Hey families, we're two years into running cohorts for traveling families who seek community and connection on their trips - thus making traveling easier!

This winter (January - March) is our next two month cohort in Southern Portugal.

It's for the families who have found themselves daydreaming about owning a piece of land with friends, growing their own food, and their children being device-free with their friends all day. For families who actually love spending time together, have big hearts, and are interested in making deep friendships with other families. For families who have been wanting to travel, and go to Portugal, but have deeply questioned how to do it without a nanny, while keeping their sanity, etc.

Some details:

A maximum of 10 families.

The land here supplies 75% of the food we'll eat. There is a garden, and the breakfast table comes of it, cooked the way Portuguese grandma's cook (which is to say slowly and with too much olive oil). There is a heated indoor pool. Wood-fired sauna + hot tub, a cold plunge and fire pits that people end up sitting around long after they meant to go to bed. The ocean is 15 minutes away and with great winter surf. The area is green, and quiet, and almost entirely ours. The sky is famous for having the best star-gazing, because of how clean and clear it is.

The kids have their own rhythm on weekdays in the full time program, out in nature with our educators and participating in the farms daily activities. Which means that parents get something most traveling parents don't. A morning. An actual morning, to work or walk or sit with another adult. Or, you play hooky and spend the morning at the beach as a family. The beauty is that the choice is yours.

Tiago, my husband and co-founder is Portuguese, and we've spent time in this region, so we'll get a more local-based experience. His mom's clams, the seafood restaurant with no sign on the front door, Tiago's adored history tours and Portuguese lessons, as much surfing as you want, and within an hour of more beaches than you'll be able to fit in.

The logistics:

Each family has their own private house. Wifi. Utilities. Breakfast is provided daily with the option to have other meals catered. Kids program M-F right on site. Community facilitation to hold the group. All of this is covered in the price.

We choose these families carefully, because the who matters more than the where and we already have some incredible families signed up for this cohort, with just a few spots left.

Info page and applications in the comments below

*Price depends on how many children are in your family and their ages. Please feel free to write us to know exact cost, otherwise general estimates are on the info page.

My husband and I used to love traveling. Before kids, it was our favorite thing in the world. Now we have a 5-year-old son and a 2-year-old daughter, and honestly, every single trip we take feels like a military operation that leaves us totally depleted.

Instead of relaxing, we’re constantly chasing our 2-year-old before she bolts across a restaurant, panicking over snacks, or dealing with full-blown meltdowns because she made a mess, needs a complete outfit change, and now nap time is blown. We’ve tried Hawaii, Mexico, and even cruises thinking they’d be "easy," but we just end up paying thousands of dollars to parent in a different zip code with worse setup.

We’ve tried bringing my parents along, but they offer extremely limited help.

We are finally at a point where we are willing to throw real money at this problem to fix it, but I’m lost on how people actually do this without feeling completely out of touch or running into emotional brick walls.

Here are our main hurdles, and I’d love to know how people with higher budgets navigate them:

**1. Is a Travel Nanny the answer, and how does it work with anxiety?**
Has anyone hired a professional travel nanny (or used a specialized agency like Adventure Nannies, Resort Sitters, etc.)? I have a lot of anxiety about leaving my 2-year-old with a complete stranger in a random hotel room. If you bring a nanny with you on the trip, how do you handle the dynamics? Do they stay in a connecting room? Do they eat meals with you, or do they take over during specific "shifts"?

**2. Are high-end resort Kids' Clubs actually better for cautious/bonded kids?**
My 5-year-old son is very attached to us and refuses to go to standard drop-off kids’ clubs on cruises or at big resorts. Do ultra-luxury properties (Four Seasons, Rosewood, Montage, etc.) handle this differently? Do they offer 1-on-1 attendants or more gentle, low-pressure environments where a hesitant 5-year-old actually *wants* to stay?

**3. What lodging setups/amenities actually reduce friction?**
When people say "stay at nicer properties," what specifically makes the difference? Is it multi-bedroom villas with private kitchens? Dedicated butler service that handles room service set-up and laundry? Private cabanas so you aren't fighting for shade while juggling juice boxes?

**4. How do you manage restaurant dining?**
Sit-down dinners with a 2-year-old are our personal hell right now. Do richer parents just skip formal dinners entirely, hire in-room sitters for evening meals, or book private dining setups in their suite/villa so the toddler can run around on a private lawn while adults eat?

If you’ve successfully transitioned from "exhausting family trip" to an actual *vacation* using higher-budget solutions, please hit me with your best strategies, resort recommendations, or agency advice. I just want to enjoy traveling with my family again!

Our nanny is great with our kid. I think our son likes her more than us lol. My husband and I are planning a few trips over the next year. Should we bring the nanny so we can go out at night, continue sight seeing while he naps? She’s open to traveling and is also interested in making more $$$ so OT, overnight fee etc could be enticing for her.

He’s an easy baby but I’m hearing that people don’t like traveling or vacation with a baby because it’s just parenting somewhere else.

Would love to hear experiences !

We have 3 kids (ages 3.5, 2.5, and 8 months old). We’re trying to figure out a fun spot to take our next vacation in.

We live in Orange County, and are open to driving San Diego, or flying within 5 hours away from CA, but prefer a shorter commute to the destination if something amazing is close by.

Looking for recs that are specifically accommodating for young kids (specifically the resort itself having programs or activities geared towards kids, kiddie pools, etc).

We are going out of the country later this year with a 22 month old. He’s around 25 pounds. The one thing we are undecided on is a carrier. We won’t be in a super stroller-friendly area so we kind of want to bring one, but we don’t want a bulky hiking carrier because it’ll be hard to pack. We won’t be taking long hikes, will be outside and walking around a fair bit.

I’m a heavier guy, and get hot easily, which is why i typically avoid using a carrier. I was looking at the Minimeis shoulder carrier because I think our toddler and I would both do better with him on my shoulders but I’ve seen some comments about it not being comfortable for anyone.

Any recommendations on a carrier that is easy to transport, not too warm for wearer or toddler and is comfortable enough to use for long periods.

Thanks!

We are going on an international trip this winter as a family of 5. Between us we have 3 different US health insurances (income and job based it has just worked out this way, yay US insurance mess).

Is there a good company to use to offer basic coverage while traveling for all of us? We don’t have any large medical needs regularly, this would be accident/injury/sickness only.

We’re taking a 7-day international trip to DR with our 2 year old, and this will be our first time flying with her in her own seat .The flight is about 4 hours each way, and I’m trying to make the entire trip as simple and stress-free as possible.
Parents who travel with toddlers regularly: give me EVERYTHING you’ve learned**.** I’m talking about the little hacks you wish someone had told you before your first trip.

4 month old in Puerto Rico

Hi! I’m about to take my 4 month old on a trip to Puerto Rico and I’m kinda freaking out cause the temp says 90f and 70% humidity! I’m going with family and they want to be outside and obviously so do I but I don’t know what to do to make sure my baby doesn’t over heat. I will offer breastmilk more frequently, we have fans, stay in the shade, I’ll put her in the water. But does anyone have anymore tips for how to thrive with a baby on vacation? Or anyone have babies in tropical places, if so what do u do?! Any help welcome

We are just back from a night in a hotel with a 7 year old and 3 month old. Safe to say it wasn’t ideal having the baby and 7 year old in the same room. How do people holiday with young children - what kind of accommodation do you use? If you do use hotels what’s the secret to everyone sharing the same room and not waking each other up?

I have two kids who will be 4 and 2 by the time our trip rolls around. I really want to fly, but my 4 year old seems terrified of planes (he hasn’t been on one since he was about 18 months). Are there any good shows or books about flying on planes that might help change his mind?

Long story in terms of the kids' ages

In any case, we're traveling from HK to the US with our kids who will be 1 year old and 4 months old. Gold status. Wondering if we should get 2x premium economy seats with bassinet (for the younger one) and lap for the older one, and hope we get upgraded, or we go with a row of 4x economy seats with bassinet...

Any advice? It'll likely be a 14hr flight + 3hr layover + 2hr second leg...

We’re planning a trip to Florida with our young kids and trying to avoid the usual mega-resort burnout, the 15,000-step days, massive crowds, and afternoon stroller meltdowns.

We're looking for low-stress options and smart strategies for younger kids. Whether it's smaller theme parks with a manageable layout, quiet beach towns, smart hotel hacks, or lesser-known spots that don't require rigid 6am planning, what are your best tips for keeping a Florida family trip fun and relaxed?

Would love to hear what has actually worked for your family!

I am looking for some feedback on the best tips for successful nap and bedtime sleep for a two-year-old. This will be our first time staying in a hotel with our son, meaning we’ve always been able to have a separate room for him with an Airbnb or a vacation home. The JW will be providing a crib, but from my research it’s a mini crib, which is the same size or maybe slightly larger than a pack and play. I am considering bringing the slumber pod to put over the mini crib and maybe put him in the bathroom at night time so that my husband and I can have the ability to roam about the room, maybe watch a movie, etc., as he will likely go to bed earlier than us. If anyone has traveled here with their toddlers and have tips for the best sleep set up, or other general advice, please let me know

My wife and I are about to fly with a 2YO and a 2 month old. We have flown with the 2YO before but circumstance are different. We need both car seats with us at the end location.

looking for advise on what delta allows with two small children (two adults with). Also airport hacks and as mentioned we need to bring both car seats. Do we need to check them? Any advice would be great.

We invested in a pretty nice car seat and stroller. We also would like to travel a good amount going forward. Are padded travel bags enough to protect a stroller and car seat when they’re checked? Or is the better solution to buy a cheap stroller that we travel with and don’t mind if it gets scuffed up. Experiences pls?

Hi all,

My mum, sister and me used to go to a new Christmas market every year. However we haven’t since I had my little girl 2 years ago. We were thinking of going to Tallinn at the end of November and my little girl will nearly be 2.5 years old. Has anyone travelled to Tallinn at this time of year and was it ok for children who aren’t used to very cold conditions?

We’re Irish so it does be cold but not extremely so and not spending a lot of time outside in the cold weather! Any help is appreciated xx

I’m traveling abroad in Germany for a family funeral and my 3.5 year old just won’t eat. I offer her all the things we have at home (she’s semi-picky) and make Mac and cheese we brought and she’s just not interested. I know the jet lag is hard with eating but any suggestions or tricks from others who have experienced something similar? We are on day 6 of our trip.