Where To Stay

5 Last Minute Labor Day Weekend Escapes

The Kimpton Seafire poolscape on Grand Cayman's Seven Mile Beach.
The Kimpton Seafire poolscape on Grand Cayman's Seven Mile Beach.

Labor Day Weekend is around the corner and we want you to make that three-day weekend count. Here are a handful of last minute vacation ideas.

Arial Pool Beach
An aerial shot of The Diplomat's iconic poolscape.

1. Hollywood Beach

Staycation close to home this Labor Day Weekend at one of Hollywood Beach’s newest resorts. Take your pick from wasting away again in Margaritaville, a culinary journey through the newly renovated Diplomat or pool party vibes at Hyde Beach Hollywood. 

Key West staple, The Green Parrot.

2. Key West

Hop in the car and drive south until you reach the end of the road. Spend the weekend in Key West at classic haunts like the Green Parrot and discover all the new restaurants, bars and shops that have popped up recently. We’ve got you covered on where to stay, including a pair of fancy new resorts on Stock Island. If you’d rather not make the drive all the way to Key West, hide away at a resort in the Upper Keys.

Oasis Pool Sunset – Photo Credit, Kimpton Seafire Resort + Spa
A stunning sunset over Grand Cayman's Seven Mile Beach at the Kimpton Seafire's pool. TanyaJane

3. Grand Cayman

If the Caribbean is calling, might we suggest the hourlong flight to Grand Cayman and a stay at the new Kimpton Seafire on Seven Mile Beach? The resort is to die for and you can even tack on a trip to the remote Cayman Brac for some off the grid relaxation.

The Lobby of El San Juan Thomas Hart Shelby

4. Puerto Rico

Take your Labor Day celebrations to Puerto Rico and leave your passport at home when vacationing at this US territory. Discover San Juan and its charming Old Town from the comforts of the newly renovated El San Juan Hotel complete with a restaurant by Miami’s own Barceloneta and nightlife by former Opium Group kingpins.

Surf's up with the bros at Rockaway Beach's Locals Surf.

5. New York City

New York is always a good idea. And there’s plenty to discover in New York’s outer boroughs from the New York Botanical Garden in The Bronx to a surfing safari in Rockaway Beach, Queens. There are also plenty of hip new hotels to check into, including the stunning new 1 Hotel Brooklyn Bridge.