Cookie Statement

This website uses cookies to ensure users get the best experience on our website. LEARN MORE

Where to Go

5 Places to Celebrate a Graduation

Commemorate all the hard work and achievement that it takes to graduate with these graduation vacation ideas

The Vacationeer
A group of young adults smiling posing with their arms up while on vacation.

Editor’s Note: These are unusual times, and some businesses are currently closed. No matter what you do, practice safe travels, follow CDC and local guidelines, and call ahead to confirm operational hours.

Whether you're a recent graduate or it's been some time since you've donned a cap and gown, graduation is undoubtedly a time of excitement and hopefulness for life's next chapter.  

It marks the culmination of hard work and dedication and is worthy of a proper celebration (read: a vacation). 

Here are five graduation vacation ideas. 

Maui, Hawaii

Plan a trip to Maui to treat yourself to a getaway complete with far-flung feelings. As the second-largest of the Hawaiian Islands and home to a long list of unique things to do and stunning scenery, it's easy to see why it's the top island vacation destination in the world

Add these activities to your "things to do in Maui" shortlist:

  • Watch in awe as humpback whales make their migration during the winter months. 
  • Enjoy a taste of Hawaiian culture with local farm-to-table fare at one of the many locally owned and operated eateries.  
  • Bask in the glow of breathtaking sunrises and sunsets from Haleakala.
  • Kick-off your flip-flops for a stroll in the sand — you have more than 30 miles of shoreline from which to choose.

Where to stay in Maui: Opening in September 2021, the eagerly awaited Maui Bay Villas by Hilton Grand Vacations provides the ideal launchpad to experience all this beloved island offers. 

Read Hilton Grand Vacations' 9-Step Guide to Maui to discover more about our new property and more Maui graduation vacation ideas. 

Charleston, South Carolina

This Southern jewel is crawling with history, fantastic food, and boutiques. Take a horse-drawn carriage ride around the historic city and eat your way down King Street.

Here are a few of our top Charleston spots to go after graduation:

  • Spend a few days on the beach on Sullivan’s Island or the Isle of Palms.
  • Rent a kayak or paddleboard and explore the waterways around the city.
  • Participate in a Second Sunday Street Fair.

Where to stay in Charleston: Be on the lookout for the opening of the Hilton Grand Vacations, Liberty Place Charleston by Hilton Club

Breckenridge, Colorado

Plan a visit to this historic gold rush town for an opportunity to let loose and reconnect with nature. This small but mighty Rocky Mountain town, just seven miles long and two miles wide, is packed with plenty to do year-round.

Here are a few must-do's in Breckenridge:

  • Enjoy the small-town hospitality at any of the local restaurants and bars. You'll have more than 100 from which to choose, including breweries and a distillery. 
  • During wintertime, visitors have their pick of ways to enjoy the town's powder days. Activities range from shredding the legendary slopes to sipping hot cocoa by the fireplace. 
  • Visit during summertime and disconnect with the every day as you hike, fish, raft the whitewater, cycle or indulge yourself at one of the areas many spas. 

Where to stay in Breckenridge: Hilton Grand Vacations' resort Valdoro Mountain Lodge is a quintessential Rocky Mountains experience. Boasting spacious condo-like accommodations, including a full kitchen and breathtaking views, and located at the base of Breckenridge Ski Resort, you'll have idea access to the area's top things to do. 

Chicago, Illinois 

If you're looking to travel to a city that celebrates all summer long, Chicago is a clear winner. From farmers’ markets to street festivals, Chicago provides a fun getaway to celebrate all of your hard work:

Where to stay in Chicago: Book a studio or suite at our new resort, Hilton Grand Vacations Club Chicago Downtown/Magnificent Mile


When considering places to go after graduation, the islands of the Caribbean might be top of mind. But, with so many islands to choose from, it can be hard to decide on one.

If you love the beach and also appreciate history, Barbados is the perfect place. This charming island in the West Indies is small in size but provides a long list of things to do along its shores.

  • Bottom Bay is a peaceful beach to unwind and relax.
  • Immerse yourself in natural pools and waterfalls at Harrison’s Cave.
  • Dive with sea turtles and discover a shipwreck in Carlisle Bay.
  • Enjoy a celebration dinner at Oistins seaside fish market to experience a traditional Barbados fish fry

Where to stay in Barbados: Founded as Barbados’ first hotel in 1887, The Crane, now Hilton Grand Vacations at The Crane, remains the oldest operating resort in the Caribbean.

Read on to explore these trending experiential vacations around the world. 



The Vacationeer

The Vacationeer is a collective of Hilton Grand Vacations storytellers whose goal is to inspire travelers to go further. We're always on the lookout for new destinations to explore, useful travel tips, and unique ideas to help you plan the most memorable vacations possible.

Popular Articles