🗝️ The Upgrade | Weekly by Anne Marie Brown.
Issue 10 · I Love You, But I Won’t Travel With You
In The Upgrade this week:
Pre-Departure – I love you, but I won’t travel with you. Not every friend is a travel friend, especially when you have kids.
The Room Report – Reporting Live From Estelle Manor with My Kids
The Lobby Bar – Four Seasons is coming to Sevilla, the Sagrada Família's completion, Mandarin Oriental's Mallorca debut, a Kerzner leadership move, the World Cup hotel flop, and what's happening at U.S. international airports this summer.
Travelers,
I’m reporting live from Estelle Manor with my Bougie Bunnies this week - read the Room Report to see how it’s lived up to my expectations a year later and with my children in tow this time.
Given the complexities of traveling with my own children, how do I select another family to spend the kind of concentrated time together that travel demands?
The answer is my rubric below. After my 20’s and 30’s spent learning how I travel with others, and what works best for my style of travel, here’s my unfiltered take on traveling with friends
Happy travels! Anne Marie
My little family on a Land Rover experience at Estelle Manor
🗝️ Pre-Departure — Hospitality Hot Takes
I love you, but I won’t travel with you
After some very number-heavy articles the last few weeks, this week’s The Upgrade | Weekly is more of a personal essay / rant. I’m currently traveling on a 3.5-week trip with my children and husband through Europe, and have observed families traveling together in the wild.
I like to think my kids are great travelers. The truth is, they are kids. Jack is basically Calvin from Calvin and Hobbes and is just as likely to launch a stick at his sister’s head as to agree to wear an adorable suit jacket (see my IG this week). Malia is easily one of my favorite people to travel with, but is in constant need of my 100% attention - which makes it difficult to produce work like The Upgrade or you know, trips that I design as part of my actual job.
From the safety of my sunglasses, I silently judge other people’s children as they throw their spaghetti at each other, while praying my own children won’t do the exact same thing in five minutes. We swear we won’t break out the iPads, and then by day 3 we are so desperate for a meal where no one has a meltdown due to the time change that we cave and we are that family.
We will meet up with another family towards the end of our trip and share a villa for a week. I am certain that after 2 weeks of concentrated time with my own children sans childcare, we will be more than ready for a week with our friends.
We have traveled with these friends several times over the duration of our friendship. Our kids get along great whether we are in the mountains of Colorado or in a villa on Lake Como. They are up for spending similar amounts as we are on things like restaurants, memorable experiences, and hotels, and they keep similar schedules. This is pretty much a unicorn situation.
Friends at home and travel friends are distinct groups, and they do not necessarily overlap.
When you find a fellow travel family who approaches parenting, airport timing, travel budget, and trip pacing the same way you do, hold on tight. Treasure them forever.
Traveling with a mismatched friend or family, on the other hand, can ruin a friendship or relationship.
Over time, I have identified certain things worth discussing before you go overseas with another family or friend. Have these conversations early, (and be honest). It will save the friendship and your sanity.
1. Be Super Clear About Your Accommodation Budget.
This is perhaps the most obvious and yet most difficult discussion to have ahead of time. You need to ask your friends:
“How do you allocate your budget for a trip? Are you looking to maximize your dining experience and don’t care about the hotel? Are you a business-class-only traveler who prefers Airbnbs over dropping $2k per night on hotel rooms for your family? What is an amount that would feel shocking to you to spend on a restaurant bill or an excursion?”
I have many friends that are perfectly comfortable sharing a queen bed with their spouse in an Airbnb. I am not that person. My spouse is like a giant furnace, and queen beds spell disaster for us. Trust me, no one is happy when I don’t sleep.
My travel is precious to me, and I would sacrifice a lot of other comforts at home (or maybe a limb), to have a more ideal experience when traveling.
Table stakes for me include: a king bed for us, a real bed for my kids (not a couch), air conditioning in bedrooms and main area, and good pillows. I undoubtedly prefer hotels to rental homes, but will make an exception and share an Airbnb if I’m traveling with another family that I know and trust will travel the same way we do.
If you are considering travel with other friends, get on the same page about what you are comfortable paying per night for lodging before you book anything.
I have made this mistake before and been out more money than I’d like to admit when a friend changes their mind and I’m stuck with a non-refundable hotel room or rental house that I wouldn’t have booked if it were just my own family.
The bottom line is this: never take the financial risk for accommodations until the other family has confirmed they are 100% in and the day they will pay you by (preferably the same day you pay the deposit).
Get travel insurance – specifically cancel for any reason coverage - in case they cancel, and include it in the total amount of the trip that you split from the beginning.
Also, make sure they have looked at flight pricing before booking anything. A surprising number of people don’t factor in flight costs and then pull out of a trip because the flights end up being too high.
If this is a difficult discussion to have, don’t travel with that friend and move on.
2. What’s better – rental home or hotel?
Rental homes can be great for common spaces and cooking meals in, but they almost always create uneven room situations that nobody wants to negotiate on arrival.
Who gets the Master? Who gets the pullout? The unspoken rule seems to be that the person who books the rental home gets the Master bedroom. However, there may be occasions where one family has a baby that needs space for a pack-n-play that only the Master has, etc.
Different friends may also have a different understanding of dividing costs based on which rooms each person get. I found this was more common in my 20’s on bachelorette trips when budgets were tight, but this disagreement rears its head even today for friends who travel with extended family and are expected to pay the same when they have been delegated to the trundle bed as the cousin/sibling/family who take over two rooms for themselves and their children. At that point, you’re just subsidizing someone else’s vacation. Go with a hotel.
Make sure to discuss room allocations and price per family before anyone books the rental home.
I’m typically team hotel for this reason: everyone gets the room they paid for, and there’s no awkward conversation after a long travel day.
3. Match your pacing and routines.
My children are early risers. I’ve lived an entire lifetime by the time a 10am sleeper emerges. I have some family members that are like this and it drives me crazy on a trip. I find myself asking my kids to tiptoe around in the morning to avoid waking them up, we push activities to accommodate their late starts, and I just end up feeling resentful.
I completely understand if they want to sleep in on a vacation, but that trip will not be with me and my kids.
Have a frank discussion with your friends about daily routines and expectations before you travel together. If you’re a morning lark and they are a mid-afternoon pigeon or a night owl, it’s not going to work.
4. Set a commitment timeline.
I know my travel plans six months to a year in advance. If I ask a friend or another family to join us on a trip, I need a commitment or a “no” as soon as possible.
I am, admittedly, a speedy decision maker. If I bring up a trip with another friend and they say, “Yeah, let’s do it,” I’m going to take that seriously and begin making plans. I have learned that for a lot of people, “Let’s do it” really can mean anything from “I’m in, let’s go on the date you mentioned, I’m ready to book” to “I would like to do that before I die but I can’t believe you took that discussion seriously – how could you be so obtuse?”
Friends, there are other people I can ask, and if it’s going to be just our family, I’ll plan accordingly.
One of my biggest pet peeves is when a friend won’t say “yes” or “no” within 1-2 weeks. Their indecision gums up the planning gears. I have learned to set a deadline and ask for a “yes” or “no” within that time frame.
Yes, I am incredibly privileged to have the financial resources to hire child and pet care if we are going to be out of town. I also co-own a company, so don’t have to request PTO. My parents are no longer alive and my family all lives in another state very far away, so I occasionally have to rely on my in-laws, who are absolute saints.
That said, I’ve never understood people who can’t commit to things quickly outside of those constraints.
Keeping someone waiting while you decide is not a small ask. Clear is kind.
5. Share the mental load.
I plan travel for hundreds of clients every year. I love the initial planning stage: choosing the hotels, selecting the activities. There is a reason this is my chosen career.
However, my vacation is my vacation from work. I do not love being the sole person on a trip who: navigates where we are going on Google Maps, changes restaurant reservations, texts everyone what we are doing the next day because people would rather borrow my brain than pull up the itinerary in their email, herds the group like a kindergarten teacher.
The time for input from the other travelers on a trip is during the early planning process, not mid-trip, not the day before the activity, not when we check in to a hotel. If you wanted to do something else, you should have brought that up during the 20 emails we exchanged 6 months ago.
I am not the tour director on a trip that I am not being paid to travel on.
Everyone should listen to the house or hotel orientation.
Everyone should be willing to look up directions on their phone and navigate, not just the person who decided to pay a data plan.
Everyone should read the itinerary and check it every night, so there aren’t nonstop questions of “Where are we going tomorrow? What are we doing next?”
The best travel companions take ownership of something, whether that’s booking restaurant reservations, being the navigator, or handling the group’s activity payments and tipping.
Share the mental load and don’t just be a passenger princess. If you want to add someone to the dinner reservation, you make the call to the restaurant – you don’t ask the person who made the res to make adjustments because your plans changed.
6. Be responsible for your own stuff.
You did not leave your brain at home. You are an adult. I am not here to remind you to get your passport out of the safe or track down the sunglasses you left in an Uber.
7. Practice time management.
If everyone is waiting on you, that is a problem. If you know you need to use the restroom before a drive, handle it before you come downstairs. Don’t wait until everyone is loaded in the car to disappear. You are not my child and I will leave without you.
8. Read your texts.
A trip requires communication. Pay for international cell service, charge your phone, and bring a battery pack charger out with you each day.
I should not be the only person on the trip with a charged phone and an international data plan. You should not rely on hotel wi-fi for your phone data.
9. Your friends are not your bank.
Split everything or take turns paying for meals. Decide which of these options you will commit to with your friends before you depart.
Use Splitwise and make sure everyone knows how to set it up before you leave so there’s no excuse that they didn’t understand it.
Everybody on the trips settles their Splitwise before you fly home. Don’t make your friends chase you down for payments.
Go to your local bank and pull out enough of cash in the local currency of your destination at least a week in advance – sometimes, you have to order it for the branch to get it in. Plan accordingly.
Get enough cash before the trip (if going to a country with sketchy ATMs) that you aren’t relying on other people to be your bank. This seems to be on an ongoing issue we encounter when traveling with friends even in our 40’s, such that I’ve now taken to texting everyone a week before hand and reminding them we are pulling out enough cash for our own family, but everyone should be prepared with enough to tip etc.
Practice all the above and you will have a better time. These are lessons we all have to learn at some point between age 21 and 40, but hopefully this article shortened that learning curve a bit for some of you.
🗝️ Room Report — Reporting Live From Estelle Manor with Kids
It’s rare that I make it back to the same hotel twice in one year. However, I had such a spectacular time at Estelle Manor over my birthday a year ago, that I left saying I wanted to bring my children to experience the hotel.
In an unusual Room Report this week, here is my experience as to whether the hotel lived up to the hype in my head. I will caveat this review with calling out that we had a great a time this week during our stay. Estelle Manor has only been around for 3 years, and does a lot of things really well that drive me nuts at other places with higher ADRs (read my article “What Luxury Hotels Get Wrong” for my punch list). They are figuring out their identity between members club, luxury hotel, and family-friendly resort. This is a difficult task. Since they’ve decided to make the family friendly aspect a priority, my review is an honest report of our family’s experience.
Unit we stayed in: Woodland Cabin
Children are not allowed to stay in the main Manor house, but can stay in the Stable Rooms, Garden Rooms, houses, or Woodland Cabins. The Woodland Cabins are little wooden octagonal homes with two bedrooms, two bathrooms, and a central fireplace.
Room Positives:
Much more space to spread out than the Garden Room I stayed in last year. Having two bedrooms has been amazing as everyone adjusts to the time zone. We have loved our evenings around the fire, watching the rain from the rocking chairs on the front porch, and letting the kids adventure in the woods out back.
Room Negatives:
There is a surprising lack of clothes storage. Each bedroom has a large wardrobe with two drawers and an area to hang things….and that’s it. If you are a packing-cube evangelist like me, you will need to resort to floor organization. Our situation started out ok… now it’s chaos. No one can find their underwear. We are missing a single shoe. My anxiety is high.
The cabins are very dark. They seriously need more lighting in here - especially the bathrooms. I have completely given up on makeup.
The fireplaces are made of glass, in the center of the room, immediately at little kid height. My son is 5 and the amount of times we say “Don’t touch that!” after lighting a cozy fire in the evenings is…stressful, to say the least.
Dining:
For some inexplicable reason, most dining outlets do not open for lunch until 12. For any parents of young children, this is a major issue. By then, my kids are losing their ever loving tiny minds. You can’t even order from the pool QR code until 12pm on the dot. Give me fries or give me death. If Estelle Manor hopes to develop their kid-friendly reputation, this needs to change immediately as it’s torture. There are grab-and-go sandwiches and a handful of options from the Potting Shed, but they need to add kid-friendly options to this menu.
The brasserie - one of the better meals we have had with our kids. Service was fast. Breakfast is a simple buffet that’s not blowing anyone away, but it’s included and honestly, my kids mostly survive on a diet of croissants and prosciutto for breakfast during trips anyway.
The Armoury (Japanese) was as good as I remembered it, but the tables are tiny and my kids dropped their chopsticks about every five minutes.
The Billiard Room does not allow children - we are eating there tomorrow on a much-needed date night.
The pool food situation needs help - the menu is small and it takes a long time.
The terrace would be a better option if it opened earlier.
The Glass House - this is their casual pizza and burger option. We ate on the patio and that was great so our kids could go explore the garden and make friends at other tables of families also trying to get their children to not throw pasta at each other.
It is important to note that photos are not allowed inside the Manor House or the restaurants, apparently. This is a shame as they are such beautiful spaces, but thankfully, I have some photos from my last time here.
Activities -
We were looking forward to lead-led horseback riding for our Bougie Bunnies, but the hotel has a different pony that can accommodate kids under 6, and apparently that pony just retired. So, I was left with the choice of watching my littlest lose his mind while his sister rode and he didn’t, or scratching the whole exercise. I chose the latter.
We did the falconry walk in the forest and my kids loved it. I liked that it was different from the falconry displays we’ve done at places like Adare Manor.
Last year, my girlfriends and I did the Ineos Grenadier Off Roading course and that was SO much fun. They have since stopped that activity, sadly. We were able to take a vintage Land Rover out with a guide for a woodland walk and picnic. The kids loved it, and we learned a lot from Mac, our guide, about the flora and fauna in the area.
We rented a James Bond car – My husband and I were the first guests to take out the hotel’s snazzy new Morgan car for a 3 hour spin through the villages of the Cotswolds. I LOVED it. We would have kept it out all day, except we had to be back to pick up our children at the Nook. This is a stellar option to live your Grace Kelley dreams.
Be advised that a lot of the activities have age limits that start at 7 or 8 (archery, ax throwing, ropes courses). I’m going to work with their adventure team to put together a Travel Dispatch guide with the perfect three days for each age group to feature here on The Upgrade.
The pool - in another blow to the family-friendly nature of the hotel, they only allow kids to swim in the pool from 9-11am and from 4-5pm. The British countryside has been freezing at 9am, so my kids haven’t been willing to hit up that first slot. By the 4pm hour, every other kid in the whole resort jumps in for their brief splash time, and I honestly think the funneling of kids into these time periods is making the whole thing worse. To temporarily solve this problem, the hotel has built a play fountain. They do have plans for another pool for kids in the future, but these sorts of projects take a while. We absolutely utilized the play fountain, though our kids required frequent warming up in the little shower beach hut.
The spa - kids are not allowed in the Eynsham baths at all. No one under 18. I would lower this to 15 if it were me, but it just means this won’t be on my mom-daughter hit list when Malia is a teen.
Childcare options:
The Nook is the kids’ club for kids under age 8. They allow you to book for 2 hour increments max, and you have to sign up quite far in advance of your stay. Also important to note that they don’t take the kids outside at all during that time period. My kids love a good craft project, but they are pretty over being inside by now. Babysitters are bookable but also have to be booked quite far in advance. We tried to book one for an additional activity on arrival, and they couldn’t find anyone.
They also have this inexplicable penchant to book massages and activities for the exact moment you are allowed to check in your child to the Nook. The spa is on the opposite side of the estate, so logistically, this just doesn’t work.
Which brings me to pre-planning.
Again, I am a professional planner. I’m highly organized. I love spreadsheets, and make the majority of my travel plans weeks or months in advance. Planning with the Estelle Manor team was a bit of a cluster. I was sent a link to activity options, which I then laid out in an email to the Friends of Estelle team (because I had stayed here before, I was put in touch with these wonderful people). Things started out fine, although they didn’t have some of the activities and dining on the days I requested. Then, it became a “who’s on first” situation where the Adventure Team, Spa Team, and Reservations teams were all copied in and told to respond to me with options for what was available.
This is not a luxury experience. What a concierge or luxury-level hotel pre-planning team should do in such a case is to work with those various teams themselves, have one person own the client communication, and then reach back out to the client with a proposed itinerary that has been reviewed for feasibility and accuracy.
We ended up with activities missing, things double booked on different days, overlapping activities, and about 15 more emails than was necessary.
To the hotel’s credit, the GM did come meet with me on arrival after I expressed my frustration with the process. A lot of how I judge a hotel is not in their mistakes, but in how they recover. And so far, they have done a great job winning me back on this trip.
Overall:
TLDR - Estelle Manor has a lot going for it, and we’ve had a lot of fun with our kids. Some frustrations need to be addressed - the pool hours, the kids club only allowing 2 hour increments and not having any outside time, how hard it is to book babysitters, lunch options not opening until 12pm, not enough options for kids under 7 for activities. The pre-planning situation should be overhauled as soon as possible.
Would I recommend this to clients still? Yes, with a lot more discussion about these restrictions so they know what they are booking. I think the hard product is still lovely and I’d come back with my girlfriends or husband again. My kids would also love to return, if they change the pool hours.
I’ll post some more photos and videos from our stay here over the next couple of days.
🗝️ The Lobby Bar — Hospitality updates, promotions, and the occasional pun
Four Seasons is coming to Sevilla. Opening in 2028, developed with Spanish investment firm Blasson, the property sits on Plaza Nueva in the Arenal Quarter. 55 rooms across five stories, architecture by Madrid-based Lamela, interiors by AD100 honoree Belén Domecq. Three outlets, a rooftop restaurant and pool, a spa, and skyline views. If Sevilla is on your list, start planning now.
The Sagrada Família is structurally complete. On February 20, 2026, the final piece of the Tower of Jesus Christ was installed, bringing Gaudí’s basilica to its full height of 172.5 meters, now the tallest church in the world. Construction began in 1882.
Mandarin Oriental has opened in Mallorca. Mandarin Oriental Punta Negra is now open on the Costa d’en Blanes peninsula, the brand’s first property in the Balearic Islands. 131 rooms, suites, and bungalows, six restaurants, seven acres of gardens, direct access to two secluded coves, and a seaside wellness retreat overlooking the Mediterranean.
Kerzner has a new head of global operations. Kerzner, owned by the Investment Corporation of Dubai and the group behind One&Only Resorts, Atlantis, and fitness-focused SIRO, has promoted Mattheos Georgiou to oversee all three brands, reporting directly to CEO Philippe Zuber. Georgiou joined Kerzner in 2022 as Global VP of Operations and has been instrumental in elevating service standards across the portfolio. Three very different brands, one person accountable for all of them.
Pay attention to this if you're flying internationally this summer. DHS Secretary Mullin has proposed pulling Customs and Border Protection staff from airports in sanctuary cities, including Newark, New York, Chicago, LA, and San Francisco. Not enacted yet, but the industry is taking it seriously. If you're routing international itineraries through any of these airports, build in flexibility now.
The World Cup hospitality boom didn't materialize the way anyone expected. According to the American Hotel and Lodging Association, 80% of hoteliers in U.S. host cities reported bookings tracking below initial forecasts, with Kansas City seeing nearly 90% of properties running behind normal June and July levels. Visa barriers, geopolitical concerns, and high ticket prices all suppressed international demand. In cities like Boston, Philadelphia, and Seattle, survey respondents described the tournament as a "non-event." FIFA also quietly cancelled a large portion of its block-booked hotel rooms across host cities, which had inflated early demand signals. The takeaway for anyone still trying to book: rates in several markets have actually dropped, and availability that looked impossible a year ago is now there.
The friends who travel well together are worth more than the trip itself. Figure out who those people are before you buy the plane tickets.
Alpenglow Travel | alpenglowtravel.com | AnneMarie@alpenglowtravel.com |
Enjoyed reading this article and especially the bit about Estelle Manor! Also, how adorable does Jack look in that suit coat😭 Your kids are really cute! 🧿💗
We just got back from 3 English country stays with our toddler and I loved your Estelle breakdown. Love comparing notes and hearing where others are enjoying taking their kids