GABE + IVY: NINE DAYS IN CHILE THEIR WAY

A nine-day trip shaped around how they actually wanted to travel—with room for individual experiences, slow mornings, and a change of plans that became a highlight.

For Gabe and Ivy, a trip to Chile wasn't about seeing as much as possible in nine days. They wanted to explore Santiago and Valparaiso, experience the food and wine, and have enough flexibility to enjoy the trip at their own pace.

They also didn't want to spend the months leading up to it sorting through hotels, activities, transportation, and everything else it would take to make the trip work. In the months before they left, they had limited time to research and plan—and having someone take on that work made a trip that felt difficult to pull off possible.

The result was a trip with enough structure to make each day easy, enough flexibility to sleep in when they wanted, and support when the plan needed to change.

PLANNING AROUND HOW THEY TRAVEL

Gabe was already traveling to South America for work when he and Ivy decided to turn the opportunity into a nine-day trip through Santiago and Valparaiso.

From the beginning, Amy knew they didn't need every hour of every day mapped out. Gabe and Ivy described their travel style as laid-back, so the itinerary gave them a sense of what each day could hold without locking them into a rigid schedule. They could sleep in when they wanted without feeling like they'd thrown off the rest of the day's plans.

The same thinking applied before the trip. Rather than asking them to sort through countless accommodations themselves, Amy curated a shortlist of hotels that fit what they were looking for. Gabe and Ivy later identified that shortlist as one of the most helpful parts of the planning process because it meant they didn't have to take on as much research themselves.

The goal wasn't to plan every minute for them. It was to make the decisions that needed to be made easier, while leaving enough room for them to experience the trip the way they wanted.

MAKING ROOM FOR EACH TRAVELER

Planning around Gabe and Ivy also meant recognizing that the best experience for them as a couple didn't require every part of the trip to look the same for both of them.

Ivy has dietary restrictions that Amy considered throughout the trip. But Gabe was arriving in Santiago before her, which created an opportunity to plan something specifically around what he wanted to experience. When Amy asked what he might enjoy while traveling on his own, two things came up that wouldn't normally be part of their plans together: seafood and gluten.

Amy built his day around both. Gabe visited Santiago's historic fish market for lunch and later took an empanada-making class with a local chef—an experience Amy says he still talks about.

It was one day within a larger trip, but it reflected something important about how the itinerary came together.

Planning for two people doesn't always mean finding the compromise that works for both. Sometimes it means creating room for each person to have an experience that's distinctly theirs.

WHEN THE PLAN NEEDED TO CHANGE

Not every good plan needs to stay exactly as planned.

After walking through options and preferences for traveling between cities, Gabe and Ivy originally planned to travel by bus. Amy had mapped out the logistics, but the day before the transfer, they realized that navigating the bus station with their luggage wasn't how they wanted to spend that part of the trip. They asked if any of those original options would still work.

Amy found a local tour operator that could turn its Santiago-to-Valparaiso excursion into a one-way transfer, with a winery stop along the way. Knowing Gabe and Ivy enjoyed wine, it wasn't simply a more convenient way to get from one place to another—it was an alternative that still fit the experience Amy had planned around them.

As it turned out, they were the only guests booked that day, turning the small-group tour into a private experience. They had time for lunch, wine, and views of the vineyard before continuing on to Valparaiso.

Gabe and Ivy later called the change one of the most personal parts of the trip and said they were glad they chose the tour instead of trying to DIY the transfer.

Sometimes making a plan work isn't about preserving the original plan. It's recognizing when something no longer fits—and knowing what to do instead.

THE TRIP THEY WANTED TO TAKE

The details came together in a trip that Gabe and Ivy felt reflected their goals, preferences, and travel style. They rated the overall experience five out of five and described the accommodations, activities, and flow as cohesive and well curated.

Some of what they appreciated most was also the simplest: having a plan for each day without feeling tied to a clock, knowing the research had already been narrowed for them, and being able to change course when something no longer felt right.

And some of their favorite moments weren't necessarily the biggest ones. In Valparaiso, Ivy's highlight was sitting on the patio of their hotel taking in the views—exactly the kind of unhurried moment the itinerary was designed to leave room for.

By the end of the trip, the value of the planning wasn't just what Gabe and Ivy had done or where they had stayed. It was how much less they had needed to manage in order to enjoy it. As they shared afterward, having support with the research and planning took a significant amount of stress off their shoulders and let them simply enjoy their trip.

IN THEIR WORDS

“Working with Amy was a great experience! Having support with the research and planning took a huge load of stress off and increased my enjoyment of the entire travel experience. She was responsive to our laid back travel style and crafted an itinerary that worked perfect for us.”

— Gabe + Ivy

IT'S ALL IN THE HOW

A good itinerary isn't measured by how much you can fit into it. Before you start booking, think about how you actually want to travel. Do you want full days or slow mornings? Reservations mapped out in advance or vetted options to help you decide as you go? Does that structure make the trip easier—and when will it start to feel restrictive?

For Gabe and Ivy, getting that balance right meant having a plan without having every hour dictated. It meant making room for experiences that reflected them individually as well as together. And when the original plan for getting to Valparaiso stopped working for them, it meant having the flexibility—and support—to change it.

The itinerary should support the way you want to experience the trip—not become something you have to manage once you're there.