Wellington Society of Madrid: Join one of the dozen walks offered by Stephen Drake-Jones, a history professor and longtime resident. You’ll get his lively perspective on topics including Hemingway’s Madrid (past clients include the writer’s niece, Hilary), the Hapsburgs, the Prado and Modern Arts museums, and the curiosities and anecdotes of old Madrid, with stops at historic taverns. From $76.
Send your dilemmas to news editor Amy Farley at tripdoctor@aexp.com. Follow @afarles on Twitter.