Overhead view of much needed travel purchases.

2008: Our first timeshare – we had zero knowledge of (or interest in) the concept, only responding because it was free. Likely not a unique story, but we’re forever thankful our initial exposure was with Hilton. “Sour grape” timeshare stories abound, but in interacting with other Owners I’ve found two common “dissatisfaction themes”: lack of engagement with the tools that help maximize points and frustration over recurring expenses. On the latter, I share the obvious: timeshare ownership isn’t free. Better to view it as a structured way to prepay vacations you otherwise might not have taken. My wife and I are in full agreement that we’ve traveled more in the past decade than we ever would have “alone.” Also, take time to compare your expenses to owning – outright – even one vacation property: mortgage, taxes, upkeep and dealing with emergencies. When hurricane Irma made landfall at our Marco Island property we experienced all of the anxiety one might normally expect – but, really, none of the worry: the property management took care of everything.

My main observation on “engagement” is this: managing points takes time and effort. It’s fun work; nonetheless, you do need to be an active participant. I’m constantly surprised hearing frustration at “having to” return to the same place every year. When I ask people why they aren’t swapping points to other locations, I get either: “We didn’t know we could,” or “We don’t know how.” We use less than 28% of our Club Points on recurring locations – the rest we use for our “bucket list.” So whether you’ve just purchased, or are long-time owners, (re)commit to fully embracing the ownership sites (www.club.hiltongrandvacation.com; www.rci.com). You will find great flexibility with your points if you really dig in. My best advice is: log on, get familiar with your points dashboard, and start to proactively manage your vacation experiences.

Let’s talk about other ways to maximize vacation planning, and some general travel expense tips:

  • Plan as far ahead as possible. HGV locations have 9- and 6-month windows (exceptions: “Home Week” properties as much as a year and RCI windows are 24 months). By planning your next vacation as soon as you return from the current one, you can anticipate related expenses (not the least expensive of which being airfare).
  • No matter your ownership level, use the toll-free booking line to help you through the process; Club Counselors are very helpful. While some locations require that you book by phone, keep in mind that the more you become familiar with the website reserving properties online (where eligible) can reduce or eliminate booking fees. Also, points typically will go farther in RCI, although location and/or date options may be more limited.
  • Mind expiration deadlines! Move unused points into the next year rather than losing them; such “rescued” points will expire 12/31 of that next year – but better than losing them altogether. You also can convert to Hilton Honors points that can be used for hotels (see next bullet). And if you’re short on Club Points, borrow from the upcoming year! Note that these transactions will incur a small fee.
  • Channel everyday expenses through a points-earning credit card (we pay ours off monthly, as interest charges rather defeat the purpose). Even vacation expenses can amass points to cover future vacation expenses! Our Hilton Honors card earns hotel points. We just returned from Scotland and Iceland, where we covered all of our accommodations (14 nights) with Club and Hotel points. In selecting cards, look for additional benefits: airport lounge membership, rental car insurance, lost luggage support, shuttle discounts, etc.
  • Within Hilton, make time for Owner presentations – especially when there are perks.
  • Check ahead for on-property rental car availability. We learned this the hard way on our last trip to Honolulu: we rented a car for the whole week and ended up not using it much, only to learn we could have day rented right from the lobby.
  • Lastly, if your time is flexible (retirees?) play a fun game I call “A Vacation in Search of Two People”: use Google Flights, Kayak’s budget explorer, or Skiplagged to search for cheap airfare to locations that interest you, then book your accommodations around those dates. Oftentimes, wanting to go to a particular place at a particular time comes with exorbitant airfare; this is one way to turn the tables.

In an upcoming issue, I’ll share tips about fun travel apps!

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