1. An African Safari
Safaris look simple online, but they are anything but. Lodge pricing is rarely transparent, inclusions vary widely, and transportation often involves charter flights, private transfers, and strict luggage limits. Wildlife viewing depends on the season, the type of reserve, guide quality, and whether you’re in a public park or a private concession, and not all lodges allow off-road driving or night safaris. A safari planned by someone without first-hand knowledge can look perfect on paper and fall flat in reality. This is one trip where experience is everything.
2. A Cruise
Cruises are not one-size-fits-all. Cabin location, ship size, itinerary flow, port logistics, and embarkation details matter far more than most people expect, and on longer or expedition cruises, flights, weather, and ship capabilities add another layer of complexity. A knowledgeable cruise advisor knows which itineraries sell out first, which ships match different travel styles, and how to avoid mistakes that can affect the entire voyage. Once the ship sails, there are no do-overs.
3. Your First Trip to a Complex Country like China or India
Some destinations are incredible but logistically demanding, and China and India are prime examples. Visas, internal flights or trains, guides, language barriers, cultural norms, and pacing all require careful planning, and without experience it’s easy to underestimate travel times, overload your itinerary, or miss what truly makes these places special. A travel agent who has actually been there understands what’s realistic, what’s overwhelming, and how to design a trip that feels immersive rather than exhausting. Reading is fundamental, and experience reads best.
4. A Remote Expedition like Antarctica or Galapagos
Antarctica and the Galapagos are not typical vacations, they’re complex expeditions. Weather windows, ship capabilities, landing permissions, safety protocols, and strict passenger limits all shape the experience, and the differences between operators are not always clear online. I’m planning a Galápagos trip as we speak, and it’s a perfect example of how complicated this kind of travel can be, from routing flights and choosing the right vessel to aligning itineraries with wildlife seasons. This is not the place to guess or bargain hunt. You want someone who understands the nuances and matches you with the right operator, timing, and expedition style, because when you’re traveling to the edge of the world, details matter.
5. Multi-Country, Multi-Transport Trips
Trips that involve multiple countries, trains, ferries, and short flights can unravel quickly without proper planning. Europe by rail, island hopping itineraries, or routes that weave through places like Slovenia and often connect with Italy, Austria, or Croatia require smart sequencing, realistic pacing, and a clear sense of how travel days actually feel on the ground. A well planned route feels effortless, while a poorly planned one feels rushed and chaotic. First hand experience makes the difference, creating itineraries that flow, protect your energy, and maximize your time in each destination.
