Just out of the helicopter, planning the first hike with our guide


Bon giorno Traveler,

Today I’m heading home from a blissful two weeks in Madrid, the Dolomites, Lake Garda and Milan. 

They are such different destinations, but so complementary when you like a trip full of contrasts.

As our kids grow, their time with us shortens, making the time we spend together that much more important. So I plan trips that I know our kids (and Jason and I) will love.

Allison, Jessie and Trevor love being active, great food, exploring new places, stepping a bit outside their comfort zone and doing cool things. 

With that in mind, for our family vacation this summer, I planned us a trip to the Dolomite Mountains of Italy. 

Your family may be similar to some or all of the above, but with other unique traits. The fun of creating a custom trip is learning about what makes each member of your family tick – what do you love to do? What pace of travel is just right? How much activity do you want to balance with your free time? Do you want to be active every day? Do you want to immerse yourself in the local culture? Learn about history? Speak the language? Meet locals?

What did our Dolomite Mountains trip look like?

There's not enough time to share everything so I've included below a page from my journal on day 3 and here are a few more highlights...

I chose to start us with a couple of nights in Cortina. We stayed at a new boutique hotel (with a great spa), went e-mountain biking (the kids LOVED this!) and enjoyed a Michelin star dinner. 

That was followed by a helicopter ride up to our first hut, four days of guided refugio to refugio hiking (with our bags transported for us) through spectacular landscapes, exploring WWI tunnels and staying in mountain refugios (I picked quality ones with private rooms, great food and in unique locations). There was a spectacular view at every turn.

Then two nights in La Villa, a small town in Alta Badia, in a family owned boutique hotel, with a three story spa.  We took a helicopter to see the Marmolada Glacier from above, waving at the hikers who had scaled it early that morning (see video HERE) and were dropped off at a via Ferrata.

After our final day of intense activity there were massages for all and time to soak in the hot tub and cold plunge pool (my feet particularly appreciated the cold plunge) or lounge in the sauna. More delicious food and local wines. 

After La Villa, Jason departed for home with two of our kids and Jessie and I went to Lake Garda and Milan. More on that in the next few weeks. 

You know when your 17-21 year old kids are on vacation, waking up at 7:30a, hiking 6-14 miles/day for 5+ hours, including vertical ascents of 2500+ feet, with no complaints, you've succeeded in planning a great adventure!

The above might be a lot for some people, but it was perfect for us. And that is the key for you – figuring out what combination of experiences, places, people and pace is just right for your family!

We all loved our dinner at San Brite, the Michelin star restaurant in Cortina, so much that I’ve chosen it for this week’s highlight. Read more about it below.  There were so many highlights that more will show up in the coming weeks.

As you can tell, I’m in love with the Dolomites!

They offer so much and in so many ways! 

So many adventures – hiking, mountain (or e-mountain) biking, via ferratas, paragliding, rock climbing, helicopters.

And WWI history, incredible food, welcoming people, a cultural blend of Italian, Ladin and Austrian/German, wine tasting and cooking classes. 

The brilliance of this destination is there are so many options and levels on how you “do” the Dolomites:


  • Most basic – staying in bunk rooms in refugios 
  • Moderate – staying in private rooms in refugios
  • Luxury – staying in 4-5* hotels


  • Staying in a new place each night
  • Staying in a string of a few places for two nights each
  • Having a base in just one or two places

Activity Level

  • Hiking from place to place
  • Day hikes and other adventures from your hotel


  • Unguided
  • Guided


  • Carry your own luggage
  • Have your luggage transferred for you

There are also so many places you can do a pre/post Dolomites stay. A city like Venice or Milan (easy because you may fly into those airports) are great options. Or consider by the water in Lake Garda or Lake Como or further out on the coast, Cinque Terra. Those are all doable, but of course you can combine with other parts of Italy, Switzerland, Austria or even Spain, as we did. The possibilities are truly endless. 

As you enjoy your summer vacation this year, make it a point to dream about what you want to do next summer. Because the time to begin planning it is as soon as this one is over! 

I encourage you to open up your calendar and select a date and time the first week of September and schedule in time to brainstorm, talk with your family, look at dates and then reach out to start planning. You will get your choice of the best places, guides and accommodations! And once it’s confirmed you will feel a tremendous sense of relief that you have it “on the calendar!”

The Inspiration articles below include BBC pictures of the world's best treks, France's most beautiful countryside villages, Bali's best hotels and a NYT article on the Azores.

And information regarding extreme tourism for billionaires, why walking helps us think (I did a lot walking and thinking in the Dolomites) and a hack on bypassing long waits for passport renewals. I will 100% be taking advantage of this tip!


Reach out to schedule a date in September to plan your summer 2024 trip


  • A glimpse into my journal from day 3 of our hike
  • This week's highlight - San Brite in Cortina d'Ampezzo
  • Hot New Hotel Opening - Flockhill Lodge in New Zealand
  • Inspiration + Information

I wrote this in my journal after day 3. This was the only day of the trip that wasn't spectacular weather. But even with that, we had a great time!

Can you spy Refugio Nuvolau below? (hint: it's perched on the very far left peak)

Cowbells jingling. The occasional moo of a cow.

The rising sun is reflecting off of Nuvolau mountain and in the distance, perched high up on a cliff, I get a glimpse of Rifugio Nuvolau. It was originally built 140 years ago, destroyed during the first World War and then rebuilt. It’s on my list to visit (by via ferrata) when I return.

Today and tomorrow we will continue hiking and also get an experiential history lesson climbing through bunkers and hideouts from WWI.

We have a briefing with our guide, Evaristo. Today’s weather will take a turn – clouds are already approaching. Nothing like the last two bluebird days. Evaristo shows us the radar on his phone AND glances out the window. Then he looks back at his phone – and the window again. We modify the plan. We want to beat the rain (and more importantly potential thunderstorms) that is coming later today.

We decide to take the chairlift up to start our hike (saving about 2 hours). From there we continue to climb, checking out WWI tunnels along the way. We miss out on our via ferrata today because of the weather. But luckily we have another scheduled in two days.

We walk through terrain that looks like smurfs are hiding around each flowery hill. Family debate ensues about the name of Gargamel’s cat. We come up with many ideas, but not are quite right. Finally Jason remembers it - Azrael.

After several hours we reach a decision – hike up Lagazuoi or take the gondola? Because of the weather we opt for the gondola. We spy many WWI tunnels on the ride up to Rifugio Lagazuoi. Just before landing, you get the sense you are about to to crash into the mountain, but it is an illusion and we arrive safely.

We are socked in by clouds in three directions, in what normally is a spectacular view. But as always we can’t control the weather.

I ask Evaristo lots of questions about what it’s like in winter. I learn there is a 7KM ski run off the backside of Lagazuoi. After skiing the long descent you are greeted by horses with trailing ropes and you grab on, being pulled to the next lift on your skis behind the horses (added to my list for a winter visit).

This is the highest we’ve been so far and there are a few remaining patches of snow. The spots without snow look like a lunar landscape – grey and rocky. We explore WWI tunnels and bunkers (fascinating!), getting a history lesson en route.

Two hours later we arrive a beautiful lake for a rest (and more photos-but today's just don't compare because of the grey skies). From there it’s 45 minutes of hiking steep, rocky switchbacks to reach our rifugio. We pass by natural springs that feed the rifugio’s spring water.

Thanks to the weather, this has been our lightest hiking day so far (just over 6 miles) and we feel it. Not nearly as exhausted as the other days.

For dinner I try something new - canederli pressati al formaggio. They are pressed vegetarian cheese dumplings. Very dense but delicious.

This trip reminds me of how different the various areas of Italy are. The Dolomites are nothing like Venice, Tuscany, Rome, Amalfi Coast, Puglia etc. The Ladin, German and Austrian influences are felt in the food, language, design and people that you meet.


When I was looking at restaurant options for our trip I sought out recommendations from colleagues and my partners in Italy. There are no shortage of incredible restaurants in Italy! When I decided I wanted to take the kids to a Michelin star restaurant, that helped narrow it down. I was looking for one that was well known for delicious food but also had more of a casual feel than many do. With San Brite, I found the absolute best option!

There were about 18 people dining there that night. It felt cozy, almost cabin like, up in the mountain above Cortina. 

Their chef/owner says...

"The secret of a story lies within its own existence. Mine starts from the story of a land and a family who chose this land as its home. Our barns, our animals are the memories of my grandparents. They are my father's story, they are my story. My father taught me that work means sacrifice and that without sacrifice there would be no gratification. For this reason, I try to elevate the work of my family and to celebrate my land through my dishes."

Other comments about the chef...

"Riccardo is a man who lives out of his passions. He is humble, pragmatic, and a perfectionist. When he decides to go down a path, he does it with his heart but also with total determination and commitment"

Subscribe to their instagram page if you want to fill your feed with beautiful photos that exude warmth and delicious food.

They grow many of their own items – including raising the cows that provide for the butter. Which in itself is a bit of a show. The server walks over with a bowl piled high with fluffy whiteness (picture above). It reminded me of marshmallow fluff. She lifts out a scoop and places it on top of a rock on your table. Pair that with the incredible bread and I’m already happy. 

Next arrives the amouse bouche and several other delights before our first course (we chose to do a la carte instead of the tasting menu). 

The sommelier helped Jason select a perfect wine that we all enjoyed drinking out of the most beautiful wine glasses with sky high stems. There's something about sharing an elegant dinner with delicious wine with your adult kids that is just magical.

Everyone loved everything.  

It was a wonderful experience and I highly recommend a visit if you come to the Dolomites!

📷 San Brite

🌟In January, Flockhill Lodge opened in Craigiburn Valley, South Island, New Zealand. This remote lodge was quickly named one of AFAR's top new hotels in 2023.

Why visit FLOCKHILL Lodge?

  • The lodge sits on a 36,000 acre working sheep farm. Located near Arthur's Pass National Park, the property is surrounded by mountains, rivers and lakes for views in every direction.
  • Each chic lodge is appointed with rugs and blankets handmade locally with whisper-light New Zealand alpaca wool and includes a private chef to prepare all meals, an outdoor terrace, access to the wine cellar and a swimming pool.
  • Spend your time outdoors hiking, mountain biking, kayaking, bouldering and fly-fishing.
  • Enjoy active culinary experiences including truffle-hunting or an alpine glacier picnic.
  • Free from light pollution in its remote location, stargazing is a can't miss activity. With a fire pit, hot beverages, open bar, outdoor furniture and blankets, cozy up on your terrace and get lost looking for the Southern Cross in the expansive sky.

Of course it comes with usual perks and VIP treatment when booking your stay through Truvay Travel.

📷 Flockhill Lodge

Reach out to plan your trip to New Zealand 


Super-Yacht Charters Shift to Exotic Locations at (Slightly) More Affordable Rates, Skift

The 11 Most Beautiful Villages in the French Countryside, AFAR

9 Best Bali Hotels, From Private Island Hideaways to Tree Houses,

Condé Nast

In the Azores: Earth, Water, Fire and Air, Sometimes All at Once, NYT

In Pictures: Five of the world's most remarkable treks, BBC


How to Watch Wimbledon 2023, Town & Country

This trick could help you bypass long waits for passport renewals waits for passport renewals,

The Points Guy

TSA Security Screenings Will Be Self-Service in Select Airports, AFAR

The Wild World of Extreme Tourism for Billionaires, Wired

Should You Put AirTags in Your Luggage?, Town & Country

Why Walking Helps Us Think (throwback), The New Yorker

(If you aren't able to access an NYT or Washington Post article, send me a note and I'll send it to you in a PDF.)


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