First name / friend, I’ve got a hangover.

The kind that comes from the best time.

 

Not a physical hangover. A heart hangover. The one I get every time I have to say goodbye to my brother after we’ve spent quality days together somewhere in the world.

 

I always dread this part, but it reminds me every single time how important it is to make space for the people you love… on purpose.

 

It’s not easy. Everyone’s busy. Schedules don’t line up. Flights leap in price. Life gets full, routines get comfortable, and suddenly six months or a year go by without seeing the people who matter most.

 

If relationships are something you value, you have to make room for trips to be together---those for the laughs, the stories you’ve told a hundred times, the new memories, the occasional tears, the moments where you remember exactly why these people are yours. 

 

Even when it’s inconvenient. Even when it costs more than you want. Even when it means stepping out of your normal rhythm for a few days.

So this week, in honor of those we love most, I'm thinking about the kinds of places that are especially good for trips to share with them.

 

No bucket list trips.

No over-scheduled itineraries. Places where it’s easy to fall into step together again, no matter how long it’s been.
 

The trips where you walk a lot, eat a lot, talk a lot…and where you don’t need a plan to have a good time together.

 

 

A less obvious city trip
Retro Euro beach town
Low-country Southern living
A road trip in Spain

Montreal has that perfect mix of energy and ease. Great food, walkable neighborhoods, cafés that let you linger, and just enough European feeling to make it feel like you went somewhere without actually going that far for the US crowd. You can do a lot or nothing at all and still feel like the trip was full.

 

📍Stay: Hôtel William Gray or Four Seasons Montreal

Forte is summer the way it used to be. Bikes everywhere, beach clubs with the same families that have been coming for decades, long lunches that turn into late dinners. It’s social, relaxed, but plenty to do if you choose, and once you’re there, the days fall into place easily.

 

📍 Stay: Villa Roma Imperiale or Pensione America

This is a trip for slowing down. Mornings with coffee on the porch, long dinners, time on the water, warm air, and an easy Southern pace for the conversations that stretch for hours. Pair a few days in Charleston for charm, drool-inducing food, art, and sweet Southern hospitality, then head out to the islands for porch days.

 

📍Stay: The Dunlin (the islands) and The Pinch (Charleston)

One of my favorite parts of Spain for trips where the plan is simply to gently explore. Mountains, wild coastline, small cities like Oviedo and Gijón, seafood, cider, long meals, and drives where you pull over just to look around. It’s beautiful without being showy, and perfect for the kind of trip where the best moments happen in between the stops.

 

📍 Stay: Palacio de Luces and Solo Palacio

You don’t need a big reason or lots of fuss for these trips.

No milestone required. No once-in-a-lifetime excuse.

 

Just a few days carved out on purpose with the people who know you best.

 

If you’ve been thinking about a sibling trip, a friends trip, or finally getting something on the calendar with someone you never see enough, carve out the time.

 

The right place makes all the difference and I'm happy to help you find it. Send this to your travel mate and click below to tell me what kind of trip is on your mind.