tips for trip planning.

May 8, 2017

tips for trip planning | reading my tea leavesFirst you should know that you’re getting advice on trip planning from someone who has a verified case of FOTP. (That’s Fear of Trip Planning, and no, it’s not actually a thing, it’s just something James likes to bring up on the eve of our trips while I bluster around the place removing items from my bag.)

It’s not that I don’t like to travel, and not that I don’t care where we end up, but I haven’t historically been very terribly good at getting around to making an itinerary or researching a place before boarding the plane to get there.

But, if you’ll allow me a very dorky post, I thought it might be helpful to share some of the resources I’ve tapped into in recent years that have helped my trip planning (and taking) go a little bit more smoothly.

I’m very sure I’m not the only person who has found myself walking down a street in a new city (or, often, right here in New York), hungry, maybe a little grumbly, but not wanting to dip in just anywhere for a bite to eat or a spot to rest my feet because I’m afraid that I’ll end up eating in a ho-hum café when just a few minutes away there’s a sweet spot that’s much loved and deservedly so. (Fear of missing out at may or may not also be at play.) And while I’ll concede that part of the fun of visiting a new place is to explore it haphazardly with a heart opened wide enough for spontaneity, if you ask me, one of the happiest results of the 21st century obsession with social media is an ability to plan a trip tailored to your particular tastes. Especially when you’re on the road, it can be awfully nice to know that you’re about to sit down for a meal or enjoy a quiet cup of tea, or lay your head to rest in a spot that someone you know or admire has also loved. 

Here are a few ways that I use a bit of 21st century sorcery when planning trips, in hopes they might also be helpful to some of you:

Travel Books: 

My mom wrote travel guides when I was growing up, so I feel inclined to mention that investing in an excellent travel guide by a thoughtful writer can still be a useful endeavor. Still, I’m not convinced that toting around an encyclopedia-sized Lonely Planet is the only way to go. Wildsam and Cereal both publish (slim) print guides that are very lovely indeed (and make very sweet gifts). Long live books,etc.

City Guides:

In the digital realm, I’ve relied on city guides on sites like Design Sponge and Remodelista for years. And yes, they’ve been around long enough that I actually remember my sister printing Design Sponge recommendations before either of us had smart phones. Before I head to a new city, I’ll still often poke around on those sites first and see if there’s anything that I might want to visit myself. 

Social Media:

Maybe best of all, I love doing a little bit of social media sleuthing to find gems to visit. While I find that general geo tags are usually too chaotic to wade through, I have had luck following Instagram accounts from folks I admire to get a sense of their favorite spots in a city I might be headed toward. Before we went to Seattle, for instance, I looked through Aran Goyoaga’s beautiful feed and through her, I found Jordan Carlson’s gorgeous Seattle-centric account. Both feeds gave us lots of inspiration for our trip (the lighthouse we visited above I first spotted on Aran’s feed) and we even ended up renting Jordan’s home through Airbnb! Put another way: It pays to snoop around a bit.

Beyond finding local experts, it’s nice to put out a direct call for tips. It’s not lost on me that as a writer in an online space, I have access to a lot of recommendations from readers, but the best part is that those recommendations are available to everyone else, too. Open up the comments section on travel posts and you’ll likely find a whole slew of local folks chiming in to give tips on their local favorites. More succinctly: Rely on folks with larger followings to do the work for you. When you notice that someone else has crowd-sourced a travel question or documented a trip they’ve taken, make a note and return to their posts later for more tips.

Taking notes:

Because a lot of the places that I’m intrigued by are in locations I have no immediate plans to visit, it’s nice to have a system for stashing away finds for later. My favorite tool lately is on Instagram. A few months ago, they launched a Pinterest-like bookmarking feature that lets users save posts to named collections. I’ve made four collections so far (Places to Eat, Places to Stay, Places to See, and Spaces to Admire) and whenever I stumble upon a post that features a spot I’d love to consider visiting myself, I save it to the collection to revisit later. 90% of my saves are purely aspirational, but it’s so nice to know that they’re there if ever I find myself, say, planning a trip to Mexico City. (Screenshots above for the uninitiated.)

Getting there: 

Here’s where I get really dorky. Once I’ve gotten together a list of places that I’m eager to check out, and before we head off on a trip, James and I like to make a dedicated Google Map, full of the places we’re hoping to check out. We tag all the spots that we’re eager to see and then refer to the map as we bop around a place. It makes actually finding the spot a breeze, of course, but it’s also super useful for getting our bearings in a new place more generally. 

What about you guys? Favorite techniques for trip planning? Fellow FOTP sufferers out there? All ears and then some.

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35 Comments

  • Reply todaysouhaila May 8, 2017 at 10:53 am

    this post is so helpful ,I like to plan my trips and next time I’m gonna use your tips x

  • Reply Camila May 8, 2017 at 11:05 am

    We’re getting ready for a trip to Brazil, and while packing I’m already miserable failing to be a minimalist packer. I may have to dig into the suitcases today and remove some items hahahaha. I love you tips no matter how dorky. Thank you for sharing.

    Happy Monday!

  • Reply Erin May 8, 2017 at 11:09 am

    I am definitely a planner. I used to travel all over the country for work and I would often Travelzoo the top places to eat before I went (my thing is making sure to try a local food – think cheesesteak for Philly – when I go somewhere new). This has led me to some amazing, amazing meals. Can anyone say Louisville Hot Brown?

    Another thing I would do is ask people in town, while I was there, where to go. A stop at Sucre in NOLA led me to Joey K’s for dinner for Eggplant Napoleon, and a trolley tour through Anchorage led me to Humpy’s for a blackened salmon salad that one can only dream about returning to.

    So, while I agree with super planning 100% – don’t forget to build in opportunities to be spontaneous and organic!

  • Reply Kim R May 8, 2017 at 11:36 am

    You’re definitely not the only person who is looking for a place to eat (or drink, or whatever) and won’t just settle for anywhere. On an unplanned stop in Paris (no international phone reception) on a road trip with my husband and brother, I made them both extremely angry (hangry?) with me because I refused all of the restaurants we walked past. I even went so far as to make us leave a restaurant where we had already sat down and received water because I realized it was not going to be a good experience when I looked at the menu. I ended up settling on an Indian restaurant that turned out to be very good but my co-travelers will never forgive me for it.

  • Reply Emily May 8, 2017 at 11:47 am

    I love this post, as I am planning to pack up house and family to travel out west for a month this summer. Also, on your note about using people you admire for travel tips- we recently stayed at the cottage in Venice that you recommended last spring and it was a dream! We also loved your dining recommendations: Superba is also one of my new favorite places to eat ever!

    • Reply ERIN BOYLE May 8, 2017 at 12:04 pm

      Oh, yay! So, so glad to hear that!

  • Reply Hannah May 8, 2017 at 12:22 pm

    I really like On the Grid (onthegridcity.com) ! It is a global neighborhood guide put together by locals. While it is a work in progress with many neighborhood guides still to come, I find it feels relatable in the sense that it’s live and current, and put together by fellow designers, although non-designers would certainly also benefit 🙂

    I’m visiting the west coast – including a first-time trip to Seattle – in a little over a month, and have been excitedly checking out your trip and reader suggestions, Erin — so glad our trips happened to almost coincide!

  • Reply Angela May 8, 2017 at 12:33 pm

    Oh, I am a type A planner (former teacher and curriculum writer), and I plan in a very similar style to you! Don’t sell yourself short! I planned an extended family trip through Ireland and relied on google maps, Instagram and blogs (god bless grace bonney). My trick is to always plan one meal and one activity each day. Leaves room for adventure but also allows for you to recover from terrible museum cafe lunches.

  • Reply megan May 8, 2017 at 12:47 pm

    Pre-travel stressing is always better than while-travel stressing in my book! Before kids, I was much happier with winging it, but toting around two little boys for the past couple of years has amplified my planning efforts. I love the idea of the dedicated google map to pair with my google sheet I prep for each trip we take – I may or may not divide our trips by day that include options for different weather conditions and general rowdiness of my little tribe.

  • Reply Claire May 8, 2017 at 1:09 pm

    Yes! I love the google maps idea! I found Rachel Ball’s Seattle map really helpful and I love here! She always has great ideas. I then put together my own map of NYC when I lived there last summer.

    Agreed that it’s hard to settle on a place when you know there’s lots out there. I find myself hangry most days I travel because I want to have the most idyllic ice cream (Paris!) or best dumplings (San Francisco), or most worthy coffee (Portland). I will walk miles for the top rated coffee shop on yelp! To each their own. Instagram is certainly helping with travel planning these days and I do love digital travel guides for the ease of fact checking and updating prices/conversions.

    Will you share some of your favorites from Seattle? I’d love to see what you enjoyed in case there’s something I’ve never been to before!

    • Reply ERIN BOYLE May 8, 2017 at 1:16 pm

      Yes! Working on it!

  • Reply allison May 8, 2017 at 1:20 pm

    Perfect timing! We are heading to Charleston soon, so I just ordered a Wildsam guide. Thanks for the tip!

  • Reply Sarah M May 8, 2017 at 1:22 pm

    We went to London last year and the best decision I made was to break up our days by area of the city. We made lists of all the places we’d like to go (definite, hopeful and maybe) and then narrowed down the area. We’d spend all day in that area, and see what we could get to! That helped us get to most of the places we really wanted to see and left room to explore as we went from place to place. Allowed us to find cool extra things without just wandering aimlessly since we only had 2 1/2 days! I like the top 10 travel books too. Gives good overviews of sites, including prices in many cases, and has fold out maps that are so helpful if you don’t have great phone coverage.

    • Reply Emma May 8, 2017 at 10:21 pm

      Hi Sarah! I love your idea to break up days by area of the city. I am heading to London this July – do you have any recommendations? I would really appreciate it – feeling so overwhelmed at the moment!

      • Reply Sarah M May 9, 2017 at 12:50 pm

        We were there in June last year. I definitely recommend going to the Globe Theater as a groundling, standing by the stage. It’s a cheap way to see a great play, but not good if the kids are in tow (too much time/standing)! There is a wonderful restaurant right around the corner from the Globe that we found by accident and it was our favorite! I think it was Turkish food, and had great service. If you can’t see a play, stop by for lunch or dinner and maybe look through the gift shop/museum. We also took a ferry down the Thames to get there. It was a fun intro on our first day in the city.

        We wandered through the South Bank one day, but it is VERY touristy. And expensive, so I wouldn’t spend much time there. The Tate Modern was our favorite museum. Great for kids too, because there are plenty of tactile exhibits. All the museums are donation based, no ticket cost, so those are good options.

        If you love tea, try the Fortnum & Mason shop. It’s huge and a fun experience. My favorite bookstores were Daunt and Hatchard’s.

        Public transit there is really easy. Get an Oyster card at the airport for 5 pounds, that you’ll get back when you return it to the desk when you leave. That way you don’t have to pay for a temporary card (nonrefundable). And you add as much money as you need onto that. We went everywhere for three days, using buses and the tube and only spent about 35 pounds for two of us.

        • Reply Emma May 9, 2017 at 11:08 pm

          Thank you so much Sarah; I am so grateful for your recommendations! I am can’t wait to start planning now 🙂

    • Reply Emma May 8, 2017 at 10:22 pm

      Hi Sarah! I love this idea. I am travelling to London in July; do you have any recommendations? I am feeling so overwhelmed at the moment!

  • Reply Lindsay May 8, 2017 at 3:23 pm

    Oh, I get really dorky with Google docs for trip planning. On a recent 2-week trip to Italy, I had a full-on spreadsheet with a tab for each city we were visiting. And then on each city spreadsheet, I had lists: things to see, restaurants to go to, and because I love food and Italy is so regional, I kept a list of each place’s regional specialties. But the other thing that really helped was divvying up the planning with my husband. It was really important to him that we see particular artists and pieces throughout the trip, but visiting every museum is exhausting. So he was in charge of identifying the key pieces we wanted to see in each city, which made it much more manageable. That way we could pop in to, say, the Vatican museums and make a beeline for the Sistine Chapel while not waiting in crowds winding our way through the whole building. It was great because then we could spend a good 20 minutes just lost in thought staring at the ceiling. I was in charge of food planning. I’m actually not a fan of spontaneity when it comes to restaurants in new places. If you’re abroad and visiting touristy spots, you’re very likely to end up in the equivalent of that place’s TGI Friday, because these are the kinds of places that locate themselves where the tourists are. So to avoid hangry moments, plan out where you’re going to eat based on where you are in the city ahead of time. We had such good food everywhere because we relied on recommendations and not empty belly instincts.

  • Reply Cle May 8, 2017 at 11:24 pm

    I use the google maps approach as well! Bonus that it is saved so you can go back and reference where you went…has not failed me yet.

    We also also stopped using yelp years ago after repeatedly ending up in lengthy lines with every other tourist and finding mediocre results at the end. I tend to ask a cab driver or other local about what to eat/do and have had great suggestions that way as well.

  • Reply cait May 9, 2017 at 12:23 am

    Woo! Thank you for this post – I’m trying to plan my trip to Scotland in July. Trying meaning that I don’t know where to start so haven’t yet. These are good tips!

    • Reply Sarah M May 9, 2017 at 2:08 pm

      I’m starting to plan for Scotland too, though I don’t have a travel date yet! 🙂 I really like the Eyewitness Travel Top 10 books. Just bought one for Scotland. They aren’t too bulky and have lots of good pictures, prices, maps, etc. And Pinterest is always a fun way to look around.

  • Reply Kizzy May 9, 2017 at 1:30 am

    Great tips, I want to start traveling more but the thought of planning and packing is the part that puts me off. I also didn’t know there was that tool on Instagram, I need a new phone so maybe that’s why I hadn’t seen it.

  • Reply Jamie May 9, 2017 at 7:06 am

    Have you tried jauntful.com? Love their sharable maps, and while I lived in Rome I made one for all my visitors. I’d get requests for advice all the time, and it was so nice to be able to send people a link to a map of all my favorite spots. Now I use it for tips on things to do in new cities.

  • Reply Willow Westwood May 9, 2017 at 7:31 am

    Thanks for sharing such helpful advice! My boyfriend and I are going to Germany this summer and I’m starting to feel excited to do some planning! Normally more of one to prefer sitting around in cafes and wandering aimlessly to seeing all the museums, etc…
    I have one question for Erin/all the much smarter-than-me minimalist packers in this little community: what do you do about toiletries on a long trip? I always aspire to pack just a carry-on but then am thrown by the TSA 3.4 (or whatever it is) ounces in a quart-sized ziplock rule. I’m certainly no beauty hound but just trying to pack shampoo conditioner, face wash, oil, moisturizer, deodorant, dry shampoo, sunscreen… it never fits in one of those little bags! And this time I’m going away for two weeks so I think I’ll have to wash my hair at some point. Tips?

    • Reply Rachael May 9, 2017 at 8:17 am

      I don’t think bar soaps need to go in your liquids bag (you should check the tsa website or with someone who flies frequently to be sure, though, I don’t fly much), and there are some great bar shampoos out there. You might look into those. I’ve got a great one from Mountain Madness Soap Co that I use every day, but you can usually also find them at health food stores and at Lush. There are also some pretty great lotion bars. Handmade soap is one of my favorite little luxuries.

    • Reply Anna May 9, 2017 at 8:30 am

      I put everything in a clear plastic cosmetics bag from Muji, which is bigger than the ziplocks provided at the airport and saves you from decanting everything from your bag – just pull out the Muji and you’re good to go through security. I’ve never seen them rigidly enforce the quart sized bag rule but perhaps it depends on where you fly.

    • Reply ERIN BOYLE May 9, 2017 at 9:53 am

      Hi Willow! I have two small silicone bottles for shampoo and conditioner (though on this last trip I forwent conditioner and packed tearless shampoo for the little guys in one bottle instead!) I travel with a small glass jar with a face/body cream combo, a tiny jar with coconut oil for makeup removal, my deodorant, mascara, lip/cheek tint and that’s about it! That said, I also put everything in my regular canvas Dopp kit! Haven’t packed a clear plastic ziploc in years!

  • Reply MA May 9, 2017 at 10:58 am

    Great tips! Such a good idea to use Instagram collections to take notes. Our family is gearing up for an extended family adventure in Norway this summer and I’m already following people/tags on Instagram to get ideas.

  • Reply Jenna May 9, 2017 at 2:54 pm

    When you say you make a “dedicated map” in Google Maps, what does that look like? Is it just saving locations? I love the idea and want to use it for an upcoming trip, but I’m not sure what it means. Thanks!

  • Reply Emma May 10, 2017 at 6:40 am

    Currently on a very laissez-faire trip to London, and saving desired spots on google maps has been my favorite planning tool so far. I have lists, named pins, and starred spots (if we ended up really liking something), and I like that we’ll be able to refer back to it in the future and see the shape of our trip.

    • Reply Emma May 11, 2017 at 2:24 am

      Any recommendations Emma? Sarah M has given me some great ones for my trip to London in July and I’d love to hear yours as well if you feel inclined to share?

  • Reply Carolee May 10, 2017 at 9:49 am

    Maybe I’m totally old school but I actually still print out recommendations like DesignSponge’s city guides before a trip. I have two kids and I am hyper-sensitive to them seeing me on my phone and I try to minimize the amount of time I need to use it in front of them, especially when we’re exploring a new city together. It bums me out how “digital” everything is – I like having a physical print-out to refer to rather than constantly getting out my phone. And I think it’s nice for kids to look at the print-outs and circle things that seem interesting to them. I dunno, kind of think we’ve gone way too far in using phones for everything (google maps! pinterest! instagram!) and it frankly seems to shut kids out from participating in a lot of the fun of trip planning.

    • Reply ERIN BOYLE May 10, 2017 at 10:01 am

      So nice to think of finding a way to involve kids in trip planning!

  • Reply Brooke May 13, 2017 at 8:35 am

    Oh I do the google map thing too! I do it not only for trip planning, but for everyday life. Inside Google Maps App for iPhone I use the newish feature Save > Save in your lists: Favorites, Want To Go, Starred Places, etc. It’s great for when my husband and I read about a place, restaurant, or experience we want to try in our hometown in London. I save it and it’s there on the map waiting for me the next time I’m in that neighborhood. Thanks Erin for another great post.

  • Reply La Shell June 4, 2017 at 12:53 pm

    Loved this article. I recently made a trip to Paris and I spent 10 days with only a carryon and it was very early spring. Very impressed with myself for the minimal packing! I used alot of these things while doing my own planning so reading this post has jogged my memory a bit for when I travel next in a few weeks. I’m yet to do any planning for that. I only have my ticket and apartment (staying with a friend).

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