It’s January, which means Wendy and I are about to embark on our annual birthday getaway.
A little background: Wendy and I are practically birthday twins, born a week apart. In high school, we even had a Doublemint-themed joint birthday party at our friend Ebbie’s house.
At some point, Wendy pitched the idea of us going to Las Vegas for our 35th birthdays. The idea became a reality and marked our first birthday trip together. We had such an amazing time that we were like, “We should do this EVERY year!” So, now we do.
Subsequent birthday getaways included:
- Road trip to Savannah, GA and Charleston, SC
- Long weekend in NYC
- Epic Texas adventure in San Antonio and Austin
This year’s destination is Washington, D.C. A place we’ve both been to many times, both separately and together. But this time is different.
This time, it’s our birthdays, yo.
There ain’t no party like a Wendy-n-Lara party because a Wendy-n-Lara party don’t stop.
I thought it might be fun to share how we actually plan these little getaways. Keep in mind that we’re the weirdos who make a full-on spreadsheet for Cookiepalooza each year. There are definite methods to our madness.
STEP 1: Choose the Destination
The conversation about next year’s destination starts during the current year’s trip. We knew, for instance, that we wanted to do a Savannah/Charleston trip while we were on the plane home from Vegas. In Savannah, we spent a tipsy night making a long list of future birthday destinations. NYC was an easy choice; we had agreed we wouldn’t get on a plane two years in a row to try to cut down on costs.
This year’s destination took a little while to nail down. For about three weeks over the summer, we were certain that we were headed for a cruise somewhere. I’d even found a crazy good deal through U.S. Airways, but missed the deadline for the rock-bottom prize. When it shot up $300, it didn’t seem so appealing anymore. We’d also talked about heading to the Poconos or doing a spa weekend in Hershey – some place really local – but in the end, we decided to head back to D.C.
STEP 2: Take it to Pinterest
Once the destination has been selected, we create a joint Pinterest board to start marking things we want to do, places we want to see, food we want to eat. We didn’t actually start this until our NYC trip; I think I was on Pinterest when we did our road trip to the South but hadn’t really started using it until I was planning my wedding. We also have a board for Future Getaways.
We aim for a mix of quintessential experiences (like horseback riding after a barbecue lunch at the Salt Lick in Driftwood, Texas) and things that just really appeal to us (like spending an afternoon wandering around the foodie haven that is Chelsea Market). The cool thing about going back to a city we’ve been to before is that we’ve done a lot of the quintessential things already. This allows us to focus on a couple of the Smithsonians instead of feeling like we have to do all of them in a long weekend.
STEP 3: Make Your Travel Arrangements
If we’re flying somewhere, I book the flight first. And yes, I said “I” – I tend to make a lot of the arrangements for these trips. One, because I’m a bit of a control freak and two, because Wendy is the same way and gets stuck in this role for all of her family vacations, so she enjoys relinquishing the duties to me once a year. We live by a big U.S. Airways hub and I have a U.S. Airways travel rewards credit card, so we typically fly U.S. Airways.
Next comes the hotel (or hotels, if we’re doing multiple destinations). I use Hotwire almost exclusively for travel. In 14 years of using the service, I can count on one hand the number of times I’ve had bad experiences. We usually stay in 3-5 star hotels for wicked cheap. These are places we likely wouldn’t foot the bill for at full price. Or we’ll opt to save even more money though Hotwire, and get a place like a La Quinta for like $47/night.
I don’t only use Hotwire for the birthday getaways. I used it for Joe’s and my trip to Chicago this summer. I’ve used it to book Girl Scout trips with my old troop. Seriously, if I’m staying in a hotel that’s not related to work travel, odds are I’ve booked it through Hotwire.
Finally, I go after any necessary rental cars. This usually involves me Googling to find coupon codes and/or ongoing sales. Rentals are easy; I’m very short and prefer a compact. These tend to be on the cheaper side.
STEP 4: Find All of the Deals
I love using Groupon when I’m planning vacations, because you can usually find deep discounts on touristy things you’d balk at paying full price for. In San Antonio, we found a crazy good deal on tickets to the Tower of Americas. And for our upcoming trip, Wendy and I are doing a half day at a posh salon for a ridiculously low price (also courtesy of Groupon).
We also stalk deals on Living Social and Goldstar. When we went to NYC, we got half price tickets to see Avenue Q Off-Broadway. This year, we got an excellent price on a nighttime tour of the Washington monuments and half-price entry to the Newseum.
Here’s my favorite tip that won’t help most of you: a lot of cities have Restaurant Weeks in January, to encourage people to eat out. Charleston and New York were two cities that we just happened to visit during such weeks. You can get amazing menus at fancy restaurants for a low prix fixe rate. Like, would I have had a gourmet dinner at Nougatine at Jean-Georges without the Restaurant Week deal? (The answer is no, I probably wouldn’t have.)
Sadly, I found out too late that Washington D.C.’s Restaurant Week starts the day after we head home.
STEP 5: Build Your Itinerary
This is where my control-freak nerdiness comes out. Each year, I build an exhaustive itinerary for our birthday trips. It includes information about our flight and rental car (if applicable), all hotels, and a day-by-day breakdown of what we have planned. For each destination I include addresses, phone numbers, web and email addresses, hours of operation, and any estimated costs. At the end, there is a list of additional places that we might want to see, things we might want to do, and food we might want to eat. This allows for flexibility if one of the choices doesn’t work out or we change our minds.
Just to clarify, I don’t go all Clark Griswold on Wendy. It’s not like I say, “OH MY GOD, it’s 8:45 and we should be at X destination!” It’s more like, “On Thursday, we’re going to the spa for three hours. Here’s where we would like to eat dinner. This is what we’ll do after dinner.” Believe it or not, it can actually be way MORE relaxing to know where you’re getting your next meal than to have limitless options.
This year, Wendy has been more hands-on with the planning part. Today she came over and we sat at my dining room table, laptop to laptop, trying to put the pieces of the puzzle together. Index cards were involved, breaking desired destinations up into neighborhoods to consolidate travel time. Three hours later, we had an almost-full itinerary.
STEP 6: Make Your Reservations
I’m not going to lie: we do a lot of good eating on our birthday trips. It’s a mix of classic locales and Chowhound favorites. In NYC, we hit up Gray’s Papaya and Katz’s Deli in addition to places like Pastis and Big Gay Ice Cream. None of THOSE places required reservations, but a lot of stops on our list do. Today, for instance, we made reservations for Oyamel Cocina Mexicana (dinner on Friday), Dukem (dinner on Saturday), and Farmers Fishers Bakers (Sunday brunch).
If there’s a restaurant that requires reservations way ahead of time, it’s best to make the reservation and then build that day’s activities around it. Confession: at least one of our D.C. days was literally planned around breakfast, lunch, and dinner. (I told you, we eat GOOD on these trips!)
STEP 7: Map Out Your Routes
On cities where we don’t plan to drive, like NYC and our upcoming D.C. trip, we’ll also take some time to plan out our public transportation. Like, “We’ll take the red line to this stop and then walk three blocks to our destination.” This doesn’t always work out for us, so we’ll both have backup aps on our phones.
STEP 8: Make Your Packing List
This is more me than Wendy, but I’m someone who needs packing lists to make sure I remember everything I need to bring. This includes things that are easily overlooked, like my mini hair straightener, the adapter I need to charge my camera, and my allergy eye drops. My anxiety over forgetting stuff is far more heightened when I’m getting on a plane, though I’m not entirely sure why. But you better believe I’ll be printing out two copies of my packing list this weekend (because I need one for the return trip home, duh).
And that’s pretty much all there is to it.
I’m thinking I might try to blog our trip while we’re actually on it. This will depend on how tired I am when we get back to the hotel each night. This year’s itinerary isn’t nearly as cracked out as the ones from previous years’, because as I mentioned, we purposely tried to plan something a little more low-key. Next year is the big 4-0; I suppose we’re saving up our money and our strength for the big birthday blow out. We’re thinking Europe. Wendy says she doesn’t care where we go, as long as she gets to use a passport.
Now, if you’ll excuse me, I’ve got a packing list to finish up.