Trips to Book Now: Where to Travel in 2020 (Part I)

2020 might seem light years away, but you guys… it’s not. It’s actually, seriously, almost here. For those who like to plan ahead—or do just the eensiest bit of vacay daydreaming while at your desk—now is the time to book your trips for the first half of the next decade’s new year. (Seriously though, HOW is it the year 2020?! Wasn’t it just, like 2004?)

• January: Florida Keys

  Why: If you’re traveling over the holidays, another trip in January might be tough to justify, but a quickie to Key West, which is relatively easy to reach and a pretty low-maintenance destination, is totally acceptable. We’re hearing good things about the new Oceans Edge Resort.

  Must do: snorkel in Dry Tortugas National Park

• February: Malibu, California

  Why: Airbnb alone lists over a thousand rentable properties in the Malibu area, many for less than $100/night. There’s a cottage on a goat farm, tiny houses, a camper van parked on the beach, and sick guest houses on estates. You can hike in Topanga in the morning, grab fish tacos for lunch, then spend the afternoon on the beach. Not bad for the suckiest month of the year.

  Must do: GOAT. YOGA. I don’t want to have to tell you again.

• March: Austin, Texas

  Why: For ten days each March, SXSW, the conference/festival that celebrates all things cool, takes over Austin. Expect music, art, talks and various awesome experiences. For a little extra Texas time, road trip to Dallas.

  Must do: it’ll be tough to drag yourself away from the event, but to experience a bit of authentic Austin weirdness, go play chicken shit bingo at Little Longhorn Saloon. You read that right.

• April: Savannah, Georgia

  Why: If you had to sum up Southern Charm in one city, Savannah would might be it. Think: Spanish moss–covered trees, hushed town squares, killer comfort food and wide nearby beaches. The Savannah Music Festival runs from late March into early April.

  Must do: read John Berendt’s Midnight in the Garden of Good and Evil and tour the Mercer Williams House Museum

• May: New Orleans

  Why: We don’t need to tell you how the Big Easy is a good time all year round, but Jazz Fest, which runs from late April into early May, is one of the best times to visit—and slightly less hectic than Mardi Gras. (Here’s a good primer on what to know.)

  Must do: There might actually be a rule that you’re not allowed to leave New Orleans without having a beignet and a po-boy. Don’t mess this up.

• June: Jackson Hole, WY

  Why: It might be most famous for attracting chi-chi skiers, but Jackson Hole is also a great summer destination, especially when the wildflowers bloom each June. The town ranks up there with Aspen in terms of pricing, but the newish Anvil Hotel is super cool, geared towards a younger client and rates start around $150.

  Must do: grab a saddle at Million Dollar Cowboy Bar

Where are you thinking about heading next year? Tell us in the comments… there’s literally nothing we love more than talking travel. And check back in Feb/March for our travel recommendations for the rest of 2020.