incahuasi ©
Isla Incahuasi

3
nights
La Paz, Bolivia

La Paz ©
Take a moment to catch your breath as you commence your holiday in La Paz.
Spend the 11th (Mon) exploring the striking scenery along WMDR Yungas Road. There's lots more to do: delve into the distant past at Tiwanaku, push the limits with an extreme tour, take in the dramatic natural features at Valley of the Moon, and make a trip to Mercado de Las Brujas.

For traveler tips, ratings, and other tourist information, you can read our La Paz sightseeing planner.

Getting from Uyuni to La Paz by combination of taxi and flight takes about 4 hours. Other options: drive; or do a combination of taxi and bus. Traveling from Uyuni in November, expect nights in La Paz to be little chillier, around 2°C, while days are a bit warmer, around 20°C. Finish your sightseeing early on the 12th (Tue) to allow enough time to travel to Bogota.

Things to do in La Paz

Outdoors Scenic Drive Tours
Find places to stay Nov 9 — 12:
Highlights from your plan
Urban Rush Bolivia ©
Urban Rush Bolivia
Tiwanaku ©
Tiwanaku
WMDR Yungas Road ©
WMDR Yungas Road

3
nights
Bogota, Colombia

Bogota ©
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.
Take a break from Bogota with a short trip to Catedral de Sal in Zipaquira, about 54 minutes away. There's still lots to do: examine the collection at Gold Museum (Museo del Oro), expand your horizons at Whee Institute, steep yourself in history at Bolivar plaza, and make a trip to Mount Monserrate.

For where to stay, ratings, photos, and more tourist information, refer to the Bogota day trip tool .

Getting from La Paz to Bogota by flight takes about 5 hours. Other options: drive; or do a combination of train, car, and bus. The time zone difference moving from Bolivia Time to Colombia Time is minus 1 hour. Traveling from La Paz in November, expect a bit warmer with lows of 10°C in Bogota. Wrap up your sightseeing on the 15th (Fri) early enough to travel to Panama City.

Things to do in Bogota

Museums Classes Historic Sites

Side Trip

Catedral de Sal de Zipaquira
Find places to stay Nov 12 — 15:
Highlights from your plan
Gold Museum (Museo del Oro) ©
Gold Museum (Museo del Oro)
Museo Botero del Banco de la Republica ©
Monserrate ©
Monserrate

3
nights
Panama City, Panama

Panama City ©
Arguably the most modern of Central American cities, Panama City boasts a shimmering skyline of glass skyscrapers.
Spend the 18th (Mon) exploring nature at Parque Nacional de Soberania. There's lots more to do: make a trip to Panama Canal, take a stroll through Casco Viejo, get engrossed in the history at Museo del Canal Interoceanico de Panama, and stop by PTYlocal.

To find where to stay, ratings, more things to do, and more tourist information, read Panama City itinerary planner .

Traveling by combination of flight and taxi from Bogota to Panama City takes 2.5 hours. Alternatively, you can do a combination of flight and shuttle; or do a combination of bus, car, and ferry. Traveling from Bogota in November, you will find days in Panama City are somewhat warmer (35°C), and nights are warmer (28°C). Wrap up your sightseeing on the 18th (Mon) early enough to travel to Cancun.

Things to do in Panama City

Nature Parks Neighborhoods
Find places to stay Nov 15 — 18:
Highlights from your plan
Soberania National Park ©
Soberania National Park
Panama Canal ©
Panama Canal
Casco Viejo ©
Casco Viejo

4
nights
Cancun, Mexico

Few destinations in Mexico dazzle visitors quite like Cancun, a modern resort town filled with glitzy hotels sitting on picturesque and well-developed Caribbean beaches.
Get out of town with these interesting Cancun side-trips: Playa del Carmen (Scuba & Snorkeling, Zipline, & more) and Akumal Beach (in Akumal). Spend the 22nd (Fri) in unforgettable company with a swim-with-the-dolphins experience. There's lots more to do: browse the different shops at La Isla Shopping Village, enjoy the sand and surf at Playa Delfines, and take in the pleasant sights at Av Kukulkan.

To see traveler tips, reviews, where to stay, and tourist information, go to the Cancun holiday planner.

Getting from Panama City to Cancun by flight takes about 6 hours. Other options: drive. Plan for little chillier nights when traveling from Panama City in November since evenings lows in Cancun dip to 24°C. Finish up your sightseeing early on the 23rd (Sat) so you can travel to Havana.

Things to do in Cancun

Outdoors Tours Wildlife

Side Trips

Playa del Carmen, Akumal Beach
Find places to stay Nov 18 — 23:
Highlights from your plan
Zipline
Scuba & Snorkeling
La Isla Shopping Village ©
La Isla Shopping Village

5
nights
Havana, Cuba

Havana ©
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, museums, nightlife, beaches, and parks. Your plan includes some of its best attractions: get to know the fascinating history of El Malecon, explore the world behind art at Museu Nacional de Belas Artes de Cuba, admire the landmark architecture of Casa de la Amistad, and stroll the grounds of Christopher Columbus Cemetery (Cemetario de Colon).

For traveler tips, reviews, and more tourist information, read our Havana trip itinerary builder tool .

Fly from Cancun to Havana in 4 hours. Traveling from Cancun in November, Havana is a bit cooler at night with lows of 21°C. Wrap up your sightseeing on the 28th (Thu) early enough to travel back home.

Things to do in Havana

Historic Sites Museums Neighborhoods
Find places to stay Nov 23 — 28:
Highlights from your plan
El Malecon ©
El Malecon
Old Havana ©
Old Havana
Plaza de la Catedral ©
Plaza de la Catedral

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