Travel Itineraries
Real two-week itineraries I'd book myself — Italy, Greece, Croatia, Scotland, Alaska, and a comfort-first de Camino Francés walk. With Mexico next. Steal whatever's useful.
- Italy — The only road trip of the bunch. Tuscany's greatest hits, then over the Apennines into Le Marche — the same scenery, art, and food with a fraction of the tourists, and white truffle season just opening in September.
- Greece and a two-option detailed itinerary — Athens plus a Cyclades island-hop through Paros, Naxos, and Santorini (Paros being the anti-Mykonos). The detail page adds the full alternative: skip the ferries and post up at one all-inclusive resort in Crete, Rhodes, or Kos.
- Croatia — An open-jaw Dalmatian run: fly into Dubrovnik, ferry north island by island through Korčula and Hvar, fly home from Split. No backtracking, and the cheapest island ferries in Europe.
- Scotland — Edinburgh to Glasgow by car through the Highlands, Loch Ness, and the Isle of Skye — timed for September, when the midges fade, the crowds thin, and the light goes autumn gold. Pack waterproof everything.
- Alaska — The one cruise on the list. Round-trip from Seattle up the Inside Passage — Ketchikan, Juneau, Skagway — capped by a full day of glacier cruising in Glacier Bay, plus a cruise-line shortlist built for a small group.
- Camino de Santiago — September/October. A 10-day "best of" the Camino Francés (Roncesvalles to Burgos) built for comfort, not suffering: boutique hotels and paradors, bags transferred ahead, walk the great stretches and taxi the dull ones — and you land right inside Logroño's San Mateo wine harvest festival.
- CDMX and San Miguel de Allende (coming soon) — Mexico City's food, art, and altitude paired with the colonial calm of San Miguel de Allende. Less a two-week vacation than a scouting trip for somewhere you might actually want to stay a while.