The blog.

Skye · Jul 19, 2026 · 8 min read · Milwaukee, Wisconsin

Milwaukee in summer, from someone who grew up here: the weekend I'd actually give you

Every other post on this site is me arriving somewhere as a visitor, figuring it out, and reporting back. This one's different. I was born and raised in Milwaukee, I've lived downtown, and I still live in southeast Wisconsin. So I'm not going to review a hotel room I've never slept in — I've never needed one here. What I can give you is the version of a Milwaukee summer weekend that locals actually live, which is not quite the one the guidebooks sell.

Start here — Milwaukee is a summer city. I say that with love. From roughly June through September this place is genuinely one of the best small cities in the country: festivals on the lakefront nearly every weekend, a walkable downtown, and a Great Lake that behaves like an ocean. Come in February and you'll have a perfectly nice time in some excellent bars and museums, but you'll be seeing a different city. Plan for summer if you can.

Where to base yourself: Downtown or the Historic Third Ward, and I say that from having lived downtown rather than from a booking site. What made it work day to day was how much was on foot — the lakefront for a morning walk, shopping and restaurants without moving the car, and friends able to meet you halfway without anyone committing to a drive. That's the same reason it works for a visitor. Stay downtown or in the Third Ward and you can leave the car parked for two full days.

The lakefront is the thing people underestimate. Lake Michigan doesn't read like a lake — no far shore, real waves, actual beaches. The path along the lakefront was my default walk when I lived downtown, and it's still the first thing I'd send someone to do. Do it in the morning before the day heats up. The Milwaukee Art Museum sits right on it, and its "wings" — the Calatrava brise soleil — open and close on a schedule through the day. Yes, it's the thing everyone photographs. It's also genuinely worth standing there for.

Kayak the Milwaukee River. This is my favorite thing to recommend because almost no visitor thinks of it. You paddle straight through downtown — under bridges, past the Riverwalk, past bars where people are sitting outside — and the city looks completely different three feet off the water. It's flat, it's slow, and you don't need to be an experienced paddler. If you do one thing from this list that isn't on a standard itinerary, do this one.

The festivals are the whole personality. Summerfest runs on the lakefront festival grounds around late June into early July and bills itself as the world's largest music festival, which is the kind of claim that turns out to be roughly true. The Wisconsin State Fair follows in August out in West Allis, and it is an entirely different animal — livestock barns, absurd food on sticks, cream puffs that people genuinely plan their day around. If your dates land on either, build the weekend around it rather than trying to fit it in around other things.

A Brewers game is an easy yes. American Family Field has a retractable roof, which in practice means a game is never rained out and never unbearably hot — a real advantage over most summer ballparks. It's a short drive or a game-day shuttle from downtown. If you're visiting in winter instead, the Bucks play at Fiserv Forum right downtown, and that arena district has become one of the better places in the city to spend an evening.

Two neighborhoods, two different nights. The Third Ward is the polished one — Milwaukee Public Market, boutiques, the Riverwalk, easy to wander with anyone. Brady Street is the scruffier, more characterful counterpart on the East Side, and it's where I'd go for a night out that doesn't feel curated. Do the Third Ward in daylight and Brady Street after dark and you've seen both halves of the city's temperament.

The one I'm still sad about: there used to be a factory tour where you could watch actual foam cheeseheads get made. I did it, it was gloriously silly, and it's not running anymore. I mention it because it's the most Wisconsin sentence I will ever write, and because it's a reminder to do the odd small thing while it's still there.

If you have an extra day: Lake Country. Half an hour or so west of the city there's a cluster of lakes — Pewaukee, Okauchee, Lac La Belle and others — where the summer ritual is getting out on the water and then boating up to a restaurant or bar and tying off. Arriving somewhere for dinner by boat is a genuinely different experience, and it's the part of a Wisconsin summer visitors almost never see because it requires knowing someone or renting something. You'll want a car for this one.

Coming outside of summer? Then you probably want to keep driving. Wisconsin's real off-season answer is "up north" — the lake country, the cranberry marshes, the ski trails — and none of it is close enough to Milwaukee to squeeze into a city weekend. I wrote that up separately: Up North in Wisconsin — what we actually do the rest of the year.

The bottom line: Milwaukee is an easy city to spend a summer weekend in and a hard one to appreciate from a list of attractions. It's a lakefront, a river you can paddle, a festival schedule that's genuinely world-class for a city this size, and two very different neighborhoods for dinner. Base yourself downtown, come between June and September, and don't over-plan it.

Skye · Jul 18, 2026 · 7 min read · Northern Wisconsin

"Up north" in Wisconsin: what we actually do the rest of the year

If you grow up in Wisconsin, "up north" isn't a place on a map — it's a direction and a whole mode of being. It means leaving the southeast corner where most of the state's people live and driving into lake country, where the plan is usually just a cabin, a body of water, and no particular schedule. I've been doing it my whole life. This is the honest version, including the drive times, because that's the part nobody tells you.

First, the distances are real. Wisconsin looks compact and isn't. From Milwaukee, Door County is about three hours, the cranberry country around Warrens is roughly two and a half, Minocqua and Eagle River are about four, and the Apostle Islands are a solid six. None of these is a day trip from the city. Each one is its own weekend, and treating them otherwise is the classic visitor mistake.

Door County is the one everyone starts with — and it's a year-round destination. It's a peninsula sticking into Lake Michigan, lined with small villages, orchards, shoreline, and state parks. Summer is water and the cherry crop, fall is color and apples, and the shoulder seasons are quiet in a way that's the entire point for some people. One timing note that trips visitors up constantly: the famous pick-your-own cherries are a July thing, roughly mid-July through mid-August, with the sweet varieties first and the tart Montmorency cherries the county is known for following. If you arrive in October expecting to pick cherries, you've missed it by two months — but you'll have landed in a genuinely lovely fall trip instead.

The Warrens Cranberry Festival is the strangest good time in the state. Warrens is a tiny town about two and a half hours northwest of Milwaukee, and on the last full weekend of September it hosts a cranberry festival that pulls in a crowd wildly out of proportion to its size. Wisconsin grows more cranberries than anywhere else in the country, and the festival runs tours out to the marshes during harvest. Seeing a flooded bed with the berries floating on top — an absolutely solid red surface stretching out in front of you — is genuinely unlike anything else. We went as a family and got to put waders on and stand out among the berries, which produced the best photograph anyone in my family owns. Worth checking what's on offer the year you go, since the wader access depends on the grower and the weekend.

Minocqua and Eagle River are the winter half of the answer. They sit about four hours north, roughly 25 miles apart, in the middle of the Northwoods lake country. In summer they're cabins-and-boats towns. In winter they turn into one of the better cross-country skiing regions in the Midwest — Minocqua Winter Park on one side, and around Eagle River the Anvil trails and the Nordmarka system. Eagle River also calls itself the snowmobile capital of the world, and spends the season making a solid case for it.

I learned to ski at Minocqua, which mostly meant learning to fall. I want to be honest about this because cross-country skiing gets sold as the gentle, meditative winter sport, and my first day was neither. What I actually spent the day getting good at was the specific technique of getting back up off the snow with long skis attached to your feet, on a slope, with no dignity available to you. It's a real skill. Nobody mentions it. By the end of the trip I could ski a bit, and the payoff — being out in a silent snow-covered forest under your own power — was worth every fall. Just book two days, not one, because day one is tuition.

The Apostle Islands are the serious commitment. Up on Lake Superior at the very top of the state, about six hours from Milwaukee, the Apostle Islands National Lakeshore is a cluster of islands known for sea caves, sandstone cliffs, and water that behaves nothing like the rest of the Midwest. It's the most spectacular landscape in Wisconsin and it is genuinely far away. Don't tack it onto anything. Give it its own trip and a few days.

A few things worth knowing before you go: cell service gets patchy the further north you get, and that's a feature as much as a problem. Supper clubs are a real Wisconsin institution and you should eat at one — expect an old-fashioned before dinner and no rush about any of it. And book lodging early for summer weekends and for anything near a festival date, because inventory in small northern towns is genuinely limited in a way it isn't in a city.

The bottom line: if you only ever see Milwaukee and Madison, you've seen the part of Wisconsin that looks like everywhere else. Up north is where the state is actually itself. Pick one destination, give it a full weekend, and don't try to chain them together on a map that lies about how big this place is.

Skye · Jun 10, 2026 · 6 min read · London, UK

London three ways: my first trip with my parents, two work trips, and the walk I'd do every single time

I've been to London a few times now — the first back in 2007 with my parents, and then twice more for work. Each trip taught me a little more, and it's become one of those cities I'm always happy to land in. Here's what I've figured out across all three.

Where we stayed: That first trip, we stayed at a Holiday Inn — and honestly? For a first London trip, it did exactly what we needed. Clean, reliable, and a solid base to come back to after long days on our feet. It's not glamorous, but when you're figuring out a big, brand-new city with your parents, "predictable and comfortable" is worth a lot. I'd happily recommend a no-drama chain hotel for a first visit; save the boutique splurge for when you already know the neighborhoods.

Getting around: On that first trip, the hop-on/hop-off bus was a lifesaver. It let us get our bearings, see the big sights, and rest our legs all at once — the perfect day-one move when everything still feels overwhelming. After that initial orientation, though, London is genuinely easy to get around. The Tube covers everything, and the central core is far more walkable than it looks on a map. By my later work trips, I barely thought about logistics at all.

The one thing I'd tell a friend to do: My favorite London memory is deceptively simple — walking from Buckingham Palace to Trafalgar Square, then down past Parliament and Big Ben to the London Eye. It strings together the postcard sights in one relaxed, mostly flat stroll, and it never felt rushed or stressful. If you only have one afternoon, do that walk. It's the trip in miniature.

One hard-won tip: Check whether there's a football match on. British football fans are gloriously dedicated, and on one of our walks there was a group celebrating right down the street — we didn't want to get in the way of their moment, and it's genuinely good to know before you wander into it. It's not a safety scare, just a "read the room" thing: match days change the whole energy of a neighborhood, so it helps to know the calendar and plan around it.

The bottom line: London rewards a little orientation up front and then basically runs itself. Grab a hop-on/hop-off pass on day one, pick a reliable central base, do the Buckingham-to-Eye walk at an easy pace, and glance at the football schedule. It's one of the easiest big cities to fall for.

Skye · Mar 25, 2026 · 7 min read · Boston, Massachusetts

Boston with my parents: 4 nights on the waterfront and why the Long Wharf location changed everything

I just got back from Boston with my folks and I'm still thinking about it. We flew Delta out of Milwaukee into Logan, checked into the Boston Marriott Long Wharf, and spent four nights walking the waterfront, eating way too much chowder, and actually enjoying the pace. This one's for anyone traveling with parents or older family members and wondering if Boston is doable without a car.

Where we stayed: The Marriott Long Wharf, right on the harbor. I picked it because of the location — the Freedom Trail literally starts a few blocks away, the New England Aquarium is next door, and the North End (cannoli, pasta, more cannoli) is a flat 10-minute walk. My mom can't do long distances on her feet, so being able to walk out the front door and be at something interesting within minutes was everything. We only needed a rideshare once the entire trip.

What worked: One big thing per morning, lunch somewhere sit-down, then an easy afternoon. Monday was the Freedom Trail (we did about half of it, then caught an Uber back when Mom's knees said no). Tuesday was the Aquarium and a harbor walk. Wednesday we took the ferry to Charlestown to see the USS Constitution — the ferry ride itself was the highlight. Thursday was the Museum of Fine Arts, which has benches in every room, bless them.

What I'd do differently: I'd skip the Faneuil Hall food court — it's fine, but we wasted a lunch there when we could have been at a North End restaurant. Also, book a harbor dinner cruise in advance if you're going in March. We tried to walk up and they were sold out.

The bottom line: Boston might be the most underrated walkable city on the East Coast. Compact, flat near the waterfront, great transit when you need it, and restaurants that don't require a reservation three weeks out. If you're traveling with family members who need a slower pace, pick a harbor hotel and you're set.

Skye · Nov 5, 2025 · 8 min read · New York City

The Marriott Marquis in Times Square: is it worth staying in the middle of the chaos?

I know what you're thinking. Times Square? Really? Hear me out. I stayed at the New York Marriott Marquis for about four nights at the end of October and I have thoughts. Some good, some "I will never do this on a Saturday night again."

The location: Right in Times Square, which means you are in it. All of it. The lights, the noise, the people dressed as Elmo. But here's the thing — the subway access is unbeatable. The N/Q/R, 1/2/3, and 7 trains are all within a block or two. I got to Central Park in about 10 minutes, downtown in 20, and the Met in a little under half an hour. If you're the kind of traveler who wants to see a lot without exhausting yourself, being right on top of a transit hub matters more than a quiet street.

The hotel itself: The lobby is up on the 8th floor, which is disorienting at first but actually nice — you escape the street-level madness. The rooms are standard Marriott (clean, comfortable, not exciting), but the views from the upper floors are genuinely incredible. I watched the city light up at sunset from my window and it was one of those "oh right, this is why people come here" moments.

What I did: This was partly a work trip, so my sightseeing was squeezed into mornings and evenings. Best move: walking south from the hotel to Bryant Park for coffee in the morning — it's only 3 blocks and it's a completely different vibe from Times Square. Worst move: trying to get dinner near the hotel on a Friday night without a reservation. Just don't.

Would I stay here again? For a short trip where I need to get around efficiently, yes. For a relaxed vacation where I want to stroll and feel the neighborhood, I'd go to the West Village or the Upper West Side instead. Context matters.

Skye · Jul 8, 2024 · 8 min read · Pigeon Forge, Tennessee

The Dollywood road trip with my nieces: Cincinnati, Purdue, small-town Indiana, and way too many roller coasters

Most of my trips are with my parents, at a deliberately gentle pace. This one was the opposite: a road trip from Wisconsin to Dollywood with my nieces, which meant coasters, pool time, and snack stops instead of museum benches. Same approach to planning, completely different speed — and honestly, it's the best argument I know for why "family-friendly" and "parent-friendly" aren't the same thing.

When someone suggests driving from Wisconsin to Tennessee, the first question is usually "why not just fly?" Fair. But the drive is the trip. We turned it into a multi-stop adventure in late June 2024, and the stops along the way ended up being just as good as the destination.

Stop 1 — Cincinnati (The Lytle Park Hotel): We stayed at The Lytle Park Hotel, an Autograph Collection property downtown. The concierge team emailed before we arrived asking if we needed anything, which was a nice touch. The hotel itself is stunning — it's in a renovated historic building right on Lytle Park. We walked to Findlay Market, ate our weight in Cincinnati chili (Skyline, if you must know), and let the girls run around Smale Riverfront Park, which has incredible playground equipment right on the Ohio River.

Stop 2 — Purdue / West Lafayette (The Union Club Hotel): A quick overnight, but the Union Club at Purdue is gorgeous. Another Autograph Collection spot — old-school collegiate charm, right on campus. If you've got a kid who's even vaguely thinking about college, this is a fun excuse to walk through. We grabbed dinner at a spot on the main drag and called it early.

Stop 3 — Madison, Indiana (Fairfield Inn): This was the surprise hit. Madison is a tiny historic river town that most people have never heard of. The Fairfield is in a converted cotton mill (the Eagle Cotton Mill), and it's way more charming than any Fairfield has a right to be. We walked along the Ohio River, found a little ice cream shop, and my nieces were thrilled. Sometimes the small stops are the best ones.

The main event — Dollywood (HeartSong Resort): We stayed at Dollywood's HeartSong Resort in Pigeon Forge and it was worth every penny. The theming is beautiful, the rooms are spacious, and you get early entry to the park. Dollywood itself is fantastic — the roller coasters are legit, the live music is everywhere, and the cinnamon bread at the Grist Mill is not optional. We also hit Dolly Parton's Stampede one evening, which is exactly as over-the-top as it sounds, but the girls were mesmerized.

Would I do the road trip again? In a heartbeat. The mix of cities, small towns, and a theme park at the end is close to a perfect kids' trip. Just don't try to do it all in one day of driving — spread it out, enjoy the stops, and let them swim at every hotel pool along the way. (My parents would have hated this itinerary, and that's exactly the point: match the trip to who's actually coming.)

Skye · Jul 18, 2022 · 9 min read · South Dakota

The South Dakota road trip nobody told me to take (and I'd do again tomorrow)

I'll be honest — South Dakota was not on my bucket list. It ended up being one of my favorite trips I've ever taken. We did a full loop in July 2022: Milwaukee to La Crosse, then west through the Badlands to Deadwood, down to Rapid City, Wind Cave, and back through Sioux Falls. About 10 days, four hotels, one rental car, and zero regrets.

La Crosse (The Charmant Hotel): We broke the drive at The Charmant in La Crosse, Wisconsin — both on the way out and the way back. I cannot say enough about this hotel. It's a converted candy factory, and the rooms have these gorgeous exposed brick walls and massive windows. The welcome email said to expect something "as whimsical as a child walking into a candy store" and they delivered. Parking is tight (heads up), but they'll give you directions to the lot nearby. We did the breakfast reservation and it was worth it.

Deadwood (Four Points by Sheraton): This was our main base — four nights. Deadwood itself is a trip. It's a historic gold rush town with casinos and saloons on every block, but it's also genuinely charming. We ate at The Lucky Horse multiple times because the food was solid and the portions were big. The town is walkable if you stay on Main Street, but you'll want the car for anything outside of downtown.

Wind Cave National Park: Book the cave tour in advance on Recreation.gov. Seriously. We almost missed it. The cave itself is fascinating — one of the longest in the world — and the ranger-led tour was well paced. Not too strenuous, though there are some stairs.

Fort Hays and the Buffalo Hunt: This one surprised us. It's a reenactment-style experience where you ride out with a herd of buffalo (from a vehicle — you're not on horseback). They even sent us photos and media afterward. My mom still talks about it.

Rapid City & Sioux Falls: Quick overnight at the Hilton Garden Inn in Rapid City (clean, easy, close to everything). Then a night in Sioux Falls — we stayed at Hotel on Phillips downtown, which is a nice boutique spot. Falls Park is free and worth the stop, even if you're just passing through.

The bottom line: South Dakota is wide open, gorgeous, and way less crowded than the national parks out west. If you like road trips and don't mind driving, it's a perfect week-long trip from the Midwest. Pack sunscreen, bring a cooler for the car, and don't skip Deadwood.

Skye · Jan 2, 2019 · 10 min read · Warsaw, Kraków & Zakopane

Christmas markets in Poland: 10 days, three cities, and my dad seeing where his family came from

In December 2018, I took my parents to Poland for their 40th wedding anniversary. My dad's family came from near Kraków, and he'd never been. So when I found a 10-day guided culinary tour through Poland's Christmas markets — Warsaw, Kraków, and Zakopane — I booked it before I could talk myself out of the price tag.

The setup: The trip was organized through Milwaukee Food & City Tours and run by Poland Culinary Vacations. Our guide, Sarna, met us at Warsaw's Chopin Airport holding a sign that said "Milwaukee Guests" — and from that moment on, we didn't have to think about a single thing. Our group of 16 traveled in a Mercedes Sprinter van, which sounds cramped but was actually comfortable, and Sarna handled every hotel, every meal reservation, every weird currency question.

The highlights: Warsaw's Old Town market at night was magical — the lights, the handmade ornaments, the smell of mulled wine everywhere. Kraków was the one that mattered most; we spent two full days there, walking the same streets my dad's family left generations ago. Then Zakopane, in the Tatra Mountains, where my dad stood in the town square, looked around at the wooden architecture and the peaks behind it, and just went quiet. That was worth the entire trip.

Practical stuff: We flew LOT Polish Airlines out of O'Hare (direct to Warsaw, which was clutch). I exchanged currency at Travelex before we left but honestly, ATMs in Poland give you a better rate — look for Bank Polski PKO machines. Visa and Mastercard worked everywhere; AmEx not so much. Tipping is about $10/day for guides and $5 for the driver, which felt reasonable for the level of care we got.

What I'd tell you before you go: Layer everything. It was December and the weather swung from "pleasant walk" to "I can't feel my face" within the same afternoon. Bring a rain jacket even if it's not in the forecast. And if you're doing a guided tour, lean into it — let someone else handle the logistics so you can actually be present. That's what made this trip special. I wasn't staring at Google Maps. I was watching my dad take in a country he'd only ever heard about.