How to plan an awesome trip

The absolute joy of my life is planning. I thrill at the opportunity to put an agenda together. There are times when I don’t have a trip on the calendar and I can feel happiness and sense of purpose gradually evaporating from my body.

I share my travel guides on here sometimes because I know that I have painstakingly combed the internet, talked to friends, and tested and tried all the best places at a destination. I do so much work before a vacation because I genuinely enjoy it, but even more than that, I do it because the trip is so much more satisfying to me when I know we’ve done all the best there is to do in that destination. All that work that I put into my own vacation surely can’t just die in my Google Calendar. Perhaps you’ve even referenced one of my travel guides before. But now, I want to share the very near-and-dear-to-my-heart process of how I plan a trip.

First, here are the general assumptions: I already know where I’m going and when and with whom. Maybe I’ve also booked flights, but everything else is totally undecided.

1. DECIDE WHERE TO STAY. Where you stay is extremely important to the overall success of the trip. I don’t care what your accommodation preference is, or what your price point is, but I do care that you stay in an area that’s central to the things that you care about. Because I recently traveled there, let’s use Maui as an example. I know that a trip to Maui for me means relaxation and the luxury of being able to walk to dinner and drinks and leisurely make my way home at night. It also means being able to take in the ocean’s natural beauty. While I enjoy the lush foliage of some parts of the island, I don’t want it to be rainy. So, I take to Google. I’m going to search something generic, like “best areas to stay in Maui.” This will not be a definitive list, because someone else’s definition of the best place can be very different from mine. I’ll read the description of each of the “best places” and pick one that sounds like what I want. Then, I’ll go to Google Maps and zoom in on that area. Are there lots of restaurants? How well are they rated? Do the menus and hours look compatible? If so, then it’s time to start seeing what else is in the area. Are the beaches in this area accessible? Can I snorkel and boogie board, or do I have to just watch the waves from shore? If everything checks out on Google Maps, then I’m going to move to hotels.com or airbnb to start searching for a place that’s walking distance to these restaurants and beaches. Filter by price and date, and you’ll have a location decided easily.

2. CREATE A GOOGLE DOC. I plan every trip by creating a Google doc for it. I will keep tabs on what restaurants I want to try, sights I need to see, and beaches I want to visit. Use this sort of as a scratch pad. I might clean it up later and add a schedule, but usually I’m not doing much else but writing down all my ideas here.

3. GET ON EATER.COM AND THRILLIST. Food is one of the most important experiences to me when traveling. Eater and Thrillist both are extremely reliable sources for me when I’m planning a trip. Eater is fantastic for mapping out restaurants: They have moveable maps with their restaurant recommendations, and often their posts are VERY specific categories, like “Best Bottomless Mimosa Brunches on the Las Vegas Strip.” First of all, hell yes I want bottomless mimosas whenever I’m on vacation. But also, all these places are vouched for by a site I trust, and it helps narrow down the wasteland that is Google Maps when I’m looking for fantastic food. Thrillist is fantastic and I find it generally has more content overall, though they don’t do the moveable maps. I’ve used Thrillist to plan wine trips (like my upcoming one in Paso Robles), ensure that I’m updated on the best places in Miami whenever I visit, and I even recently found that they sent a writer to test all the subway toilets in New York and share which ones aren’t just a boiling pit of filth (aka doing the Lord’s work). It enumerates art exhibits worth seeing, parks worth frolicking, beaches worth beaching. Eater and Thrillist aren’t the only sites I use, though. Also try the web pages for Conde Nast Traveler, Food & Wine, and the New York Times “36 Hours in” series. Any place you want to visit, add it to your Google Doc!

4. SCHEDULE EVERYTHING BEFORE YOU BOOK IT. Now’s the time to start making a visual for what you’re going to do and when. I use Google Calendar to schedule out my days. In some cities, I’ll want to do an “excursion,” like the day-long Road to Hana drive in Maui or a trip to Aconcagua in the Andes of South America. Suss out what day you want to do that, and add it to the calendar. Start to build around that: What night do you want to go to that amazing restaurant? What day will you make it to the renowned winery? Will you set aside a day to just lounge? I love to decide what “events” I’m doing first, like excursions or winery visits. Then, I see what restaurants are nearby that I can visit before or after that event. This way, you don’t spend too much of your vacation in transit to different places, and you can be a bit more relaxed. If you’re going to a very busy city like New York, London, or Miami, you’ll want to book everything in advance after you’ve finished sketching out your trip. But if you’re going somewhere relaxed, like Maui or Mendoza, you can be a little more lax with actually booking.

5. BUILD IN OPTIONS. Sometimes, you don’t want to book everything in advance. Maybe you’re not sure how much downtime you’ll want, or if you’ll need to catch up on work, or if your travel companion will need a day to sleep in, or whatever. Build in options wherever you can! This is my favorite thing to do when I’m traveling with my husband, because we have different travel styles. I love to be on the go and do everything, and while he definitely loves to adventure with me, he needs a bit more downtime to recharge. This can be a blocked-off few hours in Maui that gives the option of doing a coastal drive, or heading a nearby beach and reading our books; it can be going to dinner and then heading back to the condo, or staying out after dinner and getting a drink nearby. When I’m traveling with girlfriends, this can mean making two dinner reservations, one at a higher-end place and one at a more affordable spot, and letting them take a look at the menus to decide without judgment or pressure. It sounds simple, but the key is that I always know where we’d go if we took advantage of either option. You avoid the dance of figuring out where to go and then giving up or having a less-than experience.

Great planning is the key to the best vacation. Everyone’s relaxed, because all you have to do is show up. Plus, the next time a friend visits one of your favorite places, you can send them your recommendations, because you know that they’re the best of the best.

What are your secrets to planning a fantastic vacation? What did I miss?

Featured image: my calendar from a May 2018 trip to Disney World. Every. Ride. Was. Scheduled. (But had those good good options built in.) And it was amazing.

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