HomeTripsPlacesPhotos
bothwaysGet started
Home/Travel answers/How do you pick trip dates everyone can actually do?

How do you pick trip dates everyone can actually do?

Short answer

Offer two or three specific windows and ask people to pick, rather than asking when they're free. Open-ended availability questions produce vague answers and endless follow-ups; a short list of real options gets a decision in a day.

Why 'when are you free?' never works

Asked openly, most people answer with a hedge — "probably most of June?" — which isn't a commitment and can't be booked against. Asked to choose between the 12th–19th and the 3rd–10th, the same person gives you a real answer.

How to run it

  • Pick two or three windows yourself, based on price and season
  • State the length up front: a five-night trip, not "about a week"
  • Set a reply deadline, and say what happens if someone misses it
Get the bothways app
On Android, download it from Google Play. On iPhone, add it to your home screen straight from the browser.
Download onGoogle Play
bothways
HomeExplore everythingBlogFree templatesTravel questionsTermsPrivacy
Who it's for
For couplesFor group tripsCollaborative planningFor family vacationsFor bachelorette tripsFor honeymoonsFor reunion tripsFor road trips
Compare
vs Wanderlogvs TripIt
Accept that the wrong answer for one person is better than no answer for everyone

The person who can't commit

There's usually one. Decide early whether the trip waits for them or goes ahead — and tell them that's the situation, kindly and clearly. A group of five that books beats a group of seven that never does.

Try bothways free
One shared plan, everyone edits, nothing to learn.

Related questions

How far in advance should you plan a group trip?
What do you do when someone drops out of a group trip?
How do you choose a destination as a group?
Keep exploring: All travel questions · Best places to visit · Blog
vs a Google Sheet
vs Notion
vs Google Maps lists
vs Tripsy
vs Roadtrippers
Trip planners by destination
Lisbon trip plannerTokyo trip plannerMexico City trip plannerBarcelona trip plannerRome trip plannerParis trip plannerAmsterdam trip plannerIceland trip plannerAll destinations
Travel itinerary guides
3 days in Lisbon3 days in Tokyo3 days in Mexico City3 days in Barcelona3 days in Rome3 days in Paris3 days in Amsterdam3 days in IcelandAll itineraries
Best places to visit by category
Beach destinationsFood citiesWalkable citiesBudget destinationsRomantic getawaysGroup trip destinationsOutdoors and national parksNightlife citiesFirst trip abroadWinter sunAll categories
Destinations by time of year
Travel in JanuaryTravel in FebruaryTravel in MarchTravel in AprilTravel in MayTravel in JuneTravel in JulyTravel in AugustTravel in SeptemberTravel in OctoberTravel in NovemberTravel in December
Road trips by destination
Pacific Coast HighwayThe Iceland Ring RoadThe Amalfi Coast driveThe North Coast 500The Blue Ridge ParkwayThe Great Ocean RoadRoad trip planner
Travel questions & answers
How far in advance should you plan a group trip?How do you pick trip dates everyone can actually do?How should you split costs on a group trip?How do you plan a trip when everyone has a different budget?How many days do you need in a city?How many activities should you plan per day?What is shoulder season, and is it worth travelling then?How do you choose a destination as a group?All questions
Free planning templates
Flight & Arrival TrackerDay-by-Day ItineraryShared Packing ListBudget SplitterAll templates
© 2026 bothways · plan trips with your people