How to plan the perfect travel day

How to plan the perfect travel day itinerary

In an age of extreme FOMO and limited vacations, it’s easy to stress about the perfect itinerary. Here are a few tips on how to feel the most satisfied with your plans while you are traveling.

In an age of extreme FOMO and limited vacations, it’s easy to stress about the perfect itinerary. Inevitably you will either miss out on something your desperately wanted to see, or you will drive yourself into the ground by binging on activities, and become exhausted after a few days.

Here are a few tips on how to feel the most satisfied with your plans while you are traveling.

How to plan the perfect travel day itinerary. Step 1: Prioritize and filter your travel itinerary so that you don't get overwhelmed

  1. Prioritize and filter.
    In the age of too much information, it’s ridiculously easy to rack up a huge list of “must-dos” and become overwhelmed and disappointed when you can’t get to it all. Take a moment to sit back and think about what you really want to do, not what some Buzzfeed list says you must do. Love art? Focus on the museums. Need souvenirs? Take a little time to research the flea markets. Don’t care for the outdoors? Maybe skip the bungee jumping, even if you don’t get bragging rights and a new Instagram pic.

  3. Balance your day.
    If you have a really long day of walking through museums or hiking and you don’t usually walk that much, try to catch a live show somewhere in the evening so you can rest your feet. Or find a good spot to people watch. I like to find a place to sit outside with a coffee or dessert, and these quiet moments usually ends up being some of my favorite memories of a place. Let go of the compulsion to “go” all the time, and take time to just soak in the flavor of a city or place.

  5. Research transit.
    I’ve seen so many people just go with the flow when it comes to trains and buses and cabs. Then they get to a station and panic because they don’t know how to work a machine or read the route maps. Or they may opt for a cab during rush hour in a city with insane traffic. There’s so much info out there on what to expect, so spend a little time upfront learning how a city operates before diving right in. You’ll save so much money not using cabs all the time, and so much stress when you know how to get around without any help.

  7. Research admissions.
    Most museums and many other attractions charge a ticketing fee. These are almost always cheaper online, and there are often free days. If you opt for a free day though, be prepared to wait much longer to see what you want. For example: you can skip the crazy line at the Vatican with an online ticket. Saves hours.

  9. Eat!
    You burn extra calories walking around and taking in all of those sites. It’s easier to get confused and grouchy when you don’t keep your tums full. I’m not a huge breakfast eater but I make sure to load up on protein if I am going to be walking much more than usual. Snack away guilt free on gelatos, coffees, kebabs, or whatever to keep your strength up. Also make sure to look up local mealtimes and practices. Having to wait for dinner until 11pm when you expected it to be served at 5 in Spain is going to be a downer.

    How to plan the perfect travel day. Step 5: Eat! Make sure you know what the typical mealtimes and courses are so you are not left hungry by the end of the day.
    Chocolate and churros for breakfast in Madrid. My kind of breakfast.


  11. Go with the flow.
    Sometimes that restaurant you were dying to try is completely full with a two hour wait. Sometimes the attraction you wanted to visit is closed for crazy weather. Just go down your list to the lower priority places you picked and try again another day. Or just walk around (if you are in a safe area) and see if you can find another adventure. My classic example is Grimaldi’s Pizza in Brooklyn… it has 2 hour long lines but around the corner is Juliana’s, started by the founder of Grimaldi’s after he saw what the new owners did to his old place. Better pizza with only a short wait. The guidebooks would never tell you about Juliana’s.

    Search flight deals under $100 round-trip with Skyscanner!

  13. Nap.
    It’s okay to take a little nap. Jet lag will have you all sorts of f-d up and there is no point in being tired and miserable all day. You won’t appreciate whatever you drag yourself to. Keep it under 30 minutes or in 90 minute chunks so you wake up in the middle of an REM cycle and stay groggy.

    How to plan the prefect travel day. Step 5: Nap and regain your strength.
    Nap during the Moroccan afternoon… too hot to do much else.
  15. Split up.
    If you are dying to go to a local dive bar but your friend or partner wants to go shopping, it’s okay to split off and meet up later. No point in dragging each other along to things and staying bitter. Meet up later for lunch or dinner and you will still feel like you are vacationing together rather than holding each other as itinerary hostages. Plus you will have amazing stories to share at the end of the day!

  17. Ask a local.
    You can ask people before you get there for highlights and recommendations, and no one will know better than a local. You can visit a forum online such as TripAdvisor, join a travel oriented Facebook group, or ask your AirBnB host (most are happy to help). There are all kinds of niche Facebook groups based on interests, from women oriented groups to working nomads to adventure hikers.

  19. Save shopping for the last day.
    You will have seen most of the typical souvenirs by now and have a decent idea of good prices. It’s tempting to reach for the shiny on the first day (FOMO), but unless there is some kind of special market, you almost certainly can find that souvenir again towards the end of your trip (or even after you get home).

  21. Save a free day or two.
    You will know much more about a place after you arrive than when you are Googling around, so pad an extra day in for spur of the moment impulses, changes of heart, or merely random wanderings. Spelling out every hour is a perfectionist impulse, and a painfully easy way to set yourself up for a letdown. When I went with my family to Scotland to check out our family heritage we already knew of a few Pringle sites, but once we got there locals kept pointing us to more and more buildings with Pringle history. My favorite place was an abbey we never had even heard of before that had a whole crypt full of Pringles from hundreds of years ago.

    How to plan the perfect travel day itinerary. Step 10: Save time for the unexpected.
    The family crypt we never even knew about.
  23. Keep your eyes peeled.
    Follow your instincts when you are on the ground. This applies both ways. Stay safe by leaving an area when something doesn’t feel “right”, but also stay open to something that may not be on the agenda. One of my favorite memories is wandering into an occult bookstore in Rome. I couldn’t read a word of Italian, but the tension between the city’s heavy Catholicism and this tiny bookstore’s reaction to that was awesome to think about as I paged through weird old books.


Hopefully all of this advice wasn’t too basic, but it’s easy to get swept up and disappointed in our traveling if all doesn’t go completely perfectly.

Studies actually show that the anticipation of a vacation is much more gratifying than the vacation itself. That’s sad to me. I think if we let go of our need for perfection we can make our travels into happy experiences in the moment rather than slogging and panicking from monument to monument. Here’s to mindful traveling.

This post contains affiliate links


Artist-scholar with a passion for travel.

View stories

Leave a reply

Your email address will not be published. Required fields are marked *

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