City weekend itineraries for groups
Trip ideas · City weekends
A city weekend with friends works when each day stays in one part of town: less time on the subway, more time together. These plans hit the classics, mark what to book ahead, and leave ideas for if there's time.
Itineraries
- New York, NYCity weekendNew York in 3 days with friendsGrand Central TerminalBrooklyn BridgeThe High LineTimes Square3 days15 stopsSee the plan
- Chicago, ILCity weekendChicago in 3 days with friendsMillennium ParkLincoln Park ZooGriffin Museum of Science and IndustryThe Art Institute of Chicago3 days13 stopsSee the plan
- San Francisco, CACity weekendSan Francisco in 3 days with friendsAlcatraz IslandGolden Gate Bridge Welcome CenterMission Dolores ParkCity Lights Booksellers3 days15 stopsSee the plan
- Washington, DCCity weekendWashington, DC in 3 days with friendsWashington MonumentU.S. Capitol Visitor CenterGeorgetown Waterfront ParkWorld War II Memorial3 days19 stopsSee the plan
- Seattle, WACity weekendSeattle in 3 days with friendsPike Place MarketBainbridge Island Museum of ArtVolunteer ParkChihuly Garden and Glass3 days18 stopsSee the plan
- New Orleans, LACity weekendA New Orleans weekend with friendsJackson SquareGarden District Book ShopNew Orleans Museum of ArtThe Historic New Orleans Collection3 days16 stopsSee the plan
- Nashville, TNCity weekendA Nashville weekend with friendsRyman AuditoriumThe ParthenonNashville Farmers' MarketCountry Music Hall of Fame and Museum3 days11 stopsSee the plan
- Charleston, SCCity weekendA Charleston bachelorette weekendRainbow RowFolly Beach County ParkKing StreetWhite Point Garden3 days14 stopsSee the plan
Planning tips
One area per day
Group days that are close together, so nobody spends the trip in rideshares.
Book the timed tickets
Observation decks, museums and popular restaurants sell timed slots. Note them on the plan so someone books them.
Leave room
Two or three planned stops a day is plenty for a group. Keep the rest under If we have time.
Travel light on planning
Add the itinerary to Freya and everyone has directions, drive times and the weather for each stop.
City weekend packing list
A light list for a long weekend in a city with friends. Add it to Freya and friends claim what they’re bringing.
Questions
How many days do you need for a city weekend?
Three days covers the highlights of most cities for a first visit, especially if each day stays in one neighborhood.
How do you plan a city trip with a group of friends?
Start from an itinerary, add it to Freya, and let everyone swap stops and vote on dinner. Friends join from a link with just their first name.