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5 Destinations To Celebrate A Graduation With Hilton Grand Vacations

Commemorate all the hard work it takes to graduate with these vacation ideas

The Vacationeer
Aerial view of The Crane, a Hilton Grand Vacations Club in Barbados, including the resort and outdoor pool and gardens

Graduation is undoubtedly a time of excitement and hopefulness for life's next chapter, whether you’re a recent graduate or celebrating a loved one’s accomplishments. It marks the culmination of hard work and dedication — worthy of a proper celebration.

There’s no better way to celebrate a milestone than with an unforgettable getaway. Here are five graduation trip ideas to congratulate the student in your life on their journey.

A young woman on the beach in Maui, Hawaii 

1. Maui, Hawaii

Plan a trip to Maui and treat your graduate to a getaway complete with far-flung feelings. It's easy to see why Maui is a sought-after island vacation destination with scenic landscapes and a list of unique things to do. 

Things to do in Maui:

Where to stay in Maui: Pick your paradise from the perfectly pink Hilton Vacation Club Ka’anapali Beach or the lush Maui Bay Villas, a Hilton Grand Vacations Club.

A mother and son walking along one of Charleston's waterways in South Carolina 

2. Charleston, South Carolina

This Southern jewel is teeming with history, fantastic food and boutiques. It’s also a family-friendly destination if you’re celebrating multiple graduations — from kindergarten to doctoral degrees.

Things to do in Charleston:

Where to stay in Charleston: Stay close to both Charleston’s historic district and charming waterfront at Liberty Place Charleston, a Hilton Club

Exterior of Valdoro Mountain Lodge, a Hilton Grand Vacations Club in Breckenridge, Colorado 

3. Breckenridge, Colorado

Visit this historic gold rush town 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.

Things to do in Breckenridge:

  • Enjoy the small-town hospitality at the local restaurants, bars and breweries
  • During wintertime, choose from shredding the legendary slopes to sipping hot cocoa by the fireplace. 
  • In the summer, disconnect from the every day as you hike, fish, cycle or indulge at one of the area’s many spas

Where to stay in Breckenridge: Valdoro Mountain Lodge, a Hilton Grand Vacations Club is a quintessential Rocky Mountains experience located at the base of Breckenridge Ski Resort.

Ferris wheel and boat at Chicago's Navy Pier 

4. Chicago, Illinois 

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

Things to do in Chicago:

Where to stay in Chicago: Book a Suite at Chicago Magnificent Mile, a Hilton Grand Vacations Club near the city’s top attractions and restaurants.

The pool overlooking the Caribbean at The Crane, a Hilton Grand Vacations Club in Barbados 

5. Barbados

If you love the beach and want a taste of history, Barbados should be at the top of your bucket list. This charming island in the West Indies provides plenty of things to do along its shores.

Things to do in Barbados:

  • Bottom Bay is a peaceful beach to unwind and relax.
  • Immerse yourself in natural pools and waterfalls at Harrison’s Cave.
  • Discover a shipwreck in Carlisle Bay by scuba diving or kayaking.
  • Enjoy a celebration dinner at Oistins Fish Fry to experience a traditional Barbados fish fry, beloved by locals and visitors alike.

Where to stay in Barbados: The Crane, a Hilton Grand Vacations Club — founded as Barbados’ first hotel in 1887 — offers unparalleled access to golden beaches and Caribbean water.

Read “Add These 10 Unique Vacation Destinations In The United States To Your Bucket List” for places off the beaten path to celebrate your recent graduation.



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.

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