Budget Travel

Vacation Planning: DO IT EARLY

February 12, 2020

I have grown to love vacation planning. I enjoy the searching almost as much as the vacation itself. And as I’ve become more cost-conscious in other areas of my life, I enjoy making travel (and not necessarily cheap travel) a priority for our family.

Last night I asked Josh: “So we have a hotel for our mini-trip, right?”

In early March, I am going to the last 2 days of a conference in Amelia Island with Josh (maybe trying to make up for this trip!). He asked me to “tag along”, which sounds fun and lovely and I am going to use some of this time as the ‘personal retreat’ days that I mentioned yesterday! I had not really thought about it, but he had mentioned the host hotel for the conference and I had just assumed we’d be staying there.

BUT, I recognize that not everyone obsesses about their travel plans months in advance. Including my husband. So, he hadn’t booked it. No problem; there’d be other options, right? We hit up TripAdvisor and . . .

almost everything was booked including all of the above. Even Residence Inn!!! AGHGH.

AGHGH, very few. We lucked out and found what appeared to be the last remaining room in a non-sketchy place. It wasn’t ideal (mostly because it’s a ground floor room at a B&B), but the place looks very nice.

ANYWAY, I felt vindicated. I have currently already booked:

  • AirBnB for our family spring break trip in NC (booked last fall) + flight (booked in Jan)
  • Super nice restaurant & hotel (well, one night — reminds me, I need to book the rest of the trip!) for my 40th birthday trip
  • A resort trip for the family in August (driving distance, so no flights needed)
  • A very cool hotel suite for a family ‘fall leaves’ trip we are taking up north
  • Not yet booked, but I have attempted to book (and am in a queue) for a Disney villa for our trip in December. If I don’t come off the waiting list by June, I will just book directly with Disney.

I know it wouldn’t be a tragedy if we couldn’t stay in our choice of hotel. BUT especially with a family of 5 now, accommodations can be challenging and it is SO MUCH EASIER to find them when we are one of the first ones looking.

PLUS, it’s so much fun to think about and plan the year of travel in advance! It’s like getting to go on all of these trips twice 🙂

I actually feel ready to start thinking about 2021. (I know, don’t get TOO crazy. But it’s also fun to think about what we will be able to do as G — our weakest travel link — gets older.)

Non-sponsored note: I finally sprang for a Chase Sapphire Preferred card (I’m going to let our Citibank American Airlines card lapse and close it because I can’t stand having 3984723 cards and we don’t fly AA much anymore since JetBlue and Southwest fly to so many places from Fort Lauderdale). It has an annual fee of $95 but spending $4000 in the first 3 months yields $750 worth of completely flexible travel points (!) and 2% points are earned on all travel & restaurant purchases.

Since we are both traveling a bit for work too in the next couple of months, we can put this card to work to help pay for future travel. I am not into extreme “travel hacking” but I had read so many raves about this card that I figured it was worth it (ie not getting it felt like throwing $ away).


  • Reply Laura February 12, 2020 at 7:17 am

    Yes, this can be a problem when people you travel with have a different time horizon. Not even a spouse question – doing trips with friends and family members can bring up the same issues!

  • Reply omdg February 12, 2020 at 8:12 am

    I end up doing all vacation planning because my husband is incapable of it, and tend to find it stressful because of too many choices. I’m not doing any big Disney or national park trips any time soon which seem to require much more advance planning, so generally speaking, booking 3 months in advance has worked well for us in the past. We also don’t tend to travel with friends/family. I think this is something I need to get better about. OTOH I have no idea when I will even be able to schedule vacation for next year because — new job, so there is that too.

  • Reply Kaye February 12, 2020 at 9:26 am

    I have a hard time thinking TOO far ahead, but generally plan bigger travel ideally at least 6 months in advance. I booked our spring break lodging in early November 2019 for a mid March 2020 Europe trip, so this was slightly later than ideal for me. But I find it takes me a long time to research, read about locations, figure out where what area of the city we want to stay, etc.., especially if it’s a trip where we are moving around to various cities! Then I usually get going on researching and booking any attractions that require advance tickets (places like museums that required timed entry or popular sites that can sell out to get those nailed down). I usually book flights a few months in advance. Then I spend the few months before the trip reading travel guides/ Trip Advisor forums trying to make time to sketch out rough daily itineraries, what things we all want to see/ do, and research transportation options (like airport transfer or figuring out the metro systems, for example). It’s so much work but our trips usually turn out great! I try to alternate some easier/ plan-free beach trips with more “planning intensive” trips like big cities, international trips or U.S. national park road trips.

  • Reply Erica S February 12, 2020 at 10:39 am

    We got the Chase Sapphire Reserve car. Slightly (okay a lot) higher fee, but We also get free DashPass, some Lyft credits, free TSA pre-check fee, a $300 travel credit, and access to some airport lounges. I’m also not into Travel Hacking but I feel like at least we’re getting some more services. All of our spending is now on this card, so we’re rackign up the points!

    • Reply Sarah Hart-Unger February 12, 2020 at 10:50 am

      Actually with the $300 travel credit that’s not bad! Maybe next year I’ll consider an upgrade 🙂

  • Reply Lisa of Lisa's Yarns February 12, 2020 at 10:41 am

    I also do 100% of the travel planning in my family. My husband has no sense of urgency about things and always assumes it will work out. We are going to the Tampa area next week and I booked everything in October and that was on the late side as lots of things were booking up very fast. I do kind of hate being the planner because then my husband will ask me questions about the cost and other details and I get a little annoyed. But I’ve just accepted that if we are ever going to go anywhere, I have to plan/book/push my husband to book things.

    I’m glad you were able to find a place for the extension of your stay! Hopefully ground floor of a B&B works out fine!

  • Reply Elisabeth February 12, 2020 at 12:06 pm

    I find it hard to gauge how important it is to book ahead.
    We wanted to take a family vacation to an island off the coast of Canada (Isle de la Madeleine) this summer and were trying to book 8 months out and EVERYTHING (including the ferry there and back) was already booked for all the date ranges we were considering. So frustrating, because we thought we were planning plenty early.
    On the other hand, my hubby and I had a whirlwind week in Paris this summer – we booked everything last minute and got an incredible (large room, VERY inexpensive, in the heart of the city) hotel, with literally the most comfortable bed I have ever slept on. I guess we got lucky with that situation…

    • Reply Sarah Hart-Unger February 12, 2020 at 12:26 pm

      I have found it’s very location dependent. Big city and 2 people – no big deal. Small specific location and 5 people – early a MUST.

    • Reply Sarah Hart-Unger February 12, 2020 at 12:26 pm

      Ps week in Paris sounds AMAZING!!

      • Reply Elisabeth February 19, 2020 at 8:15 am

        Great point about the smaller/specific destination filling up faster. We are usually travelling to big cities and in that context, there are just SO many choices of hotels that you’re bound to find a good one.

  • Reply Melissa Holmes February 12, 2020 at 1:29 pm

    I will turn 50 in 2023 and want to go on a several week family trip to Europe. My kids will be 14 and 12 by then so they’ll be ready. It is bringing me such great pleasure and enjoyment just thinking about itineraries; this give me 3.5 years to look forward to this trip! My husband and I went to Galapagos for my 40th. It’s so true that having something to look forward to brings happiness!

  • Reply Sarah K February 12, 2020 at 3:37 pm

    We fly from Europe to the USA every summer. I usually buy our tickets and book hotels 6-9 months ahead. I am the family travel Nazi and am kind of a control freak about hotels etc, despite being a pretty relaxed person in my day-to-day life.

  • Reply A. February 13, 2020 at 1:19 pm

    My husband is the planner/booker, I am the one who looks for restaurants/bar/coffee shops, good team. But Disney… I don’t know how you do it, never in my life, my kid doesn’t know it exists and I hope it stays that way hahah (sorry if this sounds cruel, never loved the films, the vibe, the capitalism of it, the gendered imagination, etc.)

    • Reply Sarah Hart-Unger February 13, 2020 at 3:02 pm

      I totally get it. But … our kids love it. And it’s driving distance. So, yeah.

      • Reply A. February 14, 2020 at 12:09 pm

        Driving distance, good point…

  • Reply Nikki February 13, 2020 at 1:28 pm

    haha totally the opposite, we are the royal family of last minute travel. 3 – 5 weeks out is our current average. But, like you said, always to major cities with lots of options, and we are only a family of 4 right now, one of whom still rocks the travel crib (ages 2 & 3.5) so any hotel room or air bnb will usually do the trick. Also – have had great success with the chase sapphire! In the past 6 months we’ve used points for our roundtrip flights for 3 trips, including one cross country and one international; I think you’ll like it! I was reading on the points guy that the points are worth even more if you use them to transfer as mileage directly to certain airlines, I haven’t tried this yet, but plan to now that I know.

  • Reply vj February 14, 2020 at 10:55 am

    Love your podcast and now following your blog! (I’m a physician and mom). I do all the vacation planning for our family. I too enjoy the process and having something to look forward to though with a toddler our trips are pretty basic…Need to look into Chase Sapphire! We primarily use Prime Visa ( Amazon and Whole Foods takes all our money). As far as travel goes, I have a side gig that gives me a limited number of codes to share for free. The code gives lifetime access to a travel savings website ( save up to 35% on hotels, car rentals, weeks etc. They price-match and give back 110% of the difference if you find it cheaper elsewhere
    so I always start my search on this platform!

  • Reply Jessie R February 20, 2020 at 2:06 pm

    Yes! I’m also the travel planner for our family and love booking in advance. We just got back from a week in Jamaica that I booked in July 2019 and I booked two smaller trips for the first half of the year around Christmas. It is such a relief to have things booked and paid for so you don’t have to do the last minute scramble and ensures you get to do fun things!

  • Leave a Reply

    This site uses Akismet to reduce spam. Learn how your comment data is processed.