Best Weekend Trips for Groups That Don't Want to Take PTO
Friday night out, Sunday night back, and it still feels like you went somewhere.
Sam Whitaker
Contributing writer
April 30, 2026 · 7 min read
A weekend trip lives or dies on the Friday flight. If you land at 11pm and everyone's exhausted, you've bought two days, not three. Get the Friday afternoon flight and eat the cost of leaving work early.
From the Northeast
Portland, Maine. Ninety minutes to two hours by car from Boston, or a cheap short flight. Excellent food, walkable, and a group of six can rent a whole place in town for the price of two hotel rooms. Best May through October.
Washington DC. Train from New York, no airport at all, and museums that are free. Good for the group that includes two people who'd rather look at something than sit by a pool.
From the South
Charleston. Small enough to do properly in two days, and the restaurant scene is the point. Book Saturday dinner four weeks out or you'll be eating at 5pm.
Nashville, Sunday to Tuesday. Half the price of a Friday arrival, and the honky-tonks are still open.
From the West
Palm Springs from LA. Two hours by car, a house with a pool, and no flights involved. The purest form of weekend trip: arrive, get in the pool, leave.
Vancouver from Seattle. Three hours by car with a border crossing that can add an hour on Fridays, so leave earlier than you think.
Weekend logistics that matter
- Carry-on only. Bag reclaim for six people costs 40 minutes you don't have on a two-day trip
- One restaurant booked before you leave, ideally Saturday
- Pre-arrange the airport ride both ways rather than negotiating it in a terminal
- Pick one anchor activity, not four. Weekends collapse under ambitious itineraries
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