The beginning of a new year is a great time to plan out your travels in the coming months and to mentally transport yourself out of the doldrums of January and February. Better yet, book a last minute trip to a warm weather locale, or visit a popular attraction during the offseason for better prices and fewer crowds. Here’s our monthly bucket list for 2019.
No passport required perfect temps, and an underrated Caribbean island waiting to explore. The city of Christiansted is lively and full of culture, not to mention the beautiful and clear waters of the surrounding beaches. The island was once a thriving port of call thanks to the rum trade and the African slave population that farmed the lands made up more than half of the city’s original population. Much of that African heritage remains today in their vibrant art, food, and overall culture. Speaking of the food, this isn’t an island where all inclusive is advised—the local restaurant scene is full of gems, including fresh seafood (don’t miss the conch), farm-to-table restaurants, and even an internationally acclaimed chef, Digby Stridiron, with his contemporary West-Indian dishes at the restaurant Braata.
Austin, Texas has been an “it” city to visit for music, tech, and food for the past decade; unfortunately, this notoriety has made visiting ATX a pricey getaway most months. February is a great time to check out what all the fuss is about, with cheaper flight options, a mild climate, and none of the big crowds. The only drawback to visiting in February is the temps won’t be hot enough to enjoy boating or any water activities on the surrounding lakes and river, but hey, you can still layout poolside and enjoy a LoneStar or six. Make sure to spend at least a long weekend in Austin to have ample time to enjoy the ATX nightlife, green trails, live music, and tacos on every corner.
This bustling beach town sits 20 minutes north of West Palm Beach and is home to a variety of water activities, beautiful beaches, spring training games, golf courses, and great restaurants. What was once a quaint beach town for families and retired athletes (Tiger Woods and Michael Jordan have had homes here for almost 20 years) has seen an explosion in tourism in the last decade. Book your accommodations early or consider the surrounding cities of Palm Beach Gardens and Tequesta. The best part of Jupiter is the flexibility; if you want to ball out, you can! If you want to just hang on the beach, you can! Paddleboard up and down the intercoastal, charter a boat for a day, catch a baseball game—just make sure you end it with dinner at one of the (many) beach bars and restaurants serving fresh fish and a lively atmosphere.
If bourbon and horse racing are your thing, Lexington, Kentucky and the surrounding Bourbon Trail are a must visit. If neither of these things interests you, well, take a trip to the beautiful Bluegrass State and let them (try to) change your mind. The Keeneland race track runs every April and October, making it an ideal time to visit. Pack a fancy hat or your seersucker suit and head to the track to see some of the Kentucky Derby contestants get primed for the big race. For the remainder of your stay, spend a day exploring the gorgeous Kentucky countryside going from distillery to distillery, tasting the state's most famous export. If you have the time (and a DD) follow the Bourbon Trail to Louisville and spend a night at the 21c Hotel.
There’s no better time to be in DC than May. The cold has passed and summer’s humidity hasn’t yet hit, so outdoor activities are a “go”. That means you can don your finest tourist hat, hit the National Mall and take selfies with your favorite monuments. Stop and smell the flowers at the US National Arboretum, and enjoy a Washington Nationals game without being drenched in sweat. May’s perfect temps also mean that the city’s numerous patios will be open, letting you dine al fresco—which is good news because DC has some of the best and most exciting restaurants in the country. It also will make waiting outside for one of our favorite restaurants on Earth, Little Serow, much less painful.
Southern charm, home cooking, and live music are what makes Nashville so special—so no surprise it exploded in popularity in the last decade. Music City is the perfect weekend escape, and June is a great time to visit before the temperature and humidity reach their peak. The food and drink options are staggering, so choosing where to eat will prove challenging, but hey, you can always come back. The nightlife is unlike anything you’ve experienced. The honky tonks off Broadway are full of (interesting) people, country music, and karaoke. Don’t miss all our guides to get the most out of the Nashville. [LINK TO GUIDES]
Welcome to the culinary capital of the Napa Valley! Yountville is a cozy town nestled amongst the gorgeous surrounding vineyards and the Mayacamas Mountains. When planning your Napa trip, staying in Yountville is a must. You can easily walk up and down Washington Street to its many restaurants (including two Michelin starred gems—The French Laundry and Bouchon Bistro), galleries, and shops, or bike to the countless nearby vineyards...though biking home drunk isn’t exactly fun. Peak months are August through October, so you should find some great deals.
“It’s a place where the beer flows like the salmon of Capistrano.” When waxing poetically about Portland, the beer scene tops the list with the local brewery count topping 80. Just stepping foot in Portland makes you feel that much cooler. It’s a liberal bastion, full of free love, street art, great music venues, beautiful mountain scenery, great coffee, and a food scene that will make you despise your hometown. August sees the lowest rainfall of any month of the year, and the temps top out around 80 degrees, making it a welcome escape from the dog days of summer in most parts of the country.
The Gateway City has so much to offer beyond the Arch and seeing a Cardinals game...but you should probably still do both. Once that’s checked off your list, explore the eclectic and growing food scene that has put the city on the national radar; with everything from its James Beard award-winning chefs, to one of the only contemporary Bosnian spots in the country. September is an especially great time to visit, thanks to events like the St. Louis Symphony performing free concerts in beautiful Forest Park and the Great Forest Park Balloon Race. If you have children in tow, St. Louis is one of the best cities in the country for kids’ activities, including the Magic House, City Museum, St. Louis Zoo (the second best zoo in the US), and an aquarium opening in Fall 2019.
Palm Springs has long been a favorite retreat for the rich and famous, and more recently an art and design mecca. Nearby Joshua Tree National Park, the landscape is a beautiful mix of lush California flora and desert. The laid back, California-cool area is filled with top-notch golf courses, swimming pools, and stunning architecture. The city was built on mid-century modern design—a trend that has continued to this day. October is typically when they hold their Modernism Week, a must for design buffs. Just prepare your wallet, because you’re not going to be able to resist some of the incredible gallery and furniture showrooms. During October the temps can still get up into the 90s but dip into the low 60s at night, so come ready to swim, but also bring a sweater. Make dinner reservations as soon as you can; there are some incredible spots, but most are tiny and book up quickly.
While the crowds flock to the Smoky Mountains for fall foliage in October, early November has actually been peak time for foliage the past few years. You’ll be able to escape the crowds and be delighted in mountains awash with red, yellow, and orange. Rent a chalet in the mountains (a hot tub is a requirement), grab your hiking boots, and set off into the heart of the Smoky Mountains with a visit to Gatlinburg and Pigeon Forge. It’s most suited for a romantic or family getaway, as there isn’t much nightlife to speak of. Ride the lift to the top of Anakeesta Mountain and enjoy the restaurants and shops at the top, or just take in the gorgeous views.
Nothing will get you in the holiday spirit like a visit to NYC when it’s all dolled up for Christmas. Go ice skating in Central Park or Rockefeller Plaza, see The Rockettes, shop on 5th Avenue...the list goes on and on. All five boroughs host Christmas markets throughout December, so no matter when you visit you will have plenty to choose from. If you get lucky, a December snow in New York is magical, but otherwise, the weather shouldn’t be bitter cold just yet.