I learned a long time ago that “if you don’t ask, the answer will always be no!”
And this can be especially true when it comes to travel plans. Fortunately, neither Chuck nor I are shy, and Chuck’s OCD (only slightly) often pays off.
Here are a few tips than can pay big travel dividends.
Brand Loyalty
Unfortunately, we don’t seem to stay in any one hotel chain too frequently. We like smaller boutique hotels and find that our tour packages are often aligned with smaller local properties.
However, regardless of where we might be staying, we always head to their website and sign up for their loyalty program. If you are traveling with a tour group, you can often find a list of the hotels for each city you will visit.
I was heading into New York City for a wedding industry event and stayed outside of the city in a major chain hotel, a short train ride away.
I signed up for their loyalty program just before leaving and added it to my reservation. Upon arrival, the front desk clerk thanked me for being a member and upgraded me to the club level.
For the two days I was there, I had breakfast, evening snacks, and wine — not a bad perk for signing up a few days before my stay.
With tour groups, it’s not typically going to be the same. The travel company is already getting volume rates and perks. When you check in to the hotel, be sure to give them your rewards number when you talk to them. It might get you a slightly upgraded hotel room.
Ask Upon Arrival
Always ask about available upgrades when you arrive. Hotels and even cruise ships are sometimes willing to give you amazing prices on a vacant space.
On our tour of China last year we heard that the Yangtze riverboat company often offered super affordable suite upgrades. When we arrived, we made to get on the ship ASAP.
We were able to secure one of the six suites on the boat for about $60 US total for the three nights. Not only was there more space, but it was located next to the VIP lounge with coffee, tea, and snacks. We each also got a bag of laundry as well. Clean laundry in the middle of a 12-day trip is AMAZING!


We have also found that airlines upgrades, when available, are often much less expensive at the airport than in advance or even calling the day of travel.

Just remember, when they quote a price, you don’t have to take it if it’s still over your budget.
Check and Double-Check
Checking back is where Chuck’s slightly obsessive nature really pays off.
We frequently get e-blasts and mailings from tour companies and cruise lines we have traveled with previously. We look well in advance of our bookings for sale patterns. Black Friday Sales, Memorial Day, there are surprisingly a lot of specials out there.
But, he has also discovered that, especially with cruise lines, after you have booked you are eligible for any specials, promos and price drops up until the time you make your final payment.
We have a cruise booked and received a substantial promotional discount because the line had to cancel cruises to Cuba. Yes, we booked another cruise to go back, with a different cruise line.
But, he also found that they were running an additional promo for past cruisers and took advantage of this discount.
AND, somewhere in the middle, he saw a price drop online that went away after just one day. So, be diligent and check back.
Traveling the world can be quite affordable if you look for pricing deals, specials, and ask for any available upgrades.