My Dream Trip Planning Guide

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Some people might think they don’t need a My Dream Trip Planning Guide. They think they don’t need to plan a trip because they like to roll up into town at the last minute without a hotel reservation and just see which greasy hippie will let them crash at their pad at the night in exchange for a large bag of Doritos. They think “planning” makes you a “tourist”, whereas they are a sophisticated “traveler”. I don’t like these people.

On the other hand, it’s possible to overplan My Dream Trip. If you have a color-coded binder detailing what you and your travel buddies will be doing every second of the day, this doesn’t leave room for spontaneous adventures like getting drunk with an old couple from South Bend, Indiana.

Plus if I over plan My Dream Trip, I’ll likely be one of those people who gets home and says, “I need a vacation from my vacation!”

My Dream Trip

But how to plan My Dream Trip, you ask? You want to see as much of a place as possible, but you don’t want to cram in so many sights that you end up wasting vast sums on transportation or get burned out.

You want to eat as much as possible, but not so much that you vomit, like I did that one time in the bathroom at the Metropolitan Opera. Basically, you want to do a Goldilocks amount of traveling: not too much, not too little, just right.

After over five years of traveling solo and trying to create the most exquisite itineraries that I can, I believe I have learned the secret for how to make My Dream Trip your dream trip. So I’m excited to share with you…

My Dream Trip Planning Guide

My Dream Trip Planning Guide 1
step one: Eat Breakfast

My Dream Trip needs to start with breakfast! It’s the most important meal of the day! If you don’t eat breakfast, you’ll faint! Also, trying local breakfast traditions is the best. I have enjoyed all kinds of breakfasts, from miso soup and fish in Japan to chocolate croissant in Paris.

My best recommendation is to either stay in a hotel that serves a good local breakfast or find a cute breakfast place somewhere near your hotel and go there every morning. Then you can pretend you live in the neighborhood! You’ll feel as cool as a cucumber at a Beatnik poetry slam.

When I was in Buenos Aires, I ate cafe con leche and three medialunas every morning, and after two days, the waitress at the cafe would just bring my order without me having to say anything. This was the most fun thing that happened to me in Buenos Aires and that’s saying a lot because I also spent an evening drinking beer and eating steak with a group of British con artists.

24 hour travel itinerary
step two: select the three big “must dos” for each day

This is my most important secret for making My Dream Trip. You must plan three and only three things you want to do in a day! These can range from taking a walking tour, visiting a museum, seeing a performance, dining at a restaurant, or exploring a neighborhood on your own. Do one of these things in the morning, one in the afternoon, and one in the evening.

How do you find your big three? There’s lots of ways! Maybe there was something you were already dying to see in a particular destination. Most people don’t need to be told to visit the Colosseum in Rome or the Mummer Museum in Philadelphia. But I like to brainstorm as many ideas as possible before I settle on My Dream Trip. And that means reading other people’s lists!

Some of my favorite resources for attractions are TripAdvisor, Lonely Planet, Time Out, Thrillist, Conde Nast Traveler, and Travel and Leisure. Culture Trip and Pinterest are good for more obscure destinations that won’t have articles on the larger sites.

And if you’re a foodie, don’t miss Eater, the Michelin guide, and the James Beard award winners, for US only. Finally, I’d be remiss if I didn’t mention the NY Times 36 Hours series, which I am clearly obsessed with.

I read as many of these lists as I can, and while I read, I write down attractions and restaurants that look interesting to me. When I finish, I highlight my top choices and try to fit as many as I can into the number of 24 hour travel itineraries I have for the trip. And voila! The perfect Goldilocks way to plan just enough but not too much.

24 hour travel itinerary
step three: balance your activities

I don’t want My Dream Trip to be monotonous. Doing too much of the same thing all day will get you burned out. There’s such a thing as Museum Fatigue, so unless the museums are really different, you probably don’t want to see two museums in one day. And going on two walking tours in the same day will probably make your brain explode from too much information and also tire out your tootsies.

Ideally, you have one activity where you stay put in one place, like a museum, one activity that gets you walking, like a guided tour, and either dinner or a show in the evening. If you were to have one day in my hometown of NYC, you might spend the morning at the Natural History Museum, the afternoon exploring Central Park, and the evening at the Metropolitan Opera (not vomiting in the bathroom).

24 hour travel itinerary
step four: have some free exploring time

I found this poster of a cat when I was wandering through the Kreuzberg neighborhood of Berlin. I have no idea who he is or what he means, but I like him so I kept him. The photo of course, not the cat.

Another time I was wandering in St. Petersburg, Russia and I ended up finding a boat tour for under ten dollars that gives you free champagne. The world is full of wonders like these.

You need to make sure you spend at least a little time every day to have random adventures on your own. I refuse to give you more advice than that because then it would defeat the purpose of telling you to go on your own and have adventures. I demand that you do as I say and be spontaneous!

24 hour travel itinerary
step five: get in rest time!

Almost every attraction/restaurant all over the world is closed between the hours of 5-7. So these hours should be precious free hours during which you can do what you want.

You can go for a drink, walk in a park, go back to your hotel and nap/do your hair, or just do what I did in San Diego and spend two hours walking down an ugly highway. This is the time to do you.

24 hour travel itinerary
step six: either do a big dinner or a show, not both

In the evening, it can be tempting to cram in as many exciting events as possible. After all, how often are you going to experience the nightlife of Las Vegas/Paris/Scranton, etc.? But overbooking your evenings is a recipe for disaster.

Having a big dinner reservation and tickets for a performance in the same evening can lead to timing issues that cause you to miss your show. And if you have a big dinner and then go see a show, you might fall asleep, which will make you look an An Old Person.

That’s why I strongly urge you to stick to one big thing per evening: dinner, a show, a concert, a fireworks spectacular…whatever you want! Of course you need to eat something if your big event is a show, but make it something light and casual.

Then you should sleep. Sleep is necessary for health, unless you are a robot. And if you are a robot, please let me know because I really want this to be the world’s first travel blog that caters to robots.

You can also check out my trip around the world itinerary!

That’s My Dream Trip Planning Guide!

How would you like to plan YOUR dream trip? Have you ever vomited in an opera house? And seriously, where my robot readers at? Please email me at and let me know!

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