Transportation & Activities. Reach out to your resort concierge team ~2 weeks before travel (usually by email) to book airport/hotel transfers and any special activities that you're particularly excited about. These include private experiences like sails and beach dinners, behind-the-scenes tours and VIP access to sites. Routine things like spa treatments or group snorkles can usually be left until your arrival and typically, if available, butlers and the concierge are helpful with arranging these things upon your arrival.

Alternatively, I cannot praise Wendy Perrin Travel and one of her partners, Queen of Clubs Lifestyle Luxury Services, enough. They have together organized some of the most exclusive, special and luxurious experiences with the most phenomenally knowledgeable and professional drivers and guides. Some of my dearest memories are thanks to their foresight, insight and execution at a level that exceeded every dream and expectation. Wendy Perrin calls these her WOW! moments, and they are aptly named.

A valuable lesson: the people are the heart of any place. If you do have a private guide for a half or whole day, invite them to lunch with you (I usually insist on buying their meal). My father has made a habit of this and I now follow suit. You will learn more than you could have imagined about the true spirit of a place by getting to know your local guide. Dining with them is an opportunity to explore their personal experience as a local or to go further in depth regarding tour sites you saw earlier. When in Bellagio, we shared lunch with our tour guide for our day-long private Lake Como wooden boat tour. I never would have imagined that this detailed and highly intelligent guide was once a marketing executive for Maurizio Gucci and Tom Ford before leaving her position to pursue motherhood and then luxury guiding. I was as impressed with her as I was with the timeless and meticulous Villa Del Balbianello. We stopped with another Lake Como guide -  this time on an 8 mile walking tour - for a coffee and she saw a friend who had since had a baby. Watching them embrace as I sipped an espresso 50 ft from the lapping shores of Lake Como made me feel part of their local world, if only for a moment. Another example? Our driver from Milan to Lake Como had driven Formula 1 drivers - and we were literally there for the Monza race. My guide in London shared an anecdote about a tour he had recently given to Bill Gates and we found out we had both recently been to the same Arizona resort (Enchantment Resort, post coming soon). 

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Flights. I recommend Premium Plus/Premium Economy or First Class, especially for 4+ hour or indirect/connecting flights. Both United and American Airlines are my airlines of choice and serve all of the destinations listed on my travel page. While I have flown Economy round trip to Rome and Hawaii before, it is not preferable. The best value is for Premium Economy/Plus seating, but a splurge on First Class is always fun. The longest flight I have ever taken was to Australia from the United States and the space allowed by First Class was beyond helpful.

 

Booking Timetables. For flights, ~6 months before travel. For hotels, ideally about 6-8 months in advance. This timetable should grant you access to Early Booking rates (if offered). With that said, there are also last minute booking deals at many properties but availability and room choice may be limited by then. Either way, I recommend checking for hotel discount offers and packages on the pages linked in my articles.

If you're interested in working with a luxury planner, I encourage you to contact them at least 6-8 months in advance. The client experience is much more fun when unhurried.