Originally Posted by
Offshore171
Really curious to see how people have made this work for them, as it strikes me as a very awkward departure time.
Arrange late checkout. Have your meetings during the day, return to the hotel to shower, relax, maybe a cocktail, etc. Then have dinner in the North End (Italian). The North End is a fun neighborhood, good for walking, and really close to the airport (in driving time), so when you're ready to go, Uber or taxi will serve you just fine.