As he sat on his balcony, against a backdrop of palm trees and bird songs on the peaceful island of Kauai, Hawaii, Cliff B. exuded the travel lifestyle to which so many people aspire.

“I travel periodically for six months at a time,” Cliff began his story. “I rented out my house, so this is my home — this week and next week.”

His travel is planned through the end of the year in a calendar his kids named: “Where’s Cliff?” The calendar is their go-to if they want to know where he’s staying. Already this year, he’s been in Hawaii since March. 

   

Where’s Cliff?

“So, where am I going to be?” Cliff asked the question. “I’ll be in Hawaii until June, and staying at The Bay Club, Kings’ Land and Kohala Suites, all Hilton Grand Vacations Clubs on the Big Island. Then, I’m off to my 50th high school reunion in Indiana and my family reunion in Ohio. So I’ll take a trip across the country.”

His strategy is simple: Stay in one destination for three days, and drive for one as he makes his way through the trip. The first leg of his journey will include stops in Southern California; Flagstaff, Arizona; and Dallas. 

“I’m going to stop at a swing dance in Dallas, and then I’m going to Branson, Missouri. On the way back, I have a week planned in Colorado,” Cliff explained. “And then I come back to Hawaii in September, and I’ll be on Maui for another two months.”

Cliff values as family time as much as he values travel. He’ll take a break from the road to spend Thanksgiving with his kids, after which he’ll be off to enjoy a Myrtle Beach, South Carolina, vacation with his brother. 

“I’ll fly to Myrtle Beach and stay at Ocean Enclave, a Hilton Grand Vacations Club, and Ocean 22, a Hilton Grand Vacations Club — one week each — and my brother will join me then like he did last year,” Cliff shared.

Rounding out the year, he’s booked a couple of places for Christmas for his kids. 

“That’s my life this year, and then I need to buy a house at some point,” Cliff said with a chuckle.

Many travelers build travel bucket lists in hopes of one day making it to their coveted destinations. But Cliff has found a way to realize his travel dreams through vacation ownership. 

The Ultimate Destination

   

“Hawaii is always the place for me because it’s relaxed. So my bucket list always includes Hawaii,” Cliff began. “I like to walk by the ocean and listen to the waves, and my favorite is Waikoloa Beach. My favorite places to stay are the Hilton Grand Vacations resorts in Waikoloa.

“When you listen to the waves crash on the lava rocks, it sounds like a Japanese water fountain, which is very calming. And because every wave is different, it creates a rhythm, and every wave is like a different song,” Cliff explained.

“I just want to meditate, sitting on the beach. It allows me to do the real estate investing I’m doing to build a legacy for my kids. It allows me to do many things because I’m grounded and calmer,” he said. “So that’s my bucket list.”

Outside of spending his fair share of time in Hawaii, his top travel priorities include doing things with his family. 

“I’m the organizer for our reunions, so I like to go with my cousins and brother to different places,” Cliff shared. “They live on the East Coast, so I’d like to try Ocean Oak Resort, a Hilton Grand Vacations Club, on Hilton Head Island.”

   

The Journey to Making Travel Dreams Come True

“Originally, I wanted to go to all the main Hawaiian islands: Big Island, Maui, Oahu and Kauai,” Cliff said. “So, I bought Hilton Grand Vacations timeshare because it covered Oahu and the Big Island. So I’ve been with Hilton Grand Vacations for at least 10 years now.”

But Cliff's portfolio includes more than just Hilton Grand Vacations timeshare products. He feels so strongly about the benefits of timeshare that he started a blog dedicated to the topic. 

“I traveled for work a lot. I lived in Singapore for two and a half years, traveling through Europe and Asia and throughout the United States. As I got closer to retirement, I was like, ‘Well, I wonder who will pay for this?’ ” he said. 

As he researched the different ways to continue traveling through his retirement, he shared his learnings on his blog. For example, he wrote a story early on compared RVs and timeshare. 

“Obviously, I chose timeshare,” Cliff said matter-of-factly. “The logic is pretty straightforward. I looked at RVs, and I found out that they cost about $400,000-$800,000. You can buy them used, but I said, ‘No, if I’m going to be doing this on a serious basis, I want to get a new one.’ ” 

Not convinced a $400,000 price tag was worth it, Cliff started to investigate further — factoring in the overall costs of traveling this way for the rest of his life. 

   

“I have an uncle who’s 94 years old, and I’m a generation behind him, and of course, there are no guarantees in life, but the odds are good that I’m going to live another 20 years,” Cliff said. “So, if I use the RV, I will have to buy two.”

From that thought process, he determined his timeshare budget — anything less than $800,000. Not only would timeshare be far less expensive for him in the long run, but he’d also have the flexibility to travel to Hawaii and Europe. 

To further reinforce his decision, he diligently tracked the overall costs of vacation ownership during his first seven years as an Owner, and he found that he’d recouped his costs. 

“When I stayed at a resort, I’d figure out how much it would’ve cost if I had rented it versus what I paid as an Owner, plus my maintenance costs and how much I paid upfront,” Cliff explained. “In about seven years, I had made it back.”

Cliff’s Number One Tip for Those Considering a Timeshare

Part of what makes Hilton Grand Vacations timeshare work so well for Cliff is that he’s taken the time to learn how to maximize the benefits. 

"Know what you want going in and do your research."

“It’s a lot like buying a car or a house or any major purchase,” he started. “And I find that the people who struggle with it never take the time to do the research. 

“It would be like if you walked onto a car lot without knowing what kind of car you wanted, and then you just walked out with a car,” Cliff continued. “But then you refused to look at the owner’s manual to figure out how to use it and wonder why you don’t like your car.” 

   

 The Decision to Upgrade from Elite to Elite Plus and HGV Max 

When Hilton Grand Vacations first announced that a new program called HGV Max would be launching, Cliff was intrigued. At the time, he was an Elite Owner, affording him travel to his favorite destinations: Hawaii, San Diego, Las Vegas, Orlando and Myrtle Beach. But after the announcement, he realized just how much his options could grow. 

“I upgraded to Elite Plus and HGV Max for the number of locations. That makes it completely worth it,” Cliff said. 

“So basically, I dropped my cost to stay. Now, instead of $140 a night, I pay $120 a night to be in Hawaii in a 1-Bedroom Suite,” he explained. “So that was the value I saw.”

It all came back to his love of travel for Cliff. 

“Again, I’m looking at it long term and saying this will be a lot less expensive than if I was staying at hotels,” Cliff said. 

"One of the other reasons I did this is because I worked pretty hard and wanted to reward myself. It was my present to myself."

Finally, Cliff shared one of his most memorable moments as a Hilton Grand Vacations Owner. 

“I’m a Hilton Diamond customer, and I got to stay at the Waldorf Astoria Monarch Beach Resort & Club in California. And I stayed for free for two nights, and I got free breakfast. I would never stay in these luxurious Hilton properties if it wasn’t for my memberships.”

Read “More Than Just Vacations: Why Two Childhood Friends Chose Hilton Grand Vacations Timeshare” to discover more benefits of timeshare.