Wayfarly
North America travel guide
North America

North America travel guide

Wayfarly's third continent starts where a lot of people's actual travel planning starts: white-sand beaches and warm water. Most of these destinations run on all-inclusive resort economies, so the transport comparisons here focus on realistic flight routes and airport transfer logistics rather than trains and buses — a genuinely different kind of trip than Europe or South America, and worth planning for differently.

10 destinations, ready to compare

Aruba, Aruba
Aruba

Aruba

Aruba

Mid-range

Aruba sits just outside the Caribbean hurricane belt and gets some of the lowest rainfall of any Caribbean island — locals call it "One Happy Island," and the arid, cactus-dotted landscape looks more like a desert than the lush jungle most people picture when they think Caribbean.

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Cancún, Mexico
Cancún

Cancún

Mexico

Budget

Cancún didn't exist as a city until 1970 — Mexico's government picked the spot using a computer analysis of wind patterns, water color, and hurricane risk, then built an entire resort city from scratch on what had been an uninhabited sandbar.

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Havana, Cuba
Havana

Havana

Cuba

Budget

Havana has more 1950s American cars still running as daily transportation than almost anywhere else on Earth — not for nostalgia, but because a decades-long US trade embargo made importing new vehicles nearly impossible, so Cubans kept the same cars alive with improvised parts for over 70 years.

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Montego Bay, Jamaica
Montego Bay

Montego Bay

Jamaica

Budget

Jamaica produces some of the most influential music genres of the 20th century — reggae, ska, and dancehall all trace directly back to this island — and Montego Bay's studios and live venues still shape sounds that show up in pop charts worldwide decades later.

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Nassau, Bahamas
Nassau

Nassau

Bahamas

Mid-range

The Bahamas has a beach where wild pigs swim out to greet arriving boats — Exuma's swimming pigs are a short flight from Nassau, and nobody fully agrees on how they got there, though the leading theory is far less romantic than the tourist photos suggest.

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Punta Cana, Dominican Republic
Punta Cana

Punta Cana

Dominican Republic

Mid-range

Punta Cana didn't have a single hotel until the 1970s — today it holds one of the largest concentrations of all-inclusive resorts on Earth, strung along roughly 30 uninterrupted miles of white sand that most visitors never leave for the entire trip.

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San Juan, Puerto Rico
San Juan

San Juan

Puerto Rico

Budget

Old San Juan's fortress walls have defended the same seven blocks for over 400 years without ever being taken by force in a direct siege — not by Francis Drake in 1595, not by the Dutch in 1625, not by the British in 1797 — making it one of the most successfully defended cities in the Americas.

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Santo Domingo, Dominican Republic
Santo Domingo

Santo Domingo

Dominican Republic

Budget

Santo Domingo's Zona Colonial holds the oldest cathedral, the oldest paved street, and the oldest fortress built by Europeans anywhere in the Americas — Columbus's own son governed the city from here while Europeans back home still had no real idea how big the continent they'd just found actually was.

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Tulum, Mexico
Tulum

Tulum

Mexico

Budget

Tulum is the only major Mayan ruin site built directly on a Caribbean cliff overlooking the sea — everywhere else the Maya built inland, but here you can stand in a 13th-century watchtower and look straight down at turquoise water and a beach most resorts would kill for.

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Varadero, Cuba
Varadero

Varadero

Cuba

Mid-range

Varadero sits on a narrow peninsula so consistently lined with white sand and turquoise water that Cuba built its entire international beach-tourism industry around this one 20-kilometer strip, largely separate from the rest of the country's economy.

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