Need destination recommendations! Looking to go to a warm, beach-y destination in early September with my boyfriend for 7 days. Want somewhere easy to get to from Chicago (probably in the Caribbean or Central America?) with good Marriott properties. Looking to spend a few days by the resort pool / beach with a couple of excursions. Not looking for anything ultra expensive, but not looking to stay at a courtyard either. Any recommendations or suggestions?!

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Dominican Republican (Punta Cana, La Romana)

Cartagena

St. Kitts

St. Lucia

Turks & Caicos

Riviera Maya

(just keep in mind September is likely the busiest month in hurricane season)

Bermuda in September usually has nice weather! Not sure about Marriott properties though.

We loved Sint Maarten so you could check that out. Note, though, that September is prime hurricane season, so a spot like St. Lucia or Aruba, which are both not in the primary path of hurricanes, would be smart.

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