Destination Guides

10 ways to extend your summer beyond Labor Day weekend

On the academic calendar, Labor Day is often flagged as the last day of summer. But the long days of sunshine, beach swims and outdoor adventure don’t have to end just yet. Thankfully, for the sun-worshippers among us, the summer season doesn’t actually finish until late September. So there’s plenty of time to squeeze in one last vacation (or two!) before the chill of fall sets in. It’s also a great way to beat the crowds for a fuss-free getaway. Here are 10 ways you can extend your summer beyond Labor Day weekend.

Book a Beach Getaway

St Augustine, Florida

St Augustine, Florida

For a charming combination of small-town atmosphere and world-class beaches, look no further than St Augustine in Florida. In September, the summer crowds have thinned, but the warm, balmy weather remains. It’s the perfect time to stretch out by the water and enjoy undisturbed relaxation under the Floridian sun. This time of year, the town is particularly lovely as native tropicals like Birds of Paradise and Hibiscus begin to bloom. As if you needed any more reason to visit St Augustine, the local craft beer scene hits its stride in late September with the advent of Oktoberfest.

Falmouth, Massachusetts

On the tip of Cape Cod lies Falmouth, the ideal beach town to extend summer holidays. This pleasant-weathered seaside gem offers the best boating, cycling and swimming on the Cape. Falmouth is also in prime position to reach the island of Martha’s Vineyard. Here, travellers can enjoy days wandering the harbor towns, searching for lighthouses, and strolling by charming farmlands. Do your ideas of extending the Labor Day weekend involve a little more beachside adventure? We suggest a day trip from Falmouth to the Cape Cod National Sea Shore for a 4WD escapade on the dunes.

You can discover the pristine coastal beauty of Cape Cod with Trafalgar on the Boston, Cape Cod and Martha’s Vineyard tour

Holland, Michigan

For a trip to Europe without the fuss, we recommend Holland! Nope, not that Holland. We’re talking about Holland, Michigan, the Dutch-settled town that calls the shores of Lake Michigan home. This cultured town offers all the trappings of a beach getaway with an extra dash of European history thrown in for good measure. After days splashing, sailing or sunbathing at one of America’s Great Lakes, the 250-year-old Dutch windmill, DeZwaan, is also a must-visit. This authentic windmill and the surrounding gardens make for a picture-perfect picnic spot. Follow up with a visit to a local museum, and you will have found yourself the perfect way to extend the Labor Day weekend.

Wine and Dine

Napa Valley, California

green gold vineyard Napa Valley California USA

It’s impossible to say “wine” and not think about the expansive vineyards of Napa Valley. In September, the region is awash in classic Californian sunshine. This makes for perfect harvest season conditions and an even better way to extend summer holidays. Travellers can explore wineries and vineyards at their own pace, diving into the history and cuisine unique to each locale. To see the highlights of the Valley, however, a ride on the Napa Valley Wine Train through the lush landscape of vineyards is essential. The Wine Train is more than just a railroad ride, it is a luxury adventure to the Valley’s most celebrated wineries.

Experience the delights of California when you travel with Trafalgar on the Northern California tour

Sonoma, California

Photo by Trent Erwin on Unsplash

For travellers who prefer to enjoy their vino in a more rustic and down-to-earth setting, we recommend Sonoma. Filled with sun-drenched vineyards alongside awe-inspiring redwood forests, visitors to Sonoma are spoilt for choice, as the area is home to more than 400 premium wineries which scatter around the county. Foodies will love pairing their reds and whites with Sonoma’s farm-to-table cuisine that celebrates the flavours of local produce. For those wondering how to extend summer holidays in delicious style, Sonoma is the place to go.

GET INSPIRED: 9 epic things to do in Northern California

New Orleans, Louisiana

The creole cuisine of New Orleans will make your taste buds sing. The rich and spicy fusion of French, West African, Spanish and Native American cooking is a staple of the city’s culture. Only in The Big Easy, as the city is fondly termed, will travellers experience food as effervescent as the city it’s made in. Under clear summer-like skies, travellers can spend days gorging themselves on zesty jambalaya, okra-packed gumbo and sugar-dusted beignets. To keep the fun and flavour of Labor Day weekend rolling, New Orleans is impossible to pass up.

Take your tastebuds on a journey and discover the best of New Orleans and Creole Cuisine when you travel with Trafalgar on the ‘Tastes and Sounds of the South tour

Head Off the Beaten Track

Sedona, Arizona


If you like to spend every second of summer exploring the great outdoors, then Sedona is the perfect place to extend your Labor Day weekend. September in Sedona is bathed in mild Arizonan weather. It is the ideal time to rumble across the red landscape on a Jeep tour, bike over the tumbling rocks past arid greenery, and hike to the monumental Devil’s Bridge in Red Rock State Park. If you prefer to explore at a more leisurely pace, Slide Rock National Park will be more your speed. It’s the perfect place to picnic by bubbling, rocky streams and take in the raw beauty of nature.

Traverse the natural wonders of the Sedona with Trafalgar on The Trailblazer tour

Lake Tahoe, California/Nevada

Trailblazers wondering how to extend summer after Labor Day need look no further than Lake Tahoe. As families pack up for another year of school, the number of tourists at the lake slumps. It’s the perfect opportunity to take advantage of the lingering warmth before snow powders the landscape in November. The sapphire of Lake Tahoe is bordered by evergreens and cracked mountains on all sides. In this robust landscape, travellers can kayak, canoe, parasail and hike to their heart’s content. 

GET INSPIRED: 10 of North America’s most epic views

Explore the Tropics

Honolulu, Hawaii

Aerial view of Hawaiian Island

September is the hottest month in Hawaii, making it the perfect destination to extend summer holidays. The capital city of Honolulu offers cosmopolitan comforts like luxury shopping, premium restaurants and five star hotels. But it’s tropical beaches and lush rainforests are the true star of the show. There are plenty of centrally located beaches to enjoy at the doorstep of the city. But, a short drive from Honolulu lies the fine sands of Kailua Beach. A day spent sunbathing and paddling at this cerulean gem is well worth the travel. If you can tear yourself away from the beach for a few hours, we recommend a hike up Diamond Head. This extinct volcanic cone, accessed by ninety-nine steps that cut across the cliffside jungle, offers panoramic vistas over the gorgeous city below.

GET INSPIRED: 7 sun-kissed adventures you can only have in Hawaii


Photo by Reilly Durfy on Unsplash

The sunny shores of Bermuda are the ideal destination to extend Labor Day weekend abroad! The warm beaches in this Caribbean paradise are perfect for swimming and snorkelling from sunrise to sunset. Punctuate your trip by exploring the UNESCO listed town of St George, the Crystal Caves, and the pink sands of Horseshoe Bay Beach. There’s so much to discover on this archipelago that travellers will never want to leave.

Inspired to find out more? Contact our Travel Advisors to request a quote to unlock the best of the USA and beyond

Which incredible destination will you choose to extend your Labor Day Weekend? Let us know in the comments below! Or, if you’re still looking for inspiration, head to our website so you can read more about how you can discover the best summer holiday destinations when you travel with Trafalgar.

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