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This U.S. city is the top Labor Day destination, says Chase Travel

San Juan came out on top

By Amanda Teague Published August 19, 2025

A "parade" of umbrellas above the street in San Juan, Puerto Rico. — Andrew Davey / The Manual

Looking for a tropical escape without leaving U.S. borders? San Juan, Puerto Rico, is the top trending Labor Day destination of 2025, according to Chase Travel. The Caribbean city saw a 116% year-over-year growth in bookings, thanks to its easy access from major U.S. hubs and unique experiences that you can’t find elsewhere in the country.

From the cobblestone streets of Old San Juan to the beautiful trails of El Yunque National Forest (the only tropical rainforest in the U.S. National Forest System) San Juan offers experiences you can’t find anywhere else. Visitors can explore the historic Castillo San Felipe del Morro, browse colorful local markets, or dive into the island’s growing fine dining scene, where acclaimed chefs like Juan José Cuevas bring world-class flavors to the table.

Miami and Maui follow closely behind

Trailing San Juan, Miami, Florida, has seen a 55% year-over-year growth in Labor Day travel interest. Known for its nightlife, the city will be buzzing over the holiday weekend with hotspots like LIV at the Fontainebleau, E11EVEN, and Club Space drawing partygoers from around the world. But Miami offers more than clubbing. Visitors can stroll through the street art at Wynwood Walls, explore the Pérez Art Museum Miami, or simply enjoy the sun along the iconic shores of South Beach.

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Maui, Hawaii, comes in third with a 37% increase in popularity. Famous for its more than 80 accessible beaches, Maui is ideal for travelers seeking a slower pace and incredible scenery. Visitors can unwind at world-class resorts like Grand Wailea, A Waldorf Astoria Resort, or Four Seasons Resort Maui at Wailea, or embark on experiences such as driving the Road to Hana, snorkeling at Molokini Crater, or catching a sunrise at Haleakalā National Park.

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Amanda, an accomplished freelance writer from Columbus, Ohio, is a dedicated explorer of both the world and the written word…

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