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How to Plan a Trip | Tips + Best Sites

How to Plan a Trip

How to Plan a Trip:

I am so happy to finally make myself sit-down and write this post. I have gotten several requests for a post detailing “how to plan a trip.” So I hope that you find this post beneficial! Planning a trip should be exiting and fun. Don’t let all of the choices and options stress you out!

e0fdb543-3c47-4042-b8c7-5ac20c3fe207How to Plan a Trip

How to Pick a Location:

Of course, not everyone will have this problem. More often than not, you will probably know where you want to go. However, in the event that you are feeling spontaneous, let Google and Trip Advisor do some work for you. I often simply type into Google Search: “Trip Advisor Best places to visit in [USA, VA, East Coast, etc.]”. Read reviews, look at photos, and enjoy the search.

How to Pick a Hotel:

First, I use to narrow down my options. I filter my options based on a combination of their ratings and my budget. Personally, I won’t stay anywhere that has less than a 4-star rating. Once I pick a few standouts, I type the names into Trip Advisor to read a few reviews. Then eventually, I book with

I like because they have an extremely easy to use reward program. For every 10 nights you book, you get one night free. The “free” hotel night that you can redeem is valued at the average price of your 10 paid hotel nights.

How to Plan a Trip

What about an Airbnb?

Typically, I prefer a Hotel in bigger cities and an Airbnb in beach areas or small towns. It’s typically more convenient to be in a hotel when in buggier cities. While it’s usually more enjoyable to be in an ocean-front house at the beach or a house/cabin in a smaller town.

Airbnb is totally safe and easy to use. Of course, use common sense… and read reviews. Also, I never choose a house that has no reviews. If you are interested in signing up, you can use my link to get $40 off your first booking.

How to Book a Flight:

Always do flight searches on Tuesdays. If you are ever going to get a deal, it will usually happen around 90 – 60 days out and on a Tuesday. I use Google Flights to compare airlines, and it is really easy to use. Once I decide on which airline to go with, I book directly through that airline’s website.

Also, always sign up for the airline’s rewards program. Even if you think you will never fly with them again, do it anyway. You never know!

How to Decide What to Do:

You will likely already have a few things in mind. However, once again let Trip Advisor be your new best friend. Type in any city and click on “things to do” and Trip Advisor will list the top things to do from most popular to least.

Once I decide on a few different things that I am interested in, I use Google Maps to compare their locations and decide the order that I should do them in and possible time slots. I am not saying that you need to pinpoint an exact time for everything and create a formal itinerary. However, having a ballpark idea of times and distances allows you to maximize the amount of activities that you are able to do in a given day.

As a blogger, another suggestion I have is to type into google: “[insert city here] travel guide or itinerary”. Since you are here reading my blog, maybe you’d enjoy reading someone else’s. There are a lot of people on the internet that love sharing their experiences with other people. Take advantage of that! Need some help picking your next vacation? Check out my list of destination suggestions and tips.


I hope this gives you a little insight into how to plan a trip. Of course, there are plenty of other factors that I can’t easily put into words. So if you still have questions or would like my opinion on something, please ask! I would love to talk with you; DM me on Instagram.

Thanks, as always, for reading my tips on how to plan a trip. Stay tuned for the next Adventure: Aruba! I actually planned this one through Cheap Caribbean; so I will likely write a review of that after the trip.

Until next time,


This post contains affiliate linking, where I might make a small commission on things purchased through my links. However, as always, all opinions are honestly and organically my own.

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