The blog.

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 didn't take a single cab 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 10 minutes, the Met in 15, and downtown in 20. 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 · Jan 2, 2019 · 10 min read · Poland

Christmas Markets in Poland: the trip that made my parents cry (in the best way)

In December 2018, I took my parents to Poland. It was their 40th wedding anniversary, and both of them are Polish — my dad's family came from near Krakow, my mom's from the Tatra region. Neither of them had ever been. So when I found a 10-day guided culinary tour through Poland's Christmas markets, 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. Krakow was stunning and we spent two full days there. But the moment that got my parents was Zakopane, in the Tatra Mountains. My dad stood in the town square, looked around at the wooden architecture and the mountains 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 tear up in a mountain town.

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

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

When someone suggests a road trip from Wisconsin to Dollywood, 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 it ended up being one of those vacations where the stops along the way were 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 kids 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 the kids were happy. 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 the Dixie Stampede one evening, which is exactly as over-the-top as it sounds but the kids were mesmerized.

Would I do the road trip again? In a heartbeat. The mix of cities, small towns, and theme park at the end felt like the perfect family trip. Just don't try to do it all in one day of driving — spread it out, enjoy the stops, and let the kids swim at every hotel pool along the way.

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.