Top 5 Labor Day Weekend Getaways

Labor Day weekend offers travelers one last chance to enjoy the sweet taste of summer. Bask in the sun, enjoy a cocktail, or relax beachside at these top Labor Day weekend destinations.

Where to Spend Your Long Weekend

1. Martha’s Vineyard, Massachusetts

Accessible only by boat or plane, Martha’s Vineyard is the ultimate haven for your Labor Day weekend getaway. The island is located just south of Cape Cod and has long been a popular destination for New Englanders searching for a summer escape. 

With several shorelines to choose from, you can enjoy beautiful beaches on almost all sides of the island. The Aquinnah Cliffs are another popular spot with massive clay cliffs carved by glaciers thousands of years ago. 

2. Vail, Colorado

You’ve likely already experienced Vail throughout the winter months, but the city is equally as beautiful throughout summer, too. This Labor Day weekend, enjoy hiking the beautiful trails along Vail Mountain or take in the view from above with a gondola ride.

Summer is also the perfect time to bike on and around the mountain, explore the area’s botanical gardens, or venture into Vail’s villages for shopping, dining, and more. 

3. Savannah, Georgia

This beautiful, southern city oozes charm with antebellum architecture and cobblestone streets blanketed by hundred-year-old live oaks and Spanish moss. Savannah is also famous for its dozens of lush parks scattered throughout the city and beautiful riverfront district. 

Spend your Labor Day weekend in Savannah and enjoy delicious southern cuisine, peruse local boutiques, or, for a more thrilling adventure, partake in a ghost tour around the historic city. 

4. Chatham, Massachusetts

Located on the southeastern tip of Cape Cod, Chatham offers all the allure of a vacation to the Cape minus all the crowds. 

This Labor Day weekend, stay at one of the many quaint bed and breakfasts in and around the area and explore the old Chatham lighthouse – standing since 1808. And, for the outdoor enthusiasts, the city offers many nature trails and parks for you to explore.

5. Delray Beach, Florida

For a Labor Day weekend spent beachside, consider traveling south to Florida’s stunning east coast. Located just north of Fort Lauderdale, Delray Beach offers a welcoming downtown scene with several bars, restaurants, and shops at your disposal.

The city also boasts incredible beaches with beautiful turquoise waters – perfect for a day spent fishing, boating, and more.

Ensure this Labor Day weekend is the best one yet when you ship your luggage ahead of your arrival. Learn more about shipping ahead or generate a quote to start planning your next getaway.