How to Maximize Your Vacation With a Well-Planned Itinerary

Vacation Itinerary Planning made our Alaska trip a real success

It’s probably not a secret to any of you who actually know me in real life, but…I’m definitely  a planner. Like, intensely so. If someone tells me their grand vision for anything, I immediately start trying to work out the logistics in my mind.

And the same goes for vacations. I’m not a “hop-a-last-minute-flight-to-wherever-and-then-see-where-fate-takes-me” type of vacationer. When I go somewhere, I will have researched the hell out of it before my feet ever touch the ground in my vacation destination.

Now, that doesn’t mean that I can’t be spontaneous. For our upcoming trip to Cancun, for example, I’ve booked our flights, resort, and airport transfer — but that’s all. Because I know that is a trip focused more on relaxing and unwinding instead of sight-seeing, I’m happy to leave our day-to-day plan until we get there. But that doesn’t mean I haven’t extensively researched each and every bar and restaurant on the resort property, explored the tours you can purchase for nearby attractions, and read reviews of pretty much everything I can find on the area.

Because to me, being prepared allows you to be spontaneous without feeling like you might be missing something. 

Generally speaking, though, I do build a more detailed trip itinerary for most trips, regardless of whether they’re 3-day weekends or 14-day international epics. Here’s an example from last year’s Las Vegas trip:

Vacation Itinerary Planning Example - Las Vegas 2016

Some things you may notice here: 1) I build these in Google Drive. That allows me to have access to it from my phone, and I always make sure to make my itineraries available offline, so I can access them even if I don’t have data or wifi. 2) I include confirmation numbers everywhere I can, and reminders for myself on where to find any needed paperwork. A lot of times you’re booking months in advance, you may not remember where things are located.

I also find that putting it on paper lets me see how everything fits together. For example, if I see I have an action-packed, early-rising morning one day, I can make sure to plan a quieter, low-key night the evening before. This helps make it feel like I’ve planned a cohesive trip, instead of just a series of activities that we “have to get to”.

So how do I compile these? Here’s the order I go in:

  1. First, book your flights

As soon as I book my flights for a trip, I create my itinerary document. The flights bookend the travel, so it helps create a frame for everything else that will be added later. I also like to include flight numbers, confirmation numbers, and any loyalty program numbers that I think I might need along the way.

  1. Next, hotels and any ground transportation

Once I know the dates I’ll be arriving and departing, it’s time to figure out where to stay. Generally speaking, I let my points guide where I search: if I have a lot of Hyatt points, I’ll search Hyatt first; if I have a lot of Starwood points, I’ll search Starwood points. Once I find a couple options that look promising, I read through at least the 10 most recent reviews for the property on both the hotel’s website (if offered) and a third-party review site like TripAdvisor or Yelp.

The other big question at this step is any ground transportation. Are you visiting more than one location/hotel during your stay? How will you get between them? How will you get from the airport to your hotel? Do you need to reserve a rental car, or buy any train passes? And of course, how can you maximize these bookings to give you the most points in return?

  1. Book “big activities”

After you’ve nailed down your flights and hotel situation, it’s time to figure out what you want to do. If you’re familiar with your destination, you may have some activities already in mind, otherwise I like to look at TripAdvisor, Lonely Planet, and Thrillist for the “can’t miss” items. (Note: Lonely Planet advertises on this site. It doesn’t affect our review. See our About page for additional information.) Once I’ve found the majority of touristy options on those commercial sites, I check out what my favorite vloggers, bloggers, and ‘grammers have highlighted about the destination as well.

Then, once I’ve figured out some of the activities you want to participate in, I lump them into two categories: “big” meaning they either take more than three hours to complete and/or will require considerable physical effort or expense and “little” meaning they’re lower-key activities that I may be able to squeeze in whenever. I book “big” activities now, and save “little” activities for later in the itinerary planning process.

  1. Pick your restaurants

Next on my list is to research restaurants. My go-to sources here include Eater, Time Out (particularly in Europe), and Food & Wine magazine. I like to mix it up with “fancy” restaurants and hole-in-the-wall type places. And if a particular location is really associated with a specific dish (i.e. Nashville with Hot Chicken) I try to make sure we get to try it from at least two different locations.

For fancier places, I go ahead and make a reservation in advance, if they offer one.

  1. Fill in open spaces with “small activities”

By now, your itinerary should be really starting to fill in. I take a look and see where it looks like we still might have room to add in another activity or two, keeping in mind where we’re likely to be tired and just want to relax. When possible, I look for smaller activities that you don’t have to book in advance, so you can blow them off if you feel like it.

It’s also important to keep in mind where activities are located in this step. For smaller activities (for example, a museum that will only take you an hour or so to tour), you want to try to visit it when you’ll already be in that area of the location. Going really far out of your way for smaller activities doesn’t always make sense, especially if you can re-shuffle other activities to keep nearby activities together in the same day.

  1. Add confirmation numbers, addresses, and tips for yourself. 

Finally, once you have a fully-filled out itinerary, it’s time to make it easier for yourself when you’re onsite. I add confirmation numbers for everything that has one. For international destinations where I’m unlikely to have cell signal, I also add addresses for each location. And if I’ve learned anything during my research that may be useful (e.g. this establishment has an upstairs bar that’s often less crowded; the crab cake is legendary; you have a printed voucher for this event you need to take with you, etc.), I make sure to note that on my itinerary document as well.

  1. For longer trips, include some backup options

So now you’re done, right? Well, hold on. One final recommendation is that for vacation itinerary planning on longer trips — anything more than 3 days — keep a shortlist of back up options as well, particularly for small indoor activities and casual restaurants. That way, if you just aren’t feeling something you’d planned, and/or something stressful pops up (like a bad storm on the day you planned to visit the Botanical Gardens, or an hour-long wait at the hole-in-the-wall oyster bar you had planned to visit) you can sub in an alternative.

With these tips, I think you’ll find not only do you have a flaw-free vacation, but it also helps you to get more excited about your trip. All the planning and researching makes you anticipate the great time you’ll have on your trip, and further extends the joy you get from going. So enjoy!

Whitney