Fun Summer Getaways

May 23, 2019 | Jamie Rowley

Summer is almost here! Haven’t planned a summer vacation yet? Have no fear! It’s not too late to plan a summer getaway. Here are some of our favorite summer destinations. 


Looking for a weekend city getaway this summer? Boston is the perfect place to explore in a weekend. Dive into history with the Freedom Trail, shop & eat at Faneuil Hall and Quincy Market, meander through the Boston Public Garden and Boston Common, go by land & sea on the Boston Duck Tour, and enjoy a baseball game at historic Fenway Park. Want to stay longer? Boston is the perfect jumping off point for heading to Maine or Cape Cod - more fun summer destinations!

Door County, Wisconsin

This is one of our favorite getaways in the Midwest. Can’t make it to Cape Cod? Try the “Cape Cod of the Midwest.” This peninsula is only 4 hours from Chicago or 50 minutes from nearby Green Bay Airport. Dreaming of an old-fashioned summer vacation? This is the place to escape from the modern day hustle and bustle. Allow yourself to get lost in time. Shop on the Main Streets, take a scenic boat or trolley tour, wine taste at Orchard Country winery, explore the state parks, see a movie at the Skyway Drive-In, have ice cream at Wilson’s, enjoy a stunning sunsets on Sunset Beach, try a traditional fish boil at the White Gull Inn, and indulge in cherry pie. Take yourself back to those lazy summer days when you didn't have a care in the world and relax while visiting the Midwest's best kept secret.

Colorado Springs & Rocky Mountain National Park

Want to head to the mountains? Fly into Denver and spend a day or two in Colorado Springs. Hike the Garden of the Gods, stay in the small town of Manitou Springs, and take the train up to Pike’s Peak. Don’t forget to grab one of their famous highest elevation donuts! Then head up to Rocky Mountain National Park. Whether you’re a leisurely hiker or a pro, there’s a hiking trail for everyone. Soak up all the views and wildlife before spending the night at park’s base town: Estes Park.

Seattle and Portland

Get two great cities for the price of one on an extended weekend trip. Start your trip off in Seattle exploring Pike’s Place Market, grabbing coffee at the original Starbucks and then go local coffee tasting, take in the view from the top of the infamous Space Needle, and then take in an even better view at the lesser known Sky View Observatory in the Columbia Center. From Seattle, drive just under 3 hours to Portland. Enjoy the endless breweries and delicious VooDoo Doughnuts in downtown Portland. Endless possibilities await outside of downtown. Looking for wine? Head to Willamette Valley. Looking for mountains, waterfalls, and vistas? Head to Mount Hood, Columbia River Gorge, and Multnomah Falls. Need a beach escape? Head to Cannon Beach for a beautiful pacific coast sunset.


It’s never too late to head to Europe. That’s our mantra. July may be the busiest (and most expensive) month, but sometimes you can sneak in a trip after Memorial Day or right before school starts in August. The more flexibility you have, the better deal you’ll find. Think you need months to plan a European trip? You don’t! What better way to end your summer by hopping around London, climbing the Swiss Alps, or relaxing in a Tuscan villa.

Want more travel inspiration? Check out our Instagram page

Follow us on Instagram

Newsletter Sign-Up

Join our email list of fellow travelers to get our tips, tricks and latest travel news.