3,355 Nights
I’m Vickie, the Money Chick half of Money Chick & Wine Guy. For 30+ years, work kept me on the road: Marriott member since 1991, 3,355 nights in their hotels alone, and Lifetime Titanium Elite — earned across those work years. My husband Oren did the same in the wine business. On United alone we’ve flown 3,351,646 lifetime miles between us; we’re both Premier 1K and 1 Million Milers.
I’ll be honest about what those numbers are. They’re not a highlight reel — a lot of them were nights away from home. We’re retired now, and the second act is spending what those years earned — the points, the status, and the timeshare weeks I started buying in 2001 — traveling together, slowly, on purpose.
Everything here is one move at a time: what we did, our real numbers, and how you’d copy it. Start with Playbook No. 1: twelve nights, four tools, $1,159 all in.
Playbook No. 1 · 12 Nights, Under $100 a Night
The Move
One size does not fit all. Just shop and compare — Marriott, Booking.com, Expedia, VRBO, Airbnb, RedWeek — plus your own points, weeks and certificates. The best tool changes by the night. Use what wins, and book it.
How We Did It
Our drive from Napa to Denver and back: 12 nights on the road, four different tools, $1,159 of lodging all in — $97 a night.
| Winnemucca · 1 Night | Cash, via Booking.com — $180. |
|---|---|
| Park City · 7 Nights | An Interval International certificate at Marriott’s Summit Watch — $448 all in, about $64 a night. The same week on Marriott’s site: $1,487. |
| Steamboat · 3 Nights | Two nights on VRBO in a two-bedroom ($373); the third direct with the hotel at a studio rate ($157) — $531. Asking nicely — never entitled — kept us in the two-bedroom. |
| Salt Lake City · 1 Night | A Marriott free-night award from our Bonvoy card — $0. The only stop on the drive home. |
| Total Lodging · 12 Nights | $1,159 — $97 a night |
Loyalty to one brand over years, if you can do it, does pay off.
How to Copy It
- Shop and compare. The tool that won last trip may not win this night — check the channels and your own inventory side by side.
- Inventory first. Points, weeks and certificates are prepaid travel, and they expire. Know what you already hold before you price a single room.
- Let the night pick the tool. A certificate week for the long stop, a shoulder-season rental for the short one, an award for the one-night hop — and plain cash when cash is cheapest.
One size does not fit all. Shop and compare — and use what wins.
What we share here is about our own travel spending — educational, not individualized advice.