Opinionated trips, curated by us and drafted by our AI. Filter by what you want to do, how long you have, or how you want to get there. Showing train and drive trips only.
11 picks across the catalog.
Old streets, new restaurants, the kind of walking that earns dinner.
Three hours south on I-35, Austin stops being a tech-bro punch line the second you check into the Carpenter Hotel and walk to Launderette for dinner. East Sixth is still a mess, but Rainey Street after 10pm and Franklin's at 9am are both worth the specific effort.
A Michigan harbor town that figured out how to be a beach destination without losing its mind. Galleries on Water Street, a dune climb that earns the lake view, and a hotel that used to be a chain saw factory. Two hours from Chicago and it feels like you crossed a border.
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Two hours up I-95 to the Maine coast city that figured out how to be a food town without turning into a food scene. Lobster rolls that locals actually eat, a walkable peninsula, and a harbor that still works for a living. Stay at the Press Hotel in the old newspaper building and eat like you mean it.
Colonial Williamsburg is still there, and it's still good — better, actually, when you're the one choosing to go. Stay at the Williamsburg Inn, where the lobby fireplace has been lit since 1937. Walk Duke of Gloucester Street at 8am before the interpreters clock in. This is the version of Williamsburg your teacher couldn't afford.
Sand, oysters, the kind of porch where the day just goes.
A Michigan harbor town that figured out how to be a beach destination without losing its mind. Galleries on Water Street, a dune climb that earns the lake view, and a hotel that used to be a chain saw factory. Two hours from Chicago and it feels like you crossed a border.
Two hours up I-95 to the Maine coast city that figured out how to be a food town without turning into a food scene. Lobster rolls that locals actually eat, a walkable peninsula, and a harbor that still works for a living. Stay at the Press Hotel in the old newspaper building and eat like you mean it.
Drafted by our agent, kept on the list when they hold up. Labeled honestly.
Two hours south, the desert city that got food right before Phoenix did. Sonoran hot dogs at midnight, a tasting menu in a converted gas station, and a mid-century motel with a pool that photographs better than it has any right to. Stay downtown, walk 4th Avenue twice.
Red rocks that photograph better in person, a spa town that earned it, and hiking that starts at your hotel door. Three nights gets you past the vortex tour buses and into the version of Sedona where the light at 7am is the main event.
Six hours west of Austin, a town of 1,700 people has better art installations than most cities and a taco truck that closes when it closes. Three nights gets you past the Prada hoax and into the version of Marfa where you're up at sunrise for the light, not the Instagram.
Two hours on Amtrak and you're in Park Slope or Williamsburg without touching Manhattan. Coffee roasters that ship nationwide, a natural wine bar where the bartender remembers your second glass, oysters at a corner spot that doesn't take reservations because it doesn't need to. Brooklyn is the weekend move when you want a city trip that doesn't feel like sightseeing.
Mass MoCA in the morning before the busses arrive, a long lunch at Allium, James Turrell's sky-space at sunset. Three nights in the Berkshires is the culture weekend that doesn't make you choose between the museum and the hike — you do both, then eat dinner somewhere that sources from farms you drove past.
Two hours up the coast, you walk off the bus into a port town that got serious about food before anyone else was paying attention. Lobster rolls that cost what they should, a small hotel overlooking Casco Bay, and a Friday night that ends at Eventide around 9pm because that's when the oyster counter gets good.
Two hours north of Atlanta, a riverfront city that fixed itself without turning into Asheville. Rock City if you're into that, but the real move is the St. Elmo neighborhood for dinner, a night at the Dwell Hotel, and a morning coffee at Velo that makes you wonder why you don't leave town more often.
Three hours south on I-35, Austin stops being a tech-bro punch line the second you check into the Carpenter Hotel and walk to Launderette for dinner. East Sixth is still a mess, but Rainey Street after 10pm and Franklin's at 9am are both worth the specific effort.
A Michigan harbor town that figured out how to be a beach destination without losing its mind. Galleries on Water Street, a dune climb that earns the lake view, and a hotel that used to be a chain saw factory. Two hours from Chicago and it feels like you crossed a border.
Two hours up I-95 to the Maine coast city that figured out how to be a food town without turning into a food scene. Lobster rolls that locals actually eat, a walkable peninsula, and a harbor that still works for a living. Stay at the Press Hotel in the old newspaper building and eat like you mean it.
Colonial Williamsburg is still there, and it's still good — better, actually, when you're the one choosing to go. Stay at the Williamsburg Inn, where the lobby fireplace has been lit since 1937. Walk Duke of Gloucester Street at 8am before the interpreters clock in. This is the version of Williamsburg your teacher couldn't afford.
