Where to Go

3 Road Trips To Celebrate Your Retirement

Cruise from the coastline to national parks and exciting cities

The Vacationeer
Willow Creek Bridge along the coast of Big Sur, California

Every season is vacation-season when you’re a Hilton Grand Vacations Member celebrating retirement with a road trip.

The definition of off-season changes from destination to destination: Winter tends to be a less-crowded season in beach towns while skiing hot spots empty out around summer.

That’s great news for retirees: You can plan a road trip with the full map and calendar at your disposal.

Fall foliage along a highway in South Carolina 

Explore iconic cities, unspoilt landscapes and hidden gems across the United States with these American road trip itineraries featuring Hilton Grand Vacations properties.

1. A Slow Southern Drive In South Carolina

A South Carolina road trip is an underrated win for off-season travelers, especially retirees who have time to appreciate the Palmetto State’s dazzling landscapes.

"I've been racking up my Hilton Honors™ Points and saving them for retirement. So, when we're driving around the country during retirement, we can stay with the Hilton portfolio in almost any town we stop."

— Laurie L., Member since 2013

Start and end: Embrace slow travel — the concept of seeing more while traveling less — during a three-hour drive from Greenville to Charleston where you’ll see South Carolina’s upstate, midlands and Lowcountry.

Sunset view of the cascades at Reedy Fall Park in Greenville, South Carolina 

Stop: After you gaze at the gorgeous Reedy River Falls cascading through downtown Greenville, drive directly to another hidden gem in South Carolina: Congaree National Park. Flat boardwalks cut through the largest tract of old growth bottomland hardwood forest in the country.

Stay: Liberty Place Charleston, a Hilton Club is located on the edge of the historic district and features a marketplace and a lively lobby bar. Charleston’s walkable streets allow you to leave behind your Studio or 1- or 2-Bedroom Suite and quickly walk to the Fort Sumter Visitor Education Center, South Carolina Aquarium and The Charleston Museum.

Extend your trip: Charleston’s laid-back waterfront vibes make for an excellent vacation destination, but don’t limit yourself to one part of South Carolina’s coastline. Drive two hours south to Hilton Head Island where you can play golf and stay at Ocean Oak Resort, a Hilton Grand Vacations Club. Head the same distance north to Myrtle Beach where the Broadway at the Beach entertainment complex is as fun as our Hilton Grand Vacations resorts are relaxing.

Moose in autumnal lake at Rocky Mountain National Park 

2. Tackle Iconic National Parks

Turning a Colorado road trip into a multi-state national park road trip is easy thanks to the Centennial State’s neighbor, Utah.

"When you plan your next vacation, I highly encourage you to road trip between two Hilton Grand Vacations properties. You can go for the great American road trip experience or try a mini-road trip to get started."

Start and end: See mountains, deserts, red rocks and more when you begin in the forests of Estes Park, Colorado, and make your way to the high-altitude town of Brian Head, Utah.

Stop: Start with a drive through Rocky Mountain National Park and continue west through Dinosaur National Monument and Ashley National Forest as you cross into Utah.

Take your time getting to Brian Head: Canyonlands National Park and Capitol Reef National Park are on the way. The exploration doesn’t stop when you reach Brian Head; Bryce Canyon National Park and Zion National Park are each between 60 and 90 minutes away.

Bryce Canyon National Park in Utah 

Stay: Wake up at The Historic Crags Lodge in Estes Park, which is minutes away from the entrance to Rocky Mountain National Park.

Stop in Park City, Utah, at Sunrise Lodge, a Hilton Grand Vacations Club for a rest after a full day’s drive. Finally, settle in to Cedar Breaks Lodge & Spa in Brian Head to soak in some R&R before heading out into the canyons.

Extend your trip: Continue on from Brian Head down to Grand Canyon National Park then stay at one of Hilton Grand Vacation’s glamorous Las Vegas properties like The Boulevard, a Hilton Grand Vacations Club or Flamingo, a Hilton Grand Vacations Club.

3. Explore America’s Colonial History

Take an East Coast road trip through United States history from the nation’s capital to the site where the first English colonists landed in 1607.

Washington Monument in winter in Washington, D.C. 

"My bucket list includes good old-fashioned American road trips. I use my Hilton Honors account as a strategy for retirement that allows me to travel wherever and whenever I want."

— Laurie L., Member since 2013

Start and end: Add Arlington National Cemetery, the Lincoln Memorial and the Smithsonian museums to your Washington, D.C., trip itinerary before making your way down to the Virginia Beach Boardwalk.

Stop: Pay a visit to Virginia’s capital, Richmond, and stop by the Edgar Allen Poe Museum or the Science Museum of Virginia before getting a glimpse into what life was like in Colonial Williamsburg.

Stay: The District, a Hilton Club offers a capital experience in the capital city with an 8th floor Owner’s Lounge for D.C. visitors. Be one of the first to stay at a new addition to the Hilton portfolio, Greensprings, a Hilton Vacation Club near Colonial Williamsburg.

Aerial view of the beach and boardwalk at Virginia Beach 

Finally, rest your head on the shores of Virginia Beach at a Hilton Grand Vacations property on the Virginia Beach Boardwalk like Oceanaire, a Hilton Vacation Club and Ocean Beach Club, a Hilton Vacation Club.

Extend your trip: Even in the off-season, an East Coast road trip is scenic and relaxing. Continue your cruise down the Atlantic seaboard to North Carolina’s Outer Banks and stay at Beachwoods, a Hilton Vacation Club.

Planning a cross-country road trip to see this nation from sea to shining sea? Make the most of your Hilton Grand Vacations membership with three more memorable family road trips to celebrate your retirement: 

  1. Tackle the Pacific Coast Highway on a California road trip and enjoy breathtaking stays at Club Donatello in San Francisco and San Luis Bay Inn, a Hilton Vacation Club in Avila Beach.
  2. Turn a visit to New York into a New England road trip by spending the night at one of Hilton Grand Vacations’ NYC timeshares then take a relaxed five-hour drive to Boston, stopping in Connecticut and Rhode Island along the way.
  3. Nothing says “happy retirement” like a long Florida road trip. Start with a round of golf at Hilton Grand Vacations Club in Sandestin Golf and Beach Resort™, followed by boat rides around Marco Island and, finally, dance the night away in Miami at Crescent on South Beach, a Hilton Vacation Club.

Celebrate your retirement with the gift of travel, and use your HGV ClubPoints to their fullest potential. Read “Level-Up Your Road Trip And Stay With Hilton Grand Vacations” to discover how other Members are turning miles into memories in their retirement years.

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Vacationeer

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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