Planning Note 17 · 5 min read · By Scot, Operations & Production
What dates to avoid when booking your 2027 retreat
The dates are the first decision and the hardest to undo. Here is the 2027 calendar, and the windows we would book.
2027 at a glance Tap a month
Tap a month to see what to plan around.
Best windows Mixed Avoid
Pick the wrong week and you lose people before you have even chosen a venue. Pick too late and the best places are gone. Here is what to plan around in 2027.
Federal holidays and long weekends
| Holiday | 2027 |
|---|---|
| New Year’s Day | Friday, January 1 |
| Martin Luther King Jr. Day | Monday, January 18 |
| Presidents’ Day | Monday, February 15 |
| Memorial Day | Monday, May 31 |
| Juneteenth | Saturday, June 19 (observed Friday, June 18) |
| Independence Day | Sunday, July 4 (observed Monday, July 5) |
| Labor Day | Monday, September 6 |
| Indigenous Peoples’ Day | Monday, October 11 |
| Veterans Day | Thursday, November 11 |
| Thanksgiving | Thursday, November 25 |
| Christmas | Saturday, December 25 (observed Friday, December 24) |
Observances that matter to your team
Some dates shift by a day depending on the moon, and Jewish holidays begin at sundown the evening before, so confirm closer to the time.
- Lunar New Year: February 6
- Ramadan: about February 8 to March 9. If it overlaps, plan for evening meals.
- Easter: March 28
- Passover: sundown April 21 to nightfall April 29
- Rosh Hashanah: sundown October 1 to nightfall October 3
- Yom Kippur: sundown October 10 to nightfall October 11
- Diwali: October 29
Weeks people are busy
- Spring break, early March to mid-April.
- Summer, late June through August, when family travel peaks.
- Thanksgiving week and December 20 through January 1.
- The last week of every quarter, when sales and finance are closing.
- Tax week, around Thursday, April 15, for finance teams.
For our favorite places
- Palm Springs and the desert: the best weather runs October to May. Avoid the Coachella and Stagecoach festival weekends in April, when rates spike across the valley, and the summer heat from June to September.
- Napa: harvest in September and October is beautiful and busy, with premium rates. Late spring is calmer.
- Lake Tahoe: plan around ski season weekends, or embrace them.
- Ojai: lovely most of the year. Spring is green and quiet.
The windows we would book
- Mid-January to early February: sales kickoffs and Map the Year. The most competitive weeks, so book early.
- Late April to mid-May: spring planning and Recharge, once Passover ends.
- Mid to late September: fall leadership offsites, before quarter-end and Rosh Hashanah.
- Late October to mid-November: year-end Celebrate retreats, around Diwali and before Thanksgiving week.
How far ahead
Start looking 6 to 9 months out and sign the venue 4 to 6 months out. Larger groups and peak weeks need the longer end. Smaller teams in quieter weeks can move faster.
For the astrologically curious
We would not move a retreat for it, but some of you will ask. Mercury is retrograde in 2027 from about February 10 to March 3, June 11 to July 5, and October 7 to October 28. Traditionally a time to review rather than launch. A good excuse for a reflective retreat, if you need one.
