Itinerary tips: How to create the perfect itinerary

walking through the Singapore Botanic Gardens

I am a huge planner — I genuinely enjoy planning our travel itineraries. That said, there are certain elements that can be really frustrating. One of them is the rigidity of the itineraries you find online and in guidebooks when trying to plan a trip.

While I do often use others’ published itineraries as inspiration, sometimes they visit places we’re not interested in or skip places that are on our must-go list. It can be overwhelming to figure out how to customize your own trip, ensure you see as much as you can, and not completely exhaust yourself. After doing this for Alex and I for years, including shorter and longer vacations as well as this long-term trip, I think I’ve finally nailed it. This is my magical formula for planning an itinerary for anywhere in the world and any amount of time.

1 part major destination + 2 parts short city visits + 3 parts pit stop

What does that mean? Here’s what it looks like for a variety of different trip durations:

Creating the perfect 1 week itinerary

  • 1 part major destination: If you’ve only got one week, you need to give yourself one key destination where you’ll spend 3-4 days. It’s best if this is your arrival city so you can get acclimated to the area upon arriving.
  • 2 parts short city visits: Then you can add a max of two more destinations where you’ll spend 1-2 nights each.
  • 3 parts pit stop: On a short trip like this, your pit stops are organized excursions (not overnights) built into the time you spend in the three destinations we’ve already covered. Think: a full-day snorkeling trip, half-day jungle trek, or a cooking class. These are awesome, because they take some of the planning off of your plate. You just have to find the tour and show up.

What’s this look like in practice? Here’s a sample itinerary for a Southern U.S. foodie road trip:

  • 3-4 nights in New Orleans (including a half-day bike tour — that’s “pit stop” number 1)
  • 1 night in Memphis (including a half-day at Graceland)
  • 2 nights in Nashville (including a cooking or beer-brewing class)

Tips for 1-week itineraries:

  • I don’t recommend more than one single-night stop on a week-long itinerary or you’re likely to feel rushed and not get as much out of that stop anyway.
  • Avoid traveling for more than 2-3 hours between destinations unless you’re a die-hard roadtripper and you enjoy the travel process.
  • Avoid plane travel and/or border crossings on shorter one-week itineraries unless you know it’s a very common route. You lose a lot of time in transit that way, unless it will save you significant time versus driving, bus or train.

Creating the perfect 2-week itinerary

  • 1 part major destination: Just as in a one-week trip, you’ll want one flagship destination where you’ll spend a fair amount of time. On a longer two-week trip, though, you can give this destination about 5-7 days. This is really nice for actually getting to relax on your vacation, getting to know a city, and not feeling like you’re constantly on the move.
  • 2 parts short city visits: In addition to your one key destination, add in two additional cities/towns for 2-3 nights each.
  • 3 parts pit stop: On a longer itinerary, I suggest doing a mix of day-trip excursions and one-night stops for a total of three “extra” destinations besides the stops covered above.

Here’s a sample itinerary for a 2-week adventure in Australia:

  • 5-7 days in Sydney, including a day-trip to Bondi Beach and day-trip or overnight in Port Stephens.
  • 3 nights in the Red Centre to see Ayer’s Rock and the Olgas.
  • 3 nights in Melbourne plus an overnight along the Great Ocean Road OR 3 nights in Cairns including a day-trip to dive the Great Barrier Reef.

Tips for 2-week itineraries:

  • Avoid traveling for more than half a day between destinations, and keep the majority of trans-city hops to no more than 2-3 hours.
  • Try to mix up the types of places you visit — e.g. city, country, beach, etc. — or things may start blending together.
  • Spend some time in a place where you have a kitchen and some personal space (like an AirBnB), as spending two weeks staying in hotels and going out for every meal can be a little maddening and expensive.
  • I’d recommend only one one-night stop on a two-week trip, but definitely a max of two.

An extended one-month itinerary

30 days is the perfect amount of time to see a few countries within a region (Southeast Asia, Central America, and Eastern or Western Europe come to mind), or one large country (say, the U.S. or Australia). Many itineraries will have you switching cities every few days, but you would go crazy trying to spend 3-4 days each in, for example, London + Paris + Barcelona + Rome + Berlin + Amsterdam… you get the idea. Do yourself a favor and follow the formula; you’ll basically multiply the two-week itinerary above by two.

  • 1 part major destination: Pick two key destinations where you’ll spend about a full week (5-7 days) each. It’s nice if these are spaced out and at least one of them is either your arrival or departure destination. You can include day-trips to the surrounding region within these weeks as well.
  • 2 parts short city/region visits: I would argue that 3-5 days is long enough to get a really good “feel” for any major world city. If you’ve got a month to travel, pick four places (they can be cities or even rural regions) you want to really sink your teeth into in addition to your two week-long destinations.
  • 3 parts pit stop: Give yourself a total of six days across a few places where you spend 1-2 nights each. Six one-night stays would make you absolutely crazy — so try to stick to roughly 3-5 destinations for a total of 6 nights.

As an example, here’s what a Western Europe backpacking trip would look like if you used the formula:

  • 5 days in Rome (flagship destination #1)
  • 4 days in Tuscany (short city/region visit #1)
  • 1 day in Venice (pit stop day #1)
  • 2 days in Munich (pit stop days #2-3)
  • 3 days in Berlin (short city/region visit #2)
  • 3 days in Amsterdam (short city/region visit #3)
  • 1 day in Brussels (pit stop day #4)
  • 6 days in Paris (flagship destination #2)
  • 2 days in Barcelona (pit stop day #5-6)
  • 4 days in London (short city/region visit #4)

Traveling for 2+ months

Once you go longer than a month, simply take the above monthly formula and multiply it by the number of months you’re traveling. The one caveat I’d offer is that once you get to 6 months, I recommend settling down somewhere for a full month to decompress, take stock of how you’re feeling, and plan the next 6 months. It’s what we plan to do this summer.

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