Nov 06

Need a Vacation From Planning My Vacation


This past weekend I spent many hours planning the details of a family trip with my grandparents.

Neither of them have traveled very much (grandma’s first flight was last year when my grandparents came to NYC to visit bf and I for Christmas) and we’ve never been on a family vacation together. Both of them are healthy and pretty adventurous (for 80-year-olds!) so I think we’re going to give Mexico a try. I’ve never been to Mexico and neither has the bf, so this is probably going to be quite the adventure. I’ve also never seen either of my grandparents in shorts or a bathing suit, so this could be pretty horrifying and entertaining all at the same time.

Because I’m anal retentive detail oriented and cheap frugal, it’s important to me that every detail of the trip is planned perfectly. As you’d probably imagine, this makes trip planning pretty stressful for me.ย  Basically I hate it when things are out of my control, and vacations are usually completely out of my control (the irony). The flights, the hotels and the food can be planned to a certain extent, but the majority of those factors can’t be control once you’re “on the road.”

What does that mean? Well, basically it means that I stayed up most of the night on Saturday worrying about planning this trip.

Here’s a vague outline of what my crazed thought process looked like:

  • My grandparents would probably like to go on a cruise, but departing from NYC in the winter means “losing” several days to the cold on both ends of the trip.
  • Called grandparents, confirmed that they’d be fine with not doing a cruise.
  • Check average temperatures of Cancun in February.
  • Check Expedia, kayak and jet blue travel sites (among many many others) for package deals.
  • Check reviews of each hotel/resort offered as part of the package.
  • Check hotel amenities and guesstimate local food/restaurant prices.
  • Check reviews of local restaurants.
  • Find local attractions and activities that would be fun/age appropriate for my grandparents (no zip-lining this trip!)
  • Compare package deal prices with individual flight and hotel prices to figure out if the package deal is really cheaper (this includes changing the dates of the trip and the departure airports multiple times, to figure out what’s cheapest and most convenient).
  • Make sure dog sitter (a dear friend) is available the week we’d want to go.
  • Check what travel insurance will cover if someone gets sick.

Yes I understand that planning a beautiful getaway isn’t exactly something to get stressed out about. I guess I just feel a lot of pressure to make sure that this trip is really fun and really memorable for them. Tough problem to have right? Yeah I know, #FirstWorldProblems. Right now we’re considering staying at the Westin Spa and Resort in Cancun. It has a mixture of good and bad reviews, but the nightly rates are inexpensive and the reviews of the beach and pools are excellent (which is what matters most to us since we won’t be in the room most of the time anyway). We debated on all-inclusive vs not and have decided that we’ll probably just pay as we go. We’re not big drinkers and we’d like to explore a little bit of the area outside of the hotel, so we’d be offsite for a bunch of the meals anyway.ย 

So that’s where we are right now. Excuse me while I go breathe into a brown paper bag…

Do you get stressed planning trips? Do you use a particular travel site to get good deals? Have you been to Mexico?

Image: Anda (:


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  1. LOL, my dear friend, you really are doing a terrific job. You’d make a great living as a travel agent if it didn’t stress you out so much, as you think of every detail, it seems, when planning a trip. We haven’t been on a trip in quite some time, so I can’t comment on the stress factor, but I would imagine I’d be a bit stressed out too, especially bringing 4 kids along for the ride. I’m quite confident that you guys will have a great time on your vacation, KK. ๐Ÿ™‚

      • KK on November 6, 2013 at 9:18 pm
      • Reply

      I think of everything because I stress about everything ๐Ÿ˜‰ Bringing two 80-year-olds who don’t travel with us might be very similar to traveling with 4 kids lol, I guess we’ll see how it goes.

  2. If you and your family are not big drinkers, perhaps a bed-and-breakfast or a smaller boutique hotel will be a nice alternative to a resort. Here’s an example in Playa del Carmen: Or, you can also rent a private house – that way you have more privacy and space, and you can cook breakfast or meals if you want, and it may turn out to be much more affordable than a resort.

    My husband and I are going to Mexico this Christmas (we’re heading to Merida, which is 2 hours from Cancun). No beaches for us, but there are cenotes! We are so excited. I’m sure you and your family will have a wonderful time.

      • KK on November 6, 2013 at 9:21 pm
      • Reply

      Thanks for the advice. I also looked up a few places on vacation rental by owner ( My uncle rents out a couple of his houses on the website and I like that I can read other peoples’ reviews of the homes they’ve stayed in. I’m not sure how much cooking I’d want to do, but I do like the idea of being able to save some money that way. Mexico for Christmas sounds lovely. Hope to read about your trip on your site.

  3. Oh by the way, you can take out the live link. I copied & pasted the text so you can paste it into your browser if you want to check it out, but it got automatically linked.

  4. I have been to Mexico, just a little south of Cancun – Playa del Carmen – for our honeymoon. We had a great time and because we went off-season, in October, we got a great deal. I’m not sure what the weather is like in February, but in late October it was hot as a summer in Georgia in the States. I’m not sure it ever gets cool there! You might want to check out the Playa del Carmen area because it’s farther away from Cancun and might be a bit cheaper. It’s still very easy to get to, there are about a million shuttles that run back and forth from the airport. We stayed at the Royal Hideaway Playacar and I would recommend it. It’s a boutique-style place, meaning it’s very small and it wasn’t crowded at all when we stayed. The only downside might be the fact that there is a much bigger resort next door that always had some sort of event going on late into the night – it always sounded fun, but the noise might bother your grandparents. Anyway, that’s my two cents based on experience – I think you’re doing an awesome job with planning this trip and I think it’s wonderful that you’re doing that for your grandparents ๐Ÿ™‚ I’m sure they’ll have a fantastic time with you!

      • KK on November 6, 2013 at 9:28 pm
      • Reply

      I think something quiet will be important. My grandparents are pretty cool and laidback, but loud pounding music and drunk college kids would not be their “scene” (nor mine). It sounds like the Westin I’d looked into is pretty calm and quiet, which is important to us. Playa del Carme sounds like a lovely place to honeymoon (I also saw some vacation package there when I was trying to figure out where to go). We still aren’t set in stone for Cancun, so I’m going to keep looking a little bit and see what we find.

  5. I have never been to Mexico but I can tell you I get stressed even planning a local vacation. This is because I try to get the best deals and also make sure the experience will be good. So trying to balance those two can be a pain.

      • KK on November 6, 2013 at 9:30 pm
      • Reply

      I feel the same way. Trying to balance frugality with good service, a nice hotel and proximity to fun amenities is pretty difficult (I’d imagine it would be much easier if cost was not object).

  6. That’s so nice of you to plan a trip with your grandparents! ๐Ÿ™‚ I was, very unfortunately, never able to do anything like this with mine.

    I have had a very similar situation when it came to planning our honeymoon (and you have to do it in the middle of wedding planning = double hell!) It was a 2 week trip to Ireland/Scotland. I’ll admit that I tried to cram too much into the trip and didn’t get to see everything we wanted. Oh well, it just means we’ll have to go again ๐Ÿ˜‰

      • KK on November 6, 2013 at 9:34 pm
      • Reply

      As frugal as I am, I know I’d regret not being able to do a trip like this with them. They’ve been so supportive of me my whole life it’s the least I can do to show my appreciation. Wedding planning sounds like a nightmare to me. I’d be super stressed and freaked out doing wedding planning and honeymoon planning at the same time. I think what you said is key about not trying to do everything. We’ll probably plan one or two little side trips, but mostly just try to relax. There are other times we can go back if we don’t get everything in in one trip.

  7. A study showed that most of your happiness boost comes from planning and anticipating a vacationโ€ฆnot necessarily the vacation itself.
    I usually enjoy planning vacations but I think it’s stressful for you since you’re planning for your grandparents as well. I can’t give any good advice for Cancun…I went there years back when I was young and single! =) I do hear good things about going to the Mayan Ruins though.

      • KK on November 6, 2013 at 9:37 pm
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      I was just actually talking about something similar the other day with a co-worker. Sometimes knowing you have time off coming up is more comforting and enjoyable then the actual day off. I definitely would like to see the Ruins and possibly do one other little trip/adventure. I know people think of Cancun as a party town (which I’m sure it is), but I’d imagine there are also a lot of things to do and enjoy if you aren’t there to party with the college kids.

    • CF on November 6, 2013 at 1:05 pm
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    For flights, I like to check I believe there’s a site for each major airport in Canada. He complies some great deals on airfares and posts them there. That’s how Brian and I got our uber-cheap flights to Europe.

      • KK on November 6, 2013 at 9:40 pm
      • Reply

      Thanks for sharing. I hadn’t heard of that one (and google analytics tells me I haven quite a few Canadian readers, Hi neighbors to the north! :-))

  8. I usually don’t get stressed planning the trip. My stress comes during the implementation phase. I have to keep myself from becoming disappointed if something doesn’t go exactly as planned on the trip (which often happens on vacations).

      • KK on November 6, 2013 at 9:44 pm
      • Reply

      I feel the same way Brian. I always imagine things going perfectly and if they don’t it’s hard for me to “recover” and appreciate the other things that have gone well. It’s something I’ve worked on as I’ve gotten older. A good trip doesn’t have to be perfect.

  9. Awe, don’t worry! I am a flight attendant and I also get stressed! LOL! Great post, you can do it!

      • KK on November 6, 2013 at 9:48 pm
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      Thanks Mary, I’m glad I’m not alone. If I was a flight attendant I’d probably be stressed all the time. All those connections and unhappy travelers trying to make their connections. Stress city!

  10. I’m pretty sure this is how the staycation was born. Things can sometimes get stressful when you are away from the house for a long period of time. It’s much easier just to take off of work and maybe visit some of the local attractions that you haven’t taken the time to see. Although this usually doesn’t include sandy white beaches and a blue ocean. ^_^

      • KK on November 6, 2013 at 9:51 pm
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      Right? lol. If we had a warm sandy beach in our back yard we’d definitely stay here. I think once I get everything booked I’ll be able to relax a little bit. For now I’m kind of a mess. It would be a lot easier if they lived here or nearby and we could all fly together. Since they’re 8 hours away things get a little more tricky planning how to ge them there and us there at the same time so they aren’t alone and don’t panic in another country where they don’t speak the language.

  11. Yes, I do get stressed while trying to plan a vacation, even if it’s just a weekend getaway! I will spend hours slaving over reviews on TripAdvisor. It’s awful. My boyfriend always tells me to stop reading reviews because they aren’t always the whole story of the place. I agree and disagree. I just don’t want to pay for a bad experience, especially if I could have prevented it with some research. It’s even harder when you’re trying to figure out a vacation for an area you’ve never been to. Planning a trip to Mexico would probably take me several days. I wish I could be one of those adventurous people and just go with it, but I do like to attempt to plan everything to a T. Sometimes that does take the fun out of it.

      • KK on November 7, 2013 at 10:45 pm
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      I totally agree with you, if there are reviews I’m gong to read them to see if it’s worth my time and money to go somewhere. If all of the reviews are terrible I don’t want to bother going somewhere. Plus sometimes you find out interesting little tidbits in those reviews (which hotel members are the most accommodating, which restaurants have good food, which companies to avoid etc).

  12. I get excited about planning trips! I always want a vacation from my vacation, just to rest and recover. I came back from Iceland at 1am and went to work the next day at 8am, all discombobulated. I’ve had some pretty awful times returning to work post-vacation, because I’m go-go-go and a workaholic. I always need more time to rest! Sounds like you have a lot to plan for a lot of people though and grandparents aren’t just anyone! I’m happy you will be able to spend some quality time together.

      • KK on November 7, 2013 at 10:47 pm
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      Good for you for even making it to work. I’d definitely have to call out. If I don’t get a full 8-hours of sleep I’m a total grouch. Returning to work post-vacation is the worst. The last day or two of my trips are always spent dreading the first day back.

  13. I also use to turn planning a vacation into a very stressful experience and two years ago I started planning our summer vacation in December, doing all the research I could do on locations, then on hotels and so on. Fortunately it paid off and we had our best vacation ever, so that’s the plan on doing it from now on. It will sound crazy to many, but it’s your vacation so you have to do all that is necessary to make it perfect.

      • KK on November 7, 2013 at 10:47 pm
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      I’m so glad you had such a nice trip. That’s exactly what I want for this trip. I want everything to be fun and happy and memorable. I know I don’t have control over that, but the things I can control I will.

  14. I do get a little stressed planning trips because I want to make sure I have every detail taken care of as far in advance as possible. I usually use Expedia but will probably branch out to other travel sites because I doubt I’m getting the best deal when I only check one website. I hope your actual vacation is relaxing and all the planning pays off!

      • KK on November 7, 2013 at 10:50 pm
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      Thanks DC, me too:-) I like using expedia but have also been using kayak and What’s annoying is many of the sites don’t include taxes and fees in their “low rates” and then once you get to the booking part everything is way more expensive.

  15. LOL… I agree about getting stressed with planning, especially if there’s so many options of where to go for resources. I usually #firstworldproblem-complain about needing a vacation after my vacation to recoup. ๐Ÿ˜‰ Cancun is fun, and I agree that non-inclusive is the way to go, especially if you want to explore outside. It’s a few hours away, but if there’s a tour bus that goes to these places, Ik-Kil Cenote is awesome, and Chichen Itza is pretty cool, too (we went on a tour that stopped at the cenote first, and then the Chichen Itza afterward). ๐Ÿ™‚

      • KK on November 7, 2013 at 10:55 pm
      • Reply

      Nobody should be stressed about planning a fun tropical vacation. Iโ€™m a total spaz, but I do want this trip to be really great for them, so Iโ€™m putting a lot of pressure on myself. Iโ€™m going to google the places you mentioned. Iโ€™ve never been to Mexico so Iโ€™m definitely excited to learn more and to plan some little trips and excursions when we get there.

  16. I don’t get stressed planning vacations because I’m so freaking EXCITED!!! I love to travel ๐Ÿ™‚ I’m so excited that you get to do such a wonderful trip with your grandparents. You’re going to have an amazing time.

      • KK on November 7, 2013 at 10:56 pm
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      I think I’ll be super excited once everything is booked and planned. We haven’t been on a trip in a while and bf and I haven’t done an international trip together.

  17. Oh man, I can sympathise. After six months of ongoing travel planning (plus of course more preplanning prior t that) I am DONE DONE DONE! First world problems indeed. ENJOY!

  18. I totally get the same way when planning a vacation. For my family’s trip to Las Vages, I start spreadsheets with hotel and airfare options.

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