Happy October Everyone,

Many of you know my love for the travel industry.

Not just “travel” itself, but the whole apparatus powering my favorite and most rewarding way to spend time and money. Traveling is one of the last great human-proof experiences.

While living and traveling through Europe in 2015-16, I used Airbnb a ton. It was still relatively fresh on the scene and provided a unique alternative to hotels/hostels.

Some of my favorite travel memories are in Airbnbs: an Italian woman making us the best bruschetta I’ve ever had after slogging through Naples trying to find her apartment. Me and 9 other friends sleeping on the floor of a makeshift photography studio/apartment in Munich for Oktoberfest. This view on NYE in Istanbul:

Ironically, some of the most memorable travel moments stick with us because they emerge outside our routine and our comfort zones. The best stories often entail something going “wrong” or at least “different” rather than being smooth, easy, and predictable.

Wander’s CEO John Andrew Entwistle put it well:

Speaking of Wander, I’ve been interested in the company since hearing about them earlier this year. I’ve discussed them a bit previously but didn’t feel I could fully comment on the experience until I stayed in one myself.

Wander is a Series B startup that offers luxury short term rentals with hotel-grade amenities and 24/7 concierge service. This resonated with me as someone who has gone from a broke college grad running around Italy to someone entrusted with designing and managing 6 figure luxury travel itineraries for UHNW clients.

I understand the nuance and intricacy of balancing “wanderlust” with reliability. When you’re dropping big money on a trip - you want to be able to count on the basics (especially accommodation) to allow room to appreciate the serendipitous moments with friends and family along the way. Not knowing where you’ll sleep tomorrow might work for a young backpacker in SE Asia - not for a family or group of friends on PTO.

This is one area where hotels have been able to build a moat against Airbnb. You know exactly what you are getting at a Belmond, Hilton, or Six Senses. The branding, the level of aesthetic quality, the service, amenities, food. Airbnb can’t offer this. Even though homes can absolutely make for a more unique and intimate experience (especially for groups), there’s not enough consistency and reliability across the Airbnb inventory.

Wander is attempting to solve this, and after my first experience this past weekend - I can see the vision.

Booking a Wander

I chatted with a few members of the Wander team over the past few weeks and was able to book 2 nights at Palm Springs Haven. The booking process was personable and straightforward. Most importantly: I felt like a VIP.

To start, I was immediately connected with a member of their concierge team who outlined the available homes over the dates of my trip. I was treating my fiance and her family to a Paul McCartney concert in the desert and needed a 3 BR home within 30 min of the arena.

Haven perfectly fit the bill and came out to ~$900 for 2 nights. That’s $450/night for 6 people. 1 hotel room for just 2 people would cost that much for the same quality.

Factor in a $500 Dining Credit from Wander in the form of a Visa gift card and we are flying.

When booking: you can of course view and seamlessly book homes through the website or app, but it’s always nice to have the human element of the concierge available. Remember, empathy can’t be automated.

24/7 Concierge

Speaking of concierge…

We got in late Sunday night. The house was meticulous and vibey. There was a handwritten note from the CEO. Everything was perfect - until the jacuzzi wouldn’t turn on.

I immediately opened the app and messaged the concierge. The response was instantaneous, friendly, and helpful. Within 5 minutes, that jacuzzi was on.

This was definitely the biggest “a-ha” moment of the trip. 

You can’t plan for everything, and sometimes things go awry. To have the 24/7 concierge on call is the type of luxury touch that I’ve seen clients pay tens of thousands of dollars for. Not even kidding.

Providing that service to every member is a huge selling point. Hotels often only reserve that service for the cream of the cream (if they even have it) and Airbnb Hosts are often regular people with jobs, families, responsibilities…they’re not your concierge.

The House

As I mentioned - the house was perfect. The pictures and descriptions are accurate, wifi is fast, all the good stuff.

Without a doubt - my favorite part of Wander homes is the subtle branding, which I feel is actually incredibly important to the guest experience.

Wander’s inventory is highly bespoke and curated. Only the best properties are approved. Some might appear more cookie cutter gentrified, other’s might have a bit more flair or personality, but they are all top-notch properties. This matters, and pulling up to a home with a Wander sign in front is the short term rental version of pulling up to the Four Seasons.

The brand represents a quality you can rely on and an experience you are excited for. You know what you’re getting thanks to the familiarity and strength of the brand, but there’s just enough difference in each stay thanks to the homes and destinations themselves.

From branded toiletries to robes to outdoor signage - it strikes the perfect balance of visibility and subtlety.

My Takeaway

Overall - an awesome experience. I’d probably give it a 9.3/10. The jacuzzi lights didn’t work and I couldn’t get late check-out. I asked for it because I know my clients do all the time (especially last minute) and I wanted to see their response.

Those are nit-picks in what was otherwise an experience that met, if not exceeded, expectations.

Wander occupies a perfect niche between hotels and Airbnb. In some ways, it offers the best of both worlds.

The challenge will be how to build their moat in an industry ripe for AI disruption. Everyone, including myself, asks Chatgpt for travel advice and suggested itineraries now. Soon, ai agents will be able to actually book our travel, not just recommend hotels or restaurants.

My biggest issue with this is where these ai tools are getting their data to make recommendations. Wander has a unique opportunity to leverage their curated inventory and community of travelers to provide recommendations and services that people can actually trust. If I use an ai chatbot to search from homes on Wander, I know they’re all going to be vetted and up to standard.

If I ask my Wander concierge for dining recommendations, they could have a restaurant list curated by previous guests, and I would be more inclined to trust it than Yelp. I’d trust the taste of fellow Wander travelers than the masses on the internet.

I want the team to win. I believe traveling is more important than ever in today’s algo-driven slopfest. The more enjoyable traveling experience, the more enjoyable people, the more enjoyable world.

This Week’s Playlist

Did I mention I booked a Wander in order to see Paul McCartney?

This week’s playlist features 10 of my favorite songs from the show.

Enjoy…

RP WEEKLY!!!!!!