Vacation Finance – Taking the Time to Plan Saves Money

by Michelle · 13 comments

In my last post I described how Aaron and I came to the decision to spend our first vacation in San Francisco and Napa Valley. Once the destination was settled, we were able to focus on the financial choices that we could make before leaving.

Let me share a few tips with you on how to save money on traveling.

We are keeping this trip relatively simple. For us that means that we haven’t lined up any big entertainments (shows, spa appointments, thrill sports, etc.), so our main preparations are just travel basics: how to get from Chicago to California, where to stay when we’re there, and how to get around between our two destination cities.


I will be the first to admit that I am very easily overwhelmed by the abundance of discount travel websites out there. More specifically, it’s the loud graphics and gazillion-plus options that intimidate me. It’s like all of those italicized headlines and flash animations are designed to speed up your heart rate and your decision!

Aaron and I are new to this whole vacation thing, but between the two of us we’ve logged a decent amount of air miles traveling for work or to see family. My airfare selection process usually comes down to four simple steps:

  1. Check prices online early and often
  2. Check a maximum of two discounts sites (Expedia and Orbitz for me)
  3. Check my budget carrier of choice
  4. Book directly with the budget carrier

I honestly can’t say that I’ve ever found an air deal on one of the discount sites that beat my trusted budget airline, and my search for California airfare was no different. I ended up finding a round trip for $330 (for one passenger), all fees included, with one stop-over to cut down the cost a bit. I continue to check a variety of sites for fares and have only found increased prices, but I still wonder how else I could have saved on airfare other than by planning even further in advance.


We did use a discount site ( to get a good deal on a two-night hotel stay in San Francisco’s Union Square neighborhood. It seems like we had an advantage in looking for a room in San Francisco because of the variety of lodging that a big city has to offer. Napa, on the other hand, has more limited options, and apparently prices go up during harvest time.

We took a friend’s advice and decided to wait. As of this writing, we are still biding our time for a last-minute deal. Hopefully, we won’t have to sleep in the rental car!

Rental Car

It turns out that renting a car is fairly straightforward if you’re all right with an economy model and have done a reasonable amount of price shopping to determine the best deal.

However, if you don’t have your own auto insurance and you’re an American Express cardholder, Aaron and I recommend that you get accident insurance and a damage waiver (separate from liability insurance) through AmEx. Just $20 covers your whole trip, whereas the same coverage purchased through a rental agency can be that much per day.

To sum up the lessons learned so far about making travel pre-arrangements:

  • Plan as much in advance as you can
  • Conduct a reasonable amount of price shopping
  • Seek advice from friends who live near your destination or travel there frequently
  • Be brave and visit those lively discount sites
  • When you are working with an actual person, ask if there are specials you can take advantage of

I suspect that when I write again after the trip, the topic will have to do with how easy (or difficult) it is to be frugal with the items that you didn’t plan for ahead of time. I am excited to find out.

(MICHELLE, THE AUTHOR’S NOTE: This is the second post in a short series chronicling the financial choices behind my first real vacation. I’m a frugal person, but will I be able to pull off a great trip to California without blowing my savings to smithereens? We will find out.)

Want some instant savings for your trip? Here are the latest coupons from the three discount travel sites mentioned in the article.

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{ read the comments below or add one }

  • kevin2jobs says:

    Vacation financing….very useful……..

  • Wilson Pon says:

    Michelle, you’re definitely a smart woman, as you knew how to search the best deals from the internet. Honestly, after reading your post, I’ve learned that there are a bunch of offers on internet waiting for us to discover…

  • Becky says:

    So glad that I stumbled across this site. My husband and I are learning more and more how to save money and how to plan, thanks to Jessica V. Psalidas’ advice, outlined in her latest book, “Financial Purity.” I just finished the book and am now on this kick to do everything I can to save. We have discussed going to Texas to visit my sister but felt that it was not possible- too extravagant. However after reading your great post, I now realize that it is possible it will jut take some time planning and going to the correct discount sites. Thanks again for your advice.

  • John DeFlumeri Jr says:

    Plan ahead, do the research, don’t be disappointed with the arrangements, and Save Money.

  • In the Money says:

    I used to travel quite a bit when I studied abroad as a student. I found a really good way to save money on the activities you on the trip is to try doing what the locals do. If there are sites that you want to see that is fine, but some places are just tourist traps. I remember I took a trip to Jamaica and we asked locals where to eat. Instead of eating at common tourist restaurants, we got great deals at more local and traditional restaurants.

  • Financial Samurai says:

    Anybody ever check out that “Couch Surfing” website idea where you sleep on people’s couches all over the world, so long as you reciprocate? I think that would be a good idea.

    Michelle, how’s the San Fran and Napa Valley vacation going btw? It’s 70 degrees and sunny here, so I hope you are loving it. Maybe in the future, if we get to know each other, or anybody, you guys can crash in one of our extra bedrooms 🙂

    Happy Weekend all.

    • Michelle says:

      I’m actually not there yet–am leaving in nine-ish hours and am very excited. I’ll keep everybody posted. And I definitely look forward to that 70-degree weather 🙂

  • Kevin says:

    Travel insurance is only one of the many reasons why I even keep my American Express credit card. They may charge high fees for merchants, but the company has the most consumer perks around.

    Keep checking their website too, because the credit card company often have promotions where they give you more reward points if you shop at certain stores or buy from certain airlines/hotels.

  • Joe says:

    The airline sites usually advertise that their prices are the lowest online, so it pays to just book over there instead of checking out those “lively” discount travel sites.

  • MoneyNing says:

    One thing I tell everyone to do is to get a ticket/room/rental that you can actually refund without consequences. I update those travel deals constantly these days and I couldn’t really believe how many discounts pop up regularly. In fact, I would keep checking prices early so I book on the low range, then check for deals that come up and book a new itinerary if the math makes sense for me to do so. Then, I usually forget about checking for a while until about two weeks beforehand and start looking at those last minute deals because if they happen to fall on the days you travel, you are going to save big.

  • David@DINKS Finance says:

    I stayed in a Super 8 for only $30. The room was originally $80 but I got $50 off. I went on their site and booked it and during the process I got an IM from an employee that said if I signed up for some rewards program that was $10/month I could get $50 off the stay. I talked for about 10 minutes making sure it was free the first month and I could cancel as soon as I wanted at no charge. I had it in writing, printed it out, signed up, and took the big discount. As soon as we got back I ended my membership, all at no charge.

    Try to find deals like these and you can save a ton.

  • Mike Piper says:

    “Lively discount sites” made me laugh.

    Great tips. Hopefully Kalinda and I get to use them soon… 🙂

  • Craig says:

    It does save and you become more educated. Planning early and booking early will definitely save money in the end and it will be worth it.

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