4–6+ months out
Lock the scarce things first
- Book the villa before anything else. Christmas–New Year's, spring break, and Thanksgiving are Cabo's tightest weeks — the best-run villas with the views take those weeks first, often a year ahead.
- Match the villa to the group, not the photos. Bedroom parity for couples, a real kids' setup if you need one, staff quarters if you want daily service — and an honest answer about the road in after dark.
- Decide staffed vs. unstaffed now. A private chef, housekeeper, and villa manager change what the week costs and what it feels like — and the good chefs book out for peak weeks.
- Hold flights into SJD. Nonstops from your city fill for holiday weeks; land by mid-afternoon and the arrival day still counts as a vacation day.
2–4 months out
Build the week
- Reserve the boat day early. Sunset sails and private charters go direct-to-owner through our Baja team — celebration weeks and whale season book well ahead.
- Plan the chef's menus and provisioning. Dietary notes, the welcome dinner, taco night, the one big night out — decided before you land, not at the counter.
- Book the tables that matter. Cabo's best rooms hold their prime slots for planners; the walk-in line is the tourist line.
- Arrange private transfers. A driver who knows the villa gate beats a rental-car counter after a travel day — and car seats must be requested, not assumed.
1–2 months out
The details that save the trip
- Check every passport now. Renewals take weeks, and one expired passport un-plans the whole villa.
- Travel insurance while it still covers you. Buy close to booking; a villa week is a real deposit to protect.
- Book spa, golf, and excursions. In-villa massages and tee times at the marquee courses book out in peak weeks.
- Set the group's one shared plan. A villa week works when there's one loose itinerary everyone can see — not six group chats.
2 weeks out
Confirm everything
- Reconfirm the chain: transfers, chef schedule, provisioning list, boat day, dinner reservations, arrival-time access to the villa.
- Send the final grocery and bar list — arriving to a stocked kitchen and cold drinks is the whole point of a villa.
- Share arrival details with the villa manager: flight numbers, headcount, and who holds the itinerary.
What people forget
The quiet misses
- Cash for tips — the staff make the week, and ATMs are not where you want to spend vacation time.
- Reef-safe sunscreen and a hat you'll actually wear — the Baja sun is not negotiable.
- A no-plans day. The best villa weeks leave one day completely empty.
- One person should hold every confirmation. (This is usually where we come in.)
Or hand us the whole list
This is what we do — the right villa, a chef we've eaten with, the boat booked direct to owner, and every line above handled by one advisor with a concierge team on the ground.