Full report↓ Edmund & DapoBachelor trip 2027
When to go
Dates

When to go

The calendar is worth more than the city. Four windows to book, four to avoid.
2027 calendar

Wednesday in, Sunday out. Four nights, five if the PTO allows.

The weddings are August 5 and 7, so May or June it is. Memorial Day is Monday May 31 and Father's Day is Sunday June 20. A Wednesday arrival gets the cheapest flights and puts golf on Thursday and Friday when tee sheets are open; stretching to Monday makes it five nights. Vegas is the one place the weekend nights roughly double the room cost, so a Sunday to Thursday pattern is the Vegas version.

Best windows

Book
Wed May 12 to Sun May 16

After graduations, before Memorial Day. The mildest window: Orlando and Austin in the mid 80s, Nashville and New Orleans at their most comfortable, Vegas and Phoenix still under 95. Myrtle Beach golf still at shoulder prices.

Book
Wed May 19 to Sun May 23

Same logic, midweek start. Barefoot drops to $135 to $149 from May 17. We-Ko-Pa is $169. Crawfish still on in New Orleans.

Book
Wed June 2 to Sun June 6

Innisbrook and Streamsong at low season, New Orleans hotels at the trough, Scottsdale resorts at summer rates from May 31. Before CMA Fest.

Book
Wed June 23 to Sun June 27

Cheapest golf: Caledonia and True Blue summer rates start June 22, We-Ko-Pa drops to about $109. Hottest of the four windows.

Avoid

Avoid
May 27 to June 1

Memorial Day weekend. Saturday hotel nights run 36 percent above midweek, flights spike, lake rentals peak.

Avoid
June 9 to 14

CMA Fest in Nashville, 100,000 fans a day at the new Nissan Stadium. Rooms vanish.

Avoid
June 17 to 21

Father's Day weekend, plus any guy with kids is out.

Avoid
July 1 to 6

July 4 week and Essence Fest in New Orleans. Peak heat in Vegas and Phoenix, peak humidity in Florida. Tahoe's celebrity golf week follows July 7 to 11.

Next step on dates: get both grooms to pick two of the four green windows in order of preference, then poll the group for blackout dates against those two. Lock by early January 2027 so room blocks and tee times can go out.