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, NY · 3 days · 15 stopsNew York in 3 days with friendsA first-timer's 3-day New York plan for a group: Midtown views, the Brooklyn Bridge at sunrise, the High Line, the Met and Central Park, with pizza and deli stops on the way.First trips to New York, long weekends, groups of 2 to 8
- Chicago, IL · 3 days · 13 stopsChicago in 3 days with friendsA 3-day Chicago plan for a group: the Bean and the Art Institute, an architecture river cruise, deep dish two ways, Lincoln Park and Wrigley Field, and the Skydeck to finish.First trips to Chicago, summer weekends, groups of 2 to 8
- San Francisco, CA · 3 days · 15 stopsSan Francisco in 3 days with friendsA 3-day San Francisco plan for a group: the Ferry Building and Alcatraz, North Beach, a walk across the Golden Gate Bridge, Lands End, Twin Peaks at sunset, and burritos in the Mission.First trips to San Francisco, long weekends, groups of 2 to 8
- Nashville, TN · 3 days · 11 stopsA Nashville weekend with friendsA 3-day Nashville plan for a group: the Country Music Hall of Fame and the Ryman, hot chicken, Lower Broadway's honky-tonks, 12 South, and a night at the Grand Ole Opry.Birthday and bachelorette weekends, music fans, groups of 4 to 12
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.
More kinds of trips
- Bachelorette weekend itineraries
- Group camping trip itineraries
- Build your own itinerary, or import one from Google Sheets or Docs