Flexible Travel Can Yield Huge Benefits

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Flexible Travel Can Yield Huge BenefitsOne of the facets of early retirement I was looking forward to the most was flexible travel.  I knew that we’d be able to save some money by not having to be so rigid in our plans.

I didn’t realize the extent of how beneficial it could be though.  We’ve been retired for less than eight months now and what we’re already experiencing is awesome!

Between cheaper flights, hotels, and cruises, the price is definitely right.

Then you throw in that the destinations are generally less crowded and that makes things even better.

Mix in a little more hassle-free travel along the way like smaller lines through security screenings and life becomes a real winner!  Vacations step up their game to become even more fun!

If you’re retired now, flexible travel will be a lot easier for you.  But even if you’re not, the ideas here can still be applied in your life by just thinking outside the box a little bit.


Flexible travel with last minute hotels

During our July adventure, we stayed at a few hotels… Ok, we stayed at eight of ’em (and that doesn’t count all the other places we stayed).

Considering we had all our possessions with us in the car, I have to say that unloading and loading the car each time really sucked.

But everything else about it was great… including the prices!  We’re a little weird in that we actually enjoy staying in hotels so getting them for a good price makes it even better.

I normally like to have everything all mapped out beforehand – it’s just my OCD at work.  It calms my nerves to know that everything’s already lined up and ready to go.

But except for our stay at Great Wolf Lodge and one other hotel near Cedar Point, we changed it up.  For this trek going from Ohio to South Carolina to Texas, we did things differently.

We decided to use our ability to leverage some flexible travel to our advantage.  In this case, we would wait until the last minute to book our hotels.

There were a couple of good reasons for this:

1)  We didn’t want to force our adventure by having hotels booked in advance.  Instead, we could stop and check things out along our trip for as long as we wanted.  Then we would just drive until we were tired or wanted to stop.  We’d then find a hotel in the area.

2) Hotels tend to drop their rates 24-48 hours before the date you’re staying.  By then, they usually have a better handle on what their occupancy will be.  If they have empty rooms, it’s better for them to drop the price than to let them sit empty… which makes it better for you as well!

I tested several different apps while we were on the road and found that Priceline’s Express Deals seemed to offer the best savings.  The Express Deals service is the one that you see all those commercials with Kaley Cuoco from the show Big Bang Theory.

This isn’t for the light-hearted if you have a lot of specifics you need, but if you’re aiming for flexible travel, it’s definitely the way to go.  The idea is that it can save you up to 60% off the list price of hotels.

The key is that you don’t know what hotel it will be before you actually book it.

You tell it where you’re going and the night(s) you want to stay as well as what quality you’re after (how many stars).  You’ll see how much you’re going to be paying and the vicinity where the hotel’s located.  Sometimes, they actually tell you a list of the hotels you’ll be getting one from and sometimes they don’t.

Regardless, you’ll know how many stars it is, the price, the amenities, and the general location.  If you book it, that’s it – no refunds or changes.

That served us well on our journey.  We ended up booking seven of our hotels through Priceline and the last five were all through the Express Deals.  On top of that, four were done as same-day bookings, which is where you can score the biggest deals.

The other reason we continued to book the Express Deals was that a bit of a chain reaction started.  Every time we’d stay at a hotel we booked through them, Priceline would email us a 10% off coupon to use on a future booking another within 30 days…

Flexible travel with last minute hotels
Woo-hoo, another 10% off!!

That ended up covering most of the taxes and fees with each booking we made.

It reminded me of Rusty as Mr. Papagiorgio in the movie “Vegas Vacation”…

“I put a dollar in I won a car, I put a dollar in I won a car, I put a dollar in I won a car, I put a dollar in I won a car.”

Some of the hotels we got were just basic places we simply needed for the night, but we also scored a couple of great deals.  We stayed at the beautiful Hyatt Regency in Birmingham for $84.87 (that’s tax and junk fees included).  And we stayed at another fancy Hyatt Regency in New Orleans for $76.97 out-the-door.

I liked the game and never want to pay full price for a hotel again.


Dodging the peak days

The other area that has benefited us greatly is booking a lot of our travel during non-peak days.

Not only is it much less expensive, but you’re dealing with fewer crowds… and I like that a lot!

Doing Great Wolf Lodge and Cedar Point during the middle of the week meant that we weren’t standing in long lines all day.  And that, obviously, translates into more time actually enjoying the rides.

Flexible Travel Can Yield Huge Benefits - Dodging the peak days
Our typical line at Cedar Point for the Millenium Force. Notice how the end of the line is already up by the coaster… sweet!

Staying at hotels during the week generally means much lower costs as well.  Except for one, all eight of our hotel stays in July dodged the busy Friday and Saturday schedules.

And then there’s the subject of flying.  Having the ability to do flexible travel makes the whole flight experience a heckuva lot easier.

Have you ever been to the airport on a Wednesday?  Believe it or not, it can be eerily quiet.  After all, who does their traveling mid-week?

We do.

Well, we’re trying to a lot more now.  When we talk about flying back and forth from Panama or between states here in the U.S., we don’t even look at the weekends anymore.

Not only are the prices significantly less expensive, but going through security is a breeze (though that should be less of an issue now that we got our Global Entry status with TSA Pre✓).

Either way, why deal with the stress if you don’t have to?

Even if you still have a regular workweek, you might want to try thinking a little more against the conventional norm.  Most folks book their trips based around a standard week (one weekend to the next).

By booking a trip from mid-week to mid-week, you could look at saving a ton of dough and headaches on flights.  With the exception of trips that only allow Sat. to Sat. or Sun. to Sun. stays such rentals on the coast, why not consider doing something like a Wed. through Tues. or Wed.?

The added benefit is that it gives you two short work weeks as well!


Our next test of flexible travel

We decided that we should keep trying to eliminate our old way of thinking.  I mean, hey, we’re retired now, right?!

So here’s a perfect example of our new mindset.  It’s time for us to start thinking of going on another cruise (my favorite kind of vacation!).

Our next test of flexible travel
Our last cruise was during Halloween… a perfect combination!

We’ll be coming back from Panama in late November and visiting family and friends in Ohio in early to mid-December.  After that, we fly back to Panama.

The flights back generally have a layover in Miami before continuing on to Panama.  So we started talking about looking for a cruise out of Miami while we’re there.

We were in the process of looking at what kind of deals were out there in December.  But then we took a step back… flexible travel, remember?

So instead of doing the same old routine, we’re probably going to handle this a little differently.

What we’re likely going to do is not book our cruise right now.  Instead, we’ll just book our flight from Cleveland to arrive in Miami on a Friday in December.  We’ll find some last-minute hotel stays in the area as needed for a night or so.

And if you know cruises, you know that most of them leave on a Saturday or Sunday.

Our game plan will be to keep an eye on the cruises from now until we get to Florida.  But we’ll likely end up trying to book a last-minute trip.  The odds should be in our favor since a lot of the best deals on cruises show up for the first couple weeks of December.

Hopefully, this flexibility pays off for us.  And if it doesn’t?  No big deal – we’ll just book our flight to Panama out of Miami using our frequent flier miles.  No harm, no foul.

Pretty cool, right?

This is just the tip of the iceberg.  There are so many ways that flexible travel can be both rewarding all around.  As we start taking advantage of this some more, I’ll keep you posted with what we’re finding to be effective and what isn’t.

Since we’re on the subject of travel, just a reminder to check out my post on travel rewards.  We’ve accumulated so many miles and points that we’re not going to be paying for flights for quite a long time.

Credit card bonuses also allowed us to attain the coveted Southwest Companion Pass earlier this year.  That means for the rest of this year, plus all of next year, we fly as a buy one, get one free any time we book a Southwest flight!

If you’re planning to get a new credit card, please consider signing up for it through my Recommended Credit Cards page.  It won’t cost you anything, but it’ll help support this site and would be truly appreciated!

You can also hit me up on the contact page if you’re looking for a card that I don’t have listed and I can get that right over to you.


Have you ever had the opportunity to use flexible travel to your advantage?  How’d it go?


Thanks for reading!!

— Jim

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16 thoughts on “Flexible Travel Can Yield Huge Benefits”

  1. We have a winter home in Hawaii and have much flexibility when we fly to and from the islands. This has allowed us to get good prices on they preferred flights (shortest time, less connections). Middle of the week bookings work well but also staying away from heavily tourist travel weeks that include a holiday are also a major consideration. As you are doing for your travel over the holidays, much of the time we book one way tickets. Southwest has changed the game for airlines and now most of them do not give breaks for round trips, so why books both ways if you have flexibility?

    1. Great point on the touristy travel times of the year, Dean! That’s interesting on the round-trip versus one-way costs. I wasn’t aware that there’s not really a discount anymore for round-trip – that’s a great reason to use that to our advantage in traveling. Thanks for the info!

  2. I hope that cruise comes through for like $100 best of luck. I also love flexible travel and in addition to saving cash have had some amazing adventures by not planning ahead. I once went to Santorini from Athens for 10 Euro since I was able to leave the next morning. Keep rocking those discount adventures and avoiding the peak 😉

    1. Ha! Would love the cruise being $100 – sign me up! 😉

      Wow, I don’t know what flights cost to normally fly between those two, but I’m betting it’s generally a lot more than 10 Euros!! That’s only a little over $11 USD (for my U.S. readers) – phenomenal!

  3. Hi Jimmy,
    I would like to give you a tip. As you know I was a travel agent for cruises many years ago. Travel agents get huge last minute deals on cruises. Some for unbelievable rates. Try checking with a couple. They don’t charge for their services.

  4. We like to keep things flexible on our travels too… but probably do less of it these days now that we have little kids.

    I think you’ll find the best deals when you’re not tied to the school year (since Faith is going to be homeschooled). The discounts are fantastic in October once the kids go back to school.

    I’m going to have to check out that express deals app you’re using. Sounds like you got some great deals Jim!

    1. Ooh, good point on the school-year tactic, Mr. Tako! It’ll be nice to just book the travel for the cheapest prices and just adjust our homeschooling dates/times accordingly.

      The Express Deals were really something – there were plenty of hotels that we could have gotten for ~$40, but at $75-80 for a 4-star, why not?! 🙂

  5. Sounds like you are almost to your final destination. Hopefully you will be able to take a nice long deserved break.

    Excellent getting the expat insurance


    Good luck, Mate

  6. Maybe you can book a one way cruise to Panama – or just jump ship in Colon at a port call. That would add to the adventure.

    We love midweek and shoulder season travel. Looking for ward to more of it upon retirement.

    1. Haha, I’m not so sure about jumping ship, but we did start to look into repositioning cruises. I didn’t do too much digging, but I didn’t see anything that ended in Panama though. That would be perfect though and save us a flight out of the deal.

      Shoulder season travel is nice – better prices, less crowds, but still good weather.

  7. Heck yeah! Faith looks so psyched to be rocking the amusement park with no lines!! We are obsessed with mid-week travel as well, and always book hotels last minute to nab the best deals. Since we mostly do fitness adventure vacations — hiking, climbing, and trail running — we’ve found the biggest benefit is that the trails are always sooooo much less crowded mid-week. Even for something super-popular like climbing Mt. Whitney, which has a once-a-year lottery for reservations, we’ve had success just showing up at the ranger station mid-week and asking for a pass. To me, the single greatest thing about FI is the ability to experience amazing places while avoiding the crowds!

    1. You could even go to Denny’s mid-week during the day and it would be nice and quiet… Ok, bad example!

      That’s really cool that you slipped into some busy places like that without reservations. Totally agree that it’s so much nicer not having to deal with crowds while traveling. It’s even fantastic doing regular chores in life like grocery shopping during the week as well!

  8. Nice job! I used Priceline and Hotwire once in a while too. But I’m too nervous to book at the last minute like that. Next time we travel around in the US, we’ll try it. International, I don’t know… I prefer to have a solid plan because our son will be with us.
    Express Deal sounds good, but are you really saving that much by waiting until the last minute? How much would it cost if you booked it earlier through Priceline? I suspect you only save 10% or so. Most rooms are already a good % off the rack rate.

    1. I agree that international travel would be a whole different ball game – I wouldn’t feel comfortable not having things lined up either.

      I think most hotels start dropping prices within 24-48 hours of the date you’re looking at (unless there’s some big event in the area and they’re near capacity). The Express Deals worked well for us because it did actually drop probably another $10-15 off of what the price would have been otherwise. Top that off with the lower prices of waiting and the coupons they kept giving us and we did pretty well.

      Clark Howard mentioned a fantastic idea on his podcast. His thought is to book a hotel well in advance of what you’re looking for, but make sure you have the ability to cancel for free up to a day or two before. Then, once the date gets closer (like a week out), start shopping around. You’re more than likely going to find a better deal and can cancel your earlier booking. But if not, you’re already covered and don’t have to worry about. Genius! 🙂

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