Cancún vs Punta Cana vs Jamaica: which is best for a first trip?

Cancún & the Riviera Maya (CUN)

Best for: variety, day trips and the most resort choice at every price.

Beaches: Turquoise water and fine white sand. The Hotel Zone's east-facing beaches can have strong waves; the north side and Isla Mujeres are calmer.
Getting there: Cancún airport has the most flight options of the three. Hotel Zone resorts are about 20 to 30 minutes away; Playa del Carmen and Akumal are roughly an hour or more.
Things to do: Mayan ruins (Chichén Itzá, Tulum, Cobá), cenotes, snorkeling, Isla Mujeres and Cozumel.
Watch out for: Sargassum seaweed from spring to late summer, especially south of Cancún, and the VISITAX state fee.

Best for: long, calm beaches and lower prices outside winter.

Beaches: Wide stretches of soft sand lined with palm trees, mostly in Bávaro. Reefs offshore keep many beaches calm.
Getting there: Punta Cana airport is close to most resorts, often 15 to 40 minutes.
Things to do: Saona Island boat trips, catamaran cruises and golf. Less culture right on the doorstep than Cancún.
Watch out for: Some beaches get sargassum in summer. Resorts are large and spread out, and you'll spend most of your time on the property.
Entry: You need to fill in the free online e-Ticket entry form before you fly.

Best for: personality, music and food, and smaller resorts.

Beaches: Generally calm, with smaller private beaches at many resorts. Negril's Seven Mile Beach is the famous one, about 1.5 hours from the airport.
Getting there: Montego Bay resorts are close to the airport. Negril, Lucea and Ocho Rios take longer, so check the transfer time.
Things to do: Dunn's River Falls, rafting on the Martha Brae, Rick's Café in Negril and plenty of jerk chicken.
Watch out for: Resort prices vary more, and the budget end can be basic. Stay on resort or use licensed tour operators for trips.