Since retiring from my full-time job in 2018, I have not worked
a day. I have lived comfortably on my pension and Social Security while still
managing to save a substantial amount. This financial stability has allowed me
to travel extensively over the past eight years, which is the focus of this
edition.
Although I travel without a fixed schedule, I always have a
plan. For long-distance trips, I begin months in advance by choosing a broad
area to visit and marking possible stops on Google Maps. I then narrow the area
and develop a basic route.
For nearly 20 years, I have found that my most enjoyable
trips average 250 to 300 miles per day. This pace keeps me from feeling rushed and
gives me time to explore both planned attractions and unexpected discoveries
along the way.
One of the first travel lessons I learned was to always book
directly with the hotel, either by phone or through its website. I avoid third-party
sites such as Priceline and Hotels.com.
There are several reasons to book with the hotel directly.
Most importantly, if a problem arises during your stay—especially with the
reservation or billing, the hotel can resolve it.
If you booked through a third-party site, however, hotel
management will simply direct you back to that service to resolve reservation
or billing problems—and reaching these third party sites support team can be
nearly impossible.
A few years ago, while checking into an Ohio hotel, I
watched the guest ahead of me learn that he had use a third-party site and had mistakenly
booked his room at a hotel in Colorado.
When the Ohio hotel could not find his reservation, the
staff checked his confirmation number and discovered the Colorado booking.
Because he had booked through a third party, the clerk could
neither cancel the Colorado room nor transfer the reservation to the Ohio hotel.
She could only direct him to the booking service.
I checked in and settled into my room without difficulty.
Two hours later, he was still in the lobby trying to get the booking service to
correct the error. When I returned from dinner that evening, I asked the clerk what
had happened.
She said that, as far as she knew, he was still trying to
resolve the issue with the booking service. She eventually gave him a room, but
the erroneous Colorado reservation remained active because she could not cancel
it.
Had he booked directly with the hotel, the clerk could have canceled
the mistaken reservation and created a new one. Because he used a third-party
booking site, however, she could not access the reservation to correct it.
Another lesson I learned early was the value of joining hotel
rewards programs. At first, I dismissed them as gimmicks with few practical
benefits, but I was wrong.
I currently belong to three rewards programs and have enough
points for multiple free nights with each one. All three work similarly: You earn
points based on how much you spend each night. Usually, it is something like 10
points for every dollar spent, excluding taxes.
Once you accumulate enough points, you can redeem them for
free nights. In my experience, roughly 10 paid nights earn one free night.
During the off-season, some hotel chains also offer promotions such as double
points per night or double or triple points after a set number of stays within
a specified period.
I also earn rewards by linking my memberships to partner
companies. For example, connecting my Hilton Honors membership to my Lyft
account earns me additional Hilton Honors points on every ride, along with a
small Lyft discount.
I currently have enough Choice Hotels points for about five
free nights. Through the Holiday Inn rewards program, I have also accumulated
enough points to cover nearly my entire four-night stay at the 2027 NCAA
Basketball Tournament in Pittsburgh. I will stay at a downtown hotel within
walking distance of PPG Arena.
Without rewards points, my four-night stay—including the
room, daily parking, and taxes—would have cost $1,940. Because points cover the
room, I will pay only $344 for parking and city and state hotel taxes. That is
a substantial savings, don’t you think?
Hotel loyalty programs offer another advantage: membership
tiers that award bonus points, helping members earn free stays more quickly.
One program begins with basic membership. After 10 paid
nights, members reach silver status and earn 10% more points per stay. After 20
paid nights, they reach gold status and earn 40% more points.
I have attained the equivalent of gold status in all three
programs. Along with bonus points, this status often brings recognition, room
upgrades, and food-and-beverage vouchers.
These vouchers are particularly valuable at hotels with
on-site restaurants. A few years ago, while staying at a hotel in New York
State, the clerk recognized my gold status at check-in and gave me vouchers for
dinner that evening and breakfast the next morning.
The vouchers saved me about $35 on dinner and $15 on
breakfast. Because they did not cover gratuities, I tipped the servers more
generously—a win for everyone.
I strongly recommend booking directly with the hotel. The
savings offered by third-party sites are usually minimal, and as a rewards-program
member, I often receive the hotel’s best rate—frequently lower than third-party
prices.
Do third-party booking sites offer any real advantage? For
me, the answer is a resounding no.
