Retirement is my favorite 10-letter word in the English language. I am a little young to be retiring, and the number one question everyone asks me when they hear that I am retiring is, "What are you going to do with your time?"

I just look at them in the eyes, and they say, "You're going to be traveling even more in retirement, aren't you?" Typically, they follow up by saying, "I wish I could." 

The second most common statement I get from people is, "I thought you were already retired with how much you travel."

   

Admittedly, I've made it a goal to use every vacation day I get on a fantastic vacation with friends and family. I don't spend holidays or vacation days at home, and I take family and friends with me on my excursions.          

Hilton Grand Vacations has helped make this a reality. My strategy while working full time included butting my short vacations against official off days, such as holidays, so it was possible to get the most out of my vacation days. So for some short trips, I only use one or two vacation days. 

I've had to plan further in advance to do this successfully, but retirement will change this philosophy. 

My New Retirement Travel Strategy

Weekdays are now the prime bookings since they require fewer Points, and it's usually cheaper to fly in the middle of the week. While I'm still planning on traveling with friends and family, I'll just be staying longer than most. My goal will be to fly during less expensive times, and they can stay as long as their vacation days permit.

However, whether I'm retired or not, it’ll be different to book a vacation seven days in a row unless I use my Home Week. For example, I love Hawaii and own in Hawaii, but I rarely book seven days in a row at the same resort. 

I love to island-hop, which Hilton Grand Vacations makes easy to do. I chose my island days based on what's available around the days I want to be on vacation. Three days minimum is perfect, and I try to go to at least two islands when I visit — three days when I plan a Hawaii vacation with more than 10 days.  

And as an HGV Max Owner, I can't wait to see what new resorts open up in Hawaii for us.

Putting My Hilton Honor™ Points to Work

   

I've been racking up my Hilton Honors™ Points and saving them for retirement. I plan to use Hilton Honors Points when we need to stay somewhere just for a day. So, when we're driving around the country during retirement, we can stay with the Hilton portfolio of brands in almost any town we stop.

Staying for free is most important to me and being treated like a Diamond member will be the cherry on top.

Elara, a Hilton Grand Vacations Club in Las Vegas, is my favorite Hilton Grand Vacations resort. I booked a 4-Bedroom Penthouse Suite for the Big Game weekend three months before the trip. For me, this was the last minute. It was also Valentine's weekend, so there wasn't availability Saturday night due to the holiday. 

But Resorts World Las Vegas had just opened, and I wanted to check out Crockfords Las Vegas LXR Hotels & Resorts. The timing to stay at Resorts World was perfect since I had a free night certificate, and we could choose between Las Vegas Hilton, Conrad Las Vegas or Crockfords. 

I taught my friend traveling with us how to use her free night certificate and educated her on when to use a free night certificate and when to use points or cash. Switching resorts ended up being fun.

   

First up: Florida  

Next, I'll try my resort hopping tactic in Florida. There are many resorts around the big state of Florida, and I want to book some of the resorts with less availability to get seven days in a row. These bookings will dictate how we travel and explore Florida.

One thing is for sure; I'll use my free night certificates and some Hilton Honors Points to stay in Key West during this time also.

By the time you read this, I'll already be retired. While I don't have all the ins and outs of retirement travel yet, I'm looking forward to learning all the secrets and maximizing my Hilton Grand Vacation timeshares to the fullest.

Read "Using Hilton Grand Vacations Timeshare Plus Hilton Honors Points as a Retirement Travel Plan" for more retirement travel inspiration.