The Best Picnic Baskets and Coolers for Outdoor Drinking in Style

T-minus two days until March, which means we’re already thinking about outdoor drinking season—otherwise known as lurk season, hot girl spring (which is, by the way, gender-neutral), and aperitivo time. However you celebrate (and whatever you drink), one thing we can all agree on is that there is absolutely nothing better than rounding up your buds, busting out your best coolers, packing some snacks and brewskis (or natty wine and charcoots) and soaking up all that glorious vitamin D our bodies have been missing for the last six months. Unfortunately, the coolers you thought you owned were actually your parents’, and Mom already cleaned out the garage. So it's time to grow up, stop mooching, and buy your own. 

Now, the sheer amount of cooler and picnic basket options available online may be a little daunting, but we’ve sifted through the best (and the worst) and sorted the choice ones into categories for every kind of park hang and getaway, so don’t fret. There are big, heavy-duty rolling coolers for epic beach days or longer camping trips, and some super incognito picks for public parks, sports venues, the library—you name it.

Whether it’s croquet and cricket you're after or an afternoon of whitewater rafting, these coolers will keep the good times rolling, the drinks chilled, and the friends smiling. 

Talk about a party in a box, am I right? The Seismic audio cooler box comes with two built-in Bluetooth speakers with a charge that lasts four hours, plus a remote! But the thing that’s most impressive about this ice box is the fact that it will keep ice cold for up to 10 days, thanks to the freezer-quality gasket that creates a form-fitting seal to lock out heat. We’re not saying it’s the perfect excuse for a rager, but we’re definitely not not saying that, either. Plus, there’s a handy side drain that empties all the gnarly cooler water once the party is finally over.  

The big daddy of wheeled coolers, the BrüTank, has one feature that we haven’t seen anywhere else—a removable 2.8-gallon drink tank with a built-in tap. Did somebody say margaritas? The all-terrain wheels and foam benchtop make this the perfect companion for any outdoor adventure.

Although the Igloo trailmate may look like the Mars rover, it unfortunately cannot move on its own accord—but what it lacks in space travel tech, it definitely makes up for in features. The telescopic sliding handle makes it super easy to pull even through mud or sand, and when parked, it transforms into a stand for the butler tray. Igloo really has thought of everything; the trailmate also includes a water-resistant storage pouch, two pole slots for umbrellas or fishing, and a 70-quart capacity that can hold a whopping 112 cans.  

Cult favorite of fishermen, outdoorsy types, and yachters alike, YETI products have been trusted by so many because they just plain work. They’re ultra-durable, and the brand's newest model, the Tundra Haul, is its first-ever cooler on wheels, complete with non-slip feet (ideal for boating), and permafrost insulation that locks in those frigid temps. 

You get the best of both worlds with Sunnylife’s insulated picnic basket. You can cosplay as a coastal grandmother, winding along the dunes with perfect crustless sandwiches—or maybe a nice artichoke tapenade—in tow. Made from wicker and rosewood, this sleek picnic cooler zips closed to keep your rosé ice cold, and the lid does double duty as the perfect traveling fromage board.

Perfect for polo, this quaint little gingham number is ideal for when you want to show up and show out. It also includes everything you need for a perfect outing—a full set of utensils and glasses for two, a waterproof picnic mat, detachable wine bag, and a handy removable leather strap for easy carrying. One enthusiastic Amazon reviewer “bought this for a picnic at the vineyards,” and claims that it is “absolutely perfect.” 

No, it’s not just a backpack that comes in six fun colors—it’s also a super versatile, lightweight cooler bag and it’s screaming, LET’S GET IT STARTED! Designed to keep all your beverages frosty, this easy pack can hold twelve cans, or eight cans and two bottles of wine—perfect for all your buds, or one very thirsty person. 

The youths are downright obsessed with Hydro Flasks, and a lot of them (see VSCO girls) ride hard for the brand. If that sounds like you, then the 18-liter Day Escape is the holy grail. The soft cooler is ultra-light at only 2.5 pounds, and Hydro Flask’s patented zipper is watertight—meaning no leaks in or out. 

If you’re looking for a way to bring your cooler with you on a hike or to the beach, but want your hands free to grab branches or snag errant Frisbees, look no further than the Icemule. What makes this classic cooler so great is the foldable top that allows you to adjust the size of the bag based on what’s inside. It’s also the only one on this list that floats, and the medium classic size can hold four bottles of wine.

It’s not a fun day without major tunes, and for those who want a cooler with a built-in speaker (but can barely afford the beer that goes inside), this one is the way to go. The removable speaker lasts up to eight hours, and the power bank can actually charge your devices if you run out of juice. One Amazon reviewer (who’s doing our job for us) writes, “Charge lasts surprisingly long and the speakers are capable of playing LOUD. Not to mention the size of the inside which I was able to pack 4 lunches and the dogs lunch too. I’m happy with this purchase. I’ll be using it all summer.” 

A Carhartt lunch bag is the perfect low-key summer accessory. Ideal for bike trips with your bud, it’s water-repellant and has two insulated compartments—the bigger of which can fit an entire six-pack. Not to mention, Carhartt will earn you major points with all the tiny hat skate life dudes.

The Herschel cooler-insert is perfect for stashing must-stay-cold items in a bigger go-bag, or for throwing in the passenger seat as you cruise to the beach, just in time for sunset. It’s made of 100% recycled fabric and is totally leakproof—so you don’t have to worry about your brews exploding all over the rest of your gear.  

Never let them know your next move with this luxe cooler-satchel hybrid. Are we going bowling, or are we day-drinking on the lawn? No one knows—and that’s exactly what makes this cooler so… uh… cool. Made from vegan leather, this stylish option also (surprisingly) fits up to 15 cans. 

A classic for a reason, the L.L. Bean boat and tote is synonymous with boating, hiking, and general outdoor merriment. This mini insulated version is a New England mom’s wet dream, and she can monogram it for full waspy potential. 

Now, grab a bag of ice and some pals, and don’t forget to drink water! 

The Rec Room staff independently selected all of the stuff featured in this story. Want more reviews, recommendations, and red-hot deals? Sign up for our newsletter.