The Ultimate Guide to Traveling with Kids and Having Help – Should you bring a nanny, use a hotel babysitter, or travel with family?
The Ultimate Guide to Traveling with Kids and Having Help!
Should you bring a nanny, use a hotel babysitter, go for it on your own, or travel with family?
Family travel is absolutely magical. Seeing the world through your little one’s curious eyes, the new experiences together, the core memories – it’s why we do it! And I firmly believe it’s totally possible to travel well and feel relaxed on your family vacation, too. But you know what helps? Having HELP. Just like at home, the occasional babysitter for a date night or nanny during the day can work wonders on your mental state and ability to show up FULLY for your family. We travel a LOT, through our businesses (my travel blog and our clothing brand), as well as on vacations (my husband and I LOVED to travel together before we had kids and we were determined not to let having kids slow us down!), as well as traveling to things like weddings and family events, too, which means we are traveling with and without help all the time, depending on the trip. I get asked a lot about this, and how it works to travel with a nanny, how we decide to bring our nanny or not, etc. so I thought I’d chat about it all here! We’ve had great experiences with help (and we’ve learned from the not-so-great experiences, as well!) and don’t worry – I’m spilling ALL THE TEA here.
Whether you’re considering bringing your nanny for a full vacation, hiring a hotel babysitter for a night out on your trip, or inviting Nana along for the ride, having a little help can make the experience smoother, more enjoyable, and allow you to be more present for everyone, not to mention get back from vacation a rejuvenated, relaxed version of yourself – which is what we all want after all, right!?
After years of traveling with babies, toddlers, and two little ones in tow, I’ve learned how impactful navigating the right help on vacation can be. This is your guide to what works, what to consider, and how to do it Jetset-style.
Should You Bring Your Nanny on Vacation?
Pros:
Built-in trust + routine, it’s like relocating your kids’ normal routine for the week, vs them feeling totally out of whack
Smoother travel days (help with packing, airport, luggage, etc.)
Date nights, spa time, solo swims with no worries because you have your trusted nanny (yes please)
Consistency for your child in new environments
Family photos!! It may sound trivial but I love having someone to some get photos easily of all of us!
Cons:
Extra cost (travel, accommodations, food – this adds UP!! And has to be worth it!)
Management: balancing nanny’s work time vs. downtime takes scheduling and management
Tips for Bringing your Nanny on Vacation:
Bringing your nanny along for a family trip can be a total game-changer if you set it up right. Here are some tried-and-true tips that have made all the difference for us when traveling with our nanny all over the world over the years:
- Set clear expectations upfront. Outline when you’ll need your nanny “on duty” and when they’re free to relax. This helps avoid burnout and gives everyone clarity, especially on longer trips.
- Create a daily schedule. Having a loose routine helps kids stay grounded while traveling, and it gives your nanny confidence in managing the day. Include meals, naps, downtime, and family time.
- Book accommodations with space. Our nanny always has her own room. This gives your nanny privacy and rest time, which goes a long way.
- Include them in the fun (when appropriate). Invite them to join a family dinner (doesn’t have to be every one! But one would be great) or activity. It creates connection and makes the trip more enjoyable for everyone.
- Show appreciation. Whether it’s a little gift from the resort, a bonus, or even just a heartfelt thank you, small gestures go a long way.
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Give them defined “on” and “off” hours. Outline when you’ll need your nanny “on duty” and when they’re free to relax. We like to keep it to a total of 8 or fewer hours per day so it’s no more than their normal schedule!
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Bring extras for the nanny & always be generous: snacks, room service, etc. Make them feel a part of the family!!!!!
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Book a room with a separate space for them, always! If it’s a hotel, they have their own room, if it’s a villa, they have their own room in the villa.
How much to pay your nanny when they travel with you:
This depends on you and your nanny and your set up together! Since travel is always discussed as a key part of our nanny’s job upfront in their hiring, contract, etc. we pay them their normal salary for travel weeks, as well. And we cover absolutely everything while traveling (of course), from meals to activities to transportation. If travel is not a part of your nanny’s normal expectations, or if you’re hiring a babysitter to be a travel nanny for a week, etc., then you should discuss a rate that feels right to both of you! Usually in these cases, it’s a flat fee agreed upon and expectations are laid out ahead of the trip.
In our case, they are paid their normal salary but if they are working over the weekend, they’re compensated more, or if it’s more than 8 hours a day ( like if we have a particularly busy photoshoot day for Kenny Flowers or something like that, and we need a little extra help), then they are compensated for the extra hours. Nap times are a part of their ‘on’ time/hours if they’re expected to be the ones watching the babies/listening if they’re getting up, etc. (but this is a nice chance for them to relax at the villa or hotel room while the baby or toddler naps!)
What HAS and HASN’T Worked for Us When Traveling with a Nanny (the good + the bad!)
What has worked well: Having a clear schedule, nanny having their own space, having plenty of breaks for them to enjoy the destination as well (and for us to have family time), we also seek out nannies who are very go with the flow, EXTREMELY helpful (especially on travel days) and able to flex and adapt easily to changing plans (delayed flights or travel mishaps are no big deal, etc!).
What has not worked in the past: We had one nanny (very short-lived, only was with our family for 3 weeks) who only traveled with us once and let’s just say we learned a lot from that one trip. Long story short, she felt like a huge added responsibility for us – like another child, rather than the help we needed, which was an instant dealbreaker. She was also nervous around traveling and travel activities (despite telling us how excited she was about the travel aspect of the job), she was not comfortable being in the water, and on boats, etc. so now we thoroughly ask every nanny we have hired their experience with water, as that’s important to our travels that someone is comfortable both in and on the ocean. I think just open communication up front before hiring a nanny or a travel nanny is key! And sometimes you don’t know what is going to be important to you until you’ve done it a few times.
The rest of our experiences outside of that one person have been STELLAR, and we looooove our nannies who have traveled the world with us. I would say the key is knowing what’s important to you (for us it’s the children’s safety & overall ease of being around them, of course, their ability to proactively help the family wherever needed, and their ability to go-with-the-flow when things may not go to plan)
Hotel Babysitting Services, Are They Worth It? When to choose a Hotel Babysitter over Bringing a Nanny with You on Vacation
Many luxury resorts offer in-room babysitting through vetted professionals. I’ve used them many times!!! And while it definitely felt scary the first time, it can be incredible for the right situation. And I’ve had REALLY great experiences (I’ve especially had great experiences at Rosewood Mayakoba or any Rosewood hotel! But most luxury resorts offer fantastic, vetted babysitters, and you’ll be so glad you did it for just a few hours of downtime, or more!)
Best for:
One-off date nights
Day spa experiences
Hiring someone to watch your baby nap so you can hang at the pool
Parents who want a break but don’t travel with a nanny full-time!
Questions to Ask:
Is the sitter CPR certified?
Do they bring activities for your little ones?
Can I book them in advance?
Jetset Tip: Bring your baby monitor (here’s one that doesn’t use wifi) and stay on property / nearby for check ins if it’s your first time using one! This helps me ease the mama stress!
Is there a kids club at your resort? You may not need as much help if so!
A lot of kids clubs are FANTASTIC and provide care for children over 4 years old.
These clubs can be lifesavers, giving your little ones fun, social activities while giving you time to recharge. From pirate adventures and cooking classes to scavenger hunts and beach games, some of the best resorts in the world are known for truly amazing childcare programs. If your resort offers one, it might reduce how much outside help (like a nanny or sitter) you need – especially for part of the day. Just be sure to research ahead of time, confirm the age requirements, and make any necessary reservations in advance.
Here are some of the best kids clubs in the world. Look into it ahead of time when analyzing whether to bring a nanny or book a sitter!
What About Bringing Family?
Having Nana, a sister, or even a close friend join your trip can be an AMAZING experience if everyone is on the same page. We LOVE traveling with my parents, and my husband parents, depending on the trip, and I wrote a guide for Traveling with Your Grandkids as a Grandparent here full of tips that we’ve learned over the years.
Pros of Traveling with Family :
Built-in love + support + no stress help
No cost (usually! But we always like to treat to meals etc. or even their hotel room if it makes sense for the trip!)
Multigenerational memories
Pack matching outfits for the whole family! Here are these ones 🙂
Cons of Traveling with Family:
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Expectations! Are they helping or vacationing??? This NEEDS to be clear, and there should be times for them to do both.
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Less structure or clear boundaries, depending on your parents and how they usually help!
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Can get tricky if it’s not your parenting style!
How to Make It Work for You:
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Talk ahead of time about how much help you’re hoping for, and what the clear expectations are
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Make sure they get some alone time, too !!!
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Book a villa, home rental, or suite with enough space for everyone to breathe
Read up on my tips for a great multi-generational trip with grandparents and send it to them too!
What Type of Trip Are You Having?
This is a big one. Before deciding on the kind of help you bring (if any), think about the intention of the trip:
Are you working during the trip? A nanny is a game changer for us personally if we’re working on a trip.
Is it a true family vacation where you’re hoping for some downtime to relax or date nights? Help is likely essential. But cost-wise it could also make sense to do more in-room babysitters for extra hands if you don’t need FULL help, all the time.
Is it more of a ‘family trip’ vs family vacation, and you want it to be all about bonding? You may want it to just be the family!
There’s a big difference between a trip and a vacation, and both can be wonderful in their own ways. Just set expectations accordingly and build your support around that. We’ve also had many trips where we do half the trip ourselves, then have help or family meet us halfway and do some of the trip with help!
What’s Right For You?
Every family is different. Here’s a quick cheat sheet to help you decide:
| If You Want… | Consider… |
|---|---|
| Daily support + consistent routine | Bring your nanny |
| One-off breaks + date nights | Use hotel babysitting |
| Free help + multi-gen bonding time | Invite family |
| Space + flexibility | Booking multi-room suites or a villa |
Real Talk: Our Experience Bringing a Nanny
We’ve traveled with a nanny on long trips and quick weekends. And while it’s an investment, it’s given us the chance to actually enjoy the destinations we’re in as a couple, and as a family.
From poolside margaritas (while the kids nap with the nanny in the room), to breezy dinners with two happy, entertained kids… it’s not always perfect, but it’s so worth it.
How often we travel with a nanny, vs use a hotel babysitter, vs bring family, vs travel on our own – and how we decide what’s right for each trip!
We do a little bit of each!
Every trip is different, and we always think through the vibe, the destination, and what we need most before deciding who to bring. Here’s a quick look at how we typically approach it:
We bring our nanny on work trips, anytime one (or both) of us will be working and we need to have consistent day-to-day help. It’s incredibly helpful to have consistent care and the flexibility to sneak away for a date night or content shoot! Think: photoshoots, work-cations, partnerships where I’m creating content for a tourism board or brand partner, adn any time where we’re juggling family time and the family business.
We use a hotel babysitter when it’s a shorter trip or we just want one or two nights out, like a Mexico or Caribbean resort or a friend’s wedding. This is also a great option when we want to travel light and keep things simple!
We bring family when it’s somewhere my parents or Kenny’s would love to be a part of (and makes sense with their schedules) or somewhere we’re headed somewhere that lends itself to a multigenerational experience — like Hawaii, Europe, the mountains, or renting a house somewhere! Having Nana along can be a gift for everyone, especially if it’s about slowing down and making memories. And my parents don’t live near us, so we do a lot of destination bonding which is SO special for everyone!
We travel just the four of us a lot too!! We do this when the trip is more about vacation than working, and when we just feel like we want to do it just us!
The key is tuning into the purpose of the trip, your energy going into it, and what you want to walk away feeling!!!
Check out: The Best Travel Essentials for Toddlers and Babies
What to remember when deciding to travel as a family with little ones:
You don’t have to do it all alone! Whether it’s a trusted nanny, a kind hotel sitter, a kids club day, or your family pitching in, help on vacation is a game-changer. It means you’re choosing presence over burnout, and you’re leaning into the type of family vacation that works for you!
