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With their friendly locals, flavorful cuisine(s), and colorful cities, Latin America and the Caribbean seem to be at the top of every American’s travel wishlist lately, and given the monotony of suburban life, we can’t really blame them.

It’s not like many of us live in proximity to perfectly preserved 16th-century towns, not to mention greater weather and pristine beaches, but lucky for some, the Latin World’s top tourism hotspots are usually a two-to-four-hour flight away from most U.S. hubs.

This season, you can fly from your preferred point of departure to 4 of the most beautiful colonial Latin gems of the Caribbean Sea––no stopovers required:

Havana, Cuba

Panoramic View Of The Historic Port Of Havana, Cuba, Latin America

Inspiring as much intrigue among Americans as it does suspicion, the Cuban capital Havana is in fact one of the most welcoming destinations in the Global South, in spite of its clear ideological differences, that set it apart from most of the world, and unique society:

Locals are incredibly hospitable, the food is a unique blend of Spanish and Afro-Caribbean influences, and the architecture is eclectic, though irrevocably European in character, with stately Baroque and Neoclassical buildings to be admired at every corner.

View Of Old Havana, The Historic Center Of The Capital Of Cuba, Latin America

The UNESCO-listed historic center is a maze of narrow streets and colorful facades, dominated by an imposing stone-built cathedral, while the white-sand beaches to the east, outside the city’s fortifications, are lined by rows of palm trees and three-star hotels.

If you’re willing to keep an open mind, and leave your American values at the door, you’re sure to have an amazing time in Havana, particularly now that the Cuban Government has unveiled a brand new, easy-to-apply electronic visa for U.S. passport holders.

Fly To Havana (HAV), Cuba From:

Texas

  • Houston (IAH), United Airlines, 1 flight per day every day

Florida

  • Miami (MIA), American Airlines, 6-8 flights per day every day
  • Miami (MIA), Delta Airlines, 2 flights per day every day
  • Tampa (TPA), Southwest Airlines, 2 flights per day every day

San Juan, Puerto Rico

Aerial view of a huge fort on an ocean cliffside in San Juan Puerto Rico

The capital and largest city in Puerto Rico, San Juan is a fortified Spanish-built port straddling the bright-blue Caribbean, best-known for its cobblestoned center, locally known as ‘Old San Juan’, and bustling resort strip, packed with beach bars, casinos and nightclubs.

Strolling the postcard-perfect streets of the Old Town, with its brightly-painted low houses and alcapurria stalls, you’ll find all the vibrant culture you seek, and if you want to see something truly fairytale-like, make sure you pay seafront castle El Morro a visit.

Busy Street In San Juan, Puerto Rico, Latin America, United States

Now, for our fellow beach bums out there, Isla Verde is the place to be if you’re using San Juan as base: a buzzing wide beach of fine white sand boasting a high concentration of upscale resorts and high-rises, and even water parks, it is all the Caribbean fun you need.

Out of all Latin American destinations, Puerto Rico is the most convenient for U.S. citizens to fly to, not only due to its connectivity––it hosts flights from at least 15 states––but the fact that, as it is a U.S. territory, Americans can board flights there with a driver’s license or state ID.

Fly To San Juan (SJU), Puerto Rico From:

Florida

  • Orlando (MCO), Southwest Airlines, 7-8 flights per day every day
  • Orlando (MCO), JetBlue Airways, 5-7 flights per day every day
  • Orlando (MCO), Frontier Airlines, 4-5 flights per day every day
  • Orlando (MCO), Spirit Airlines, 3 flights per day every day
  • Miami (MIA), American Airlines, 5 flights per day every day
  • Miami (MIA), Frontier Airlines, 2-3 flights per day every day
  • Miami (MIA), Spirit Airlines, 2 flights per day every day
  • Fort Lauderdale (FLL), JetBlue Airways, 4 flights per day every day
  • Fort Lauderdale (FLL), Southwest Airlines, 2 flights per day every day
  • Fort Lauderdale (FLL), Spirit Airlines, 1-2 flights per day every day
  • Fort Lauderdale (FLL), Frontier Airlines, 1 flight per day every Monday, Wednesday, Friday, Saturday
  • Tampa (TPA), JetBlue Airways, 2 flights per day every day
  • Tampa (TPA), Southwest Airlines, 2 flights per day every day
  • Tampa (TPA), Frontier Airlines, 1-2 flights per day every day

woman holding us passport waiting for a flight

New York

  • New York (JFK), JetBlue Airways, 6-9 flights per day every day
  • New York (JFK), Delta Air Lines, 3 flights per day every day
  • New York (JFK), Frontier Airlines, 2 flights per day every day

Massachusetts

  • Boston (BOS), Jet Blue Airways, 5 flights per day every day
  • Boston (BOS), Spirit Airlines, 1 flight per day every day
  • Boston (BOS), Delta Air Lines, 1 flight per day every day
  • Boston (BOS), Frontier Airlines, 1 flight per day every Sunday, Tuesday, Thursday
Couple with luggage standing in an airport terminal

Georgia

  • Atlanta (ATL), Delta Air Lines, 5-7 flights per day every day
  • Atlanta (ATL), Spirit Airlines, 1 flight per day every day
  • Atlanta (ATL), Frontier Airlines, 1 flight every Monday, Wednesday, Friday, Saturday

New Jersey

  • Newark (EWR), United Airlines, 3 flights per day every day
  • Newark (EWR), JetBlue Airways, 2 flights per day every day
  • Newark (EWR), Frontier Airlines, 1-2 flights per day every day
Beautiful aerial view from the plane over Punta Cana, Dominican Republic

Pennsylvania

  • Philadelphia (PHL), Frontier Airlines, 2-3 flights per day every day
  • Philadelphia (PHL), American Airlines, 1 flight per day every day
  • Philadelphia (PHL), Spirit Airlines, 1 flight per day every day

Illinois

  • Chicago (ORD), Spirit Airlines, 2 flights per day every day
  • Chicago (ORD), United Airlines, 1 flight per day every day
  • Chicago (ORD), American Airlines, 1 flight per day every day

Beach in San Juan PR

Texas

  • Dallas/Fort Worth (DFW), American Airlines, 2-3 flights per day every day
  • Dallas/Fort Worth (DFW), Frontier Airlines, 1 flight per day every day
  • Dallas/Fort Worth (DFW), Spirit Airlines, 1 flight per day every day
  • Houston (IAH), United Airlines, 2-3 flights per day every day
  • Houston (IAH), Spirit Airlines, 1 flight per day every day
Woman looking out over San Juan del Sur beach town in Nicaragua

Maryland

  • Baltimore (BWI), Southwest Airlines, 2-3 flights per day every day
  • Baltimore (BWI), Spirit Airlines, 1 flight per day every day
  • Baltimore (BWI), Frontier Airlines, 1 flight every Monday, Wednesday, Friday

Connecticut

  • Hartford (BDL), JetBlue Airways, 2 flights per day every day
  • Hartford (BDL), Frontier Airlines, 1 flight per day every day
Old San Juan street with cool design above street

North Carolina

  • Charlotte (CLT), American Airlines, 2 flights per day every day
  • Charlotte (CLT), Frontier Airlines, 1 flight per day every day
  • Raleigh/Durham (RDU), Frontier Airlines, 1 flight per day every day
  • Raleigh/Durham (RDU), JetBlue Airways, 1 flight per day every day

Virginia

  • Washington (IAD), United Airlines, 1-2 flights per day every day

Frozen treat in old san juan

Ohio

  • Cleveland (CLE), Frontier Airlines, 1 flight per day every day

Michigan

  • Detroit (DWT), Delta Air Lines, 1 flight per day every day

Colorado

  • Denver (DEN), United Airlines, 1 flight per day every day

Santo Domingo, Dominican Republic

Santo Domingo, Capital Of The Dominican Republic, Latin America

In keeping with the theme, Santo Domingo is another lively historic city on the shores of the Caribbean. It was settled by Spaniards in the late 15th century and is distinguished for being the first European colony to be founded anywhere in the Americas.

The Colonial Zone looks like any other city in Spain, past the run-down suburbs and modern developments.

It has a monumental cathedral, impregnable city walls, and even a castle–Ozama Fortress–built as early as 1502.

Osama Fortress In The Colonial Quarter Of Santo Domingo, Colonial City And Capital Of The Dominican Republic

The celebratory Plaza de España is flanked by casual eateries, and the landmark Alcázar de Colón, the former palace, is now a museum housing Late Medieval artifacts and a short drive from the capital, you can find stunning coastal strips still mostly undisturbed by the masses.

A half-hour drive away, Playa Boca Chica is a lovely stretch of honey-colored sands that feel far wilder than the overly-polished Punta Cana, while Juan Dolio is your typical up-and-coming resort zone, with hotel towers bordering teal-colored waters.

Fly To Santo Domingo (SDQ), Dominican Republic From:

New York

  • New York (JFK), JetBlue Airways, 6 flights per day every day
  • New York (JFK), Delta Air Lines, 3 flights per day every day

Florida

  • Miami (MIA), American Airlines, 5 flights per day every day
  • Miami (MIA), Sky High Aviation Services, 1-2 flights per day every day
  • Miami (MIA), Frontier Airlines, 1 flight every Sunday, Thursday
  • Orlando (MCO), JetBlue Airways, 2 flights a day per day
  • Orlando (MCO), Spirit Airways, 1 flight every Monday, Wednesday, Friday, Saturday
  • Fort Lauderdale (FLL), JetBlue Airways, 1 flight a day per day
  • Fort Lauderdale (FLL), Spirit Airways, 1 flight a day per day

palm trees in Santo Domingo, Dominican Republic

New Jersey

  • Newark (EWR), United Airlines, 3 flights per day every day
  • Newark (EWR), JetBlue Airways, 1-2 flights per day every day

Massachusetts

  • Boston (BOS), JetBlue Airways, 2 flights per day every day

Georgia

  • Atlanta (ATL), Delta Air Lines, 1 flight per day every day

Cartagena, Colombia

Panorama Of The Old City Of Cartagena With Skyscrapers And A Modern Development Zone Seen Across The Caribbean Sea, Colombia, South America

The only mainland destination on this list, Cartagena is Colombia’s unofficial gateway to the Caribbean, and its busiest resort city on the turquoise sea, with a youthful atmosphere, and a picturesque Old Town that’s been virtually left intact as the Spanish intended:

With protective walls against pirates, a landmark gate topped with an unmissable yellow-washed clock tower, and dozens of ornately decorated Catholic shrines and winding lanes that are friendlier to pedestrians and horse carriages than they are to cars.

Cartagena, Colombia. Church of St Peter Claver

The coastline extending from the more quaint Ciudad Amurallada to the skyscraper-dotted Bocagrande may not be your typical Caribbean dreamland, with dark-colored sands and deep-blue oceans, but the Rosario Islands off the coast are:

A short 45-minute boat ride from Cartagena, these paradisiacal islands are fringed by powdered-sugar white sands and crystal-clear waters. Isla Grande and Isla Baru host overnight guests and sun-loving daytrippers alike.

Fly To Cartagena (CTG), Colombia From:

Florida

  • Miami (MIA), American Airlines, 2 flights per day per day
  • Miami (MIA), AVIANCA, 1 flight per day per day
  • Fort Lauderdale (FLL), Spirit Airlines, 1 flight per day every day
  • Orlando (MCO), Spirit Airlines, 1 flight every Monday, Friday

flying and traveling, view from airplane window on the wing on sunset time

New York

  • New York (JFK), JetBlue Airways, 1 flight per day every day
  • New York (JFK), AVIANCA, 1 flight every Monday, Tuesday, Thursday, Saturday

Georgia

  • Atlanta (ATL), Delta Air Lines, 1 flight every Tuesday, Thursday, Saturday

Have you been dreaming of fresh arepas, broken cobblestones and centuries-old churches that look as if they could belong in Europe?

Discover other incredible Latin American colonial destinations here.

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