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Top 8 family-friendly US cities to visit in 2020 by season

I don’t know about you, but I am always excited to spend time during the holiday season planning out places I want to visit as a family in the New Year. Our bucket list is so big, but the kids are small for only so long. There are fun, but important, decisions to be made!

December is a time of year to dream big about new adventures. Personally, I am feeling that 2020 will find us on the Emerald Isle listening to traditional Irish music and sipping a fresh pint of Guinness. I mean, a girl can dream can’t she?

Also, with helpful websites like FlightHub, it can be fun to browse the cheapest airfare rates to lots of different cities from your home airport to help with trip planning and sticking to a budget. So for all you moms out there that want to dream big with me this year and start planning some epic adventures, here is my list of the top US cities to book a trip with your family in 2020.

And since some places are just better to visit than others during a particular season, I’ve organized the list by time-of-year, presenting two of my favorite options to match each season.

Winter (December – February)

San Diego Coastline train
Did you know you can take the Surfliner from downtown San Diego along the gorgeous coast through Orange County and up to San Luis Obispo!?

San Diego, CA

San Diego is the birthplace of California, and as SoCal natives, it is one of our favorite places to visit as a family. San Diego is just magical and has this beautiful, temperate weather all year round. Even when much of the country is bitten by frost in those cold winter months, you will find weather suitable for eating lunch al fresco in warm sunshine, with highs in the 60-70 range and lows only in the 50’s.

No, you won’t be able to do water sports or play at the beach in the heart of winter, but trust me there is plenty to see and do in San Diego.

Old Town San Diego Guide with Kids
The Whaley House in Old Town San Diego is a haunted historical landmark my kids love visiting

One of our favorite places (like, on Earth) is Old Town San Diego. It is such a colorful and lively place full of music, history, friendly people, authentic Mexican food restaurants, a village of Victorian homes to explore (seriously!), and great views of Mission Bay. It is also home to the historic (and reportedly haunted) Whaley House, which is one of our top five family-friendly haunted sites to visit.

Other great things to do in San Diego during the winter include:

  • Relaxing at the cozy Seaport Village and touring the USS Midway Museum
  • Browsing world-class museums in Balboa Park
  • Experiencing fun nightlife in Downtown’s Gaslamp Quarter
  • Spending a day at the famed San Diego Zoo and/or Sea World
  • Relaxing in a resort with gorgeous ocean views in places like La Jolla, Del Mar, and Carlsbad (among many others)
  • Spending the day lounging at Mission Bay, Pacific Beach or Coronado Island

I promise you will fall in love with San Diego any time of the year, but especially during Winter because you just won’t believe how perfect the weather is, and how lively and friendly the city is to boot.

Downtown Scottsdale Arizona

Scottsdale, AZ

Scottsdale is a quaint city in Arizona near the capital of Phoenix with a bustling old town district and gorgeous desert vistas. It is also a great jumping off point for exploring other parts of Arizona like nearby Tucson and Tombstone. The weather can be pretty great in the winter months, with daytime highs in the 60-70 range. Because it is a dry desert climate, nighttime does tend to bring frigid temperatures in the 30’s to low 50’s, but there should be very little keeping you from enjoying the outdoors during the day.

Kids in Rusty Spur Saloon in Scottsdale AZ
We listened to live country music at the Rusty Spur Saloon with our kids for hours one afternoon. It was good times!

One of our favorite hangouts in Scottsdale is the Rusty Spur Saloon, which is a cozy, authentic cowboy saloon that is unique because it has live music 7 days a week from around noon until after midnight. We found it to be a very kid-friendly music venue (with great food) during the early afternoon, but I imagine it can get pretty rowdy at night being a cowboy saloon and all!

Other great things to do in-and-around Scottsdale in the winter include:

  • Shopping and browsing the many shops with Turquoise, leather goods, and fine jewelry
  • Exploring Native American history and culture at Pueblo Grande and Heard Museums
  • Spending a day in the historic city of Tombstone (yes, it’s a real place and family-friendly!)
  • Dining at a nice restaurant in Old Town Scottsdale

Spring (March – May)

Ultimate Guide to Visit St Pete beach FL with Kids

St Pete Beach, FL

St. Pete Beach is known as the sunset capital, located on a barrier island off the mainland of St. Petersburg. With warm average highs ranging from 88-76 and lows hovering around low 70’s to mid 60’s, spring time is the perfect time of year to visit. There isn’t even much rain this time of year with only 3 or 4 day of rain fall a month. This is probably the most popular time to visit St. Pete Beach, but it is for good reason and you’ll be able to find so many exciting things to do. Of course hanging out and enjoying the white sugar sand beaches and warm clear water is enough for us.

Hotel Review Tradewinds Island Grande St Pete Beach FL
This is the beach-side water slide at Tradewinds Island Grand that my kids LOVE!

Our of our favorite places in St. Pete Beach is staying at the Tradewinds Island Grand, a 20-acre beach front resort with five pools, several restaurants and a ton of family activities. The kids spend the day going down the 3-story high inflatable slide, swimming in the sea, splashing in the pool and making crafts at the KONK Club. At night we enjoy delicious meals, beautiful sunsets, bonfires on the beach and live music. It a true vacation in every sense of the word.

Other great things to do in-and-around St. Pete Beach in the spring include:

  • Visit lovely beach-side community of Pass-a-Grille and pop into the magnificent and historical Don Cesar Hotel as known as Pink Palace.
  • Spend the day at John’s Pass, a fun fishing village where you can eat seafood, shop and even sail on a pirate ship.
  • Explore Treasure Island, 4 miles of gulf beachfront and the Sand Sculpture Capital.
  • Play at Fort De Soto Park, where kids can explore lagoons and sandbars created by tidal variations on this beautiful stretch of sands.
Kids having fun in Nashville at Night

Nashville, TN

It is always a good time to visit Music City, but spring yields mild temperatures in Nashville ranging from highs of 62 in March to 79 in May with lows from 40 to 57 degrees. In a city that can be pretty darn humid in the summer, spring is a refreshing option for family travel. Home of the County Music Hall of fame, family-friendly Nashville live music venues and honky tonks are in no short of supply. It is great place to put your boots on and kick up a good time.

Kids dance to live music in Nashville
Kids dancing to live music at BB Kings in Nashville, TN

We are slightly obsessed with live music and a dance floor, so when we come to Nashville we are all about the nightlife, even with our kids. Luckily for us, Nashville has plenty of places that you can honky tonk with your kids and that is exactly what we like to do!

Other things to do in-and-around Nashville in spring include:

  • Visit the historical Belle Meade Plantation, built in the early 1800’s this was famous for their breeding of thoroughbred racing horses like Bonnie Scotland and Epsilon.
  • Explore Nashville music history with a visit to the Country Music Hall of Fame and the historic RCA Studio B and Ryman Auditorium.
  • Catch a show at the Grand Ole Opry where many country music greats have graced the stage.
  • Handle the heat with some Hot Chicken, a Nashville original fried chicken dish created 100 years ago. With various degrees of heat, you see how hot you can go!

Summer (June – August)

See exactly how we spent our weekend in Wildwood, NJ with absolutely perfect weather!

Wildwood, NJ

Who doesn’t love a good beach vacation during summer? Wildwood has warm mild temperatures with highs ranging from 79 to 82 degrees and lows in the mid to high 60’s. So you won’t be roasting on the sand and that’s a good thing. Wildwood isn’t just any beach – it’s an amusement park by the sea. The boardwalk is lively with exciting rides, water parks, carnival games and affordable, yummy grub everywhere. It is no wonder why summers by the shore create lasting memories!

I grew up hearing stories from my dad’s childhood summers at the Jersey shore goofing around on Wildwood Beach. For us this is a nostalgic beach escape, enjoying the warm waters, riding the Ferris wheel, getting salted pretzels and the best pizza from Mack’s. Night time sparkles with neon lights and nonstop entertainment everywhere you look.

Other things to do in-and-around Wildwood in the summer include:

  • Visit the historic Hereford Inlet Lighthouse which on the National Registers of Historic Places with beautiful museum and grounds to explore.
  • Have breakfast in the sky as eat the most important meal of the day while riding a 156-ft Ferris wheel.
  • Quench your thirst at one of the many local breweries like Mud Hen and 7 Mile Brewery
  • Explore the land with bike rentals as you ride along the 5 mile island and National Wildlife Refuge.
City National Grove of Anaheim

Anaheim, CA

Ah, no place better in the summer than my hometown of Anaheim. Not only is Anaheim home to many popular family attractions like the world famous Disneyland, but it also has perfect weather in the summer for a family vacation. Anaheim literally gets zero rain in the summer and temperatures range from the high 80’s to low 70’s. Whether you are into theme parks, beach time or lively shopping districts, Anaheim has what you are looking for in an exciting family summer getaway.

Disneyland with Kids Ultimate Guide
Summer at Disneyland is pretty crowded, but then again, it is crowded pretty much all year round.

Since we live in Anaheim we enjoy just about everything this awesome city has to offer, including regularly visiting Disneyland, one of our favorite summertime activities is catching an good old fashioned baseball game at Angel’s Stadium. On summer nights they often have an awesome firework display fitting for a grand finale to any game. Nothing screams American summer like a cold beer, peanuts, sunshine and baseball.

Other things to do in-and-around Anaheim in the summer include:

  • Hit the beach! Anaheim is only minuets from some of the best Orange County beaches, like Newport Beach, Balboa Beach, Huntington Beach and Dana Point, just to name a few.
  • Enjoy live music and global fare and craft cocktails at the Anaheim Packing House, a food hall housed in an historic citrus packing house.
  • Visit other nearby theme parks like Knott’s Berry Farm, home to famous Boysenberry
  • Enjoy outdoor shopping and entertainment at Anaheim Gardenwalk and OC Marketplace.

See our list of things to do with kids near Anaheim any time of year

Fall (September – November)

Downtown Boston

Boston, MA

If you want the glory of fall foliage then Boston is the place to visit this fall. Temperatures hover around the 70’s and 60’s in the September, but drop to the 50’s as you approach November. Early fall is the best time to catch all those magnificent colors from the turning of the leaves before winter comes. In addition, Boston is an amazing city loaded with great restaurants and American history.

List of Best Family Hotels Boston Downtown

I am huge on history and I suggest taking the free walk along the Freedom Trail. This a 2.5 mile walk through downtown that takes you all 16 important locations in American history. You take as long you want, making the stops that interest you most. Take your time and enjoy frequent beer and grub breaks at the many historic pubs along the way.

Other things to do in-and-around Boston in fall include:

  • Cruise along the Boston Harbor and take in the view from the sea
  • Visit the site of Boston Tea Party at the ship museum
  • Drink your way through a Boston brewery tour
  • Catch a baseball game at Fenway Park

Read our custom list of the Top Family Hotels in Boston

Santa Fe New Mexico

Santa Fe, NM

Santa Fe is on the other side of the country from Boston, but has similar fall temperatures. Early fall is the safest if you are looking for warmer weather at highs of mid 70’s, but by November the temperatures are dropping to the low 50’s at the highest. Santa Fe is a wonderful historic city with a major artsy and foodie scene. Known for their Pueblo-style architecture, it is a treat just to walk around taking it all in, but there is no shortage of fun things to do in Santa Fe.

You’ve got to see this place to believe it! Check out our video of kids (and a baby) exploring Meow Wolf in Santa Fe

Now, there are a ton of historic sites to visit while in Santa Fe, like the San Miguel Chapel built in the early 1600’s, but Santa Fe is also home to some quirky attractions too. When in Santa Fe you have to make a visit to Meow Wolf, a total sensory experience created by a local art collective. You could spend the whole wandering from room to room trying to figure it all out, but it is best to just let go and enjoy. Don’t forget to enjoy a crazy craft cocktail at the Float Cafe & Bar.

Other things to do in-and-around Santa Fe during fall include:

  • Visit a historical Indian Pueblo, where natives inhabited the land for centuries.
  • Visit one the 22 museums in the city, including New Mexico History Museum, The Museum of Indian Arts & Culture and New Mexico Museum of the Art
  • Stay, eat or just play the historic luxury La Fonda on The Plaza
  • Stroll through the Santa Fe Plaza, enjoying the many shops, restaurants and historic sites.

That’s a Wrap!

There you have it! These are 8 amazing places you should consider visiting with your family in 2020. We presented two of our favorite options for Winter, Spring, Summer and Fall. I hope you are as excited as me! The time to start planning an epic family adventure this year is NOW!

In the comments below, let me know where you hope 2020 will take you!

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Family-Friendly US cities to visit this year

I am a busy mama with 3 delicious babies and a serious itch for travel and writing (when I am not bartending, that is)! After graduating from Cal State San Marcos with a B.A. in Communications, I decided to start a family and pursue a career in freelance writing. I created HotMamaTravel as an outlet to do what I love while sharing useful travel tips and inspiration with others. Our mission is to show parents how to master travel with kids, while keeping your Saturday-night selves. We call it "Family travel...with a twist".

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