The Weekly Edit
walkable sandals, Chicago stays and eats, Condé Nast's top new hotels list, and AI in travel
In this week's newsletter: my top picks for walkable, chic, sandals for summer: a short list of where to stay and what to eat in Chicago; Condé Nast’s top new hotel list; and is AI good for travel planning?
Walkable sandals
As you read this I’m on my way to Greece (!). I’ve never been and I am so excited to check out. Our itinerary is PACKED - less lounging on the beach with drinks and more zipping around taking hotel tours and island hopping. Our plans include getting all 10K+ of our steps in every single day, so even though I LOVE my heels, I’ll be bringing mostly flats this round. I’ve carefully curated my collection of comfortable sandals - all of which fit my super high arches and are cute enough to wear trekking through cities but also to dinner with the GM.
The Finch sandal by Beek. This is a new to me brand (out of California - shout out to my home state), and I wore these sandals all over the Maldives last summer. They had zero break-in time, are beautiful and lightweight, and even when I broke my toe on that same trip they were the only shoes I could wear comfortably.
Reef sandals (bought on Amazon). Reef as a brand has been a go-to for me since I was a teen. These sandals manage to be cute and comfortable - and I’ve had several people ask me where I got them. Love the platform, and they are water-friendly.
Hermes Oran. I have two pairs of these and would buy more. They are elegant, very packable and break in so very nicely.
Freedom Moses slides. I have a pair of these in hot pink and they are an excellent dupe to Birkenstocks. Great for the beach or for walking around town.
Sunbeam flip flops by Beek. These are my “fancy” flip flops. I have them in black and love them. They hit the mark of being practical and stylish. Love.
Chicago Hotels + Eats
After returning from our annual academy last month in Chicago, I reached out to one of my fellow travel advisors, David Barclay, who lives in Chicago to get his take on his top spots to stay and eat in Chicago. His taste is impeccable, so if you’re headed to the windy city, bookmark this for your trip.
Hotels
In my opinion, this is the best hotel in Chicago. Impeccable service, the staff goes above and beyond for guests. It also has a great spa and is close to many boutique shops in the Gold Coast. If you like Peninsula hotels in other cities, this hotel delivers on the Peninsula experience. They also have one of the best afternoon tea services in the city, many locals go there just for tea.
A great location and great views of Chicago & the river. This hotel is great for both leisure and business travelers, and upgrading to include the Club Room is a must. Staff is very friendly and goes out of their way to make guests feel special.
A great hotel for families, as with all Four Season hotels it has many amenities focused on kids & families. I love the ice cream cart that will come by the room (or the martini cart for the adults). I have several clients that live in the Chicago suburbs and use the Four Seasons for their “staycations” as the hotel provides a relaxing experience in a great location in the city.
Restaurants
Part of the Alinea group, I think the food and presentation here is just as good and creative as at Alinea. What I like about Next is that every year there are 3-4 dinner themes (each running for 3-4 months before the restaurant switches to the next theme). Every dinner theme has been highly creative and a lot of dinner theater in addition to great food, and for travelers who visit Chicago a few times per year, it’s a great option since the menu will change for each visit.
One of Stephanie Izard’s (winner of Trop Chef) restaurants, Cabra means goat (a theme for her restaurants) and Cabra’s menu is Peruvian inspired. The food is incredible; many small plate options perfect for sharing with a group of friends. It’s located on the top of the Hoxton hotel and has great views of the city.
My favorite Japanese restaurant in the city. In addition to some of the best sushi I’ve ever had, the menu adds other Japanese foods including a variety of noodle dishes and robata. For those looking for something a little more casual, the basement is the Izakaya at Momotaro, a cozy sister restaurant that serves small plate dishes in the theme of Tokyo street food and drinks in the theme of a Japanese whiskey bar.
Condé Nast Traveler New Hotel Hot List
May means the annual new hotel hot list drops from Condé Nast Traveler. This is the 29th year of this tradition, and here’s where I’m going to highlight three on this list that I’ve been to (or will by the end of this week!).
This is one of the stops on our trip this week to Greece (pictured above), and I am so thrilled to see this space. Designed by the same architect as the Aman, and located a stone’s throw from Athens, this spot has been five years in the making and since it’s a One&Only I am expecting the service to be top notch.
The Dunlin, Auberge Resorts Collection
Located on John Island about 40 minutes from Charleston this spot is an amazing weekend getaway. Dubbed Coastal Grandma-chic by Condé Nast it is a beautiful addition to one of my very favorite hotel collections.
The Surrey, a Corinthia Hotel NYC
Being a local to NY I get a lot of inquiries for first-timers to the city, and this hotel is now one of my top recs. It’s on the UES and hits all the classic NY notes: white-glove, centrally located, classically art-deco.
Links
Here’s the entire hot list for your perusal.
The only US beach to make the world’s top 50 beaches is in Florida… which one do you think it is?
The French Riviera is still a hot spot, duh.
Is AI a good way to plan travel? Spoiler: sometimes.
This awww-inspiring meet-cute compilation of people meeting people in airport lounges.
I’m booking for summer 2025 trips right now, as well as already into the fall and festive - and already have inquiries for Spring Break 2026. Reach out if you want to get on my calendar, I’d love to work on a trip with you!
If you enjoyed this, would you be kind enough to give it a little heart? I hope you have a nice week!