Most of my work is custom, comprehensive itineraries for families and milestone gatherings, always with 4- and 5-star hotels and operators. I also happily book hotel stays and quick getaways for clients, and for those who love them, small-ship cruises and escorted journeys with lines like Silversea, Regent, and Tauck.

I'm compensated two ways: the planning fee you pay directly, and back-end compensation built into trip costs — commissions and wholesale-rate margins from our supplier partners. Trip pricing is always presented as a package total; our partners' negotiated rates are confidential.

It depends on the destination and the season, but most Dash & Ramble itineraries begin around $15,000–20,000 in land arrangements before airfare. That number is a beginning, not an estimate: a family in peak-season Italy will land well above it. The Budget Guide above gives honest starting points by destination.

Yes, and please do. Hotel-only bookings are welcome, and Virtuoso properties come with real perks when booked through me, like breakfast and property credits. You can even book on your own through my Virtuoso portal. What I don't take on is designing a fragment of an itinerary, like arranging only the tours for a trip planned elsewhere; the value of design work is in how the whole fits together.

No, and it's a quality decision. I'm accountable for your trip from beginning to end, so I only book accommodations I can stand behind: vetted hotels, resorts, and villas with professional staff and someone answerable on-site. If a villa is what your trip calls for, my network includes professionally managed villas that deliver the space and privacy people want from a rental, without gambling on a listing. If a self-managed rental is essential to your plans, I'd have to decline assisting with that portion of your trip.

Earlier than feels necessary. The best hotels and guides sell out first, and school-calendar travel puts every family in the same few weeks. For spring Japan or summer Europe, reaching out 9 to 12 months ahead keeps your first choices on the table. Shorter timelines are often workable; the tradeoff is fewer of those first choices.

I recommend it, and I buy it for my own trips. A canceled flight or a sprained ankle the week before departure is exactly the kind of thing nobody plans for, and on trips of this size, protecting the investment is worth the premium. I'll provide a quote with every trip. The decision is always yours, and if you decline, I'll ask you to sign a simple waiver so we're both clear.