Share on Facebook

The Perfect Vacation for Every Week of Summer

Don't let summer pass you by! These are the absolute best trips you can take to maximize your fun in the sun.

Every editorial product is independently selected, though we may be compensated or receive an affiliate commission if you buy something through our links. Ratings and prices are accurate and items are in stock as of time of publication.

summer vacation gradyreese/Getty Images

How to spend your summer vacation

The best season of the year is as fleeting as it is sun-filled, so you shouldn’t waste one bit of it. Need a plan? We’ve got one! Here’s how to squeeze in every last drop of sunshine and excitement from Memorial Day through Labor Day. And for the rest of the year, you’ll definitely want to check out these 20 places you need to go in 2020, according to travel experts.

Timber Cove Resortvia

May 23 to May 30: Napa Valley

Book Now

Start the season with a bang at the BottleRock Napa Valley Festival with music, food, wine, and beer all served up under the sunny California skies. The festival, which calls itself “the first taste of summer,” is headlined by the Red Hot Chili Peppers, Stevie Nicks, and the Dave Matthews Band, and the culinary stage pairs musicians with star chefs. Extra bonus: Memorial Day weekend in northern California offers perfect temps in the high 70s. Take a break from the festival at the gorgeous Timber Cove Resort, which is set on a dramatic bluff high above the Pacific Ocean across 25 acres of beautiful Sonoma coastline and has two miles of private oceanfront hiking trails on the property. Looking for a shorter trip? Start with these amazing weekend getaways in every state.

Kimpton Aertson Hotelvia

May 30 to June 7: Nashville

Book Now

The music continues in Nashville, where the CMA Fest fills lower Broadway with live country music across multiple stages from June 4 through 7. Early June is also the perfect time to explore Nashville’s expansive and scenic green areas, like Centennial Park’s rolling lawns and glistening lake (not to mention the full-size replica of the Parthenon) or the colorful blooms at the Cheekwood Botanical Gardens. Take a break from the music-loving crowds by staying in the quieter midtown neighborhood, where you’ll find hip eateries and the art-filled Kimpton Aertson Hotel, which boasts a luxurious rooftop pool for private views of the city. (Taylor Swift lives nearby, giving this hood even more country-music cache.) If music’s your thing, these are the best American cities for live music (besides Nashville).

legoland summer vacationvia

June 7 to June 14: Hudson Valley, New York

Book Now

Grab the kids and head to the verdant hills of New York State for the grand opening week of LEGOLAND New York Resort, the first major theme park to open in the Northeast in more than four decades. This epic 150-acre destination is also LEGOLAND’s largest park in the world and features seven themed lands and more than 50 rides, shows, and attractions geared toward families with children ages 2 through 12. One highlight: The LEGO Factory Adventure Ride, which utilizes the world’s most advanced motion-tracking and facial-detection technology to “shrink” guests down into mini LEGO figurine versions of themselves for a journey through the process of becoming a LEGO brick. Here are more of the most amazing theme parks attractions you’ll want to see this year.

Yachtsman Hotel & Marina Clubvia

June 14 to June 21: Kennebunk, Maine

Book Now

Stretching along a prime stretch of Maine coast, the Kennebunks are a quintessential summer destination, with lobster rolls served at scenic waterside stops, sunny beaches (although the frigid Atlantic takes some getting used to), and a good dose of Americana (this was the former summer residence of George and Barbara Bush). Kennebunkport launches its summer season with Launch, a Maritime Festival event that highlights local seafaring traditions like the Captain’s Cook-Off lobster bake, a River Lights Boat Parade, and a Blessing of the Fleet at Cape Porpoise on Sunday morning. Overlooking the Kennebunk River and a quick stroll to downtown Kennebunkport, the new Yachtsman Hotel & Marina offers not only a waterfront location but also a pool in a boat barge that floats right on the Kennebunk River. If this sounds heavenly to you, check out more of the most beautiful lakeside resorts in the world.

alaska via

June 21 to June 28: Fairbanks, Alaska

Book Now

The longest days of summer call for celebration, and in Alaska, where summer offers up just a few hours of darkness, the summer solstice is truly a call for a party. In Fairbanks, the Midnight Sun Festival offers up entertainment, music, and local food for Alaska’s largest single-day event. And Fairbanks is a summer paradise, with rafting, hiking, and access to the Arctic and several national parks, including Denali. There are also six breweries and distilleries in the area, as well as dozens of restaurants. Find out 31 things you never knew about the summer solstice.

washington DC NeoPhoto/Getty Images

June 28 to July 5: Washington, D.C.

Book Now

The best time to travel to the nation’s capital is for the country’s birthday, when you can attend the free “A Capitol Fourth” concert, line up along Constitution Avenue for the National Independence Day Parade, and take in the spectacular fireworks that light up the sky over the national museums and monuments. This patriotic week is also a good opportunity to explore the Smithsonian museums and zoo, pay your respects at Arlington National Cemetery, stroll along the Georgetown waterfront, or root for the home team at Nationals Park. The Washington Marriott Georgetown is the perfect home base to explore D.C. It’s away from the hustle and bustle of the city center, but still in a prime location to explore the quaint shops and restaurants of the Georgetown area. It’s also close to Dupont Circle and attractions such as the Lincoln Memorial. 

Tivoli Carvoeiro Algarve Resortvia

July 5 to July 12: Algarve, Portugal

Book Now

Looking for a summer destination that offers fabulous beaches as well as great summer entertainment? Portugal has it all, including the best beach in all of Europe. According to Best of Europe magazine, that would be Carvoeiro Beach in Portugal’s enchanting Algarve region, which boasts scenic fishing villages, charming seaside restaurants, hidden grottoes, and turquoise waters. And for entertainment, it’s hard to beat the AgitÁgueda Arts Festival, held July 4 to 26, a celebration art and music with more than 500 performers and artists. Stay at the Tivoli Carvoeiro Algarve Resort on the clifftop of Vale de Covo, which boasts an incredible pool with views over the sea and easy access to the beach. For more beach fun, check out these great beaches for every month of the year.

yellowstone national parkdszc/Getty Images

July 12 to July 19: Yellowstone National Park, Montana

Book Now

Adventures by Disney (AbD) offers trips to the most popular national parks across the United States and Canada, including Yellowstone National Park, which was its very first “Adventure” trip more than a decade ago and is still one of its most popular. This week, take the whole family on a summer adventure to Montana, where you’ll explore Yellowstone’s amazing natural attractions, including the soaring waters of Old Faithful, the rainbow-hued Grand Prismatic Springs, and the Grand Canyon of Yellowstone. Then, try out the adventures—horseback riding at a real dude ranch, fly-fishing, white-water rafting in the Gallatin River, and zip lining in Big Sky. Here are more VIP Disney vacations you should try at least once.

mackinac islandvia

July 19 to July 26: Mackinac Island, Michigan

Book Now

Named the number one summer destination in America by TripAdvisor, Mackinac Island is often referred to as being suspended in a more innocent time. “The Jewel of the Great Lakes,” Mackinac Island is located in Lake Huron and has a ban on motor vehicles, limiting transportation to horse and buggy, walking, and biking on its traffic-free roads—making it the perfect place to unplug and unwind. And this July week offers up plenty of amazing lake views, with the Bayview Mackinac Race featuring an array of boats sailing between islands. Take in the boats and enjoy the beautiful lake beach setting at Mission Point. The seasonal resort, set on 18 acres of lakefront property where Lake Huron meets Lake Michigan, offers bike rentals, kite-flying workshops, horseback-riding lessons, and guided sunrise hikes. It is also home to Lakeside Spa and Salon, the island’s only full-service health and wellness retreat. Don’t miss these other enchanting islands in the United States.


July 26 to August 2: Montreal, Canada

Book Now

Head north of the border to the French-influenced city of Montreal, where the stars, and festivals, align to create a cornucopia of amazing entertainment this week. Among the highlights: Catch top comics every day this week at the world’s largest comedy event, the Just for Laughs Festival. Then watch a spectacular fireworks display that lights up the night sky as part of the monthlong L’International des Feux Loto-Québec fireworks competition. Here are more of the most popular travel destinations in Canada.

vailgladassfanny/Getty Images

August 2 to August 9: Vail, Colorado

Book Now

This cosmopolitan Colorado ski town is possibly even more fabulous in the warmer months, with nearly constant sunshine and no humidity. There are more than 340 miles of mountain-bike and hiking trails to explore that traverse verdant mountain terrain, wildflowers, and towering pines, and Epic Discovery, Vail’s summer on-mountain experience, lets you try out everything from zip lining to mountain coasters. There’s also festivals aplenty all summer, including the internationally renowned Vail Dance Festival, held this week; it features performances that feature the stars of dance, so you can catch Misty Copeland pirouetting in person.

Stay right in the heart of Vail Village at The Lodge at Vail, which has a pool with mountain views as well as lovely outdoor patio dining with firepits, where you can make s’mores and watch the stars. And for the chillier months, make sure to scope out the best ski resorts in Colorado.

st. luciavia

August 9 to August 16: St. Lucia

Book Now

Spend August satisfying your sweet tooth during St. Lucia’s Chocolate Heritage Month. The Caribbean island produces some of the world’s most sought-after chocolate (a third of which is used in treats made by Hershey’s). Base your chocolate-drenched beach stay at The Landings Resort & Spa, where the 70 privately owned, airy, and luxurious one-, two-, and three-bedroom suites are elegantly appointed and have plenty of room for families. St. Lucia is also one of our favorite warm-weather destinations to escape the cold.

great smoky mountains glamping campingvia

August 16 to August 23: Great Smoky Mountains

Book Now

Head to the untouched beauty and great outdoors of the Great Smoky Mountains for the Celebrating Our Appalachian Musical Roots Festival in downtown Gatlinburg, which features hit songwriters and live music from August 20 to 23. The event and entertainment are free, and aspiring songwriters can partake in song competitions, workshops, mentoring sessions, and stage spots.

For the rest of your vacation, stay among the pines, fall asleep under the stars, and wake up in one of America’s most iconic national parks to the sounds of nature, and then spend the day on the Appalachian Trail, fly fishing or white-water rafting. Summer is the perfect time to enjoy the crisp mountain air with the ultimate glamping vacation, Under Canvas Great Smoky Mountains. At the campsite, you’ll find safari-inspired canvas lodging tents, which can hold up to seven people and are furnished with Casper mattresses, luxe linens, West Elm furniture, woodburning stoves, and full bathrooms. If you need to stay closer to home this summer, you can’t go wrong with the best campsite in your state—and every other.

minnesota state fair JoeChristensen/Getty Images

August 23 to August 30: Minnesota State Fair

Book Now

Princesses carved in butter, deep-fried food on sticks, and more than 320 acres of adorable farm animals, adrenaline-pumping rides, entertainment, shopping, and fun are all on tap at the fun and friendly Great Minnesota Get-Together (also known as the Minnesota State Fair). It opens August 27 and will feature live performances by the Doobie Brothers and Tim McGraw. When you’re done filling up on favorite fair food—like Sweet Martha’s famous cookies, cheese curds, and foot-long hot dogs (not to mention beer in flavors like Caramel Corn Cream Ale)—head to nearby Minneapolis for a luxe stay at Hotel Ivy. In addition to offering plush rooms, it has a yacht or luxury sailboat for use only by Hotel Ivy guests, so they can experience the Land of 10,000 Lakes in style. These are the other food festivals worth a pit stop.

NYCIngus Kruklitis/Getty Images

August 30 to September 7 (Labor Day): New York, New York

Book Now

Yes, we know this is longer than a week, but you’ll want the extra days here. End the summer just the right way in the Big Apple on Labor Day weekend and watch the tennis stars shine bright under the lights at the U.S. Open. The tournament starts August 31, and the first three rounds offer all-day play, happening simultaneously on dozens of courts. While there, you can sample delicious fare from some of New York City’s top chefs as you watch your favorite players.

In your free time, explore the city—there’s always something new to experience in the City That Never Sleeps. Make the most of your experience by staying at The Bowery Hotel, a quintessential Manhattan property that put the East Village on the map. Don’t be surprised if you see a celebrity or two (or a tennis star) while enjoying a cocktail in the elegant Lobby Bar or indulging in a bowl of decadent pasta at Gemma Restaurant. You should also check out these 15 NYC hidden gems most New Yorkers don’t know about.

Melissa Klurman
Melissa is an intrepid explorer and award-winning travel journalist with more than 25 years of experience. She covers topics ranging from family travel and Disney to honeymoons and romantic beaches, and everything in between.

Newsletter Unit

CMU Unit

Subscribe & SAVE Save Up To 84%!