HiFirst name / Good Sunday morning,

 

Fast forward to early January.

 

The holidays are packed away, and most everyone you know is staring at a calendar full of work, school, and birthdays, with the travel still a big question mark. 

 

Spring break needs sorting, urgently. Summer is an even bigger haul, and it's still wide open. And the end-of-year holidays book a year out now, so next December is already a deadline. 🫠

 

Meanwhile, you're on the couch sipping your coffee, reading the latest Travel Made Good Sunday Edition, your nervous system at ease, because your whole year of travel is already in motion, most of it booked.

 

Costalegre in April with your partner. Scotland in August with the whole fam. A Nile cruise for New Year's. 

 

You got every room you wanted, that hard-to-book Relais & Châteaux boat, and the best guides for your experiences. All that's left is to pack and enjoy the anticipation.

 

That's how several of my clients are heading into 2027, and it's easier to pull off than you'd think. It usually starts with one conversation about their next big trip, and a question I always ask after it.

 

Most of my client conversations start with the next big trip on their mind. 

 

Where, when, who’s coming. 

 

With my regulars, once we’ve talked it through, I ask, where else are you thinking about?

 

All of my clients are different, but most take two big trips a year, nine to fourteen days each, plus a shorter getaway of five to seven days in one place. Add a spontaneous long weekend here and there and a few business trips, and that’s a full travel year.

 

Planning it all at once may sound overwhelming, but it’s often easier on the eternally busy.

 

We cover the year in one conversation, your dates go on the calendar months ahead, and each proposal reaches you in the order we need to make decisions.

 

It often makes better investment sense too. You’d look at your portfolio as a whole before deciding where to put your money, and travel works the same way.

 

 

The three places were a safari, the Caribbean, and the Italian coast.

 

For the safari, they wanted the shoulder of the dry season, when wildlife gathers around the water and the camps open up at lower rates than in peak months. Late May is the sweet spot, just before the busy season.

 

For Italy, they wanted high season with their two twenty-something kids. August, when Italians are on holiday too and the beach clubs are energetic but not in places inundated with tour groups.

 

For the Caribbean, they wanted a week to slip away and relax, just the two of them.

 

How it played out. 

 

The safari and the Italian coast were their two meatier trips. To get the safari experience they wanted, we moved it to May 2028, which gives us the best pick of lodges.

 

The Italian coast goes in August, built around places Italians have gone for generations, and the more intimate sides of the places that can get inundated with travelers.

 

The Caribbean took April 2027, in the space the safari opened up.

 

That left room for another big trip at the end of 2027, and we’re in a great time for New Year’s.

 

We’re still deciding, but the Maldives is a strong contender for its festive celebrations. It would be their first time, there’s plenty of availability at this point, and once you arrive, everything is effortless. It’s perfect.

 

Our next steps. 

 

The Italy proposal went out first, because August is the most requested month on that coastline, and our partners are holding rooms while we finalize the flow.

 

Caribbean options went out next, they’ve chosen the hotel, and I’m calling my contact on property to lock in the perfect room.

 

Our local partners are already engaged for the safari, and that proposal goes out next week, once Italy and the Caribbean are settled. 

 

Then come the Maldives options.

 

Voilà! 

 

All they had to do was look at dreamy photos and experiences, decide where they wanted to make the bigger investments, and ensure calendars matched up.

 

I get to know your taste, how you and your favorite people travel together, and which day of the trip everyone starts getting cranky. I factor all of it into every trip, from the quick and simple to the big and beefy.

 

That’s the idea behind the Travel Portfolio. 

 

For clients who travel 25 to 30 days a year or more, I manage every trip on your calendar during the year, and an annual retainer, paid quarterly or in full, covers all of the planning, including any trips you throw in the mix during the year.

 

 

It’s open to current clients, and new clients start with an application. Click below and we’ll see if it’s a good fit for your lifestyle.

P.S. My books close December 11th every year until Jan 4th so I can recalibrate my mind, body, and business, and have some quality time with my family. That leaves seven weeks to get 2027 started with something magical on the calendar. 🖤

Good Trips began with a simple belief: the right hotel can define an entire trip. 

 

Founded by Katy Hoogerwerf, the studio merges design sensibility, wellness insight, and years of hospitality experience to create journeys that feel grounded, beautiful, and human.

 

We build trips to meet your lifestyle needs, whether you're seeking rest, inspiration, memories with loved ones, community, or simply fun. 

 

It's beyond travel management, it's lifestyle management. The perks, priority access, and room upgrades we secure are just the icing on the cake for our travelers.