Planning a Multi-Country Trip from Palm Beach: Why I Tell Clients to Get Help
Every multi-destination trip is a puzzle!
Multi-country itineraries are where DIY trip planning quietly falls apart — not because any single piece is hard, but because the connections between pieces are. The hotel you'd pick in Rome shapes the train you take to Florence, which shapes the day you arrive in Tuscany, which determines whether you have time for the wine experience you came for. And Venice? Forget Venice!
As a Palm Beach travel agent specializing in custom international itineraries, I handle all of that as one connected design problem.
I'm Krista Nannery, a Virtuoso travel advisor in Palm Beach. I lived in London for over a decade and traveled across Europe most weekends. I've personally been to 80+ countries. Italy is my #1 seller every year, and the rest of my top sellers are multi-country trips. I sell the whole world, but I also sell a lot of Switzerland, Japan, Egypt, and France. Here's what I've learned about why these trips need a real planner.
Why multi-country trips are harder than they look
Five reasons that compound on each other:
• Sequencing matters. The order of your stops determines your flight cost, your luggage situation, and whether you arrive jet-lagged in the city where it matters least or most. I usually open with the big arrival city and close with the slow-down stop.
• Borders create gaps. Trains between countries don't always run when their websites suggest. Visa requirements differ. Connecting through certain hubs is genuinely worse than others — Paris CDG is not Zurich.
• Hotel programs reset at borders. Your status at one chain doesn't translate. I match clients with hotels in each country that maximize the perks they actually use — sometimes that's Four Seasons in one city and a Belmond in the next.
• Local transport is country-specific. Japan trains, Italy trains, and Swiss trains all work differently. Booking windows, pass options, and seat reservation rules vary. Knowing this in advance saves you real headache.
• Pacing requires honesty. Most travelers pack too much in. I will tell you to drop a city. That's part of what you're paying for.
What I actually do for a multi-country itinerary
On a typical 14-day Italy + Switzerland + France trip, here's what's on my side of the file:
• Mapping the sequence — usually big-city arrival, mid-trip slow-down, big-city departure — to match flights and energy levels
• Booking hotels in each country through the strongest amenity program for that property: Virtuoso, Four Seasons Preferred Partner, Marriott STARS & Luminous, Rosewood Elite, Belmond Bellini Club, the Aman Liaison, the Peninsula and Bvlgari programs
• Booking trains and seat reservations — including the Bernina Express, the Glacier Express, and the high-speed routes that sell out
• Arranging private transfers with vetted English-speaking drivers between hotels and stations
• Booking private guides in each city — vetted, not from a generic platform
• Restaurant reservations at the spots that book up two months out
• VIP arrival and departure airport service where it's available — being met at the plane door and walked through immigration
• Travel insurance that actually covers multi-country complexity
• A clean handoff at every border so nothing falls through the cracks
None of this is hard for any single piece. All of it is hard at once!
How far in advance to plan a multi-country trip
Six to nine months for a normal trip. 12+ months if your trip includes:
• Peak Italy summer (Tuscany villas vanish months ahead)
• Cherry blossom season in Japan — late March through early April
• An Africa safari (the best camps cap at 12–18 rooms and the family tents go first)
• A Christmas-market river cruise
• A milestone trip during peak Greek island season
The popular hotels in popular destinations are not waiting for you.
Can't I just use ChatGPT or Claude to plan it?
Honestly, yes — for the brainstorming. AI tools are genuinely useful for generating itinerary options and comparing destinations. They are not useful for booking, for knowing which Lake Como hotel is currently in soft renovation, for which guide in Cairo is actually good, or for which side of the Bernina Express has the better view. AI is just making too many mistakes for anyone to rely on it. Most recently, ChatGPT suggested my clients take a gondola ride in Rome!
How to get started
Book a complimentary 30-minute Zoom consultation. We'll talk through what you're picturing, where you've been before, what your travel style is, and where you might consider going. If we're a fit, we'll move into a more formal planning conversation with a transparent planning fee disclosed upfront.
About Krista
I'm a Virtuoso travel advisor based in Palm Beach, Florida. I attended the University of Notre Dame for undergrad and have my MBA from the University of Chicago Booth School of Business. Before building my travel business, I spent 20 years in the investment management industry and over a decade living and working in London, England. I've personally traveled to 80+ countries and now design thoughtful, highly customized trips for travelers who value expertise, access, and a seamless experience.
