Chicago North Shore Moms Travel | Chicago North Shore Moms

“It’s good to have an end to journey toward, but it’s the journey that matters in the end.”
-Ernest Hemingway 

Travel adds so much to our lives.
It’s a way to come together, and a way to escape.  It’s a refresh or reset and new adventures together.  So, in the spirit of our mission “giving moms the gift of time”, we narrowed down only the places that we would stay at again, to save you hours of scrolling reviews.
Did you know that one half of Chicago North Shore Moms is part of a service-oriented luxury travel group?  That’s right, if you need vacation help, Shawn’s your gal.  Not only have we experienced each of the properties featured first hand, but we have inside knowledge on so many more.  Shawn is affiliated with Glass Slipper Concierge and Sanborn’s Travel, a member of Virtuoso’s prestigious network of the worlds best properties and travel advisors.  
Life is short, take the trip!
Florida Beaches

 



 

Ritz Carlton, Sarasota, FL

You can’t beat a Ritz with kids!  The staff really goes above and beyond with making families feel welcome at all Ritz Carlton locations.  During our last stay they had a cake with our sons name on it and balloons in the room when we arrived to celebrate his birthday that week. All the extras add up to make memorable stays.

What we love-  The property has a water view, and a fantastic pool right at the resort, which makes early morning and late day wins with kids easy- BUT the beach club really where it’s at!  Just a short walk or shuttle the beach club is on a street here of gorgeous private beach with a large pool, along with beach chairs and umbrellas.  There’s a shaded area with sand toys for kids and activities offered throughout the day on the pool deck.  The food and drinks are great, and you just feel pampered.

The resort is in a really fun area with multiple kid-friendly restaurants, a few parks and the aquarium is wonderful!  If you need a break from the beach, there are plenty of options.

Know before you go-  The rooms could use a refresh.  The grounds and beach club or beautiful and that’s where this property really shines.  The rooms feel dated and worn though.  you’ll pay a premium for this resort any time of the year- but it’s truly the only luxury resort option with a beach in Sarasota, so they have you there.


 

Naples Grande, Naples, Florida 

We have a love/hate relationship with this resort.  Located in Naples near Calm Pass, it is one of only a few true resorts in Naples with a private beach.

What we love- The resort is very family friendly!  With a zero depth entry family pool  featuring a water slide and Cabanas to rent, this is fantastic for young children.  The resort has staff-lead activities offered through the day (some with a small charge, like bracelet making) that our kids always enjoy.

The beach is gorgeous and has restrooms and a full bar and grill with shaded tables.  There are family yard/beach games set up like bags, and jenga and a large shaded area with sand toys.  We love spending the late afternoons here as the sun starts to set with cocktails while the kids relax and dig!

Know before you go-  The rooms are dated and in need of a refresh.  While large with great balconies, they feel worn.  Garden Villas are in better shape and we like that we have the option to dine on the patio at a full sized table.

The beach is almost a mile walk or there’s a complimentary tram through the mangroves down a boardwalk.  During off season this is a breeze and no trouble at all, but on busy season it can be tough with kids.  (If you have stroller age, it was an easy walk with our baby jogger!)

Restaurants can get busy, and outdoor options are limited/close early.  Our number one complaint with this resort is that the pool closes by sundown and the bar and grill at the pool earlier.  With kids on vacation from blustery Chicago, they can to swim into the evening!  Once the pool and beach close there are limited activities to keep kids entertained- which is why the garden villa with extra space is clutch!  You loose the view, but have ample space for kids to spread out.


 

Bakers Cay, Key Largo, Florida 

Bakers Cay recently underwent full renovations after multiple hurricanes and we were lucky enough to visit while the property was still slightly under the radar.  Part of the Hilton Curio Collection, this resort feels curated, boho-chic and boutique, while still offering just about everything you would want in a beach vacation.

Why we love it-  Multiple activities for kids make your days fly by!  Off the pier fishing, paddle boards, kayaks, shallow waters, a designated family pool with activities and nightly s’mores keep kids busy throughout the day.  They even offer movie night with inflatable bean bags and snacks on weekends! 

The staff go above and beyond to cater to all ages and the food is wonderful.

Know before you go-  This is a 4 star resort because of the amenities and private beach location, but the rooms are basically renovated motel rooms.   

The bathrooms are small in size, but have plenty of shelving to store everyone’s items comfortably.  We definitely suggest a suite for families.

This resort is located down a private drive and you will need a car for off the resort trips.  Ride share options are easy as well!  The bonus of being remote is that the resort has a  private beach only accessible to those staying and it’s family friendly and safe.  We felt very comfortable letting our kids run around swim while we sat in lounge chairs.

When you want to feel like you’re on a tropical island, without leaving the US, you cant beat the Florida Keys.


 

Loews Miami, South Beach, Florida

Miami with kids?!  YES!  We loved Miami with our kids!   This resort is one of the most family friendly, in a prime location right on South Beach, and we would go back in a heartbeat.

What we love-  Nestled in between the boardwalk and the beach the Loews is in a fantastic location for just about everything.

The beach is just across the boardwalk and you can rent chairs and umbrellas that are set up for you.  There is a full bar and grill and chair service on the beach to make watching kids near the water super easy.  

Take a walk down the boardwalk or beach to Collins Ave where you’ll find a playground overlooking the water.  This is a great pre-dinner stop!  Within a 15 min walk are multiple restaurant choices.  We love little Italy for gelato & an after dinner stroll through the brick streets and if you’re looking for empanadas or live music, you’ll have TONS of options!

THE KIDS CLUB!  My oldest wanted to check out the SOBE Kids Club because “it looks so cool”… Turns out, it IS so cool!  We signed him up for just a few hours and he asked to stay longer.  The staff is awesome, and took them outside for swimming & games olympics and they each went home with a medal.  They have video games, painting and sand art and more. He asked to go back each day, made friends and my youngest decided to join too!
MOM BREAK!

 

Know before you go- The rooms are clean, but small.  The beds are two doubles instead of queens and the suite options are low (so book in advance if that’s a must).

There’s just one large pool, but one side has zero depth entry + a splash zone that most kids congregate around- and being that this is a very family friendly resort, nobody is bothered by water play.  

 


 

Hyatt Regency Coconut Point, Bonita Springs

I’ve always been curious about this resort and we finally tacked on 2 days before a trip to Naples.  Just enough time to check it out!  The Hyatt Regency Coconut Point is very family friendly while still feeling luxe- and that’s tough to find on the Gulf side of Florida!

What we love-  As soon as you walk in, you feel like you’re on vacation.  The foyer and check-in area are beautiful and a good balance between grand and elegant, yet updated.  It’s bright and sunny, easy to navigate and the grounds are gorgeous.

Our room was spotless.  From the bedding to the bath, the room felt clean and well stocked.  It’s also a good size at 400 square ft with plenty of storage.

I love a resort with a designated adults pool.  Kids on vacation want to let loose and feel like they’re on vacation- and so do parents!  The last thing I want to do is worry about my child splashing someone who doesn’t want to get wet.  There are 2 kids pools.  One with zero depth entry, a water slide and a small kiddie slide and one with a lazy river, and 3 slides.  

The bonus to this inland resort is that they do have access to a beach with chairs and umbrellas provided.  The ferry runs hourly and you must book a time ahead.

Know before you go-  You can’t sugar coat it, this resort is on the pricy side for 4 stars.  That said, there are so many activities included!  

The check in time is 4, and it was actually 4:30 before we got our room assignment.  This was fine for our family because we utilized the pool well passed 5 with out ever needing to go to the room with pre-planning for this, and our luggage was promptly delivered once we picked up our keys.

The beach takes some planning ahead.  There’s no food, drink or towel service so you have to bring it all.  It’s crystal clear water with soft sand and a pleasant ride… with very young kids this could be tough.

The water slides are intense!  The height requirement is 42” and up, and they’re fast.  


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Snow and Skiing


 

Boyne Mountain, Boyne City, MI 

What we love-  This resort is themed to the max, but well done and it feels fun rather than annoying.  The ski “village” behind the sprawling resort is adorable with great food options and multiple yard games.

In the summer months, there is a bike rental right there, chair lifts to take up the mountain, and movies outside at night.  You can drive or ride bikes to Deer Lake which has chairs set up, a lawn area and a beach bar.  They also have multiple pools with hot tubs, a spa, an arcade and a full blown water park.


 

Boyne Highlands, Petosky, MI

We really have a love for this resort, and area in general.  The Highlands are technically in Petosky, but equal distance to Harbor Springs.  Both towns are gorgeous with boutiques, coffee shops and restaurants, and right on Lake Michigan.  We have both skied in the winter and enjoyed all this resort has to offer in the summer- and will keep going back not only for the activities, but the friendly staff.

What we love-  The endless activities through the summer!  Golf, hiking, swimming, yard games, campfires, kids programming- you name it!  Winter brings ski season and the kids club instructors here are my kids favorite anywhere!

Sandwiched between Harbor Springs and  Petosky this property has multiple options for beaches, dining and shopping.

The room configurations are fantastic for families.  They offer 1 bedrooms and lofted suites with full kitchens and multiple bathrooms with space to spread out.

Know before you go- The resort is a decent drive from the North Shore.  The gorgeous location and awesome ski school makes it worth it as far as Midwest skiing goes!

The rooms in the main lodge are becoming a little dated, but renovations have been underway!  The suites aren’t fancy, but clean and spacious with a mountain lodge feel & perfect for families.

Disneyland Resorts


 


 

Grand Californian, Disneyland, California

I Love this hotel!  For being a Disney property, it doesn’t feel “Disney”, it feels grand, luxe & calm- all while being a very quick walk into Disneyland when you’re ready for a few attractions!  Which is really the number one reason to love this property, along with a few more…

What we love- The second you walk in, this resort feels special.  The lobby is just beautiful with soaring ceilings, stained glass windows with light pouring in, fire places and a piano player.

The rooms are spacious and well thought out with an extra twin pullout, storage space and multiple outlets.  They somehow feel very quiet and cozy while just outside roller coasters and the monorail are zipping by.

The food options are wonderful, especially for a Disney property!  The outdoor grill, Craftsman Bar & Grill, has fantastic flatbreads and fresh California fair, and the Napa Rose has a wine list that rivals any.  Even the character breakfast feels less themed, and more of a nice restaurant with live music many mornings.  If you can splurge for a Club Level room, do.  The spread each morning and night is amazing and don’t even get me started on the deserts and mimosa bar!

The pool is the perfect balance between pretty and fun.  The quiet section has a small water feature that keeps the noise out from the kids area with the water slide and the lounge chairs are plush.

Know before you go- The location and beauty comes with a high price tag.  It’s Disney, so that’s to be expected.  What I tell people- with the proximity to the parks, you can cut your stay in half and do so much in a short 2-3 day stay.  The easy in/out of California Adventure gives you quick access in the morning to hit a few attractions (aka, rides), take a pool break, and head back when ready.

If you’ve visited Disney World before, this will feel different.  The resorts aren’t sprawling and the transportation is easy, but you’ll also have 2 less theme parks to explore.  


 

Disneyland Hotel, Anaheim, California

I’ll be honest- we just love Disneyland in general with kids and this is another resort that doesn’t dissapoint!  The Disneyland Hotel is right in the heart of Downtown Disney and has all the nostalgia with updated amenities.

What we love- It’s a short walk to Disneyland of course!  Wake up, order your Starbucks for pick up in Downtown Disney and take a 10 min stroll to the gates of Disneyland.  It’s that easy.  Really.  Plus Downtown Disney has some fantastic food options and it doesn’t feel super themed.

The rooms are spacious with an extra twin pullout/daybed, large bathroom and changing area.  Bonus- hallways are surprisingly quiet with so many families running around!

Know before you go- This isn’t Disney World.  I repeat, this isn’t Disney World!  This resort has everything you need, but it’s not sprawling.  The pool area has two awesome water slides and nice lounge areas with a fire pit, and pool service. It’s understated and lovely, but much smaller than the resorts at Disney World… which can also be a very good thing too.

The rooms don’t have a balcony.  As many parents know, that balcony becomes Netflix & wine time with earlier bedtimes and quiet before the storm coffee in the mornings.  We honestly don’t have many complaints about this property, but no balcony was a bummer.

Some of the “magic” you may love at Disney World might be missing because it’s simply not as large of a property with as many options.

 

Walt Disney World Resorts


Disney’s Grand Floridian,
Lake Buena Vista, FL 

The Grand Floridian is considered the grand dame of Disney resorts. It’s situated on Bay Lake, with a view of the Magic Kingdom!

What We Love- This property is a quick boat ride to the Magic Kingdom, and a Monorail ride to Epcot.  Easy peasy transportation with little ones! 

The grounds are beautiful with yard games and there are two large pools.  One with a water slide and one with water features, plus a splash pad and a “beach”.

The rooms are some of the largest at Disney and sleep 5- which is fantastic to separate kids!

Know Before You Go-  Transportation to Hollywood Studios and Animal Kingdom are by Bus or Ride Share only.

 
 
 

 

Disney’s Riviera Resort,
Lake Buena Vista, FL

The feel of a current boutique hotel, while at
Disney World! 

What We Love- Well, the obvious!  This property truly feels like a boutique hotel you would find in any city, but in the middle of Disney.  From the tiles to the lighting, the spaces are well done and adorable and the theming is just enough.

The pool is large enough that you don’t feel crowded, but small enough that you can sit in a lounge chair and wave to your children at all angles- and doesn’t that spell vacation?!  The water slide and splash area is great for kids of all ages and the gelato cart and bar next to the area are perfect additions to the pretty property.

The newest and best Character dining option is home to The Riviera and if your kids are Mickey and Minnie fans, it’s a must!

Know Before You Go- The Skyliner stop is just outside to whisk you to Epcot or Hollywood Studios… but the lines can be long and it’s the only transportation option to the parks at all besides the buses.


 

Disney’s Wilderness Lodge,
Lake Buena Vista, FL

We loved this property when my kids were young for the easy-to-navigate main pool area & laid back feel, and quick transportation to the Magic Kingdom. 

What We Love- The lobby is so great for younger kiddos with an adventurous side!  There’s a brook with a bridge to walk over and totem poles built into the structure to explore.

The property is just a quick ferry ride away from the Magic Kingdom, as well as Fort Wilderness.

The pool has a splash area with 2 waterslides overlooking the water and next to the pool.

One of our favorite on property food options, The Geyser Grill, is home to Wilderness Lodge with great food and ambiance.

Know Before You Go- The rooms are on the smaller side for a deluxe category at Disney.  If you have a family of 4, the bunk beds are the way to go- or a suite.

The only park with quick a transportation option is the Magic Kingdom.  Otherwise ride share, buses or transfers await.


 

Disney’s Yacht & Beach Club,
Lake Buena Vista, FL

We love this resort for Disney trips!  It’s the one we go back to year after year, for so many reasons.

What We Love- When you walk through the doors of the Yacht or Beach Club shared property, you’re immediately emerged in coastal smells and beach-y feels.

The location is amazing!  You’re a short walk into Epcot, Hollywood Studios and Disney’s Boardwalk, along with the Swan and Dolphin Resort and Disney’s Skyliner.  The dining and activity options are huge!

The pool has so many fun features, has chair service and never feels too crowded.

The rooms are perfect for a families and feel current and clean. 

Know before you go- Buses only to the Magic Kingdom and Animal Kingdom.


 

Disney’s Polynesian Village
and Resort, Lake Buena Vista, FL

The island vibes and convenience make this property another favorite at Disney World!

What We Love- The grounds are gorgeous and you truly feel like you’re at a tropical resort rather than Orlando while visiting.  Lush flowers, burning tiki torches and water views surround the buildings.

The transportation to Magic Kingdom Park and Epcot are quick and easy- and the views of Cinderellas Castle are pretty magical for both kids and nostalgic adults.

The rooms are fantastic for families with a 5th sleeper daybed and lots of storage space.

Views of the Magic Kingdom fireworks at night (especially from the pool) are so much fun!

Know Before You Go- Dining is tough here unless you’re a big planner and like to leave the resort to eat. The restaurants get very busy.  We normally stay Club Level at this resort and eat mainly there, which is wonderful, but not an option outside of that room category.


 

Mexico


Generations, Riviera Maya 

This beach front property in Riviera Maya is perfect for just what the name suggests- a resort for multiple generations!  

What We Love- While this isn’t our resort of choice when traveling with adults only, it’s a great choice for finding middle ground with family members of all ages.  It’s calm, while being lively enough, there are multiple depths of water in the pools with enough space for kids to play and the restaurant choices will satisfy everyone in the party.  

If the grandparents are up for watching the kids one night, take advantage of it and head to the adults only sister resort for live music a short walk or golf cart ride away! 

The resort is situated right on the beach so no long walks required to get from the pool to the beach.  

Swim-Out Rooms on the ground floor would be perfect for parents of kiddos who still need naps.  Lay them down then lay in a lounge poolside just outside of your door!  

Know Before You Go- This is an all inclusive in a traditional sense, which aren’t our favorite types of resort.  That said, it’s more posh than many and the food was great.  


 

Casa Dorado,
Cabo San Lucas, Mexico 

This family friendly resort is on a rare stretch of swimable beach over looking Lovers Beach and the Arches.  It’s not sprawling, but we like that.

What We Love- A family pool and lower depth on one side of the large pool is perfect for families with little ones.  Chair service and multiple restaurants within a 5 min walk provide easy options with kids.

The rooms are spacious with kitchens and large baths.  Score a walk out patio near the pool and you can sit pool side while the little ones nap!  It’s that close- but quiet enough for naps and chill time.

The views are beautiful and the location is perfect for walks to the marina, tons of great restaurants like our favorite The Office, and boutiques with handmade items and boho beach wear.

Know Before You Go- This is perfect for families, but it’s not a Luxury resort.  The staff is fantastic and location makes up for any amenities some of the bigger resorts boast though.


 

Viceroy, Riviera Maya, Mexico

This luxe boutique resort is adults only.  When mom needs a quiet break, this is the place.

What We Love- Each room is your own casita, which is a thatch roofed hut, surrounded by jungle and twinkle lit paths to each restaurant or the beach.  The resort is quiet, GORGEOUS and feels secluded- yet it’s only an hour from the Cancun airport and lively Playa del Carmen.

Each room has a private plunge pool and outdoor shower.  You can’t beat waking up to a nespresso while taking a dip in your own private pool/hot tub in the jungle!  (This is a very vegetative area. We saw monkeys everywhere!)

The resort has a beautiful beach with cushy lounge chairs and beach beds with beach service and a full restaurant overlooking the waves.

Know Before You Go- This resort is more romantic and refreshing than most in the area.  If you’re looking to party, it isn’t here.


 

Midwest (is best!)


 

Boyne Mountain, Boyne Falls, MI 

The most obvious reason to visit is skiing in the winter, but if you have active kids, summer doesn’t disappoint!  We are a ski loving family and may actually like this property more in the summer because there’s so much to offer.

What we love-  This resort is themed to the max, but well done and it feels fun rather than annoying.  The ski “village” behind the sprawling resort is adorable with great food options and multiple yard games.

In the summer months, there is a bike rental right there, chair lifts to take up the mountain, and movies outside at night.  You can drive or ride bikes to Deer Lake which has chairs set up, a lawn area and a beach bar.  They also have multiple pools with hot tubs, a spa, an arcade and a full blown water park.

 


 

Boyne Highlands, Petoskey, MI 

We really have a love for this resort, and area in general.  The Highlands are technically in Petosky, but equal distance to Harbor Springs.  Both towns are gorgeous with boutiques, coffee shops and restaurants, and right on Lake Michigan.  We have both skied in the winter and enjoyed all this resort has to offer in the summer- and will keep going back not only for the activities, but the friendly staff.

What we love-  The endless activities through the summer!  Golf, hiking, swimming, yard games, campfires, kids programming- you name it!  Winter brings ski season and the kids club instructors here are my kids favorite anywhere!

Sandwiched between Harbor Springs and  Petosky this property has multiple options for beaches, dining and shopping.

The room configurations are fantastic for families. 

Know before you go-  While this property isn’t luxurious or posh, it’s so wonderful for families and clean with an amazing staff. 

There’s no better way to end the day in the summer than smore’s with a glass of wine by the fire!

 

 

We Will Travel Again!


 

After a year of staying home, we’re ready to travel again!  Tap, tap, tap the photo to find out what to expect when you’re ready for your next adventure!

Why Disney? How I Started Planning & How the Process Works!


 

Why Disney?

I’m not a super fan, or a collector, I’m just a parent who likes nice vacations!  My Disney vacation love ironically came from a botched first trip as a parent.  By our second trip I figured out that there’s a much better way to visit and I want to pass that on!  Disney Destination planning is overwhelming, but it doesn’t have to be.

I was so excited to take my children to Disney World because of the magical memories I had visiting as a child.  I booked only a few weeks prior to traveling and wow did I learn my lesson.  It didn’t matter if we stayed at the best resort, I was clueless.  I spent the first day at the parks in frustration & tears. I had no idea what I was getting into!  The next few nights I laid awake researching the best ways to navigate each park the next day, without the coveted fast passes people booked months in advance, and it worked.  We had the best time- but I didn’t sleep the entire trip!

Sweaty, but happy!

The next year we gave it another go, but this time, beyond prepared.  We had an amazing time, parents included, and it actually felt like a vacation!  Strangely enough, Disney became our go-to for long weekends away because I had the planning down and it was such a stress free trip!  No car seats, no driving, no directions needed.  Just giant pools, life guards and entertainment galore- it’s a parents dream!  At this point we’ve visited more times than I’d like to admit and I’ve become well versed on luxe & relaxing Disney.  We don’t try to do it all each trip, we just do it the right way.

I realized how much I enjoyed the planning process of our family trips and I decided that I wanted to help others with the all-to-real struggle.  Disney or any other family adventure shouldn’t be a “have to go” trip, it should be an “excited to go” vacation, and I can help with that!

If Disney’s on your horizon, or any resort travel, let someone else do the planning!   Relax while I create a customized, full service experience without the stress of booking on your own!  I know all the tricks and tips to make your days feel like the magic they should be- all you have to do is show up & enjoy!

Ready to Start Planning?

  1. Contact me for a consultation.  Email or DM what you have in mind, with dates and a vision.
  2. Let’s chat!  We’ll have a conversation to talk details.
  3. I’ll send quotes based on our conversation.
  4. Choose your resort & I’ll book everything for you.
  5. Over the time between booking and travel I’ll create a customized itinerary for each day along with booking dining, activities and more.  One month prior I’ll send the itinerary to look over and make any necessary changes.
  6. Let the fun begin!  Your itinerary will be sent at least 5 days before travel, and you’re set to go!
  7. While there, I’m there for you!  If you run into a problem, I’ll do my best to solve it so you can do what you’re there to do- enjoy yourself!

Contact Me!

Shawn@chicagonorthshoremoms.com

Shawn@glassslipperconcierge.com

I’m happy to answer any questions you have!  Feel free to email or simply send a DM on Instagram with your contact info.

*Shawn is an independent consultant with Glass Slipper Concierge, a Platinum Level, Earmarked, Authorized Disney Vacation Planner, as well as Sanborns Travel, a member of the prestigious Virtuoso network, representing the best in travel across the world.

Ready to take the trip?

When you’re ready to travel, we’re ready to take on the planning!  We can do everything from booking and full service planing to itineraries for Walt Disney World® Resort, Disneyland® Resort, or any other destination you’re interested in!  Sit back and relax while we give you “The Gift of Time”.

Contact-  
shawn@chicagonorthshoremoms.com
shawn@glassslipperconcierge.com 


*Shawn is an independent consultant with with Glass Slipper Concierge, specializing in Disney, and luxe family travel.

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