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Welcome to my newest series, The Wanderland Guide to Travel Planning. This is the third post in a multi-part series!.

Part Three // Creating an Itinerary

Once I’ve nailed down my destination(s) and transportation, my next travel planning step is to start a rough itinerary. For short trips, this can help me get organized in case I want to, for example, make hard-to-get dinner reservations or nab a ticket to a show. For long trips, it helps me organize my time and make the most out of my travels. My first move? Grabbing a guidebook and binging on travel blogs!

Travel Blogs

• Guidebooks: If I’m still in the trip contemplation stage, I’ll sometimes take a guidebook out of the local library, but once I’ve committed to going I’ll usually buy one to take along on my travels. I’m on the Lonely Planet mailing list, and whenever they’re having a sale — usually a few times a year — I snap up guides for all my upcoming trips. My favorite feature? Being able to purchase a single downloadable chapter at a time online, or buy both a physical and digital book together at a discounted bundled price. Personally I think the more specific the better (I’d rather carry both California and Arizona guidebooks than buy a regional one for the Southwest USA).

I’m not always Lonely Planet loyal — I occasionally branch out to other guides. Moon does off-the-beaten-path stuff (my friend Kyle wrote their guide to Maui!) and I love the full color versions of Fodors, especially for regions like the Caribbean, which Lonely Planet doesn’t cover very comprehensively.

• Travel blogs and websites: I start by heading to all my favorite bloggers site’s and checking their destination pages to see if they’ve been where I’m headed. If not, I simply Google “[Destination] travel blog” and see what comes up. The New York Times travel section has a series called 36 Hours In that I always check the archives of when I’m researching. And if I’m heading to anywhere in Southeast Asia, I make sure to take a long hard look at Travelfish — if anyone knows of a similarly comprehensive resource for other parts of the world, I’d love to hear it!

Guatemala Travel

• Maps: If you or your friends or family are AAA members, ask them to go grab you a free map! For some trips I like to have one just for fun and photo-ops, but for others — like road trips in which cell service is spotty — they can be lifesavers.

• Forums: Sometimes I’ve exhausted all research options and still have a question about something related to my trip, or I just want an opinion on a part of it I’ve been weighing up in my mind. Travel forums can be a great place to go get those answers. Tripadvisor’s forums are my favorite, though the audience tends to skew more tour bus than public transit. Lonely Planet’s Thorn Tree forum is another go-to. While a little less frequented than the Tripadvisor forums overall, they’re definitely a bit more backpacker oriented. For Southeast Asia, Travelfish forums take the prize again, while for diving trips Scuba Board forums can’t be beat. Remember that what goes around comes around — if you got an answer that helped you out, try to see if there’s someone you can help out with info about a destination you already know and love. Also, follow the first commandment of forums — thou shalt search previous threads before asking thy question.

passport

Once my head is spinning with ideas and inspiration, I take pen to paper and make a list of everywhere I want to go. Then I start prioritizing. Personally, I’ve tried to adopt the “less is more” manifesto when it comes to destinations as I need time to work on the road, and I find that I’m happier after spending more time in less places. But even if you’re off on a pure vacation, don’t forget that you’ll want time to relax and unwind! Build in time to linger in cafés, read on beaches or park benches, and, you know, do laundry.

Sometimes I print out blank calendar pages and start penciling things in to get a pragmatic picture of what I can see in what time I have. Sometimes I take a map and circle the places I want to go and start building a route from there.

Bermuda Travel

For example, when I was in the daydreaming stage of my recent two-week trip to California, I considered hitting up Los Angeles, San Diego, Palm Springs, Anaheim, Santa Barbara, and even flirted with the idea of a side-trip to Tijuana. In the end, after booking my flights in and out of Los Angeles and sitting down with a calendar and a map of SoCal, I stuck with the first half of that list and dropped the second. There’s always next time. And don’t forget to be realistic about how much time it can take to transit between various cities or even hotels!

What you do with that itinerary is up to you. When I arrived in California last month, I had accommodation booked and I was on a locked schedule. That was great. When I arrived in Central America last spring, I had four months, a notebook with a list of cities I wanted to visit and a rough idea of the order in which I might do so. I didn’t have a single bed booked, not even for the night I landed. That was great too. One traveler, two different tips, and two different moods!

Reading a Guidebook

Next up: Booking accommodation, activities, and more!

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41 Comments...
  • Leah
    October 25 2015

    I’m loving these posts! It’s always interesting to see how other avid travelers do things. I’m sooo not a planner anymore, but I used to love browsing Lonely Planet guides prior to a trip. I actually haven’t bought one in ages and tend to just show up at my destination and THEN figure everything out. Obviously not practical for most travelers, but it works for me 🙂
    Leah recently posted..Pinterest for Travel Bloggers: An In-Depth Guide to Help You Drive Traffic Like a BOSS

    • Alex
      October 27 2015

      It really depends for me. For the purposes of this post I definitely gave the most all-in, extreme example, but I quite often figure it out as I go as well. However, I actually enjoy research so when that happen it’s usually more a time limitation than anything else! I’m also a lot more lax when I’m traveling alone than when I’m traveling with others — in those cases, I tend to plan and information-gather a little more vigorously as I feel somewhat responsible for making it a great trip.

  • becky hutner
    October 25 2015

    Thanks for the “36 hours in” NYT tip! And it’s good to know which forums you find useful. I usually have one burning question per trip I can’t seem to find the answer to!
    becky hutner recently posted..Canadian in…London??

    • Alex
      October 27 2015

      Me too! I probably head to Tripadvisor the most often out of those, though Scuba Board has been invaluable for planning diving trips as well.

  • Dominique
    October 25 2015

    I tackle itineraries the same! First LP (or if I’m going to a big-city-lots-of-museums-destination I use DK Eyewitness because of the comprehensive location drawings inside buildings), blogs, and I occasionally check TimeOut. Great advise on Travelfish and LP sales – that’s new to me and I’ll check it out! This is a very informative series, thanks!
    Dominique recently posted..Delphi – The World’s Belly Button

    • Alex
      October 27 2015

      You’re so welcome, Dominique. Lonely Planet has some crazy good sales — and I’m always ready to pounce when they do 😉

  • Fernando
    October 25 2015

    Sounds a lot like what I do when planning a new trip.

    Being able to buy ebook versions of guidebooks has been a massive improvement for me in terms of travelling light. Sometimes I miss the printed versions, but nothing beats the convenience of having a bunch of guidebooks on your smartphone.
    Fernando recently posted..How to Choose the Best Compact Travel Camera for Your Needs

    • Alex
      October 27 2015

      True — it’s a lot lighter! Still, I am a sucker for the printed version. I just like being able to write on the maps and flip through the pages!

  • Caity
    October 25 2015

    Creating the itinerary is my fave part of the planning process, especially looking through and getting inspired by my guidebook. In fact I get soooooooo in to it that I’ve got itineraries for places I have no immediate plans to go to! Although I have used Lonely Planet in the past personally I don’t feel as inspired by them as I do by DK Eyewitness Travel. Each company have their strengths and weaknesses but DK are definitely my go to guide. 🙂

    • Alex
      October 27 2015

      Ha, believe me — I’m almost embarrassed by the number of places I have guidebooks to/have written out itineraries for that I’ve never been to and have no immediate plans to visit. And another vote for DK guides! My parents used to have some and I did enjoy flipping through the drawings of the major sites, but I don’t find them as practical for getting around with.

  • Natasha
    October 25 2015

    I usually travel without an itinerary and decide things very last minute. The good thing about this is going somewhere unexpected. However, I would like to start traveling with a little more a rough itinerary like this to help stay more organized.

    Never knew about the NYT 36 hours. Will definitely start using that!
    Natasha recently posted..Why you should visit Zakopane

    • Alex
      October 27 2015

      I love a good mix of spontaneous trips where I can go where the wind takes me and well-planned ones where I can just kind of go into auto pilot once I get there because all the decisions are already made. It’s a nice balance!

  • Rachel
    October 25 2015

    Forums and blogs are my biggest source for planning! Itinerary planning is a tough job but also really fun!
    Rachel recently posted..Steve Jobs: Movie Review

    • Alex
      October 27 2015

      Agree! I think this step is the hardest — fleshing out where to go when — but once that’s locked into place, I love filling in the details.

  • Travel planning is my favorite. I had no idea that the New York Times has that column. I’m heading over there right now to scour it like crazy! I try Googling the destination + travel blog, but oftentimes I don’t really get the results I’m looking for. I’d love to hear some of your favorite blogs to check out. Do you have a list somewhere on the blog?
    Amanda | Chasing My Sunshine recently posted..Balance vs Priorities

    • Alex
      October 27 2015

      Actually I don’t! I’m not the blog reader I used to be and these days really only check in with my blogging buddies to see what’s going on in their lives. I do miss being a regular reader of tons of them, though! Maybe I should put out a list of my favorites, one of these days.

  • Rachel
    October 25 2015

    I’m loving these posts, it’s nice to know that even really experienced travellers have such a detailed process when planning a trip. I would love to be a show-up-and-wing-it kind of traveller but I get too excited when doing my trip research and end up booking everything in advance. It takes away some of the spontaneity but it also makes me feel organised, gives me hours of enjoyment (travel planning is FUN) and builds anticipation for the trip so I guess it’s a worthwhile trade-off for me.
    I’m a fan of Rough Guides website, it skews towards the backpacker more than other sites, and has really helpful lists of not to be missed sights and even suggested itineraries. Also addicted to Rome2Rio, which helps a lot working out the time, distance and best method of travel between each place I want to go, making it a lot easier to work out a logical itinerary

    • Alex
      October 27 2015

      I agree — I LOVE travel planning. When I am being spontaneous, it’s usually down to lack of time in the pre-planning stage 🙂 And Rome2Rio is getting a major shoutout in my next post — it’s amazing!

  • Katie
    October 25 2015

    I’m a huge fan of Travelfish! I’ve also looked for similar websites for other regions, but without any luck so far. Sometimes I think trip-planning/day dreaming is half the fun 🙂

    • Alex
      October 27 2015

      Amen. And let me know if you ever find the Travelfish of anywhere else 🙂

  • rebecca
    October 26 2015

    great list of resources. My favourite travel blogs are generally my go to for research as well. I tend to break out the spreadsheets, over fill and under complete is my moto
    rebecca recently posted..Everything ends, that is what gives it meaning

    • Alex
      October 27 2015

      Ah, girl after my own heart. I love a good spreadsheet!

  • Britt
    October 26 2015

    It’s such a coincide that you wrote this post now because I’ve just spilt the beans on where I’m planning to go for the next 15 months; roughly of course because I think it’s always important to build some flexibility into your itinerary.

    I’m a big fan of the ‘(Destination) travel blog’ search when I’m starting to plan for a specific destination. Google searching ‘how many days to spend in (insert city)’ always tends to direct me towards a good forum discussion about how much time to allocate in one place and those responses often include the things you can do as well.

    I use a word document to sketch out my rough plans and then after that I put it into an excel spreadsheet with the rough dates and then I also add budgets, booking numbers for accommodation and transport I might book, as well as final costs in each destination as I’m travelling. Spreadsheets are the best!

    • Alex
      October 27 2015

      Yes, I also Google “how many days to spend in (insert city)”! Leads to some great info. Sounds like we are kindred spirits when it comes to travel planning 🙂

  • ‘Love the post! It’s great to see how other travel bloggers do things.

    If I’m travelling with hubby and son then I travel slower and spend more time in fewer places. If not, I speed away! I tend to have a location idea, then I check out travel blogs to see who has been there before, for tips and general prices. I then buy an updated Lonely Planet Book as I really love the way they write and like collecting physical books as well as the kindle version LOL! Once location is sorted out, then it’s trying to find the cheapest form of transport but if I’m travelling solo I get the flight or train 1st and work backwards!
    Victoria@ The British Berliner recently posted..The British Berliner is 2 years old. Let’s whip out the the daisy cocktail and have some strawberries & cream!

    • Alex
      October 27 2015

      I’m also addicted to the paperbacks — who needs minimalism when you can have a full shelf full of those blue spines?!

  • Leigh
    October 26 2015

    I love the NYT 36 hours series…very helpful!

    I love staying in nice hotels, and am content to stay in and order movies and room service. For this reason, I have to have some sort of itinerary pre-planned or I fall back into “hotel mode” and end up doing nothing!
    Leigh recently posted..Chicago’s Historic Pullman Neighborhood

    • Alex
      October 27 2015

      Ha! Girl I hear ya. Staying in nice hotels is kind of a trap for me because I’m like um… why would I leave?

  • Susan
    October 26 2015

    Thank goodness for the internet, right?! I can’t imagine how people did travel planning before we had all of these amazing resources. I mean, I know they used guidebooks and printed maps obviously, but I just feel really lucky and appreciative of our resources today. (Thanks for the NYT tip! I didn’t know about that one.)
    Susan recently posted..A Weekend in the Scottish Isles

    • Alex
      October 27 2015

      I had this discussion with my mom recently and I was rolling on the floor laughing thinking about it. We were talking about our childhood trips to Martha’s Vineyard and she was telling me how they used to write away for brochures about rental properties and call and cue up over the phone to book ferry reservations, and get advice from friends on where to eat. My how things have changed!

  • Ashley
    October 26 2015

    Loving this series, and being able to get a glimpse into your travel planning process! I have almost exactly the same routine when planning an itinerary, but still struggle with the “less is more” aspect 😉
    Ashley recently posted..Expat in Edinburgh: Month 5

    • Alex
      October 27 2015

      Believe me, I do too! It is getting easier over time but I still have to fight the urge to want to go everywhere every time!

  • Diya
    October 28 2015

    I’ll echo all the others and say I’m loving this series too. It’s great to get a glimpse into your travel planning process.

    I’d also love to see a list of your recommended travel bloggers 🙂

    • Alex
      October 30 2015

      Alright, I’ll have to add that to my list of post drafts 🙂 Thanks for the suggestion!

  • Conor
    October 28 2015

    I’m currently at this stage in my travel plans. I’m super ahead of schedule as I’ll be leaving September next year for Central America but it’s still taken me ages to decide on an entry point let alone decide on a route. I followed your recent central america series of posts which have been super valuable. Thank you!

    • Alex
      October 30 2015

      That’s awesome to hear, Conor! So glad you enjoyed those posts. Have fun with your Central America planning!

  • Mary B
    October 28 2015

    I use a lot of the same sources, but Pinterest and Google Spreadsheets were my most important planning tools for this most recent trip. I read through my Lonely Planet too, but found it most useful for spur of the moment decisions once I was on the road. Even though I love to do research and plan, I also really loved not having a set itinerary for the first half of my trip – I had ideas about where I wanted to go, but was free to switch things up, especially if I met cool people or wanted to stay longer. The downside, though, is that I had 6 weeks in Georgia and still missed a couple of places I wanted to see. Guess I’ll have to go back!
    Mary B recently posted..Getting a Visa to Iran

    • Alex
      October 30 2015

      Yeah, I like to have a plan but not be afraid to break it 🙂 I don’t use Pinterest as much as I should — maybe I’ll give it a try for my next adventure!

  • Joy | Joy Goes Places
    October 30 2015

    I love this guide! Creating the itinerary is my favorite part of travel planning. I usually make a wishlist of the spots I want to visit and then check out a map to plan out my route. It’s also the most tiring because of all the time I spend on researching. But I love it! Spontaneous trips with no itineraries are great but planned ones are also fun. 🙂
    Joy | Joy Goes Places recently posted..5 Awesome Memories from My Mt. Pulag Trip

  • Nicole
    November 5 2015

    Hi Alex,

    I’m Nicole. I love your travel writing! Especially this post! I’m a producer for Thought Catalog, and would love to email you about your writing!

    • Alex
      November 8 2015

      Feel free to get in touch via my contact page. Thanks for the kind words!

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