The Calendar

2027

The events people build a whole trip around. We go deep on four. For the rest, we plan on request.

Super Bowl LXI

Sunday, February 14, 2027 · SoFi Stadium, Inglewood, California

Presidents' Day weekend, and the hardest hotel market in the country that week.
Daytona 500 Racing Passport

Sunday, February 21, 2027 · Daytona International Speedway, Daytona Beach, Florida

Handled by Racing Passport.
NCAA Men's Final Four

Semifinals Saturday, April 3. Championship Monday, April 5, 2027. · Ford Field, Detroit, Michigan

You have to book before you know whether your team is in it. Here is how that actually works.
Kentucky Derby

Saturday, May 1, 2027. Oaks Friday, April 30. · Churchill Downs, Louisville, Kentucky

The 153rd running. The infield does not see the finish line, and most people find that out too late.
Indianapolis 500 Racing Passport

Sunday, May 30, 2027 · Indianapolis Motor Speedway, Indianapolis, Indiana

Motorsport is handled by our sister site, Racing Passport, where Robert has been going to the Indianapolis 500 for 27 years.
MLB All-Star Game

Home Run Derby Monday, July 12. All-Star Game Tuesday, July 13, 2027. · Wrigley Field, Chicago, Illinois

Wrigley's fourth All-Star Game, and the first since 1990.