ORD to TPA
Updated: Apr 4
If you've been following along on our social media accounts you know that I moved to Florida with my family (temporarily). After years of negotiating with insurance we finally got approved to make some repairs and renovations to our Chicago condo after severe water damage. The work was estimated to take about 6-8 weeks and we needed to completely vacate the property. Everything from furniture to clothes to toys had to go along with us! The relocation process was not ideal either. Trying to find a comparable rental for two adults, a toddler and a dog in Chicago during the holiday season proved to be challenging. After looking at a few places we agreed to push back the repairs until the new year and head to a warmer climate for an extended stay. We knew we'd be miserable in a small rental in Chicago during the worst months of the year (January & February) so Florida just made sense. The promise of warm weather while being displaced would be worth it. I realize how fortunate we are to have come to this resolution. I also realize how fortunate my husband and I are to be able to work remotely and that Sonny isn't in school yet. This was a really awful situation for us that we ended up turning into an amazing opportunity. Luckily all the dominos fell in to place for us!
In early January we rented a house in West Bradenton. A town neither my husband nor I had heard of. As soon as we starting telling people where we were going there was an influx of recommendations. Our house was located about 10 minutes from Anna Maria Island/Bradenton Beach/Cortez, 30 minutes from Downtown Sarasota, 40 minutes from St. Petersburg and 50 minutes from Tampa. We couldn't have asked for a better location! If anyone is interested in renting the house we stayed at I'm happy to share the contact information of the owner. It's a newly renovated 3 bedroom, 2 bath ranch with a heated pool in a very convenient location. Everything you'll need is only a few minutes drive away, but a car is a necessity in this area. Depending on your length of stay it may be more cost efficient to even ship your car down like we did (we are talking thousands of dollars saved). We honestly didn't have much experience traveling on Florida's Gulf Coast so we got really excited when people told us how amazing the area was. Even though we went in blindly I would consider ourselves well versed now. So many people had reached out to give and ask for recommendations so I kept a list of all the places we visited, shopped, explored, and dined at to share with everyone when we returned.
This adorable barrier island has been gaining a lot of popularity lately. With no high rise hotels and an abundance of beaches and wildlife it's a beautiful place to vacation. The second you step foot on AMI you are on island time! The 7 mile stretch is filled with cute mom and pop restaurants, bars, and shopping. Since we were only a 10 minute drive from Anna Maria we frequented it the most to eat and hang out. The island is so charming and you feel like you are transported back to an "old school" Florida. If you stay on the island at a small hotel or rental property you'll either have a golf cart for transportation or use the FREE trolley that runs the length of Anna Maria. We rode the trolley and Sonny loved it! You can conveniently get around AMI without a rental car. One of the best things about Anna Maria Island is it's beautiful beach sunsets and one of the best places to see that is at the Moose Lounge! If you are a member in another state you still get free access and can enjoy inexpensive beverages as the sun goes down. On Bridge St make sure to check out the mini golf. Sonny had a blast and so did we! Almost every restaurant on this island is kid and pet friendly too.
Ginny & Jane E’s: We made a minimum weekly trip here to eat. The food was great, but the star of the show is their cinnamon roll. This was hands down the BEST cinnamon roll we ever had in our entire life. This place draws a crowd so the earlier you arrive the better to beat the masses (we're talking lines out the door). Attached to the restaurant is a cute retail shop too. ✔️
Anna Maria Oyster Bar (on the pier): Make sure to check out the location on Bradenton Pier! Even though it is small it's an incredible location. You can dine overlooking the water and after you eat or while you wait for a table take a walk down the pier or down Bridge Street to shop. That main street is lined with tons of restaurants, bars, boutiques and mini golf. ✔️
Donut Experiment: Watch as these mini donuts are being made. Kids will love it here since they get to customize their own donuts too!
Fudge Factory: We always made a point to stop here after dinner for homemade candy, fudge and ice cream! They also have a section of nostalgia candy. ✔️
Ugly Grouper: This place is a vibe. With only outdoor seating be prepared. They have amazing live music and a kid friendly area for littles to play. The linguini with oysters and mussels are our go to! ✔️
Sand Bar (on the beach): This is a sister restaurant to Beach House Waterfront. The food is really good and the view and vibes can't be beat. Get here in plenty of time to catch the sunset. We also saw dolphins here on the beach as we waited for our table. Like most places on AMI they do not take reservations. ✔️
Waterfront: Everything we ate here was excellent, but our favorite menu items were the calamari & grouper tacos. They have a front and back patio with ample seating. If we had to wait for a table (again no reservations) we would hang out on the City Pier and after dinner walk to Two Scoops for dessert. ✔️
Skinny’s: They are known for their dive burger.
Slim’s: They are known for their Phili cheesesteak.
Two Scoops: Cute little (homemade) ice cream shop. ✔️
Wicked Taco: We loved this place and wish we found it sooner. It had great food and a solid margarita. They have two locations; one on AMI and one in Sarasota. The Sarasota menu is far more extensive with ample vegetarian options. Pro tip since they aren't on the beach for sunset just cross the road and wait on the beach with your margarita and enjoy the view until your table is ready. We cut through Gulf Drive Cafe. ✔️
The City Pier Grill & Bait Shop: This pier is great to enjoy morning, noon, or night! We went several times and loved it. At night there is live music and a great ambiance. We had drinks and food from the grill and it was all very good. ✔️
Mademoiselle Paris: We stumbled upon this cute Parisian cafe after arriving to an insane line wrapped around the block at Ginny's and Jane E's and we are so happy we did! They have a cute patio in back and the food was incredible! ✔️
Gulf Drive Cafe: This is located on the beach with a cute vibe and incredible view. Unfortunately, the food and drinks were lacking when we went. We'd go back and give them another shot, but tbh we'd just have a drink there and wait for a table across the street at Wicked Taco. ✔️
Harry's Grill: There are plenty of options for everyone here! We had a great meal and time at Harry's. They have a fun patio with live music too. ✔️
Sarasota (St. Armand's Circle) /Siesta Key/Long Boat Key
Sonny's favorite spot we frequented was St. Armand's Circle in Sarasota! We loved walking around the circle shopping, eating, grabbing ice cream, and enjoying the live performances. St. Armand's circle is home to so many restaurants and boutiques, but it's only one part of Sarasota to visit. They also have a cute downtown area with more dining and shopping options to explore. Only a short drive away is Siesta Key and Long Boat Key. Siesta Key is home to one of the most beautiful beaches in the country and they have a really cute downtown area. All these areas a quick and easy drive from each other and all have beautiful beaches and scenery. Sarasota also has a really good shopping mall we would go to with restaurants and outdoor activities. We made sure to check out Pop Stroke, Tiger Wood's mini golf, while we were there. It was a really fun activity to enjoy in the sun while having a drink. They're so many mini golf places in Florida, but this was marketed towards adults and was more like a Top Golf atmosphere. On a cloudy, rainy day head to Mote Aquarium in Sarasota. Sonny loved seeing the fish and sea creatures. Kids under 2 (or 3) are free so check before purchasing tickets. This place was perfect for us to spend the day learning and exploring. If we ever permanently made a move to Florida I would want to live in Sarasota. We love the bigger city energy with easy access to the waterfront and beaches. Sarasota is a perfect balance!
Columbia: A must dine when in Sarasota. There are multiple locations, but don't let that deter you. Each time we dined here we loved our meals. It has a great corner location that over looks the circle. The sangria & 1905 salad are a must order. We subbed shrimp in ours instead of ham. I could live off that sangria and salad the rest of my life! ✔️
Big Olaf: We tried the St. Armand's Circle location for homemade ice cream, but there is one in Siesta Key too. There are so many places to grab ice cream and gelato in the circle that are delicious! ✔️
Siesta Key Oyster Bar: We enjoyed live music and a great laid back Florida vibe while dining. This place is worth the wait. Put your name on the list and walk around the area while you wait. I'm so happy we were able to eat here because the food and ambiance was top notch. ✔️
Ritz Carlton Beach Club: Wish we could have checked this out because it came highly recommended and the reviews are incredible.
Owen’s Fish Camp: This place is super popular and does not take reservations, but don't let the wait scare you away! Get there when they open to put your name on the list. It is oddest location for a restaurant but it's walking distance to downtown where you can grab a drink or shop while you wait. This was some of the best seafood we had all trip and worth the hype. 10/10 recommend Owen's! ✔️
Dry Dock (Long Boat Key): We loved this place. You can make a reservation, but they are pretty challenging to get so plan ahead. This oceanside restaurant had amazing food and views. We will definitely going back on our next visit. ✔️
Shore Longboat Key (Long Boat Key): We didn't get a chance to check this place out, but the person we rented from just went and said it was really good. Adding this to our list for our next visit!
Mar Vista Dockside (Long Boat Key): We didn't get a chance to check this place out, but the person we rented from just went and said it was really good. We will be checking it out next time we head to the Gulf Coast!
Le Colonne: More Italian food in St. Armand's with outdoor seating. ✔️
Grand Cru Wine Bar: Wine on tap. Need we say more?! We hung out here while waiting for our table at Owen's Fish Camp and the wine was incredible. I loved the Pinot Noir. They have nice seating options, an endless wine selection, and small bites. ✔️
Venezia: Located in St. Armand's Circle this was the best pizza and pasta we found during our trip (with the exception to Molto in Naples). You can enjoy good wine, food and company in one of the best locations of the circle overlooking the beautiful center greenery. ✔️
1592: Located in downtown Sarasota we grabbed dinner here and the vibe and service was great. It a modern twist on Greek food. ✔️
The Fat Donkey: We popped in here for dessert after dinner in downtown Sarasota. ✔️
Bradenton is huge! There are so many different areas to explore, but we lived in West Bradenton. One of our favorite areas to explore was Cortez. They had some of our favorite places to eat and we can see that area gentrifying in the next few years due to the close proximity to the ocean and beaches. The new construction in the area is already insane. Bradenton was a perfect mix of small businesses and chain restaurants which made it very easy to settle in quickly. When we weren't swimming or hanging at the beach there were plenty of kid friendly options like bowling, movies and a trampoline park to keep us occupied.
Star Fish Company (Cortez): Located in the Cortez area we think is going to be the next hot spot is Star Fish Company. The wait to dine there can be long with limited seating so we grabbed a to go order and it was amazing fresh seafood. Definitely check it out! ✔️
Slickers (Cortez): This was our absolute favorite place to eat with the BEST food. Again, it's off the beaten path and doesn't have the ambience to draw a crowd, but the food was a 100000/10 every time. We are convinced Max makes the best margarita's in the world!!! The blackberry jalapeño margarita was our favorite. I still dream of them. We recommend ordering the octopus, fish of the day and shrimp. Everything on the menu was delicious! ✔️
Pig Out: Enjoy authentic BBQ and soul food. We ordered this for Super Bowl Sunday. I just don't eat meat so I can't give you an honest review, but it looked and smelled delicious. ✔️
Beach House Waterfront: Located on Bradenton Beach this was one of our favorite places to eat. The place is gorgeous and there's no better place to catch a Florida sunset while you eat. This is a sister restaurant to Sand Bar on the Beach. ✔️
Sage Biscuits (breakfast) ✔️
Sweet Berries: We fell in love with Sweet Berries. They serve up delicious homemade custard with rotating specialty flavors. The lunch options were great too with soups, salads and sandwiches. The tuna salad was my favorite. ✔️
Pier22: Located in downtown Bradenton this was one of the first places we ate. It's on the water and has great views. The vibe was like a steakhouse and the food and drinks were solid. ✔️
Tyler’s Ice Cream: Hands down the BEST homemade ice cream we have ever had!!! Tyler's is off the beaten path, but worth the drive. You will not be disappointed! ✔️
We only ventured out to Saint Petersburg once, but it is massive and there is so much to do! They have beautiful beaches, so many restaurants to eat at or places to shop at in the downtown area and newer area by the pier and they are also home of the Ray’s baseball team.
Doc Ford (on the pier): We went to the new pier area when visiting and loved it. Sonny loved walking the pier and they had the coolest playground (with food and adult friendly beverages). We ate at Doc Ford on the pier and the food was great, but the best part is there is a small airport with choppers and planes that kept Sonny’s attention while we dined. ✔️
We took a quick day trip to Naples to visit friends. Even though we didn't have much time to explore we were able to walk down the famous downtown 5th avenue strip and enjoyed one of the best meals we had in Florida with amazing company! The options for dining and shopping on 5th are endless and we hope to make it back there again to spend more time.
Molto: This authentic Italian cuisine is what dreams are made of! Molto serves homemade pasta cooked fresh in the kitchen by the owners mother. Everything we ate and drank here was divine. If you travel to Naples it is a necessity to dine here. ✔️
The Vine Room: We brought our toddler and dog to Naples so checking out this speak easy wasn't an option, but our friends recently went and said it was awesome.
This was one of the coolest cities we have every visited. I feel like people really sleep on Tampa, but it is gorgeous! We made a point to check it out any time we got the opportunity. We even got to experience Gasparilla! Imagine Mardi Gras, but everyone is dressed up like a pirate. We wish we could have explored Tampa more and would have love to have seen a sporting event (like the Tampa Bay Lightning).
Zoo Tampa: So many people raved about this place so we made a point to check it out on a cooler 60+ degree day. It is extremely expensive but children under the age of 2 (or 3) get free admission. Everything is all inclusive with ticket pricing including rides (Sonny’s favorite part), animal interactions and more! There was some really unique and fun things to experience, but for the most part we were underwhelmed. Our local Brookfield Zoo definitely has more animals to see and this didn’t hold a candle to the San Diego Zoo. ✔️
Berns Steakhouse: The second we told our friends we were going to Tampa they emphasized how important it was to check out Bern’s! We made reservations in advance (a must) for a date night. This old school steak house has so much charm with multiple dining rooms and even a separate dessert room to experience after dinner. The dessert room featured individual “private” seating for just your party. Everything we ate was amazing, but the banana’s foster was the real star. Definitely arrive early to grab drinks in there bar area too. This is a perfect date night spot or night out with friends! ✔️
The Edition: We stayed here and it was probably one of the nicest hotels we’ve even been too. The hotel scent was so incredible we had to buy a diffuser to bring home! Side note for my electric car peeps; they are a Marriot affiliate hotel and will charge your car for free next door. ✔️
There are so many cool beaches to explore and see along the gulf coast! Make sure to experience the beaches at sunset as well. On multiple occasions we saw dolphins at each location we visited. It was one of the prettiest sights to see. A main concern while we were down there was red tide. Fortunately, our trip was not really effected. Sonny never experienced coughing and I only did once while at the beach. My husband was much more effected, but as soon as we left the beach and surrounding area he was fine. I recommend the following websites to check the red tide levels before heading out: Red Tide Current Status
Coquina: This was Sonny’s and my favorite beach! There is tons of parking, clean restrooms, a coquina cafe with drinks & food and tends to be less crowded than Holmes/Manatee Beach. Pro Tip: if you purchase reusable cups front he cafe you get discounted beverages at both Coquina and Manatee beach (alcoholic and non-alcoholic). ✔️
Whitney Beach: We didn’t make it here because it’s slightly off the beaten path. We opted for beaches with facilities like a playground, changing area, trolley service, food and ample parking. If you’re looking for a less crowded options head here.
(Holmes) Manatee Beach (limited parking / huge restaurant & bar / public restrooms) ✔️
Siesta Key: One of the most beautiful beaches I’ve ever seen and worth checking out. There is ample parking but there is an extremely long walk from your car to the actual shoreline. There is restrooms and a restaurant at the beach, but it is a bit of a hike. ✔️
We are typically not beach people, but really made and effort to go once a week because they were so clean and beautiful. Sonny loved the beaches and we felt really safe with him going in the water and playing on the shoreline. If you’re heading to the beach these following items are a must have!
Mom Beach Pro Tip: Head out to the beaches after the morning rush. The UV index will be lower, you won't have to worry about getting home for naps or beating the crowds. Instead of having lunch at the beach do a dinner picnic and enjoy a beautiful sunset. Your kids will have just as much fun playing in the sand and water with less people, well rested and with less of a chance of getting sunburnt.
✔️ indicates we were able to visit, eat and explore these places during our stay.
My hope is that these recommendations help you with future travels. We fell in love with the gulf coast and all it had to offer. If you have any additional recommendations please send them our way to add to our list! We appreciated everyone reaching out with incredible places to eat and explore. I hope your travels one day lead you to the beautiful beaches, delicious restaurants, and area we made life long memories at!
All the stress and anxiety of moving to Florida was worth it. It was worth advocating for ourselves with insurance. It was worth the complex packing process. It was worth figuring out all the logistics. Everything was worth it for this family experience and adventure! We've made so many memories and got to explore so much because of this extended stay. Our dream has always been to relocate in the winter months and we finally got the opportunity. The ability to escape seasonal depression this year was life changing. Sonny got the opportunity to spend his winter outside enjoying the sun, fresh air, beaches, pool, parks and more instead of being cooped up in the house. He got to experience things he could never have done at home during the winter (or ever)! My love and loyalty will be to the beautiful city of Chicago, but I hope to be a permanent snowbird at some point in my life. I can only hope it is sooner rather than later!
XO - Amanda