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How to Create The Perfect Travel Itinerary

travel itinerary

Planning a trip itinerary can seem overwhelming, especially if you’re traveling with multiple people. How do you pick and choose from hundreds of attractions, restaurants, and hotels? How do you find things to do that everyone in the family will enjoy?

From spending multiple long weekends in various U.S. cities to 10-14 day trips in Europe, Africa, and Asia, I’ve learned that one of the biggest causes of a successful vacation lies in the trip itinerary. I’m sharing my number one must-do on any vacation, plus a few more tips to help you create an unforgettable time away!

Plan a day of leisure

Don’t skip this one! I like to pretend I’m a resident of my destination for the day. This means I’m not rushing to tourist traps like the sucker I was the day before! Instead, I might visit a bookstore or coffee shop, walk around a park, or even go to the movies. I employ this trick on every single trip I go on, and it makes a huge difference! If I’m going away for two or three days, I make my day of rest be my last day of the trip. If my trip is longer, I like to plan pockets of rest scattered throughout.

In New York City, I spent a day in Brooklyn going to brunch and walking through a farmer’s market. For a date night in San Francisco, my husband and I went to a park to eat ice cream and then saw a movie. In Italy, we took our toddler to a park, bought gelato, and people-watched.

Other ideas: go on a picnic, rent bikes, order room service, take a long bath, read in a quiet café.

Determine everyone’s top travel desire

Let’s get one thing straight: you can rarely see it all/do it all on vacation. Don’t try to fit everything in. Instead, ask everyone going on the trip what they want to do most. It might be they want to see a specific site, or eat at a restaurant they’ve heard about online. Try to hit everyone’s number one desire, and count everything else as fun extras! (Need help budgeting? Check out these three tips!)

When my husband and I planned our San Francisco trip, his only request was that we eat at In-N-Out. He was happy to leave the rest of the planning up to me!

If your kids aren’t giving much input, I suggest looking up places that will bring the child out in everyone. Every kid loves to see their parent having fun. Try finding an arcade, mini golf course, bowling alley, or playground. I went to Dallas when I was 11 and all I remember about it was going to Dave and Busters and having the time of my life.

Map out your plans ahead of time

How are you getting around your destination? If you’ll be mostly walking and using public transportation, I highly recommend mapping out your most important plans. (I love Google Maps!) Once you learn how much time you’ll be walking or sitting on a bus, you might decide to stick to only one or two sections of the city you’re visiting. Look for restaurants within a 20 minute walking radius of your hotel and the attractions you want to see. You won’t want to walk much longer on an empty stomach, especially if you have kids with you!

Don’t be discouraged if you can only reasonably see a small section of a big city. You can always go back!

Ask for recommendations, but trust your gut

Use social media to your advantage and ask your friends if they’ve been to the place(s) you’re going. Some of my favorite meals were at restaurants recommended by friends. However, you’re bound to get some people who rave about the zoo (but your kid is terrified of monkeys), or who tell you to skip the science museum (but you’re dying to see the human body exhibit). Trust your gut! You know you and your people better than anyone else.

If vacation planning is overwhelming you, stop trying to do it alone. Contact a travel agent and let the experts do the work for you.

And be sure to check out our travel guides! We’re sharing our faves in Charleston, SC, Philadelphia, PA, Captiva, FL, Charlotte, NC, Rehoboth, DE, and Lewes, DE.

Comments (2)

  1. JEB says:

    We went on a wonderful 55 day trip to Australia and New Zealand. We packed light, wore very comfortable eco shoes, asked friends for tips and left the schedule open in some places so that we could be spontaneous and just discover. We met wonderful people along the way and even stayed two nights with a couple from New Zealand who we met while visiting Rotnest Island in Australia. We have invited two couples from the UK to visit us here in Maryland! It was perfect.

  2. admin says:

    What an incredible trip! 55 days! Wow!

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