Travel Guides | 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 

Our travel guide section is sponsored by Take The Trip Travel Chicago, part of Glass Slipper Concierge, an Authorized Disney Vacation Planner as listed by Sanborn’s. Questions about all things Disney, reach out!

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.

Our resident travel gal, Shawn, who is also a travel advisor with Glass Slipper Concierge, lists a few family travel recommendations visited within the last few years with her kids.  Are these the most luxurious and exotic of locations- no, but they are easy with kids, have loads of family activities, and have our stamp of approval for cleanliness and service.

We’ll continue to update this section as we experience new adventures!  Life is short, take the trip!

*Resorts listed have all been visited, and have only been added if we recommend!  These are not paid partnerships, just honest reviews.  

Have questions?  Don’t hesitate to reach out!

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 Planning can be complex to say the least!  These are a few of the resorts that we have enjoyed staying at and recommend for the ease, location, recreation options.  

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 plus plenty of activities to keep kids busy outside of the Theme Parks. 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!  We also love staying Club Level when visiting for the ease and extra space it provides.

Know Before You Go–  Transportation to Hollywood Studios and Animal Kingdom are by Bus or Ride Share only.  The rooms are definitely in need of a refurbishment- which starts Spring 2022.  If you go before, you’ll likely have the benefit of a lower cost before the new rooms debut… but after, the luxury of shiny new digs.



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.


Beach Resorts


Baha Mar,
Nassau, Bahamas 

This might be our families favorite beach resort yet.  Baha Mar sits on a gorgeous stretch of Cable Beach with plenty of water activities to keep every age happy.  The rooms are newer and spacious, and the grounds are sprawling with multiple pools.  The real action though is the waterpark, Baha Bay, in the center of the property shared with two other resorts, SLS and Rosewood.  Baha Bay is new as of this year and so much fun.  This property checks all the boxes for every member of our family!


What We Love
This property has so many dining and shopping choices throughout the 3 resorts, along with a spa, kids club, and even a casino- not to mention Baha Bay waterpark!  The waterpark is really well done, and almost pretty, blending into the landscaping. There are separate sections in the park for each age group, and plenty of seating within each area.



Know Before You Go
Food and drinks are pricy, but so expect a hearty tab at the end of your stay!  The resort is large, so if you like a more intimate property, this isn’t it.  The private beach area is wonderful, but it means this isn’t walking distance to town.  Taxi’s are easy to pick up though and the concierge is happy to help.


Ritz Carlton Golf Resort,
Naples, FL

The Ritz Carlton Golf Resort in Naples just underwent an enormous renovation, so everything is bright and shiny!  We’ve always enjoyed this resort for the quiet and relaxed vibe, combined with kids programming- which is a hard combination to find.  With the updates, the pool area was transformed, making the property even more kid friendly!

What we love
The rooms are spacious and new, which is obviously always a plus! The real star here though is the brand new pool area complete with a splash pad, lazy river, and bigger sides for bigger kids! The grounds and golf course are gorgeous and there’s a shuttle into downtown Naples.

Know before you go
This resort is not on the beach. That said, there’s a complementary shuttle to whisk guests to the Naples Rittz Beach Resort just a short ride away where you’re able to enjoy the pool and beach for the day.

Hyatt Regency
Huntington Beach, California 

I don’t visit the West Coast as often as I’d like.  The time change combines with a longer flight is tough for quick trips, plus my parents are in Fl for the winters, so it makes sense.  That said, I did a lot of research sifting through family friendly resorts in the area, and this one checked all of the boxes!  I love Huntington Beach for family vacations!  It’s ultra casual, but upscale and always lively!  

What we love
The grounds are expansive, as is the beach, and there  are a number of family friendly activities scattered throughout and the resort offers Camp Hyatt, the kids club.  The pools are separated into a family pool complete with dueling slides, and an adult/quiet pool.  We love a pool situation where you don’t have to apologize over and over for splashing!

Know before you go
There are still quite a few restrictions in this location, so be sure to double check what’s open before travel, along with the cancelation policy.


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!


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.  


Snow and Skiing

Crystal Mountain, Thompsonville, MI 

While small in size, this resort is less than 6 hours from Chicago’s North Shore, and gives a true resort experience with plenty of activities and lodging choices.  

What we love 
There are so many choices for accommodations that work well for families or even bigger groups.  Many with full kitchens.  We love the Mountain Market for easy grocery shopping and gourmet local goods, in addition to a number of great restaurants.  The indoor pool is great for days when it’s just too cold to be outside, but the kids need to burn off energy- and parents can relax in the adjoining hot tub.  

Know before you go
This is a smaller ski area and while you may be paying out west mountain pricing, you won’t be skiing the same terrain!  Midwest ski resorts have a captive audience and they charge for it.  

Kids lessons are shorter in time than many.  To build a full day you’ll have to pick up for lunch, and pay for a second lesson in the afternoon.  


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.


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 is the ONE adults only Resort we’ve added as of yet, because this is meant to be a family list- but it’s too good not to share! When mom needs a quiet break, or you need to reconnect with your partner, 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!



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