The Best Types of Trips to Take With a Baby (and Where You Shouldn’t Go!)

Becoming a parent changes your world in the most beautiful way. Suddenly this tiny little human becomes the center of everything… and life starts revolving around nap schedules, snack packs, and a stroller that somehow contains half your house.

But one thing I want every new parent to know is this: having a baby doesn’t mean the adventures stop.

In many ways, traveling with a baby can actually be one of the sweetest seasons of travel. Babies are surprisingly adaptable. They nap on the go, they’re happiest close to you, and they don’t need elaborate itineraries to enjoy a place. Some of our most magical family trips have been during the baby stage – slow mornings at beautiful hotels, long stroller walks by the ocean, and dinners where a baby monitor and room service turn into the easiest date night imaginable.

That said, the type of trip you choose makes a huge difference when traveling with a baby. Some destinations and travel styles make life wonderfully easy for parents, while others can quickly turn a vacation into something that feels a lot more complicated than relaxing.

After years of traveling with babies and toddlers (and helping many families plan their own trips), I’ve learned there are certain kinds of vacations that work incredibly well with a baby — and a few types of trips that are usually better saved for when your kids are a little older.

Here are the best types of trips to take with a baby… and a few I’d personally skip for now.

Traveling has always been a huge part of my life, and from the second I got pregnant, I was SO excited to travel as a family. I have been lucky enough to create such incredible memories with my family growing up as my parents took me and my brother around the world, that inspired my passion for travel, and eventually quitting my corporate job in San Francisco to move to Bali and pursue Jetset Christina full-time. I truly cannot imagine my life without travel, and neither can Kenny, so traveling with our babies and showing our child the world so that they can become a well-rounded citizen of the world is something we have always worked hard to prioritize. And we want to help you travel more (and easier!) as a family too! Travel with a baby can feel intimidating, but I promise you it’s not as complicated as people make it out to be – it’s actually really, really fun.

As a disclaimer, I just want to say that if you are not ready to travel or are not comfortable doing so with a baby, that’s perfectly okay. There is no right or wrong time to start traveling again – it is all up to you and your new little family! Only you know what is best for you and your baby, no matter what anyone else says. And hey, who says a staycation in your city (or somewhere nearby) can’t be the best vacay ever?!

For those of you who do want to travel with your baby, I’m sure you’re wracked with questions like “How soon can I travel with a baby?” and “WHERE can I travel with a baby most easily?” Which is where I come in. Here are my top Jetset-approved types of trips to take with your little one (along with a few hotel and resort recommendations for each!). I have also included a few general places that you shouldn’t go with a baby, as well as a few tips and tricks for flying with a baby for the first time.

First of all, let’s cut to the chase,

How soon can you travel with a baby?

That’s totally up to you! Talk to your doctor and see what their advice is. Assuming both mother and baby are healthy, plenty of babies fly as soon as a few weeks old. It’s a personal decision! I personally waited until both of my babies were 2.5 months old to travel with them, after their first round of immunizations at 2 months. This made me feel more comfortable taking them on planes, etc.! Plus, each time we were so excited to be home and nest with the little one for those first couple months in our newborn bubble. But then it was go time!!! We were READY to get out of the house at a couple months old – it was just what we needed as a family! Even the baby slept better on vacation !!! 

I think that the the first year is the BEST (and easiest) time to travel with a baby, so take advantage of it! At the 3-9 month old baby stage, parents really can take advantage of your baby’s flexibility, and help it to become more adaptable. Most 3-9 month old babies will still sleep a lot and even nap easily on-the-go in a carrier or car seat. Plus, babies aren’t usually mobile at this stage so you have less worries.

The Best Types of Trips to Take with a Baby

Baby-friendly beach resorts

When you dream of a luxurious, relaxing vacation, chances are, you’re dreaming of a beautiful beach (and, if you’re anything like me, an ice cold margarita). Beaches can be a great place to take a baby (as long as you are prepared with the right products to keep your baby happy and sun-safe). Be sure to grab some baby-safe sunscreen, a sun hat, baby sunglasses, a float (with a canopy!) for the pool, and a pop-up beach tent. And if you are looking for the cutest swimsuits to dress your little one in this summer, check out the best baby swimwear – and matching family vacation outfits – here! 

The Best Beach Destinations to Travel to With a Baby

Hawaii

Y’all know how much Kenny and I LOVE Hawaii! Not only did we get married here, but we also spent our final babymoon here (and we can’t wait to make more memories with our little beach babe here in the years to come!). Hawaii is great for a trip with your baby because the islands are easy to navigate, they are safe and very clean, and Hawaii prides itself on being a family-friendly vacay destination! Many of the resorts have family-friendly rooms complete with cribs, baby amenities and so much more.

Where to Stay With a Baby in Hawaii

I would specifically recommend going to either the Big Island or Maui if you are traveling with a baby and looking at which island would be best as a family in Hawaii.

On Maui, I would recommend Four Seasons Maui. Four Seasons Maui offers tons of amenities for families and couples alike (check out my post all about the FS Maui here!). 

By the way — if you’re interested in booking FS (or any of the hotels on this list), with FREE VIP Jetset Perks, you can book directly through me here. I offer complimentary hotel bookings and through my relationships with the top hotels in the world, can secure you preferred perks like daily complimentary breakfast, resort credits, and priority for room upgrades at no extra cost to you! Just shoot me an email to [email protected] with the trip you have in mind. 

On the Big Island, check our Four Seasons Hualalai (Kenny and I have stayed here in the past and it is dreamy!!). Here, you can request anything and everything to make your stay more comfortable, from a crib, playpen, diapers, wipes, a white noise machine, a bottle warmer, “little swimmers” diapers for the beach/pool, a nursing pillow, and a high chair! They also have laundry machines on property (free to use) which is an incredible convenience because it means less packing/stressing for you when traveling with a baby.

Matching family outfits by Kenny Flowers. Photo by @bebanones

Mexico

Belmond Maroma

If you’re traveling to the Riviera Maya with a baby and want a hotel that feels incredibly luxurious but also calm and easy, Belmond Maroma is one of my favorite options.

The property has one of the best beaches, and the whole atmosphere feels peaceful, beautifully-designed, intimate, and very tucked away from the bigger resort scene. It’s the kind of place where you can truly slow down with beach walks in the morning, long lunches by the pool, and relaxed dinners under the palms. It’s beautiful!!!!!!

The suites are gorgeous, spacious, and very private, many with terraces or plunge pools overlooking the jungle or the ocean. The hotel is also wonderful about thoughtful family touches — things like cribs, high chairs, and babysitting services if you want to sneak away for a date night.

If you’re looking for a luxury hotel in the Riviera Maya that feels peaceful, exclusive, and baby-friendly, Belmond Maroma is a really special one.

And if you’d like help booking Belmond Maroma or other luxury hotels in the Riviera Maya, I’m always happy to help — when you book through me as your travel advisor, you’ll receive preferred partner perks like complimentary breakfast, resort credits, room upgrades, and VIP treatment throughout your stay. Just email me at [email protected] and we can plan from there.

It’s the kind of place where you can spend slow mornings at the beach, afternoons by the pool, and just really enjoy being together.

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If you book this hotel through me via email or directly through my portal here, I can add complimentary VIP perks like daily breakfast, a $100 resort credit, complimentary room upgrades, and early check-in or late checkout when available.

The Rosewood Mayakoba

If you’re looking for a luxury resort in Mexico that will blow your expectations out of the water, and is EXCEPTIONALLY baby and kid friendly, but super luxe, it’s the Rosewood Mayakoba. We headed here when my son was just 3 months old as our first international trip with a baby, and I couldn’t be happier we did. The service at this resort is next-level, and will besure to give your family the vacation you deserve. They also have super-talented on-site nannies available, which we loved using! 

Make sure you take some time to yourselves to go to the Sense spa, which sits on its own private island overlooking beautiful, lush, limestone lagoons!

How do I get Jetset perks when booking the Rosewood Mayakoba?

For free breakfast for two at the Rosewood, a $125 resort credit, and a room upgrade (if available), contact me here and I will reach out with more information and can help book you with all kinds of fun perks (at no extra cost to you, and we don’t charge a fee to book!)

Rent a Beach House

San Diego, California

For those of you who are new around here, Kenny and I used to live in San Diego. This was our “home base” before we bought our home in Charleston, and it is a place that is near and dear to my heart as my grandparents have lived there for more than 50 years! San Diego is known for its beautiful beaches and near-perfect weather 365 days per year, making it a fabulous beach destination for families.

As an added bonus, San Diego is home to Lego Land, which is a must-see for the kids! You also definitely need to go to the San Diego Zoo (one of the best zoos in the world!), The Wild Animal Park – now called the San Diego Zoo Safari Park is absolutely amazing, or venture around Balboa Park with your little one in tow.

San Diego is a great place to rent a beach house and relax steps away from the sand. There are hundreds of great options! Personally, I would look into neighborhoods La Jolla, Del Mar, and Mission Bay. If you’re looking for a VRBO there, I would recommend something like this beach-front sanctuary or this luxury condo in the heart of the village. For those of you who are looking for a house instead of a condo, this three-bedroom home in La Jolla sleeps six!

Where Else to Stay With a Baby in San Diego

If you decide to go the hotel route, check out Hotel del Coronado, it’s great for families and I loooove the Coronado area of San Diego!

Seaside, Florida

Now that we’re living on the East Coast, the Florida panhandle has been on my radar quite a bit recently, specifically the area of 30A/Seaside. This area has some of the softest white sand and calmest, clearest blue water in the U.S., making it perfect for vacationing with your little one. When you visit, you will immediately pick up on the tranquil beach vibes as you walk past the white picket fences and quaint beach bungalows. Dreamy!

Where to Stay With a Baby in 30A

With a convenient beach entrance only a few steps away, this 2 bedroom is a great choice in Alys Beach.

Or try this adorable home in a gated community with an un-crowded beach.

I highly recommend renting a VRBO in Seaside! There are hundreds of cute beach houses that will make your stay super comfortable, especially if you are traveling with other friends or family. This beach house has free bikes and a private pool with enough room for 9 guests, while this condo is reasonably priced (only $471/night!) and is right on the water. If you are traveling with the whole fam for a reunion or family vacation, check out this incredible home where the beach is your backyard! 

If VRBOs aren’t your style, grab a room at The WaterColor Inn & Resort (rated #1 on Trip Advisor as the most kid-friendly hotel in 30A!). Hey, maybe you could wear your Watercolors Swim and matching Kenny Flowers/Kiddy Flowers at the WaterColor Inn?! 😉

Theme Park

Is there anything better than the happiest place on earth with your little one? 

Disney World

Orlando is a no-brainer when it comes to a family vacation to remember. Disney World – or Disney Land – will probably be one of their core memories from their childhood, and you can bet you’re going to have a great time, too! Also, if you are looking for a solid mix between a beach vacation and Disney, consider a Disney Cruise – consistently ranked one of the nicest cruise lines in the world!

Where to Stay With a Baby in Orlando

The Four Seasons Resort at Walt Disney World is the ULTIMATE place to stay with kids at Disney World if you value luxury and convenience. I would seriously not recommend anywhere else for a trip to Disney World!!! We stayed here and had an absolute blast with our toddler at Disney World. The FS Orlando offers top-notch relaxation with a fantastic golf course, oasis-like pool areas (both adult and family-friendly!), and even character brunches with Mickey, Goofy and friends that the kids will adore. 

Wine Country Getaway

Now I know what you’re thinking – wine country? With a baby!? But hear me out on this one, wine countries around the world are famed for their relaxing slow pace of life, delicious food, amazing hotels, and, of course, wine to keep the parents happy! I think wine country can be a great trip with a baby. Here’s where I’d go.

For my ultimate guide on Napa with a baby, check out this post here.

Sonoma, California

Sonoma isn’t just for bachelorette parties and girls’ trips! The towns surrounding Sonoma are extremely inviting, super relaxing, and many of the restaurants, although luxurious, are family-friendly. Plus, let’s face it, chances are you have been waiting a year (or more) to drink wine again when you’re pregnant. So why not enjoy California’s best wineries with your baby in tow?!

Where to Stay With a Baby in Sonoma

Montage Healdsburg

This would hands down be my pick of where to stay in Healdsburg! It’s one of wine country’s newest properties – just opened in 2020, and I think it may be my favorite in ALL of California wine country! We stayed here with my 3-month-old baby and it was just perfect. With 2 gorgeous pools surrounded by vineyard views, and modern, sophisticated, refined rooms overlooking the vines, it’s hard to beat a stay here. I also LOVED the restaurant – Hazel Hill. If you’re looking for the ultimate luxurious place to stay in Sonoma, this is your spot.

Fairmont is another brand that features family-friendly hotels and resorts all over the world. The Fairmont Sonoma Mission Inn & Spa is no exception. Here, you will enjoy spacious rooms and all of the family-friendly activities your heart desires!

Douro Valley, Portugal

On the tail-end of my honeymoon, Kenny and I visited the Douro Valley in Portugal and I was surprised at how baby-friendly Portugal is for families! It was soooo wonderful for babies.

    

We loved it so much that we returned to the Six Senses Douro Valley for a second time with our little one and when I asked if the hotel had a crib, they replied that they have absolutely everything we need for the baby, and that we should ‘bring nothing’. They also have in-room childcare available at 20 euros per hour. 

City Weekend

For those of you who can’t stand the thought of entertaining a baby at the beach and constantly wiping sand off of them, perhaps a city is more your speed! 

The Best Cities to Travel to With a Baby

Tokyo, Japan

Japan is one of the most baby-friendly travel destinations in the world. The culture is exceptionally clean, organized, and beautiful!!! It’s an amazing trip to do as a family, and they’re SO friendly toward babies and toddlers. 

We did a trip to Tokyo with our baby boy at 16 months old, but I think it would have been a good vacation spot for babies of any age! Check out our Tokyo itinerary with a toddler here.

Toronto, Canada

Canada is a fairly simple getaway for Americans looking to hop over the border for a fun international weekend. Overall, Toronto is known as a safe and clean city featuring tons of green spaces for families to relax in. It is also a very stroller-friendly city, so you won’t have any issue toting your little one around!

Where to Stay With a Baby in Toronto

The best place to stay with a baby in Toronto is Hotel X (located right on Lake Ontario!). Hotel X offers free cribs and infant beds, in-room childcare (for an additional charge), and a refrigerator to keep milk cold! Plus, their rooms are very spacious, so you and your partner will be able to have some alone time in the room after baby goes to bed without having to worry about waking him or her up.

Charleston, South Carolina

I had to put my home city in the mix! When choosing a home base, Kenny and I had several non-negotiables. Since we knew that we wanted to grow our family sooner rather than later, living somewhere family-friendly was at the top of the list. In Charleston, you’ll see babies and kids everywhere!!! From roaming around the breweries, to living their best life at the beach, Charleston is extremely baby-and-kid-friendly.

Where to Stay With a Baby in Charleston

In my opinion, the best places to stay in Charleston with your baby are Wild Dunes Resort, the Sanctuary at Kiawah, or Hotel Bennett. You can book Wild Dunes Resort via VRBO as it is a vacation rental located in Isle of Palms (known for its beaches, eateries, and sea turtles!!). 

Just be sure to have a rental car in Charleston – you’ll want it to get around if you’re planning on going to the beaches and downtown! 

Chicago, Illinois

Perhaps you are craving the busyness of New York City or Washington D.C., but you can’t quite wrap your head around what it would be like to shlep the stroller down the subway stairs – Chicago is for you! Chicago is a cleaner city than both NYC and D.C., and it is also a bit safer overall. The city is fairly compact and easy to navigate, plus, you won’t find the sky-high prices that you would experience in Manhattan.

Where to Stay With a Baby in Chicago

Warwick Allerton – Chicago was rated the #1 hotel for families in Chicago by hotels.com. This property offers free cribs and playpens for infants, babysitting services (for a surcharge), and daily housekeeping to ensure your stay is as comfortable as possible. 21c Hotel Museum Chicago also offers free cribs/beds for babies, and for mom and dad, they have a luxurious spa onsite. 

European Escape

If you’re down for an adventure with your baby, consider these dreamy European escapes

Amalfi Coast, Italy

Yes, you will use the carrier a lot (the stroller won’t work as well on those hillsides of the Amalfi Coast) but it will be worth it!!!! While many don’t consider Italy a great destination with a baby, I beg to differ – The Amalfi Coast with a baby is actually a DREAM!

Tuscany, Italy

Tuscany is known for being relaxed and serene – making it the perfect European getaway as a young family! We had a great time in Tuscany staying at Borgo Pignano as a family and spending our days by the pool, doing Italian cooking classes, going wine tasting, and going on family walks around the sprawling farm property. So fun!!!

Matching family outfits by Kenny Flowers.

Douro Valley, Portugal

We absolutely love Douro Valley in Portugal with a baby! Portugal is THE most baby-friendly European destination – you will love it!!!! We were so surprised (in a good way!) when we were rushed to the front of EVERY line in Portugal (from rental car lines to even Starbucks lines) just because we had a baby with us – they couldn’t be nicer to families. It’s amazing. 

Mountain Retreat

Once your kids turn three, they can begin to learn how to ski and/or snowboard! But even before then, the mountains are always a beautiful place to take the fam and your little snow bunny any time of year.

Vail, Colorado

Vail has beauty and luxury similar to that of the Swiss Alps without the long plane ride for those of you who live in the U.S.! It is very similar to Aspen (check out my blog post comparing the two, here!), but it seems to be more family-friendly than Aspen is. When staying at The Vail Resort, you can enjoy free childcare for infants ages two months and up!! This is a huge plus as it allows you and your partner to go hit the slopes or check out the après ski scene. Vail also has free public transportation as well as playgrounds for kids who are a bit older. 

Where to Stay With a Baby in Vail

My top two recommendations for your stay in Vail with a baby would be Four Seasons Vail or Antlers at Vail Hotel. I’ve already gushed about how great and family-friendly Four Seasons is, but here’s a little bit of info about Antlers at Vail Hotel: this resort has condominiums complete with a full kitchen, and they even offer a free shuttle to the grocery store to make cooking easy! They truly offer white-glove service when it comes to your little one – you can call ahead to pre-arrange baby monitors, car seats, and even bottle warmers!

All-Inclusive Resort

Feeling adventurous? Ready to take your baby a little further away from home? Let’s go international!! It’s time to turn that little bundle of joy into a jetsetter (just don’t forget that your baby will need a passport, too!).

Montego Bay, Jamaica

I have heard a lot of hype lately about Jamaica, and from a family perspective, I can see why! Jamaica is easy to get to (just a few hours from the U.S.), and it is peppered with all-inclusive resorts, making your stay a walk in the park.

Where to Stay With a Baby in Jamaica

All-inclusives are used to having families at their resorts, so I would opt for one of these if the idea of staying in one place sounds nice to you. Most of these resorts offer nanny services, and you can request cribs and other baby products as well! If you are open to a hotel that isn’t all-inclusive, I recommend Round Hill Hotel & Villas. This property has onsite family specialists who can arrange all family activities, particularly for your baby! Paul McCartney and Ralph Lauren have stayed here while in Jamaica, so you know it’s good!!

Puerto Vallarta, Mexico

My love for Mexico runs deep, so I can’t wait to show our little coconut all of the places we love here! Puerto Vallarta seems to be a great place for the whole family from its authentic Mexican feel to its pristine beaches and calm waters. 

Where to Stay With a Baby in Puerto Vallarta

You can’t go wrong at the Grand Velas Riviera Nayarit! This oceanfront all-inclusive really gives your baby the VIB (Very Important Baby!!) treatment. Upon check-in, you will receive toys, pool floats, and even clothes for your baby! The onsite spa offers baby’s first haircut complete with a certificate, and the chefs make fresh purees daily. Need I say more?!

Playa Mujeres, Mexico

Located just outside of Cancun, Playa Mujeres is one of the best Mexico destinations for a baby or kids!

For families and multi-generational groups, Finest Playa Mujeres is the move – since it is the only all-inclusive luxury family friendly resort in greater Cancun, and the only one of the three resorts that isn’t adults-only.

It’s easy to see why young families are drawn to Finest – not only do they have the most expansive and beautiful kids club I’ve ever seen (waterslides, movies, round-the-clock activities, full-time nannies at no additional cost (!!!!!!!) & the option to stay with your kids if you want to!), but the family-friendly atmosphere throughout the resort is one that will make every family want to come back year after year. Not to mention the relaxation that comes with not having to worry about keeping your kids occupied (or touching your wallet!!) the second you step foot onto Finest. It’s a vacation that pleases both kids and adults, with both aspects of relaxation and fun!  During my stay I also admired how many multi-generational families were traveling together and enjoying the resort together as a group, but still while doing their own things. I loved that Finest has something for everyone, so families and kids could do their own activities during the day, but meet up with their bigger groups for dinner at the end of the day.

Where You Shouldn’t Travel With a Baby

At the end of the day, where you travel is 100% up to you and your partner! However, I think that it is important to consider all of the possible cons of traveling to certain destinations with a baby.  Here are the types of destinations to avoid when traveling with a baby.

Africa

Chances are, if you are traveling to Africa, your baby may need special immunizations or malaria pills. In my opinion, this just isn’t worth the stress while juggling all that parenthood already entails! I would recommend taking the kids on an African Safari when they are older and will really remember the experience.

Somewhere With a Really Long Flight

The Maldives and Bora Bora are incredibly dreamy destinations, but traveling with your baby for 24+ hours, throwing off his/her sleep schedule, and trying to adjust to a new time zone all while caring for an infant might just be a little too much stress for you guys as a family. But, that being said, if you’re up for it, go for it! We actually DID do the Maldives and Bali with an 8-month old! And we conquered Bora Bora with a toddler!!! And we had a blast doing them, but it wasn’t for the faint of heart! I would also be sure you’re there for a long enough time to make the time zone transition worth it! 

Anywhere You Will Have to Camp or Won’t Have Necessities at Your Fingertips

Let’s be real – I don’t like the idea of camping (or even glamping), period. But staying in a tent or camper without running water or air conditioning with a baby? Forget it! Not for me. There are just too many things that you need to have at your fingertips to keep your baby comfortable IMO.

Beach Locations With High or Dangerous Waves

If you are going to the beach, you probably want the option to bring baby into the water (even if it’s just long enough to snap a cute picture for their baby book!). But if you choose a destination with high waves and dangerous rocks, your baby won’t be able to be in the water safely. Look for destinations with easy beach entrances and very little, baby-friendly waves.

Somewhere Secluded Where You Couldn’t Easily Get Help in an Emergency

The likelihood of an emergency while you are on vacation is low, but with a new baby, you can never be too cautious! Try not to choose a destination that is too secluded or is hours away from the nearest town with a doctor, just in case. And always know your ‘escape route’ in case of emergency!!!!

Check out these other blog posts

The Best Children’s Clothing Brands I’m Obsessed With

Harrison’s birth story – navigating the NICU, labor and delivery

Pregnancy must-haves

Spring baby shower inspo

The best baby registry must-haves

All about our Anguilla babymoon