Summer is officially coming to an end, and this weekend may be the last time you’ll soak up that sun before the year’s out. Here are five sunny Labor Day getaways that are easy to get to and super fun to visit for the long weekend!

San Juan, Puerto Rico

Don’t Miss: Castillo San Felipe del Morro, one of the largest Spanish fortresses in the Caribbean. This UNESCO World Heritage Site is located in Old San Juan, and is visited by more than two million travelers every year.

Cancun, Mexico

Don’t Miss: Playa Delfines, a gorgeous beach outside of Cancun’s crowded hotel zone. After taking in the amazing view, head on over to the nearby Mayan ruins to round out your day.

Montego Bay, Jamaica

Don’t Miss: The Half Moon Equestrian Center, rated first among Montego Bay attractions on TripAdvisor. A wonderful experience for family travel, the Equestrian Center offers horse and pony rides, polo lessons, and more.

Bridgetown, Barbados

Don’t Miss: Stavronikita, a deliberately wrecked Greek ship that has become an artificial reef and a must-see for divers of all skill levels.


Don’t Miss: Boca Catalina, one of the best beaches in Aruba. Perfect for couples, families, groups, and solo travelers, don’t forget to try out the snorkeling!

About the Author: Sarah Stone

As the managing director of Frayed Passport, my goal is to help you build your a lifestyle that lets you travel the world whenever you want, however long you want, and not worry about where your next paycheck will come from. I've been to 20+ countries and five continents, lived for years as a full-time digital nomad, and while I'm based in Miami now, I spend one-third of the year traveling to amazing destinations around the world and have worked completely remotely since 2013. If you would like to share your story with our community, or partner with Frayed Passport, get in touch with me at!