Hi there, friends!
First, I want to acknowledge it feels kind of trivial to be blogging right now when so many are losing so much in Houston. (To be honest, that’s why this post is so delayed.) I’ve watched more CNN in the last three days than I have all year. I have donated both money and airline miles this week, and I encourage you to donate your time, talents, or money to an organization that feels right to you. A storm of this magnitude could happen anywhere, and there’s no promise it couldn’t happen to any of us one day. I have been overwhelmed by the power of the human spirit in this time of dire need, and the sung and unsung acts of the first responders, volunteers, and neighbors helping neighbors reminds me of the Mister Rogers quote:
“When I was a boy and I would see scary things in the news, my mother would say to me, ‘Look for the helpers. You will always find people who are helping.'”
Second, despite this post coming in hot on a Thursday, I am really going to try to get my blog to a Monday, Wednesday, Friday post schedule. Some weeks there might only be a post on Monday and Friday, some on Monday and Wednesday — you know how I roll. But, I want to make it more clear to you, my dear readers, on when you should expect content from me. Of course, you can always sign up to be notified via email when a new post is live on the right sidebar, and I always share new posts on Twitter and Facebook.
Third, today I wanted to talk about a topic that was suggested in my reader survey—how I plan, afford, and get the time off work for trips. So far this year, I’ve been out of town 16 weekends (editors note—suddenly, my apartment is starting to feel like one expensive storage unit), so it’s no surprise that two of the questions I am most often asked are, “where are you going next?” (answer currently: Boston!) and “how do you travel so much?”
As such, I wanted to share tips and tricks I’ve learned over the past couple “on the road.” I will note that my post is written with domestic travel in mind since besides a respite to the Dominican Republic earlier this year, I haven’t left the country in a decade. However, getting back to Europe for an extended period of time is something I daydream about at work, and I’m hoping to make that dream a reality within the next couple years.
WHO I TRAVEL WITH /
My family and I generally take one trip in the summer, so for the majority of trips throughout the year, I travel with or go visit friends in other cities. I know this season of life will not last forever, and it will become increasingly harder to travel with my friends as our roots grow deeper, so I am really embracing this fun time.
I am lucky enough to have many friends who love to travel—sometimes I travel with my blogger friends, sometimes with my college friends, sometimes with my high school friends, sometimes with my coworkers—so I always have someone I can reach out to if there’s a shared destination I know we want to visit (or vice versa), which brings me to my next point…
HOW I SELECT DESTINATIONS /
I love writing down my goals, and I treat travel destinations as goals—meaning, I keep a running list of places I want to go. While I would love to go seemingly everywhere, it makes it a lot easier to have a list of places that are high on your list. (I literally have a journal with lists, and my list of top destinations is one of them—currently on that list is San Juan, Austin, Seaside, Newport.)
Since I often travel with friends, we obviously both have to have an interest in the destination. I’m pretty vocal about wanting to travel and where I want to go, and I feel like if my friends are interested in going on a trip, too, we make it happen. This tends to happen pretty naturally. For instance, a couple of weeks ago, my friend Emma texted me and asked if I wanted to go to San Francisco. I said yes, and we booked our flights a couple of days later. Of course, reality has some bearing on selecting destinations, too. For instance, when I went to Miami over MDW with Hilary, we both knew we wanted to go somewhere warm/tropical. We quickly identified Miami and Puerto Rico. Since we only had three days, after looking with the flight schedules, we decided Miami was the best bet so we wouldn’t have to spend half our trip in the airport. Thus, Miami was crossed of my aforementioned list—I loved it!—and San Juan will be on deck for a longer trip.
HOW I GET THE TIME OFF WORK /
When I first started working, my vacation was limited, both from a PTO and office holiday standpoint. I’d say for my first two/three years of work, I really didn’t take that much time off. I took maybe two weekend trips with my friends a year—maybe without even taking PTO, just leaving Friday after work—and saved up the rest of my vacation days for a week-long trip to the beach with my family and for the holidays.
In the past couple of years, I’ve gained more flexibility at work and my family no longer goes on a week-long trip since we’re all so busy our schedules do not align like they used to. But, what’s also happened in that time is that I’ve gotten smarter about how I use the vacation hours I do have more effectively. My work situation allows me to leave early on Fridays during the summer, which is great for weekend trips. And if I need to sneak out a couple hours early on a standard week, I have a great boss who is willing to work with me. And while it’s more expensive, I like taking advantage of long weekends—especially when traveling with friends, since everyone already has the time off.
I will also say that while it’s great to travel and go on vacation, I know when my busy times of year are—for me, that’s recruiting season during the fall. As such, I try to not request vacation during this time to show my commitment to my responsibilities, knowing that I’ll likely get that hard work back in time during a slower period of the year.
HOW I AFFORD TO TRAVEL /
I am lucky that I have a job and financial situation that provides me the disposable income to travel. I also value experiences more than things, so I prioritize travel within my budget.
But, I’m not made of money, so I am smart about how I pay for trips. You’ll notice most of my trips are quick—three, four nights at most. This keeps hotel costs lower, as well as the number of meals/drinks/activities I have to pay for. I also try to find hotels that offer complimentary breakfasts when possible. (I’m also not one to pass up an Embassy Suites happy hour.)
I also have a credit card that rewards dining out + travel, book flights well in advance—even domestic ones—for a better deal (and seat options!), head to destinations off-season, find flight/hotel bundle deals through Expedia, and use airline/hotel miles when possible. Where there is a will, there’s a way—even if it means skipping sweetgreen salads for a week and foraging at work for leftover meeting food.
In addition to being smart about buying my travel, I also save a certain percent of my paycheck each month for travel, so that when it comes time to book flights, pay for a hotel, or actually go on my trip, I don’t have to borrow from my emergency savings or disrupt my normal monthly budget. You can read more about my budgeting strategy in this post.
HOW I BUILD ITINERARIES FOR TRIPS /
For me, I find a lot of joy before the actual trip, both in looking forward to it and planning for it. I’d say I approach trips in three different ways—
1. If I’ve been to a city before and checked off the major things I want to do, I’m much more relaxed and don’t do as much planning ahead of time. I’ll probably snag a few reservations and look up a couple of shops or attractions, but there are no concrete plans. This is how I approached my trip to Charleston earlier this year.
2. If I am traveling with a fellow planner, I usually let them take the reins or we split the planning duties. For instance, no one can build a trip itinerary better than my friend Emma, so when we went to New Orleans last summer, we all threw out a few things we wanted to do, and she took charge. When Hilary and I went to Miami earlier this year, we both did research, compared notes, and then were able to put together a fun roster of restaurants and things to do.
3. If I am really excited about visiting a destination or am traveling with someone who would prefer me to plan it, I go all in. I love reading travel guides written by fellow bloggers, asking friends and coworkers for suggestions, and posting about my upcoming trips on Instagram stories to get reader advice. I also scour Open Table, Yelp, and Trip Advisor. Then, I build an itinerary around the interest/budget of the folks on the trip—but, I leave unstructured time for exploring, taking locals’ recommendations, and relaxing so that everyone enjoys the trip and I don’t come off as a drill sergeant ;].
Lastly, I’ll leave you with my top travel tip—get TSA pre-check. It’s worth every penny! Time is money after all. Let me know if you have any questions about my travel game in the comments below—or shoot me an email to chat anytime (firstname.lastname@example.org)!