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Labor Day Getaway Ideas – Travel Insurance Services

With our days of sun and swimsuits being limited and soon replaced with changing leaves and light jackets, Labor Day weekend is the ideal time to treat yourself to a break. And, if you’ve already been on a vacation, who says you can’t get away again?

There are several places to spend Labor Day weekend. It truly just depends on how far you want to travel, and what you want to do. Labor Day destinations can include beaches, cities, countryside, or simple small town USA. Although Labor Day weekend falls after many kids have returned to school, it offers one last opportunity to end the season on a high note.

Here are four fantastic places where you can get away in end-of-summer style.

September in Orlando, Florida can’t be beat. It’s a month when hotel rates are at their lowest of the year and crowds have thinned with the back-to-school season. Everyone is aware that Orlando is home to Walt Disney World and several other theme parks, but Orlando also offers many dinner shows, sightseeing adventures, outdoor activities, and other attractions that can be enjoyed by all ages. Some ideas in and around Orlando include: Kennedy Space Center Tours, Madame Tussauds, Sea Life Orlando, Legoland, Medieval Times Dinner & Tournament, and Discover Cove to name a few.


September also kicks off the fall color season in Pigeon Forge, Tennessee. With clear skies and cool weather, the Pigeon Forge area of the Smoky Mountains is ideal for outdoor activities. You can enjoy a wide range of happenings including music & variety shows, recreational activities, museums, white water rafting, horseback riding, Dixie Stampede, and so much more. The Great Smoky Mountains National Park offers a wide range of exciting things to see and do as well, including Dollywood and Dollywood's Splash Country Waterpark.


When you think of an all-inclusive resort, is Pennsylvania the first place you think of? Probably not, but the Skytop Lodge in Pennsylvania’s Pocono Mountains has been welcoming families since 1928 and offers a huge choice of activities over the Labor Day weekend, including zip-lining, kayaking, archery, tennis, boating, biking, rock climbing, and hiking. There’s also an excellent supervised children’s program, and golfers get a bonus that’s virtually unheard of: unlimited greens fees. This is the place to be for Labor Day Weekend, and events starting on Friday, September 4th include fall-themed activities for the whole family to enjoy: a beer and wine tasting, family fun grilled pizza with an interactive demonstration, live music, and a delicious Labor Day classic menu.

Skytop Lodge

Boasting the world’s longest front porch is the Grand Hotel, set on storybook Mackinac Island, Michigan. This iconic summer resort has been a favorite of vacationers since 1887. If you’re looking to take a step back in time this Labor Day Weekend, Mackinac Island will give you just that. What makes this area unique? Motorized vehicles are prohibited and folks get around on bikes and horse-drawn carriages instead. The Grand Hotel offers myriad ways for families to enjoy not only the resort, but the island as well. From biking to horseback riding, to swimming in the 220-foot pool, a Labor Day Weekend in Mackinac Island won’t disappoint. You won’t want to miss The Annual Labor Day jazz weekend either, which is a wildly popular musical event, featuring an impressive line-up of jazz and gospel artists.

The Grand Hotel


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