How to Make the Most Out of a Long Weekend


For some of us, taking a 3-4-week vacation is just not doable; and that’s ok! It might make more sense to take 3-4 smaller long weekend trips each year to make the most of your vacation days and the easiest way to do this is to add on 1-2 days to a holiday weekend. Here are some base rules:

  1. The time it takes to travel there has to be less than the time you will spend there. You don’t want to spend an entire day driving or flying, so make sure you can get to your destination in 2-4 hours.
  2. Book early…especially if you are traveling over a holiday weekend! You don’t want to end up paying double the cost for an AirbNb or hotel just because you waited until the last minute!
  3. Don’t immediately rule out international travel…if you live in certain parts of the country, you can easily get to an Island, Canada, or Mexico

I am splitting the United States into 4 categories to give ideas for each: the east coast, the Midwest, the west coast and the south.  

One of the many shelters from the Appalachian Trail that you will see on a hike through Shenandoah National Park

One of the many shelters from the Appalachian Trail that you will see on a hike through Shenandoah National Park

The East Coast

  • Upstate New York, specifically the Finger Lakes region. Base yourself in Ithaca to take in Cornell University, the Herbert F. Johnson Museum of Art, Cayuga Lake, Cascadilla Falls and wooded gorges and natural pool. This, along with some wine tasting (the area specializes in Ice Wine) would make for a great long weekend! 
  • Bermuda: This is a quick flight from NYC, Boston or the DC area, making it a great option if you are looking for a beach vacation. Check out historic St. George, take a bike ride on the 18-mile Railway Trail and eat some delicious seafood!
  • Shenandoah National Park and Charlottesville, Virginia: If you are driving from the DC area, Charlottesville is a quick 2.5-hour drive with rolling hills, UVA’s gorgeous campus, wineries and even Thomas Jefferson’s house, Monticello to see. After spending 2 nights in Charlottesville, head back the long way, through the scenic Skyline Drive through Shenandoah National Park and take a hike or two on the Appalachian Trail. 
The view from a trail in Sleeping Bear Dunes

The view from a trail in Sleeping Bear Dunes

The Midwest

  • Traverse City, Michigan and Sleeping Bear Dunes: This is a great option for people living in the Midwest. Although it’s a bit of a drive, it’s worth it once you get there. Traverse City has tons of eating and drinking options, including a number of breweries. Sleeping Bear Dunes has tons of hiking trails, calm water for swimming and a biking trail. 
  • The Bourbon Trail – Lexington and Louisville: Kentucky is still considered the Midwest to me, even though they like to so y’all down there. Take a gander at the official Bourbon trail and plot your course over 2-3 days, starting in Louisville. After sampling the urban bourbon trail, the next day hire a driver or company to take you to Four Roses, etc. (look them up) circling back to Louisville for your final evening hoping along Bardstown Road or taking in the new area of Butcher Town.
  • Toronto: Toronto is the perfect place to take a long weekend, both metropolitan and easy to navigate, anyone can find something to do and see in Toronto! Take in the view from the CN Tower, go for a walk in the 400-acre High Park and take in one of many delicious restaurants.
After a 5.6 mile hike in Rocky Mountain National Park

After a 5.6 mile hike in Rocky Mountain National Park

The West Coast

  • Vancouver: This Canadian city is a traveler’s dream…a quick drive from Seattle and a quick flight from Colorado, Southern California or Las Vegas. Vancouver is an international city with tons of shopping, great food and outdoor activities. In the summer Stanley Park is teaming with people. Rent a bike and bike through and around the park. 
  • Ojai: A few hours from San Diego and a train ride from San Francisco sits one of the newest wine regions in California…Ojai. Famous for it’s yoga retreats, hiking and winery, it’s the best place for a long weekend. Take the first day to sample wines, the second day to Los Padres National Forest, which borders the town on the north and the last day for a yoga class and spa treatments. 
  • Denver: The perfect spot for a long weekend allows you to explore both the city of Denver and Rocky Mountain National Park and the city of Estes Park or the Red Rocks. Take the first day to drive the 2 hours to Estes Park and Rocky Mountain National Park. Pick a trail that’s not too strenuous because of the elevation change and spend the evening in Estes Park. The next day, take a detour to Boulder to check out the beer scene while driving back to Denver.
The famous Albuquerque Balloon Festival

The famous Albuquerque Balloon Festival

Southern US

  • Albuquerque and Santa Fe, NM: Only an hour away from each other, you can hit up the historic Santa Fe famous for being the home of Georgia O’Keeffe (there’s even a museum to pop into) and pueblo style architecture. In Albuquerque, check out Old Town and stop by the Cibola National Forest.
  • Savannah: One of the most beautiful cities in the United States, Savannah is known for its parks, horse-drawn carriages and architecture. Make sure to walk through Forsyth Park and the historic district. Spend a day in the Wassaw National Wildlife Refuge walking the various hiking trails and finish your visit at one of Savannah’s well-known restaurants.
  • New Orleans: Named as the Top Place to Go in 2018 by the New York Times, New Orleans is a city where you can eat, drink and dance yourself into happiness. Get away from the craziness of Bourbon Street and take in the jazz on Frenchman Street, the historic homes in the Garden District and the crawfish all over the city!

These are just some starting off points and ideas to help you make the most of your vacation time! We would love to hear from you on your favorite 3-4-day trips! Comment below with them.

Because Adventure Travel Feeds the Soul,
Amy K and the Hashtag 59 Team

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