5 Best Destinations to Celebrate Life’s Annual Milestones

By Jordan Sherwood

If you’re living your best life, no occasion is too small to warrant a celebration. As our culture finally comes around to the idea of self-care, many of us are learning to reward ourselves for hard work with the occasional spa day or fancy dinner. But for life’s extra-special annual occasions — birthdays, anniversaries, reunions with family and friends — there’s no better reward than a vacation.

Treat yourself to some time away from work — with some help from your friends — by swapping coasts, exploring the best of the Midwest, or hanging down South. The Southwest Rapid Rewards® Priority Card is here to help. The Card comes with a $75 annual Southwest® travel credit you can use towards airfare plus up to four upgraded boardings per year when A1-A15 boarding positions are available. In addition to the points earned on spend, Cardmembers also receive 7,500 points each year on their anniversary to help get to your next destination faster.

Need even more inspiration? We've teamed up with Chase and the Southwest Rapid Rewards Priority Credit Card to put together a list of amazing destinations to get you started. Even better, you can check out Southwest’s low fare calendar to get the most bang for your buck (or points) to the destination of choice.

1. Take A Birthday Trip To LA


Nothing screams “I’m living my best life” more than a picture of you posing on an inflatable flamingo, surrounded by friends, in a swimming pool in Los Angeles. LA offers the perfect dose of glamour for a birthday trip, and you’ll have no trouble convincing your friends to join you at such an enviable locale. Picture it: frozen drinks poolside, delicious gourmet vegan food, and late night walks along the beach. The only way to recover from a trip to LA is to start planning the next one!

2. Head To Denver For A Winter Trip


Denver’s Rocky Mountain location makes it a prime spot for a winter getaway. If you’re the type to slap on a pair of skis and glide down the side of a mountain, you’ll be pleased to know that world-class skiing resorts surround the city. If you’re more the type to cozy up in a mountain lodge with some hot chocolate, a good book, and your boo, you're still good. It will be easy to feel disconnected from the noise of everyday life as you lounge by the fire, but if you get the urge to dive back into the city for a night, Denver’s got an amazing arts and dining scene, too. Their art museum is one of the best in the country, and the locavore food scene is seriously poppin'.

3. Plan A Spring Getaway To NOLA


If you haven't yet gone to New Orleans, now is the time to make it your new spring destination. From the moment you land, you’ll know you are in a world apart. New Orleans is buzzing with intense, kinetic energy that is nothing short of infectious. Embrace the old-school Southern glamour of the French Quarter, enjoy one of the world’s best jazz festivals, and learn about the city’s history through the many fascinating walking tours on offer. (I once followed an evening voodoo tour with a midnight ghost tour by the same local guide, and let’s just say that the city’s unofficial history makes its already wild and documented official history look tame by comparison). You’ll leave a piece of your heart in New Orleans, but you can always come back for it next year!

4. Grab Your Girls For A Summer Weekend in Chicago


Chicago comes alive in the summertime. Its location in the Midwest makes it the perfect place for your annual meet-up with your far-flung friends from college. Bordered by 26 miles of shoreline along Lake Michigan, the city provides the perfect backdrop for a weekend filled with sunbathing, shopping, and sipping cocktails. A stay in Downtown Chicago gives you access to the city’s many beaches, the shopping mecca of Michigan Avenue (“the Magnificent Mile”), world-class museums, and a bustling nightlife scene. There’s something in Chicago to suit everyone’s tastes, particularly if those tastes include eating. Chicagoans are known to be indulgent (I guess it’s the long winters), so try to keep up!

5. Family Vacay In Orlando


Orlando is the place to be when it’s time to gather for your annual family trip. Grandma and grandpa are already there, mom and dad don’t need an excuse to escape the winter weather back home, and all the kids in the family are already arguing over who gets to ride next to you at the amusement park. Something about Orlando brings out the kid in everyone; you’ll all be posing with your faces painted and your arms filled with stuffed animals before you know it. And if you want to enjoy nature, you can check out Wekiwa Springs State Park. There, you can kayak and just generally enjoy the swampy gorgeousness of Orlando!

This article is sponsored by Chase and the Southwest Rapid Rewards Priority Credit Card.