Family reunion travel scene

How to Pick Dates When Everyone's Schedule Differs

Plan your trip

5 minute read · · Published Nov 4, 2026

Family reunion travel scene

The fastest way to choose reunion dates is to collect everyone's fixed limits first, lay school calendars and long weekends over the same months, then poll the family on only two or three windows that survive. Asking "when works for you?" invites forty different answers; asking "which of these three weeks?" gets a decision.

Below is the method we use with large families, including how to handle households in different provinces or countries, how to run the poll, and when to stop waiting for the last reply.

Step 1: Collect hard limits, not preferences

Before anyone suggests a date, send one short message to each household asking for the things they cannot move. Keep it to five questions:

  1. Which school district or school calendar do your children follow?
  2. Are there any weeks you absolutely cannot travel (work shutdowns, exams, medical treatment, a wedding)?
  3. How many days of leave can you realistically take?
  4. Does anyone need to avoid heat, high altitude or long flights at certain times of year?
  5. Is there a milestone date the trip should include, such as a grandparent's birthday or anniversary?

Put the answers in a shared spreadsheet with one row per household and one column per month. Mark blocked weeks in red. Within a day or two, the impossible months show themselves.

Give a reply deadline of about ten days. Households that miss it are asked once more, then planned around using the information you have.

Step 2: Map the school calendars

School is the biggest constraint for most families, and calendars differ more than people expect. In British Columbia, for example, each school board sets its own school calendar under the province's School Calendar Regulation, so two cousins in neighbouring districts can have different spring breaks and last days of school. Don't assume one date covers a whole province or state; check every family's own district.

Ask each household for a link to its district's published calendar, then mark three things on your spreadsheet:

  • Spring break for every district. If the breaks overlap by even one week, that week becomes a candidate.
  • The last day of school in June and the first day in late August or September. The usable summer window is the period when every family is out.
  • Non-instructional days next to long weekends. A Friday professional day beside a Monday holiday turns a weekend into four days.

Teenagers add their own limits: exams, tournaments, summer jobs and camps. Ask them directly, since parents don't always know the schedule.

Step 3: Overlay the holiday map

Family reunion travel scene

Long weekends save a day of leave for working adults. When the family lives on both sides of the border, the calendars line up some weeks and not others.

PeriodCanadaUnited StatesWhat it means for a mixed family
Late MayVictoria Day, the Monday before May 25Memorial Day, the last Monday in MayUsually different weekends, so pick one and expect half the family to use a leave day
Early JulyCanada Day, July 1Independence Day, July 4Close together; a trip spanning July 1 to 4 can include both
Early AugustCivic Holiday, first Monday in August (not in Quebec)No federal holidayHelps Canadian travellers only
Early SeptemberLabour DayLabor DaySame Monday in both countries, a good shared long weekend, but in many districts school starts right after it
AutumnThanksgiving, second Monday in OctoberThanksgiving, fourth Thursday in NovemberDifferent months; a November date works for Americans, an October one for Canadians

Canada's list of public holidays and the US Office of Personnel Management's federal holidays list give the exact dates each year. Provinces also have their own days, such as Saint-Jean-Baptiste Day on June 24 in Quebec, so check those for relatives who live there.

For a broader look at seasons, weather and pricing, see our guide to the best times of year for a family reunion vacation.

Step 4: Shortlist two or three windows

From your spreadsheet, pick the two or three windows with the fewest red cells. Then check each one against the destination before anyone votes:

  • Is it peak season, with higher rates and less group space?
  • Is the weather reasonable for young children and older relatives?
  • Are flights available from the main home airports on those days of the week?

Drop any window that fails badly on cost or weather. It's better to offer two strong choices than three including one nobody should pick.

Step 5: Run a two-round poll

Online scheduling polls and shared forms make voting easy. A few rules keep the result fair:

  1. One vote per household, not per person, so a family of six doesn't outvote a couple.
  2. Ask for three answers per window: "works", "works with difficulty" and "cannot attend". A single "cannot attend" from the grandparents usually outweighs any number of "difficult" answers.
  3. Set a 7-day deadline and share the results with everyone.
  4. Round two only if needed. If two windows are close, rerun the vote between those two alone.

Decide in advance who has the final say if the vote ties. In most families it's the people the reunion is centred on, such as the grandparents or the couple celebrating a milestone.

Step 6: Lock the dates and protect them

Once a window wins, move quickly. Send a save-the-date with the exact dates and arrival and departure days, and ask every household to confirm attendance by a set day. Then place the group room block and hold air seats as soon as you have numbers, because group space tied to school holidays goes first.

Not everyone will be able to come for the whole stay. Offer a core period of at least three or four nights when the main events happen, with optional extra nights on either side. Our guide to organizing a vacation with the whole extended family covers communication and roles once the dates are set.

Planning notes

Start the date process 12 to 18 months before a large reunion, and expect it to take three to four weeks from first message to locked dates. Keep the spreadsheet; you'll use the same household list for rooms, flights and payments. If you'd like us to check candidate windows against resort availability and group air before the family votes, send us the shortlist.

Frequently asked questions

What if one household can never make any of the dates?

Choose the window that works for the most households, and offer the household that can't attend a way to join, such as a video call during the main celebration or a shorter visit with part of the group.

Should we avoid school holidays to save money?

Only if the family has no school-age children or can take them out of class. Holiday weeks cost more, but a reunion without the grandchildren rarely feels like a reunion.

Start planning

Bring your reunion plans together

Start with the people, pace and moments that matter most, then build a trip everyone can enjoy.

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