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Going Somewhere? A Guide to Trip Planning

One of my biggest pleasures in life is traveling. Once I decide to pack my bags, my enthusiasms for the next few weeks are centered around the trip. And going somewhere I’ve never been just makes me buzz with excitement.

Trip Planning Guide

And as excited as I get, a big part of it comes from preparing for the trip itself. As a Type-A girl, I really can’t enjoy myself unless I have some sort of plan as to where I’m staying, what my itinerary is, and what places to eat. I’m all for spontaneity, but I want to make the best of my time.

90% of the time I am Trip Coordinator for my girlfriends – and I’m an assistant who has booked plenty of travel for other people – so I thought today I would share some of my best tricks for putting together a trip that is relaxing to plan and go on.

Your Hassle-Free Guide to Trip Planning

1. Eat Whatever You Feel Like

There are two types of travel people. 1) Eat chain because it’s cheaper and 2) Eat only local. When I travel, it’s just about what feels most natural while you’re out and about. When I was in San Francisco I ate at the same local bistro across the street 80% of the time because it had everything, at In-N-Out at the waterfront, and Subway on our way back from exploring. When I travel I’m a “wannabe local” which means I eat like I would imagine a local would. And it’s usually budget friendly!

2. Know Your Vacation Buddies

The advantage of traveling with your friends/significant other/family is that you know them. You know if they don’t like walking, or need to have a special bed, or really can’t stand museums. Let your knowledge of them influence your itinerary and choices. If you have a group that doesn’t want to take Uber everywhere, find a hotel in the middle of everything. None of you like history? Plan out an itinerary of shopping, relaxing at the beach, and eating out. When your group feels content, your trip is already better. And if you have a divide of people, divide the group! Everyone has a better time (including you!) if they don’t feel like they’re enjoying themselves.

3. Always Look For All-Inclusive Tours

Planning an itinerary, especially in a city you haven’t visited, can be stress-inducing. That’s why I love tours. In San Francisco we signed up for one of the bus tours. For three days – and $60 – we got to ride the buses all day, every day to explore everything from downtown to the water. Actually, we took the downtown tour so much I’m pretty sure the could have hired me to give the tour! Having such an easy option for transportation, sightseeing, and fun meant we were constantly entertained, and it was really cheap!

4. Do Everything in the Morning

In 2014 a group of girlfriends and I went to Los Angeles for a weekend trip. It was the first time I’d ever planned a trip by myself, and I knew with the 36 hours we were in the city that we had to do as much as possible. This meant doing all our traveling in the morning. By afternoon, all restaurants and attractions are usually packed with all the tourists who slept in on vacation. Skip the beauty sleep and enjoy the city when things first open. No lines, cooler temperatures, and you can actually nap post-lunch!

Because we started in the morning, we were able to do the entire Hollywood Walk of Fame, Madame Tussaud’s, Hard Rock Cafe before noon! Which meant Hard Rock for lunch!

5. Always Go For the Cheapest Flight

People who spend all their money on the travel part of their trip absolutely astound me. I can’t stand it when my plane ticket was the most expensive part of the trip – especially when you’re staying in a nice hotel! You’ll generally find that the cheapest flights are at the most inconvenient of times – take those! I don’t care if I’m waking up at 3am, it was cheap! Plus, those early hours usually mean less crowded planes and quiet airports. Don’t forget to check lots of different sites for the best prices too, as I discussed in my article for Her Campus.

6. Choose Hotel Location Over Price

It’s easy to cut corners and go for cheap accommodations to keep below budget. But those inexpensive motels can mean having to pay more to get to food and your destinations. Instead, find a reasonably priced hotel that is near where you’ll be heading. In Pasadena, we stayed at a hotel only a few blocks from Colorado Boulevard, which was easy walking to breakfast, shopping, and entertainment. And in San Francisco we stayed right on Union Square, right next to all the bus tours, lots of restaurants, and a very downhill walk to all the shopping.

7. Find Bloggers in That Location

Once you’ve got all your travel accommodations made, it’s time to actually preparing for what’s going to go down while you’re there. That’s where I turn to bloggers. Locals know the city better than anyone, which is why I look to them for places to check out and what to wear. And apparel is really important, especially when you’re checking out a place with really weird weather like San Francisco or Portland. Those bloggers talk about their cities for a reason!


I hope you’ve enjoyed my trip planning tips! If you have any questions, feel free to reach out to me at or leave a comment. I love to talk travel.


Thanks for reading! Want to stay up to date with all of my crazy shenanigans, what movies I’m watching, and how to live the best life ever? Check out my Instagram @PotatoesHegarty

Stay classy, Internet,












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#organization #trip #tripplanning #planning #travel #travelplanning

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