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How to Plan a Trip: Step-by-Step Guide

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This year, my trip planning skills were put to the test. Within the span of a month, I had to figure out how to plan a trip across the U.S. and find things to do in all five cities and surrounding areas. (If you’re interested in learning more about my cross-country road trip, I’ll include the three city-specific guides I put together at the bottom of this article.)

Before this, I never thought of trip planning as something difficult to do. And it’s because I realized I’d never had to plan so many trips all at once!

I will say, however, that it can be fun to purchase a ticket to somewhere and let the trip play itself. If you’re looking to make the most out of your trip though, I’d recommend doing some planning. Follow this step-by-step guide and you’ll be a pro trip planner by the end of it!

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Table of Contents

  1. Pick Travel Dates
  2. Book Your Flight or Rental Car and Accommodation
  3. Research Things to Do & Make Reservations if Needed
  4. Create an Itinerary
  5. Prepare Travel Documents and Essentials
  6. Sign Up for Safety Alerts & Notify Friends and Family

Step 1: Pick Travel Dates

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Photo by Olya Kobruseva on

The first step in planning any trip is picking a date to travel. If you’re planning a trip to Hilton Head Island, for example, you would want to pick a time that’s warm so you can actually enjoy the beaches. On the other hand, if you’re looking to admire the fall foliage in the Pacific Northwest then you should look to see when the leaves are at their prettiest.

The date you pick to travel could also determine how much money you’ll be spending for your trip. Flight and hotel prices often go up in the summer and during the major U.S. holidays – especially Thanksgiving and Christmas.

Hopefully you can now see why determining the date of your travels is step number 1.

Wanderer Tip: Before locking in a date, it’s also a good idea to check your travel documents aren’t expiring anytime soon. Specifically, your state ID for domestic travel and passport for international travel.

Step 2: Book Your Flight or Rental Car and Accommodation

trip planning guide


If your trip requires flying, I recommend booking your flight as early as you pick out a date and as late as a month before your trip date. The reason for this is flights usually get more expensive the closer you get to your travel date. Book early and lock in better rates and your ideal flight schedule. If you don’t know what a good rate for your destination is, Hopper is a great tool that’ll allow you to track flights prices and alert you when the prices are good. It’s one of my favorite tools to plan travel!

When looking at flights, your initial travel dates may shift slightly based on the prices you see, and that is perfectly ok! Being flexible is also an important skill to have when planning a trip.

Rental Car

If you’re driving for your trip and need to rent car, it may also be wise to book your car a couple weeks to months in advance. This is especially the case for trips that are more than a couple days. Rental car companies do have a finite number of cars they can rent out after all. I’ve noticed that Hawaii has high car rental costs to begin with (since most visitors need a car to get around on the island), and the closer to your travel date you try to book a car, the more expensive the rentals get.


I think this one is pretty explanatory. You’ll need a place to stay when traveling. Book this early and you don’t have to worry about it for the rest of your planning process! If you’re looking for cool Airbnb stays, it’s especially important to book those early. They go FAST!

Step 3: Research Things to Do & Make Reservations if Needed

Here comes perhaps my favorite step of this How to Plan Your Trip Guide: figuring out what to do!

Usually when I decide to visit a place, I already have a few thoughts on activities. For instance, when I traveled to London, I knew I had to see the Big Ben and the Changing of the Guards. But it was only after I did some research, inquired my friends, and did some searching on Instagram that I realized London is known for its Indian food and that going for a ride in the London Eye is one of the best ways to see the city.

So how do you plan the best activities for a trip? Well it very much depends on the type of activity.


how to plan a trip viv the wanderer

For foodies and really anyone traveling, enjoying local cuisine and finding the best restaurants to dine is perhaps one of the most essential activities.

Eater is one of my favorite sources for finding places to eat. If you’re traveling within the U.S., you can search for Eater’s top lists by city. They also have a travel specific section that is essential for anyone who wants to eat like a local. Tripadvisor often has good recommendations for food in their destination guides too. Their lists are not as extensive as Eater’s, but will work just fine if you want to quickly find the top 3 spots to eat at your destination.

Once I’ve identified a few restaurants, I then cross-check with reviews on Yelp to see what people have to say about them. That usually helps me decide which restaurants I want to prioritize going to and making reservations for.

Last but not least, if I know someone who’s traveled to the destination before, I often ask for a list of recommendations. Nothing beats a friend, family member, or coworker vouching for a restaurant in a foreign place.

General Activities

The other category then is all other activities (haha!). Tripadvisor, blog posts, and Instagram are some of my favorite tools for looking for things to do. For almost every trip, I do a search on “things to do in [insert destination]” and that usually gives me a pretty good starting point.

Step 4: Create an Itinerary

Once I’ve gathered a list of things to do, I like to put them all in a Google Doc and highlight all the things I want to do most. I’ll also consider things like whether or not I can get a reservation before I come up with my top things to do.

I then put these top things to do into an itinerary. The places and activities that are closer in proximity and also more easily done on the same day are usually planned for the same day. Pretty straightforward right?

Wanderer Tip: Always leave room for spontaneity. Having an itinerary is great especially if you are traveling very far from home and aren’t likely to return to the same destination. However, it’s easy to plan TOO much and not have any room for spontaneity. Oftentimes my favorite memories from trips are the ones that were completely unplanned.

Step 5: Prepare Travel Documents & Essentials

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Photo by Element5 Digital on

At this point you should’ve already confirmed that your state ID or passport will still be valid by the tine you return from your trip. (If not, that means you didn’t finish reading Step 1!)

What Are Other Important Things to Check When Planning a Trip?

That depends on whether it’s an international or domestic trip. And yes, the checklist for international trips will be much longer.

International Trips

  • Tourist Visas: some destinations may require tourist visas. Look into how you can get those and if you need to have it before you arrive at the airport.
  • Local Currency: so you have spending money for all the restaurants that you want to eat at! It’s always good to be prepared with some cash
  • Power Adapter: Many international destinations’ outlets will have a different voltage from those in the U.S. Get a power adapter to make sure you can charge your electronics once you’re in your destination country. Better yet, get a universal power adapter that should cover you for most international power outlets.
  • Portable WiFi or Local SIM: If you rely on your phone for everything from looking up directions to Yelping the best places to eat, getting a Portable WiFi device or local SIM card would be a good idea.
  • Notify Bank: If you are planning on using your credit or debit cards abroad, notify your bank in advance. I have noticed that banks like Bank of America and Chase no longer you to notify them of your travel plans. I’d check their latest guidelines though just to be safe!

Traveling During COVID

  • A Negative COVID Test: Many destinations require a negative COVID test 3 days within your departure date even if you are vaccinated. Make sure you plan for this and look for a testing location that can turn results around ideally in a day.
  • Proof of Vaccination: A picture of your vaccination card will do in some cases but read the rules of your destination carefully to make sure you’re prepared to show proof of vaccination.
  • A Quarantine Plan: Some countries require you to show proof that you’ll be able to quarantine yourself if you do end up contracting COVID. While other destinations such as Taiwan require a quarantine regardless of your vaccination status. Be prepared with a physical address that will allow you to self-isolate.

Step 6: Set up Safety Alerts and Notify Friends & Family

trip safety
Smart Traveler Enrollment Program for U.S. Travelers

This last step is most applicable to those traveling solo or going to a more remote or potentially more dangerous place.

There’s a program called the Smart Traveler Enrollment Program, or STEP for short, that allows you to enter your information and travel plans so you can be alerted if something potentially dangerous is going on at your destination. It’s free and easy to sign up.

How to Plan the Best Trip Ever

camel riding in marrakech
Camel riding in Morocco

After reading this guide on How to Plan a Trip, are you feeling more confident planning your next vacation? If this was overwhelming, feel free to skip steps 3 and 4 to start. After you’ve done the rest of the steps and are ready, then come back to this post and complete steps 3 and 4. Those steps are really great to have but having a mode of transportation, place to stay, and a way to travel safely are the most important thing!

Lastly, as promised…

Guides from My Cross-Country U.S. Road Trip

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