Not every trip needs a full week to feel like an escape. Sometimes all you’ve got is a long weekend — and if you do it right, that’s more than enough.
I travel often, usually for longer stretches, but I’ve learned that some cities are especially good at delivering in a short window: great food, easy momentum, and plenty to do without overplanning. The kind of place where you can settle in fast—whether that’s chasing the perfect ribeye, grabbing a rooftop drink, or ordering something so good you’re still thinking about it weeks later.
That’s what I think of as a weekend-ish getaway. And Madison, Los Angeles and Fort Worth all fit the bill. Here’s where to stay, what to do, and what’s worth building your trip around.
Madison, Wisconsin
I end up in Madison quite often. Just 90 minutes from Milwaukee and about 2.5 hours from Chicago, Wisconsin’s capital is an easy escape with a lot to offer. There are standout restaurants, plenty of outdoor recreation—from ice fishing in the winter to lakeside lounging in the summer—and a general sense that you don’t need much of a plan to enjoy yourself.
All you really need are good sneakers and a willingness to wander. It’s a lively university town with breweries everywhere, bikes zipping past on nearly every street, and the kind of easy smiles and hellos that make Midwest nice feel real.
Where to Stay:
The Edgewater Hotel – Right on Lake Mendota near Capitol Square, this comfortable, elegant hotel makes the most of its setting. In the winter, there’s an ice rink; in the summer, live music outdoors.
The rooms are spacious, with curved walls of windows that look out over the water—truly one hell of a view. Even better, the windows actually open, which I always love in a hotel room. Our suite had a massive bathroom with a soaking tub and separate shower, and the property also has multiple restaurants and a full-service spa.
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Where to Eat:
Les Délices de Awa – A must-try spot I can’t wait to return to the next time I’m in Madison. Chef Awa Sibi cooks food from her homeland of Côte d’Ivoire, along with other West African specialties, all halal.
The pastels—reminiscent of empanadas—were filled with beef and vegetables and served with a flavorful sauce. Most dishes leaned mild in heat, but the in-house spicy sauce (which I highly recommend if you like a kick, like I do) brings everything to life. The plantain practically melted in your mouth, the goat was tender and full of flavor, and the fish beignet (a must-order) is filled with sautéed tuna and salmon and served with a savory tomato sauce.
Tornado Steak House – More of a classic supper club than a traditional steakhouse, and it absolutely delivers. The space is dimly lit and always packed, with wood-paneled walls, mounted antlers, and crisp white tablecloths setting the tone.
We started with a generous spread of complimentary bread and butter, fresh oysters, and escargot—my wife’s favorite, not mine, though the leftover sauce was perfect for dipping. Steak comes with soup or salad and a side (a detail I always appreciate), so we shared a perfectly cooked medium-rare ribeye with a cheese-topped hash brown and a Caesar loaded with anchovies. Everything, including the old fashioneds my wife ordered, was comforting and satisfying.
What to Do:
The Big Gay Market – A quarterly market that brings together artists and makers from across Wisconsin. The mix changes each time, but you might find leather belts cut to size, body candles (my wife makes those), tea blends, ceramics, prints, and tie-dye.
Beyond the shopping, events often include drag shows, photos with Santa, food trucks, clothing swaps, and even furry fashion shows. It’s consistently a good time.
Rent a Bike – Madison is one of the most bikable cities in the country, with more than 200 miles of trails. Renting a bike is an easy way to get around or spend an afternoon exploring. The 13-mile Lake Monona Loop winds through parks and along the water, with some of the best lake and skyline views in the city.
Henry Vilas Zoo – One of the only free zoos in the country, open year-round and home to more than 650 animals. You’ll find everything from red pandas to critically endangered black-and-white ruffed lemurs. Don’t miss the Tropical Rainforest Aviary for free-flight birds or the Arctic Passage, where you can watch polar bears and seals swim underwater.
Los Angeles, California
Los Angeles is a sprawling, high-energy city where you can sleep, eat, and play without ever getting in a car — or pinball across neighborhoods chasing something new at every stop. It’s a place people love to hate, but however you like to travel, there’s something here for you.
Where to Stay:
Downtown LA Proper – Location was everything for this trip, and the Proper delivered. Set in downtown LA, it’s an eclectic, colorful boutique hotel with vintage brick details and excellent service. It’s within walking distance of LA Live, Crypto.com Arena, and the Fashion District, and I even made the walk to Redbird. The room was comfortable, with a large shower, and I loved that the windows opened slightly — always a win for me — though the AC wouldn’t go below 67 degrees, much to my dismay. The hotel earned a Michelin Key in 2025 and has two on-site restaurants and a rooftop pool with city views. It made a perfect home base.
What to Eat:
Damian – From Chef Enrique Olvera of Pujol, Damian was a meal I went into with high expectations—and it delivered. We started with a Japanese Wagyu tostada, all contrast: crunchy, rich, and deeply satisfying.
The dry-aged grilled branzino was flaky and beautifully cooked, but the standout was the chicken al pastor, served with a fresh pineapple salad and pineapple butter—bright, savory, and just a little indulgent. Service was polished, the vibe felt spot-on, and yes, everything was genuinely excellent. Bonus: valet was a surprisingly reasonable $12.
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Redbird – Set inside the former rectory of Vibiana, Redbird is a modern American restaurant built for sharing. Every meal begins with a basket of hot, fresh pão de queijo—chewy, cheesy, and hard to stop eating.
Service was thoughtful, even as a solo diner, with spot-on recommendations. I had the kombu-cured Japanese hamachi with navel orange, capers, chili, and kohlrabi—bright, balanced, and just a little spicy.
I tend to order tartare whenever I see it, and Redbird’s version stands out: served over a crisp potato tosti with caramelized onion crema, egg jam, pickled pearl onion, and shaved marrow. It’s rich, layered, and more inventive than the usual. The whole crispy branzino is also worth ordering—it was perfectly flaky.
What to Do:
LA Kings Hockey Game – I somehow end up in LA often, usually for work, and this trip was no different. I was invited to a Los Angeles Kings game at Crypto.com Arena with one of their sponsors (and mine), Mercury Insurance. Hockey is a great pick if you want something fast-paced and entertaining, even if you’re not a die-hard fan. The arena is within walking distance of the Proper and right next to LA Live—grab a bite there before or after if you want to avoid arena prices.
Visit West Hollywood – Head out to West Hollywood for a different pace: sunshine, good wandering, and a little scene-y energy. Start at the The West Hollywood EDITION for a drink (and maybe a snack—the duck tacos with house hot sauce are good, but not unforgettable). It’s a beautiful hotel with art in the lobby and a rooftop with sweeping 360-degree views.
And yes — stop by the bathroom. It sounds silly, but the views really are worth it.
From there, it’s about a mile to The Woods, and the walk gives you a nice stretch of Sunset and Santa Monica to take in along the way.
The Woods – I’ve been to a handful of consumption lounges—from San Diego to Las Vegas to Richmond, Illinois—and this one is easily my favorite. Honestly, it’s worth the trip to West Hollywood on its own.
The space is mostly outdoors, with real trees, birds, koi fish, and plenty of seating, plus private cabanas if you want a more tucked-away setup ($75 for 90 minutes). The dispensary has a strong selection of outdoor-grown California flower and rental devices, including my personal favorite, the Stündenglass gravity bong. There are also plenty of infused canned drinks, though no handcrafted options, which is standard in California.
Entry is straightforward — spend $20 in the dispensary or pay a $10 cover — and you can order food or grab coffee next door. It’s an easy place to settle in, get a little (read: very) high, and spend time with friends in a setting that feels more like a garden hang than a bar. I’ve been recommending it to everyone I know—and I can’t wait to go back (this time with my bird-obsessed wife).
Fort Worth, Texas
Fort Worth is ideal for a weekend getaway. Downtown is walkable, the city leans into its Western charm, and the food scene holds its own. Between daily longhorn cattle drives, rodeos, live music, and plenty of low-key ways to relax, there’s always something going on. Wander through Sundance Square, dip into a bar or two if that’s your thing, and don’t be surprised if your trip ends up feeling packed — in the best way — even midweek.
Where to Stay:
Sheraton Fort Worth – Not a luxury property, but a recently renovated and very comfortable option in a great location. My room was huge, with a small kitchenette (sink, microwave, and fridge), which made leftovers easy. The bed was comfortable, though the shower felt surprisingly small for the size of the room. The real draw is the location: an easy, flat walk to Sundance Square, the Cultural District and Trinity Trails.
What to Do
Lookout Hill: Yarn and Art Supplies – I passed this shop a few times and couldn’t get over how charming it looked. Inside, there’s a great mix of yarn, art supplies, and classes if you’re feeling inspired. I didn’t have time to take one, but it’s an easy stop from the Sheraton — and a fun place to pick up something a little more unique to bring home.
Pete’s Dueling Piano Bar – One night, about 100 women from the Women in Auto Care conference I was attending descended on this place with zero warning — and the staff didn’t miss a beat. We were welcomed in with full Texas charm. It was my first time at a piano bar, and it absolutely delivered. It’s part dive, part performance space, with songs flying, drinks flowing, and the whole room singing along. Come ready to laugh, make requests and fully lean in.
Where to Eat
Birrieria Chalio – Chef Raul Luis comes from a long line of birrieros in Jalisco, Mexico, and his family played a role in bringing birria to a wider audience in the U.S., starting in Los Angeles in the early ’70s. His Fort Worth restaurant—named for his nickname, Chalio—features murals that reflect that family history.
The food is excellent. House-made corn tortillas, and your choice of lamb, goat, or beef birria, served traditionally or as grilled cheesy tacos with a dipping consommé. The lamb ribs are especially worth ordering.
I tried both the beef quesabirria and the lamb ribs with tortillas, and would happily order either again. Save room for dessert—the house-made churro cheesecake isn’t overly sweet and is a great way to end the meal.
Woodhouse Spa Fort Worth – If you’re looking to slow things down, this is a solid place to do it. The Woodhouse Spa offers everything from massages to facials and body treatments in a comfortable, low-key space.
I opted for a four-hand massage—something I fell in love with on my trip to Vegas—and while the coordination wasn’t perfect (it was one of the masseuse’s first), it was still deeply relaxing. I left feeling loose, calm, and very ready for a nap.
Smoke’N Ash BBQ – A bit of a trek from downtown, but absolutely worth it. Smoke’N Ash blends Texas barbecue with Ethiopian flavors, and the result is something special.
The brisket, seasoned with salt and pepper along with berbere, rosemary, garlic, and ginger, was the standout—rich, smoky, and deeply flavorful. Don’t skip the Texas toast, which somehow ties it all together.
And if you have room, get the sweet potato pie topped with berbere. It’s a little unexpected and completely works. (Honestly, get two—you’ll be thinking about it later.) They also ship nationwide through Goldbelly if you want a repeat.
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