How to Plan a Trip: 5 Steps to Create a FLEXIBLE Vacation Itinerary

There are two types of people: The one who travel plans and knows every minute of their vacation. And the one who barely knows the name of the city lol. The former knows how to plan a trip and when to leave point A to get to B, while the latter aimlessly wanders around to find the next cool thing to do.

My recommendation? Both! Create a flexible vacation itinerary.

Below are the steps I take to have direction, while also allowing for the unexpected to occur, whether it’s a day trip or a week-long vacation. I don’t get as granular as “we will be at XYZ restaurant at 6:15 PM on Saturday,” but I do want to create a list of things I’d like to cross off my list. Without any sort of planning, I miss out on things. Enter: a flexible vacation itinerary; perfect for any kind of trip you are planning!

How to Plan a Trip That Will:

Keep you on track to accomplish a few great things in the area that you’d like to do.
Leave room for (plenty!) of spontaneity.
Mix in tourist traps with experiences off the beaten path.

Here is the easy step-by-step guide you can follow before your trip, along with an example, to answer your “how to plan a trip” question. It is a good place to start!

How to Plan a Trip STEP 1: Start with What You Know

You picked your travel destination. And you may know a thing or two about it—say that you want to check out the Empire State Building in New York City, visit the Hollywood sign in L.A., or go up the Space Needle in Seattle. Maybe your friend already told you about a few of the best places to eat, you’ve seen some cool spots on social media, and/or you picked this city because of something in particular (going to a concert, game, whatever.)

This is a great starting point for your flexible vacation itinerary. The first step is to create a “Note” on your phone and list out what you have in mind. Here is an example of what I might write down if I’m going to Seattle, Washington:

TRIP TO SEATTLE

Seattle Mariners Game
Space Needle
Pike Place Market
First Starbucks

If you don’t know a thing about where you’re going, no worries at all. Start with a BLANK SLATE! Often, that’s the best thing ever.

How to Plan a Trip STEP 2: Google “things to do in [CITY]”

Once you search your destination in the Google search engine, you’ll get a nice “Top sights” section at the top of the page (scroll just a bit) and can click for more where you will get all of the popular attractions. You are going to see the main attractions right off the bat and you can add ideas and interests to your list.

Tip: Generate a list that has 3-4 experiences per day.

If you’re going for a 4-day weekend, type out 12-16 things to do. The likelihood of getting everything done on your list is SLIM, but we will narrow this down below. In reality, you’ll get to 2 things per day which will allow for some spontaneity. And of course, we need PLENTY of time for eating and drinking. 🙂

Tip: Check out the ratings and reviews

This Google page will give you an overall rating of each sight (see below), as well as the option to click it for more information and reviews. If you can’t decide if something is right for you, spend some time reading and that should help you decide. Remember, you won’t do EVERYTHING so be picky.

Tip: Use the map to the right!

Google also provides a map that comes in very handy. Zoom in on a few miles radius from where you are staying so you are only shown what’s nearby and aren’t adding things to your list that are waaaay far away.

This is also a great time to start thinking about where to stay if you aren’t sure yet. You can look to position yourself where most of the places you want to go are. (Read my travel tips on Hotel Room or Airbnb: Where Should I Stay for help with your best accommodation decision!)

After my Google search, my list looks something like this—remember, we are making a much longer list than we are going to achieve. Don’t panic.

TRIP TO SEATTLE

Seattle Mariners Game
Space Needle
Pike Place Market
First Starbucks
The Gum Wall
Chihuly Garden and Glass
Museum of Pop Culture
Alki Beach
Fremont Troll
Gas Works Park
Olympic Sculpture Park
Seattle Aquarium
The Museum of Flight
Pioneer Square
Discovery Park

NOTE: This can be as long or short as you’d like! If you only have 2-3 things, no problem! Also, keep in mind, things like Starbucks and the Gum Wall only take 10 minutes each.

How to Plan a Trip STEP 3: Find Blog Posts

Now, we want real advice and recommendations from travel bloggers. Not just the tourist traps. This is my favorite part. Put “blog” at the end of your search (“things to do in [CITY] blog”) and go through 5-10 blog posts to get a good idea or 10.

Sometimes, you can even find good posts if you search “non-tourist things to do in [city]” to make sure you get a variety of off-the-beaten-path experiences added to your list.

Use the blog information to determine if what you put on your list already is a fit. It’s a great time to start narrowing down and cutting things out that you may not be interested in after reading more about it.

Tip: Look at price.

If you have museums or experiences that cost money, make sure to check on how much it costs. It’s usually a factor that can help us make a decision on if we really want to do it or not, depending on if it’s a lot of money. (Do a quick coupon search as well to find the best deal.)

Now, Rework Your List

To make it easy, put everything you know you want to do at the top, maybe’s in the middle and no’s at the bottom (or just delete.) After my search of travel blogs, I’ve added + narrowed down my list to make it look something like this:

TRIP TO SEATTLE

Seattle Mariners Game
Space Needle
Pike Place Market
First Starbucks
Ferry to Bainbridge Island (looks awesome, adding it!)
Hike: Rattlesnake Ledge (according to bloggers, hiking is a must in Seattle)
The Gum Wall
Chihuly Garden and Glass
Fremont Troll + surrounding neighborhood (looks like an awesome place to explore)
Alki Beach (maybe…depends on the weather)
Olympic Sculpture Park (so many parks…keep them as options)
Gas Works Park (maybe list)
Discovery Park (maybe list)
Seattle Aquarium (maybe list)
Pioneer Square (maybe list)
~~Museum of Pop Culture~~(read some reviews, not into it)
~~The Museum of Flight~~ (eh, not my thing. Skip)

This leaves me with experiences I’d like to check out on my trip—including new ones, a few maybe’s, and a couple that I’m not interested in anymore after digging into some blog posts.

Remember, if you are more spontaneous, great! Have a smaller list. Your goal is to make sure you don’t miss things you REALLY want to do, even if that’s only 1-3 things.

How to Plan a Trip STEP 4: LOOK AT THE MAP

Next up is to use Google Maps and figure out where each one is located. This is going to help you figure out which one’s to pair together to create the easiest and most efficient FLEXIBLE vacation itinerary. You don’t want to plan something on the south end of the city in the morning and then something way north in the evening. You’re going to waste too much time.

The best way to maximize experiences is to plan your days by area so you have enough time. Make location notes next to each spot that is going to help you remember where they are. Here it is in my example:

TRIP TO SEATTLE

Seattle Mariners Game; Century Link Field, south of downtown
Space Needle; north of downtown and Pike Place Market
Pike Place Market; right downtown, little bit north on the water
First Starbucks; in Pike Place Market
Ferry to Bainbridge Island; hop on the ferry downtown
Hike to Rattlesnake Ledge; hour and a half southeast—requires car rental for mini road trip
The Gum Wall; downtown, right near Pike Place
Chihuly Garden and Glass; north of downtown, right by the space needle
Fremont Troll + Neighborhood; way north of downtown, need a ride
Alki Beach (maybe…depends on the weather); way southwest of downtown
Gas Works Park; way up by Fremont
Discovery Park; way north of downtown, way west of Fremont, off on its own
Seattle Aquarium; just south of Pike Place/gum wall
Pioneer Square; pretty much downtown, little bit south

Group together by location.

This is an important thing that will not only help you decide which places are close to others but with prioritization as well. Take my list above with all the parks, for example. I can keep one or two on my list that are near other attractions and delete ones that are nowhere near anything else since they aren’t as big of a priority for me.

Here is my list now with 4 general areas. Try to bunch them into the number of days you will be on your trip. And keep the maybe’s:

TRIP TO SEATTLE

Downtown

PIKE PLACE MARKET; right downtown, little bit north on the water
FIRST STARBUCKS; in Pike Place Market
THE GUM WALL; downtown, right near Pike Place
FERRY TO BAINBRIDGE ISLAND; hop on the ferry downtown
OLYMPIC SCULPTURE PARK; just north of Pike Place
SEATTLE AQUARIUM; just south of Pike Place/gum wall
PIONEER SQUARE; pretty much downtown, little bit south

Downtown—North

SPACE NEEDLE; north of downtown and Pike Place Market
CHIHULY GARDEN AND GLASS; north of downtown, right by the space needle

Father North of Downtown

FREMONT TROLL + NEIGHBORHOOD; way north of downtown, need a ride
GAS WORKS PARK; way up by Fremont

Downtown—South

SEATTLE MARINERS GAME; Century link field, south of downtown

Out of the Way

HIKE TO RATTLESNAKE LEDGE; hour and a half southeast—need a car
ALKI BEACH (maybe…depends on the weather); way southwest of downtown
DISCOVERY PARK; way north of downtown, way west of Fremont

How to Plan a Trip STEP 5: CREATE SOME DIRECTION

Now, underneath your list (still in your Note), write out the days you are going to be on your trip. Remember, this is NOT a set-in-stone plan. Maybe you do what goes with Thursday on Saturday. Or Sunday on Friday. Who knows. You must allow for flexibility. Maybe you found an awesome bar and stayed there for hours—who cares!

What this does, is gives you some direction when it’s your first time in a new place and don’t know where to start. My example, with travel dates and grouped by location so you know which top spots are near eachother:

Thursday: Downtown Seattle—hit the first Starbucks, walk around Pike Place and see the gum wall in the morning. Take the ferry over to Bainbridge Island for the afternoon.

Friday: Downtown North and Fremont—start downtown to hit some tourist traps early and then go north to explore Fremont in the afternoon.

Saturday: Hike to Rattlesnake Ledge—rent a car in the morning to go hike + explore outside the city. Leave the night open.

Sunday: Downtown South—go to the baseball game, find some things to do near there afterward.

Look at that. You have a flexible vacation itinerary that is going to give you some direction instead of aimlessly walking around. Plus, your days aren’t completely packed. They allow for good restaurants, bar hopping, and random experiences along the way!

NOTE: look into public transportation as well to maximize your time!

Tip: Keep the things you don’t plan on doing on your list.

You’ll have options that were researched beforehand for when you end up having extra time on your hands and are looking for something to do!

Tip: Do not ultra-pack your day.

You gotta leave room for flexibility. You’re going to meet people who have suggestions, run into areas you had no idea about, spend too much time eating or shopping, all of it! And I REPEAT: Your plan is only a bit of DIRECTION.

Tip: DO YOU.

Maybe you leave first thing in the morning open because you like to casually get up, find coffee, and mosey around first. For me, I usually leave from happy hour and beyond open because by then I am ready to find bars, have a few beers, and either end up partying all night or finding a place to have dinner at 8pm. (Check out Tips to Find the Best Restaurants While Traveling for a great way to find the best spots in as little as 2 minutes.)