Identify Who is Going (and if you want to go)

Before planning anything else, it’s a good idea to figure out who is participating in the trip. Do you find yourself traveling with people you butt heads with time and time again? Perhaps this is your chance to set a boundary with yourself. I’m here to tell you, it’s okay to say no. Don’t only travel with someone because they’re the only person who is available or is willing to go. Fly solo if you have to! If for whatever reason you need to travel with someone you don’t get along with, read my post on How to Travel with Friends and Family.

Make a Shareable Document

Now for the fun part – nailing down exactly where you want to go. Whether it be a google drive or a presentation, begin listing places you’d like to go, and have it accessible for others to look at it at a later time.

Use Google Map Lists

I am a visual learner. Speaking on the phone only gets me so far to figuring out where I want to go. The best way for me to nail down places is by favoriting locations on my phone:

• Open Google Maps (downloadable app),
• Click on a cafe, destination, or museum in your Google Maps
• Click “Save” and “+New List”
• Name your list such as “Palm Springs” or “Family Trip”
• Begin saving all your desired locations to the list you made
• Click “Add Note” if you need to specify activities
• Click “Share” and send to your family/friends

Once you share it, others can add to it and even access it when you are wandering around a city. For safety, I always share it with a trusted friend or family member who isn’t traveling in case something crazy happens.

Set Expectations (or don’t!)

The biggest disappointments I’ve had while traveling were when I held high expectations. When traveling with friends, it’s even more important to be flexible and lighten expectations because other people’s lives and habits are in the works. Of course there are activities you’ll want to do, so set aside 1-2 of your must-do’s and express that to the group to compromise the several other activities you’d love to do.

Plan for Downtime

Time and time again I’ve planned a hefty itinerary for my Day 1 travel days, and I end up feeling guilty for begin exhausted and skipping out. I’ve now shifted my travel plans to include rest days or blocks. On the first day I expect to do nothing (see, no expectations). Merely taking the pressure off allows to do something if I feel like it, and if not, I choose rest. Vacation is a time for relaxation anyway, right?

Divide and Conquer

Do you know your travel style? Is it checking off bucket list items like skydiving, or wandering around a city? My least favorite activity during vacation is shopping. However, many travel to do exactly that! I take that time to split ways, whether it be dividing groups or simply adventuring solo. When you’re planning, ask those types of questions and plan to go off on your own once in a while to get what you want out of the trip.

OPTIONAL: Write it Out & Text it

Type-A, visual learner here! If you are Type-B (go with the flow folk), ignore this. Now that we’re alone together, we can agree we like to know what the plan is. Mostly I plan out each day of travel and adjust day-of. Then, I text it to the group in a chat so we don’t forget in the midst of catching trains and strolling museums. Here’s an example of my last day in London:

As you can see, plans changed during the day so we switched around activities, and timing didn’t matter a that point. Writing it out made it easier for us to check off our eagerly-anticipated bucket list!