5 Amazing Fall Travel Destinations in the US for Fall Break (travel essential links included)

Today we are discussing some of the best places my family has been for fall break, along with some great travel accessories that get me through the trips!

Fall break is one of my favorite breaks my kids' get for school! Places are often less crowded, temperatures have cooled down, and leaves are starting to turn (in certain places), ushering in my favorite season, FALL!!! So, let's dive into my top five places I would go again and again.

1. Anna Maria Island, FL

Full disclosure, I am not a beach person, and neither is most of my family. BUT this island is magical and my favorite beach as a non-beach person. We flew into Sarasota, FL and then took a quick 30-minute Uber ride over to the island. From there we rented a golf cart for 4 days, about $350, and checked into our VRBO. Not only is the island easy to navigate, but it wasn't overly crowded and fairly easy to get into restaurants and find open spots on the beach to spend your days, all of these points are huge pluses to me! We didn't have a house right on the beach, but this was ok for us, there are beach access points all along the main road, which was very close to us, so we just loaded up a wagon and headed to the beach daily. The water was beautiful, and the sand was the perfect powdery white.

Another plus, we found most of the VRBO's to be more equipped with entertainment options at home than our average VRBO on the Gulf. For example, almost every house we looked at had a pool, hot tub, ping pong or pool table, and card games. When traveling with kids, especially small kids, going to the beach can be hard...you have to pack ALL THE STUFF! This is why I think having a house with some great options to entertain and swim at home is essential. I would visit this island again and again and hope you do too! Send us a message through our Contact Us page for a more in-depth travel guide for Anna Maria Island.

2. Washington, DC

If you have older children, ages 10 and up, Washington, DC would be a great place to go for fall break. I would not suggest this for younger children, it is a lot of walking, visiting museums, and learning about places that are important in United States history...not a lot of fun toddler activities. When kids start to learn about these places in school it is so fun to be able to show them the places they have seen only in textbooks (or on Chromebooks). Some of our favorite places to visit were The Bible Museum, The Capital, Arlington Memorial, and the Museum of Natural History.

We stayed at The Conrad on New York Ave when we were here, it was a great location to walk to a few things and what we couldn't walk to we were a short Uber ride from. Also, if you want to combine this trip and the below trip, we stayed in DC for a couple days then took the Amtrak to NYC for a few more days. This was a great way to see both cities that were a quick 3-hour train ride away from each other. The ride was quick, comfortable, and very affordable. This just required us to book two one-way tickets, into DC and out of NYC, which was easy to do. Send us a message through our Contact Us page for a more in-depth travel guide for Washington, DC.

3. New York, NY

This is one of my FAVORITE cities to visit, we have been during fall break, but have also been every other season. Fall break is great because the weather starts to cool down, but if you are going to take another trip there, I highly suggest closer to Christmas...the decorations really make the city come alive. When we went with our children we stayed at The Conrad in Midtown, this hotel is closed now but the Midtown location is great and there are other hotel options in that area. Some of our favorite things to do with kids in NYC is take the ferry to the Statue of Liberty and Ellis Island, visit the Lego store and FAO Schwartz, head to the top of One World Trade Observatory, catch a show on Broadway, go to Serendipity 3 for desserts, China Town and Little Italy for dinner and sights, and the 9/11 Memorial. If your children are really into museums, I highly suggest the MET, the history in that one building is fascinating and the artifacts are so interesting if history is your thing. The restaurant options are ENDLESS and there is always a great store around the corner if you want to spend your afternoon with some great food and retail therapy. If you will have an afternoon child-free then I suggest the 9/11 Museum, it is so moving but could be too heavy for children. Send us a message through our Contact Us page for a more in-depth travel guide for New York City.

4. St. Maarten, USVI

This island is going to be your typical all-inclusive resort experience, with a few things that set it apart. The island is divided into two separate sections, the French side and the Dutch side. We stayed on the Dutch side but visited the French side. The Dutch side has a more American feel, some chain restaurants, fully clothed beaches, some nightlife, and a bit busier. The French side is quieter, less English is spoken, and more of a quaint feel. We LOVED both sides, the local food was so good on both sides, and we felt completely safe to walk around on both sides. Just a heads up if you are taking kids...the French side has nude beaches...so that may or may not be something you want to put on the agenda. There isn't border control between the two areas, so you won't need a passport for one and not the other (if you are American). Definitely plan to go to Maho Beach, this is located at the end of the island's airport runway, and you stand on the beach while planes fly over. This is a surreal feeling; it feels like the planes are going to land on you (but aren't even close actually) and it takes everything in your body to stand there. This made the trip for us and created such fun memories. Unfortunately, the resort we stayed at got damaged in the hurricane in 2017 so it isn't there anymore but there are so many great resort options, and I wouldn't rule out a VRBO if you are going with a larger family. This island could easily be navigated with a rental or Uber rides. Send us a message through our Contact Us page for a more in-depth travel guide for St. Maarten.

5. Gatlinburg, TN

Gatlinburg has a little bit of everything from mountains, an amusement park and aquarium, shopping, a kitschy downtown with all the touristy flare, alpine coasters, mini-golf, and go-Karts. If you have younger and older kids, this is a great place to find entertainment for all of them. We have always done VRBO when we go to this area and prefer to be more in the mountains instead of down in Pigeon Forge with all the activities. Pigeon Forge is a quick drive so going down in the evenings wouldn't be a problem.

The Smoky Mountain National Park is beautiful and would be easy to hike with a backpack carrier for a toddler or small child. The leaves should start to turn about this time (mid-October) which will bring crowds, so keep that in mind when traveling there, getting in national parks early is always your best option. To avoid crowds and heat we like to get up and get in early then have evenings free for dinner and activities. Send us a message through our Contact Us page for a more in-depth travel guide for Gatlinburg, TN.

I know not every area of the country has fall break, I had never heard of it until I moved to the south. If you don't have fall break, don't worry, all of these places would be great to visit during different times of the year! One of my biggest tips when traveling with a family, and staying in a rental, is to find a local grocery store and place a pickup order before you get there! This has saved us so many times after a long travel day and the last thing we wanted to do was go to a grocery store to get the essentials.

Below I am adding in some of my travel essentials for myself, kids, and our whole family, make sure to check out our blog entertaining your toddler on a plane to pick up all of our most entertaining toy options!