Greece

Greece is the trip travelers say they want to do "someday" until we tell them what's actually possible in 9 nights. Three days in Athens gets you the Acropolis, Plaka, and a day trip to Cape Sounion. Three nights on Santorini covers the caldera at sunset, a winery tour at Domaine Sigalas, and a private boat day along the volcanic coast. Three nights on Mykonos gives you both ends — the windmills at sunrise, the beach clubs by afternoon, the white-and-blue lanes of Chora when the day-trippers leave.

We book the boutique cave hotels in Oia that go to friends-of-the-house first, the ferry classes that aren't visible on aggregator sites, and the private boat captains who know which Caldera spots are quiet at noon.

• Acropolis with private licensed guide, before public hours
• Santorini caldera by private sailboat with onboard lunch
• Domaine Sigalas wine tasting with the winemaker
• Mykonos beach club day at Scorpios or Nammos
• Day trip to Delos — the archaeological island
• Optional add-on: Crete or the Peloponnese

Greece runs May through October. June and September are the windows we route most — warm water, manageable crowds, no August heat or August prices.