How to Take the Stress Out of Vacation Planning (Open Thread)

We haven’t talked about how to plan a vacation in years, so here’s a fun topic for today: how do you simplify travel planning — i.e., take the stress out of vacation planning? Do you repeat trips? Copy a friend’s (or blogger’s) itinerary? Use a travel agent? Do you have any “done and DONE” kind of things where, say, if you know there’s a Kimpton hotel in that town you’ll stay there, or if your friend or a magazine or book series says Y restaurant is amazing you make it a “must do”? Take a specialty vacation package like biking or a family vacation resort something? Do you use social media like Instagram or FB? What are your best tips to take the stress out of vacation planning?

The topic kind of comes up because I just stayed at a Cambria hotel a few months ago for an alumni trip — and I mentioned how nice the hotel was for an affordable, well-located hotel to an acquaintance and she said, “Oh yes, we LOVE Cambria and ALWAYS stay there if there’s one in the city.” Interesting technique, and I could see how that would reduce a lot of the stress of vacation planning if you didn’t have any boutique hotel you were dying to stay at or you were flexible on where in town you wanted to stay. For those among you who travel often for business there’s probably a whole subtopic here — what’s your favorite hotel chain? 

For my $.02, though, in general I STINK at travel planning… so my husband and I usually share this responsibility. We usually start with travel arrangements — sometimes just getting the plane booked is the biggest hurdle! I’ve definitely grabbed a guidebook and said I would figure it out on the plane over, and I also tend to crowdsource things and ask friends on Facebook (and obviously, we get a lot of threadjacks here on Corporette with crowd-sourced vacation questions)!how to take the stress out of vacation planning I’ve tried working with travel agents twice in my life (once for my honeymoon and once more recently to try to get ideas for a nice family vacation with 6-8 people) and have yet to feel that “click” with any of the agents I’ve used. For those of you who are pros at this, though, share your secrets — how do you take the stress out of vacation planning? What are your favorite resources, tips, hacks, checklists, or more? 

(We’ve talked about how many people are using their vacation time, how to deal with pre-vacation stress at work, how to travel solo, and how to  early to start vacation planning (over at CorporetteMoms).

Stock photo via Creative Market / Barn Images.


  1. My husband and I will be going to Estonia mid-august. Any recommendations?

    • BabyAssociate :

      Ohhh, following. I’m going in November!

      • Yes! Estonia is great, depending on what you’re looking for. The old town is lovely and so is the Kadriorg palace. I recommend also renting a car and driving around the coast and to Haapsalu (day trip from Tallinn, proper castle!) Pärnu (overnight, spa town with a beach and lots of summer festivals)…

  2. London in September :

    Just wanted to thank the hive for all the suggestions yesterday – I bookmarked the thread as we’re diving into the planning.

    FWIW, my husband and I have complementary planning skills, which helps. He is happy as a clam to sift through hundreds of Airbnb listings and narrow it down to 30 or so for me to look at. He’s also great at things like figuring out the best transit passes to buy. I like browsing blogs and comments for inspiration on restaurant choices and interesting things to do that aren’t Straight Out of Guidebook Itinerary.

  3. I think you have to first figure out how you like to travel. This goes beyond hostel vs AirBnB vs luxury hotel, but also applies to how far in advance do you “need” to make plans, how much are you willing to leave up in the air, etc. I’m generally comfortable leaving things up in the air a bit so I usually pick a general destination/type of vacation, a window of time and plan things no sooner than 4-6 weeks in advance. Usually this involves looking at what cheap flights are available and then planning from there. For example, one summer I wanted to go to Europe and noticed that all the best flight deals were through Spain so we ended up just going to Spain because that was a great fare and once we had cheap flights worked out everything else fell into place. But I have friends who plan vacations up to a year in advance and for them anything so close in time would be hard either mentally or just logistically. Other friends will just take super last minute trips with little to no planning. I think knowing what stresses you out and what you don’t care about is essential.

    • BabyAssociate :

      I think this is a good way of putting it. I’m a mix of both. I usually plan trips 4-6 months in advance, but pick where I go solely based on where I’ve found a good deal (thanks, Scotts Cheap Flights). I’ll book my hotel or Airbnb a few months in advance. I usually make a list of things I want to do/see/eat, but won’t necessarily make a day-by-day plan unless I’m traveling between cities or need reservations for something.

      I also plan all my trips assuming I’m going alone. A friend will often come along, which is great, I just don’t like waiting on people to make plans.

      • Has the Premium Scott’s Cheap Flights worked well for anyone? I live in a city (STL) that rarely gets mentioned for outbound flights in the free emails and I’m not sure if I would see a benefit from paying if my city just sucks that much. Then again, my last trip I drove to Chicago in search of better fares and direct flights to London so I’d probably see them mentioned.

        • BabyAssociate :

          I have Premium. I’m in a major east coast city, but I like not having to sift through emails to find out if it even applies to me.

  4. For hotels, I rely heavily on google maps. I pull up a map of the general location I want, search for hotels, and filter by price range and star rating (that is, reviewer star rating, not hotel star rating). If people staying there don’t give it at least 3.5 stars, I’m not interested. I used to rely on guidebooks for recommendations but this is faster.

  5. cat socks :

    I like to plan in advance, but leave room for flexibility. If I’m spending time and money to travel somewhere I like to be reasonably prepared so I can enjoy the trip instead of figuring things out while I’m there. I’ll make a tentative itinerary, but I’m not a stickler for sticking to every moment of it.

    I like to use Google maps to search for restaurants around the areas I’ll be visiting and then I’ll read reviews on Google, TripAdvisor and Yelp. I save info about restaurant and places to visit in Evernote.

    I find the TripAdvisor forums to be helpful for various types of travel questions. The search feature there works reasonably well.

    I’ve found having an international plan on my phone is helpful. I use the $10/day travel pass from Verizon.

  6. Let DH plan the whole thing? ;) But seriously, trip planning stresses me the heck out. DH is just so much better at trip logistics than I am.

  7. Lost in Tuscany :

    This is timely. I’m finalizing our Italy trip for early October and I’m having a difficult time with where to stay in Tuscany for the last 3 days of the trip. We were looking at villas, but the reviews on so many of them seem mixed and I want to make sure they aren’t so remote where we can’t easily drive to vineyards. This is proving to be a little overwhelming. Any suggestions or reccs from the hive would be much appreciated. Thanks!

  8. If you don’t enjoy the planning process, or if you’re squeeze for time, my #1 tip is to use the Amex concierge. They’re fantastic.

    • If you’re still reading… what information do I need to go to them with to get the planning process started? If your card gives you access to the concierge, is there still an extra fee for using their services?

  9. Anonymous :

    I love travel planning so I guess this post isn’t really directed at me. However, I’ve got a system down for how I plan our one big trip every year (normally 10 to 14 days). First, pick location/research flights. There are way too many places I want to see in the world to repeat. Picking a location is narrowed down by whether I really just want to go there or if I found a great deal on flights. Someone mentioned a great deal to Spain above and I did the same thing last year. I was trying to figure out where to go and I saw an amazing deal so I booked it. Second, I research Airbnbs and book those. I spend a ton of time researching them, but I think it’s fun to see all the options and I’ve ended up with some amazing places (and saved tons of money compared to hotels). Third, book any travel needs once at my destination such as trains or rental cars. Fourth, research and book organized tours. Fifth, fill in the itinerary based upon all the details I already have set. This normally includes roughly sketching out places I’d like to visit, figuring out if there are restrictions on when we can do that activity, etc. I do this by using the internet, but also travel books (which I recently realized I can get from the library instead of buying). I don’t plan down to the minute, but I like to have the general day planned out with the major activities and fill the gaps based upon how we feel while we are there. I genuinely enjoy putting these trips together. My husband has pretty much no input (which he prefers) so it’s a surprise to him when we get there and he sees everything I’ve planned. I think I missed my calling as a travel agent.

    • I am almost exactly the same way, and my DH is the same. He always has input on the location and dates, budget…but beyond that, he’s usually like “…just surprise me!”

      I LOVE IT. Drunk with travel agent power!

      • Anonymous :

        “Drunk with travel agent power” I love it and that’s SO TRUE! LOL That really does sound like us – although we don’t even discuss budget because I’m more financially conservative than my husband so he doesn’t care. Dates and location are the only thing he really provides input on. It works out so well because I don’t know how my crazy system would work if someone else wanted to be involved in the planning!

      • My husband wants some input but he wants to do none of the work. And I love travel planning so that’s usually not a problem. For the most recent trip I kind of did a “This or that” powerpoint where I’d show two cities or two museums, boat versus train, or a Tour vs DIY kind of thing. It gave me enough direction for that part of planning and then I could just come to him with more specific questions, like “How important is it that we do xx?” or “What is on your must-do for yy city?” and I found out we had to do both boats and trains, art museums versus war ones, he wanted Brighton instead of Bath, and he had to try beer in London, Scotch in Scotland and crepes in Paris. It doesn’t seem like a lot but it gave me a ton of direction.

    • Anonymous :

      I should also mention that this is mostly applicable to European vacations (from US). This would be crazy overkill for something like a beach vacation. I really consider it travel much more than a vacation. I’m generally following this system for our trip to Hawaii this year, but it’s definitely a much more relaxed version.

      • I’m currently pre-planning a Hawaii 2020 trip and I’m the same way. I do barely nothing for the beach vacations we take but Hawaii is a mix of beach and activities so I need to be like Day 1 – Beach, Day 2 – AM Hike, PM – Beach…that kind of thing.

  10. I’m the total opposite. I have day-by-day itineraries in google docs with corresponding google maps of the driving route. I do a lot of planned spontaneity too – leave 2 hours open and list options (like in Portland it was either shop, stroll, or hang out at breweries), eat lunch in x district of town…that kind of thing. If it’s any vacation that involves activities, you’d better believe I planned it and know all I can about the city. I can’t take a ton of vacations and they involve a lot of money so I want to get a good value from the trip.

    It can stress me out ahead of the trip but my most recent trip to London, Paris and Scotland, the biggest issue we ran into was not being able to find a dessert shop one evening. I also plan super far in advance, even just in a super abstract way. I have pinterest boards for all the destinations I’m considering visiting. From there I put everything I’m considering on a google map and then decide what looks doable. Like Scotland had about a hundred pins but it was suddenly very clear that Isle of Skye was a must and London was already a must for flights so I worked backwards to figure out how to get from Point A to Point B. Then we chose a route to get to Edinburgh, another must from the map. Then I wrote out a schedule with just what city what day so I could book hotels. I turned off the map layers with locations we decided to skip out on and then focused on hotels with good access to transit or the destinations. Once I had that, I reviewed what needed to be booked ahead (Eiffel Tower, rental car, sleeper train, Louvre tickets, afternoon tea) and quickly made a schedule for all of that. Once the schedule was full I updated the map with separate layers by day and some route instructions on rental car days. I was able to add in some hikes and museums or a trip to the movies and beach while I was there so not everything was obsessively planned but because of my reading I totally knew what options to mention depending on the ever-changing weather.

  11. I am always in amazement by the people on this board who talk about travel planning and appear to enjoy it. Planning a trip is one of my least favorite things to do because I feel paralyzed by all of the options, combined with a fear that if I chose to focus on one item it’s to the detirment of other choices. Most of travel that I have done since being out of college has been to weddings (like 5-6 out of town weddings a year) with a few days tacked on at the front or back end, and these have worked out great.

    Now that there are less weddings, I find that we travel significantly less because of the feeling described above. When it’s added on to the wedding, you know dates, location, and have been provided with a hotel option, so you just pick a few additional activities and bam – a trip is born. When not a single one of these options is picked for me, I just don’t know where to begin and figure it’s less stressful to just not travel. For example, if I want to go to Germany, I start asking the following questions: when should I go (spring? fall? summer?)? for how long? if I chose X flight because it’s direct (but maybe the times aren’t great) am I missing out on some great experience or the ability to stay in a better hotel? If I go in the spring what am I missing out on that would be better in the summer?

    And, it doesn’t even need to be an international trip. I started looking into a trip to the grand canyon and also became overwhelmed even just trying to figure out where to fly into.

    So, now that I’ve totally complained about my first world/ 1%er problem, how do you all start planning a trip? Does anyone have a travel agent recommendation for someone who is willing to do 100% of the planning for you and basically just tells you when to show up at the airport?

    • Senior Attorney :

      If you are really a 1%-er, then this is easy. Just do a package tour. There are all kinds of fabulous high-end options and although many of them skew older, there are some that specialize in younger clients. Again, if you’re really a 1%-er then you can pick a destination and have the company customize a trip for you (and your friends). We’ve done this and it’s great.

      As far as travel agents, I’m in So Cal and I’ve been happy with The owner is a member of my Rotary Club — tell him the new club president referred you! ;)

  12. I wish I had a HUSBAND to plan my vacation. I have MYRNA, but she is a freind, and I need a HUSBAND who loves me not just a freind. If I did, I would be soooooooooo happy!

  13. I usually choose vacations based on airfare deals (hello, honeymoon in Norway), and use a guide book to get an idea of what sorts of things I want to see. I’ll then do my own research on hotels/Airbnbs, train/bus schedules, etc. However, when we recently had to cancel our Kauai trip with less than one week to go due to torrential rain and flooding, I rebooked our whole vacation to Victoria/Ucluelet instead in less than 48 hours by pretty much following the itinerary of a recent article in Sunset magazine. We had an amazing time, and now we have airline miles to Hawaii banked, probably for a babymoon next year.

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