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Guest Post: How to Make the Most of a Weekend Trip

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The other day, I was tweeting with my friend Josh @ FrugalHack.me and I asked him if he wanted to write a guest post for me.  I have been following Josh’s blog for a few months and I like his writing style and topics (he covers MS strategies and cash back deals).  If you like reading Travel with Grant, you will probably like reading FrugalHack.me as well.  With that said, take it away Josh…

There’s no doubt that my wife and I love weekend trips.  Truthfully, we’d like them to be longer, but we just don’t have the vacation time to use.  So, we just make do with what we have and it works, quite well actually.

These trips aren’t long, hence the “weekend” part, so there really needs to be a game plan in place to make sure the time off is well used.  I don’t want to brag, but now that we’ve taken quite a few of these weekend trips, we’re kind of experts at making the most of them.

Want to learn how to do it?  Of course you do! :)

Flying vs. Driving

Choosing between flying and driving all depends on where you want to go and what options you have.  I try to keep our commute under 4 hours, since we only have a couple of days to work with, which basically gives us access to most of Michigan and a bit of Canada, Ohio, Indiana, and Illinois if we choose to drive.  That’s just fine for the summer, but in the winter what’s the point?  They’re all cold!

If you do choose to drive, it may make more sense to rent a car instead of driving your own, but we’ll get to that in a minute.  I, personally, prefer to avoid driving at all costs, because it’s not very “vacationy” and it’s more expensive than flying, since we have a companion pass.

That leads me to my next point: the Southwest Airlines Companion Pass.  If you want to fly and maximize your points on a short weekend trip, the Companion Pass is the way to do it!  It gives you (and a companion) access to the whole nation at super affordable rates.  And, it’s actually not that hard to obtain, since there are many ways to do it.  Note: That’s a password protected post that you can gain access to by signing up for my newsletter.

Southwest Airlines Companion Pass

With a Companion Pass, a roundtrip ticket for two will only cost about 14,000-30,000 Rapid Rewards points and $22.40 in fees.  Considering you need 110,000 Rapid Rewards points to get a Companion Pass, that works out to about 4-8 trips for two!  Not bad eh?

As I mentioned above, you’ll want to maximize your time on vacation (i.e. not traveling). The best way to do this with a Companion Pass is to take a direct flight.  Fortunately, Southwest Airlines makes it extremely easy to find out what flights are direct from your location with their route map (red lines are nonstop flights).  All of the direct flight options I have, which I realize isn’t many, are under 3 hours.  That helps us get a lot more time actually at our destination!

Southwest Airlines Grand Rapids Route Map

Southwest Airlines Grand Rapids Route Map


The best hotel chain for weekend getaways is by far Club Carlson, assuming you have the US Bank Club Carlson Premier Credit Card and spare Gold Points in your account.  Why?  Because, Club Carlson is extremely generous with the perks they offer on that credit card. They not only give you Gold status, which offers room upgrades when available, but they give you you’re last night free on all bookings made with points that are two days or longer.  That basically makes a weekend hotel (2 nights) half the points!

If you don’t have that credit card, IHG, Hilton, and Hyatt all offer hotels costing 5,000 points per night.  That’s not very expensive either, but considering how easy Gold Points are to acquire and the free night perk, Club Carlson is my favorite weekend getaway hotel chain.

What to Do

There are two websites we check for attraction ideas when visiting a new city, Trip Advisor and Viator.  Trip Advisor is great at showing you the top things to do, whether paid or free, based on customer ratings.  Viator is good at getting you deals on attractions that cost money.

Using our last weekend trip as an example, we found things to do on both sites.  Trip Advisor suggested we visit a free manatee viewing center (which was really cool) and Viator got us a great deal on Busch Gardens tickets.  It saved us a lot of money vs. buying them at the gate.

Disclaimer: The links above are affiliate links. If you use them, cool. If not, no worries. Thanks for your support!

Car Rental vs. Uber

This all depends on what you plan on doing while on vacation.  If you only plan on going one or two places, Uber is the way to go.  That’s doubly true, if your hotel offers a shuttle to local attractions (e.g. malls, downtown, the airport).  If, however, you plan on visiting multiple locations around town or you want to take a trip longer than 30 minutes, it might be cheaper to get a car rental.

On our last trip, we rented a car from Avis for just over $60 and I’m sure glad we did, because we drove about 200 miles during that trip.  We originally planned on “Ubering” around, but we found out a friend was just one town over from ours, so we rented a last-minute vehicle at an extremely affordable rate and ended up making great use out of it.  That probably saved us hundreds of dollars over using Uber.


Our favorite weekend getaway combination consists of a Companion Pass, a US Bank Club Carlson Credit Card, and a rental car.  Those three things guarantee us a fun (and quick) weekend vacation for, on average, under $125.  That’s a pretty sweet deal for two people!

Do you have any weekend vacation tips?

Grant: if you have any questions for Josh, feel free to leave a question below.  Happy travels everyone!

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23 thoughts on “Guest Post: How to Make the Most of a Weekend Trip

  1. Jay

    Josh & Grant,
    Great post. Need your help. I’m trying to find the best way to go to carribean for 2 ppl, can be Aruba or grand cayman. I have companion pass and I heard that SW already started its international service to carribean. But I can’t seem to find a flight from SFO to Aruba nor grand cayman…..:(

    1. Joseph

      Jay, if you’re not getting any results when looking for flights during their scheduled service its likely because the flight schedules from the west coast simply don’t work with their published routes. You may need to book two separate trips (i.e. SFO to BWI, and then BWI to Aruba the next day.) At times I’ve actually found it cheaper to book it as two tickets rather than one.

    2. Josh

      I just tried SFO to AUA as well and I see what you mean. I think it’s a glitch with Southwest’s online search tool, but I did find a work around. You could do SFO-ATL-AUA, which is probably how you would be routed anyway, since SFO-ATL has a direct flight as does ATL-AUA. You’d be looking at about 30-40k points each way. You might also try calling Southwest to book the flight, because based on Southwest’s route map, SFO should be able to travel to AUA.

    3. Grant

      Southwest’s website is not smart enough to find fights from SFO to Aruba/Grand Cayman. Only certain airports have flights to those cities, so you will have to see which airports fly there. Then book a separate flight from SFO to that airport.

  2. Jay

    Joseph / Josh / Grant,

    Thank you for your help. No wonder I cannot find the published routing of SFO – AA on the Southwest’s website. I hope they fix this issue someday.
    Which route is the best way from SFO to AUA:
    1. SFO – BWI – AUA


    2. SFO – AOL – AUA

    as Josh mentioned, it supposed to be 30-40k one way, is that from SFO all the way to AUA? And do Southwest price the award separately like SFO – ATL first then another miles for ATL – AUA?

    And is there anyway to book this online or I have to call to book?

    1. Josh

      Either would work and they should both cost about the same. The only thing better about SFO-ATL-AUA is that SFO-ATL and ATL-AUA have direct flights. SFO-BWI does not have direct flights (BWI-AUA does).

      The 30k-40k estimate is one way from SFO all the way to AUA. You can book this online segment by segment (i.e. SFO-ATL and ATL-AUA or SFO-BWI and BWI-AUA and return), just make sure you leave yourself enough time to connect.

  3. Miles4MoreKenny

    If you can make dates work with SFO-HOU-AUA you can save yourself a lot of flying, and probably some points too. Again you’ll have to search separate as they do not yet have a published SFO-AUA fare. HOU-AUA is Saturday only. MCO is also a possibility.

    1. Jay

      Thanks Kenny. How many SW miles for SFO – AUA if fly via HOU?
      if HOU – AUA is Saturday only, how about AUA – HOU?

      As you mentioned, can possibly also do SFO – MCO – AUA?

      1. Grant

        The number of Southwest Airline miles will depend on the current price of the ticket, which will change almost every day. I would look at a calendar view to see which flights to Aruba are the cheapest.

  4. Brad

    For Southwest Credit Cards, can you apply for the Business Premier if you don’t have a business and a TIN?

    1. Grant

      For all Chase business credit cards, you can use your own SSN to apply as a sole proprietor. A TIN/EIN is not necessary and may just be an extra step to go through since Chase will also check your personal credit history/score to decide your application.

          1. Brad

            I currently have the personal plus card so if they say i don’t qualify for either im going to cut that limit in half or im just going to cancel it in general since ive had it since 2011 and annual fee is coming in march. i know ill qualify for 1 but they may 2nd guess the 2

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