2020 Travel So Far + How We Booked It

The first half of 2020 is already shaping up to be an exciting, jam packed few months! With my job change at the end of this month and a new work arrangement that’s going to allow for some more flexibility travel-wise, I have a few fun trips lined up and will be bopping to various parts of the country between now and mid-July. Travel content continues to be one of my strongest verticals on the blog so I’m excited to be as transparent as possible with how we pick destinations and book flights, and how much those flights cost. There’s definitely an assumption that travel is expensive and while that’s the case a lot of time, it’s a priority for us so we make it a point to find good deals, optimize credit card rewards points, and regularly visit destinations in the off-season to take advantage of lower rates.

Also, if you’re new here, an important tidbit: We have the Southwest Companion Pass for 2019-2020, which is what’s allowed us to travel so much in the past year. It’s literally saved us thousands of dollars and we definitely wouldn’t be taking this many trips without it!

New Orleans – February

New Orleans has been on my extended bucket list for years and we’re going at the end of next month! J went once in college–and his trip looked a lot different than what we’ll be doing this time around!–and I’ve always wanted to visit but honestly, other destinations always ranked higher and I figured I’d make it there eventually for a friends reunion, bachelorette party, or something like that. We’ll be there three nights and are still working out what we’ll be doing…thank you to everyone who sent recommendations on Instagram! Feel free to leave some at the end of this post, too. So far we have lunch reservations at Commander’s Palace (their weekday lunch as 25 cent martinis!), I really want to visit the Carousel Bar, and of course–Café Du Monde.

How I booked it: Southwest–$295 cash, and J flies free thanks to the Companion Pass. We found a good cash rate for a Marriott property, and paid that out of pocket since we’re saving our free night certificate + points for a trip later this spring.

Savannah – March

My bff from home and I have been talking about taking a girls trip for years. Literally years. She spent two years in grad school abroad, we both had entry-level salaries, and she lives in Dallas and I live in DC. She’s also a teacher and coaches so can’t take time off for the entire fall! It was so hard to get our schedules and lives to line up but I’m happy to report we finally did it and are heading to Savannah for two nights in March! The cherry on top is we both got engaged within a month of each other, so there’s a lot to celebrate :) A bunch of you sent recs on Instagram (thank you!) but if you have any to share, please drop them in the comments below!

How I booked it: Ugh, I hate myself for this but I booked and Basic Economy fare on American for $388. I avoid flying AA whenever possible and Basic Economy means you don’t even get a seat assignment till you’re at the airport (my nightmare), but tickets were already pricey and I didn’t want to spend $50 more to get my seat in advance. Competing for overhead storage at the back of the plane is my personal hell so I’m planning on taking just a personal item since we’re only there for two days! TBD on the hotel front–we’re still figuring it out, but a central location is a priority.

Upstate New York – March

A quick trip upstate to do a site visit for our wedding! We’re taking a Friday off from work and getting back to DC on Sunday. The plan is to tick a bunch of to-dos and meetings off the list since this is potentially the only trip we’ll be making–at least until much closer to the date!

How I booked it: We’re renting a car, and our “home base” hotel is giving us a heavily discounted rate for one night and a free night for the second.

Dallas – April

My aforementioned bff’s bridal shower is in our hometown at the end of April! I’m helping plan it with her future mother-in-law and will probably make it a long weekend in town to hang out with my parents.

How I booked it: I haven’t booked yet, but am planning to buy cash ticket on Southwest. Newfound work flexibility means I’ll be able to travel at off-peak times, but fares are still unusually high at around $295. Fingers crossed they drop! I always love that Southwest will also credit you the difference (in the form of a travel voucher) if your fare drops after you book, so plan to take advantage of that if I can.

Seattle & Vancouver – May

The second half of this year is going to be really busy for us personally–sans travel–so we wanted to take one larger trip this spring. We were going to do Europe (our friends are in London for six months and we seriously debated going back even though we were just there last year!) but decided to take full advantage of the CP while we have it and go where Southwest flies. The Bahamas were a strong contender (I’m dying to stay at the Baha Mar–you have to read Ashlee’s review!) and we considered somewhere in the southwest, but landed on Seattle + Vancouver since we’d also get a bang for our buck with BOGO flights. Seattle and western Canada have been on my bucket list for as long as I can remember but it’s an (expensive) trek from the northeast!

How I booked it: We’re flying in and out of SEA (from DCA, with one stop each way) using Southwest points + the CP again! So that means the only cash for airline travel was taxes (~$12 per person) out of pocket. We’re planning to use our Bonvoy points to cover as many hotel nights as possible. We’ve done Airbnb for longer trips in the past and sometimes it’s been great, but our last experience in London was pretty uncomfortable so we’re trying to stick with hotels when we have the points or it makes sense financially!

Charleston – June

Another trip with B–for her bachelorette! We’ll be in the Charleston area and details are still be worked out. Her other maid of honor is taking the lead on planning but I’ll be sharing a thorough recap after the fact!

How I booked it: I haven’t, but will probably head there Thursday night or early Friday morning. Flights from DC to CHS can be all over the map–I’ve seen them as low as $120 RT, and as high as $600+! We’re staying at one of the bridesmaid’s family’s home, which takes care of accommodations.


We’re also heading to Westchester, NY for a wedding in May, but we’ll just be taking the train up and staying in a room block :)

That’s where I’m traveling to in the next few months! Do you have any trips planned?

P.S. My favorite resources for budget-friendly travel.

P.P.S. What we buy on every trip.

Leave a Comment


  1. Ashlee wrote:

    So many fun trips ahead! Can’t wait to see what you guys think of Vancouver! Thanks for linking to my Baha Mar post – you’ll get there soon enough!


    Posted 1.22.20 Reply
  2. Annaliese wrote:

    Such a fun and helpful post- also love how you share the different prices on these trips! I have a lot of travel in the first half of the year that I’m so excited for, including a girls’ weekend in NYC and a wedding in Florida!

    xoxo A

    Posted 1.23.20 Reply
    • Monica wrote:

      Thanks for the feedback, I’m so glad it was helpful!! Those are two good things to look forward to, especially a pre-planned warm weather getaway!

      Posted 1.23.20 Reply