Learn How to Plan Vacations Like A Pro with These 7 Practical Tips

One seasoned Hilton Grand Vacations Owner shares his vacation planning checklist for stress-free vacations

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Eric Z.
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Summary: Want to up the ante on your vacation planning skills? Read this for a practical how-to, 7-step vacation planning checklist.

No matter what’s going on in the world, I’m almost always in vacation planning mode.

Click to expand and read.

“A s an Elite Premier Owner with Hilton Grand Vacations, I’ve had more than a decade (15 years, to be exact) to refine my process.”

The result? A stress-free vacation that runs smoothly.

Here are my vacation planning tips based on what I’ve learned over the years.

Start Planning Months Before Your Vacation

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Review your options. I have an ongoing bucket list of travel destinations ready to go. I keep it updated to reflect new properties opening, and with Hilton Grand Vacations’ ever-growing list of Travel destinations it’s even more fun to update and plan future vacations.

Start the booking process early. Think 9 to 12 months, depending on the popularity of the travel destination. This tip helps lock in the dates and suite size you want.

Insider tip: If you have a lot of points Book multiple dates or destinations at the same time and narrow it down. As long as you start planning your vacation months in advance, you’ll have plenty of time to make your final decision and cancel the other bookings without issue.

Hit the internet and do your research. See what’s new and fun to do, and read restaurant and activity reviews on sites like TripAdvisor.

Insider tip: Join Facebook groups or like Facebook pages of local businesses in the destination you’ll be visiting to stay in the know.

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Start tracking transportation prices. Making reservations early helps guarantee the best prices for flights and car rentals.

Insider tip: If you need a car rental, reserve it as soon as possible. You can always cancel and rebook car rentals at no cost.

Practical Pre-Vacation Planning Tips for a Couple of Weeks Out

Do your monthly accounting. Use the post office’s free mail hold service, so neighbors don’t have to grab it. Sign up for electronic statements and pre-pay bills online so you can truly unplug and relax while you’re away.

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Book reservations. Book your must-do activities before You arrive. Some of the more popular activities fill up weeks in advance. These reservations include dinner reservations at hot new restaurants, so you are not eating at odd hours.

Insider tip. Sign up for Open Table. You can cancel or change reservations for free, and if you have an account, you can earn free cash towards future meals.

Get your travel bag ready. Save yourself the “night before scramble.”

Locate and pack the following items ahead of time.

  • Electronics (Remember to charge them, too.)

  • Camera batteries

  • Spare phone chargers

  • Earbuds

  • Travel day must-haves (i.e., travel reads, neck pillow, water bottle, etc.)

Read 4 Extended Vacation Travel Hacks for the Ultimate Stress-Free Trip for more of Eric’s vacation planning tips.

About the Author Eric Z.
Hilton Grand Vacations Explorer profile picture

Seasoned Owner and returning Explorer, Eric made his home resort The Grand Islander by Hilton Grand Vacations in 2006 and never looked back on life before vacation ownership — quickly climbing the ownership tiers, reaching Elite Premier status. As an Elite Premier Owner, he and his family including, his wife, teenage son and parents, regularly enjoy elevated access to some of the best amenities and services offered to Members, such as extended vacations.
Over the years, his travel has afforded him unforgettable father and son trips, priceless multigenerational family vacations and even his once-in-a-lifetime destination wedding at Kings’ Land by Hilton Grand Vacations in Hilton Waikoloa Village. He’s your go-to guide for practical vacation ownership tips and says, “I love Hilton Grand Vacations and the opportunity to share what I’ve learned over the years.”

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