A Night Out in Sanford

The Waterfront Gateway City

The city of Sanford sits on the southern shore of Lake Monroe, just above the start of the St. Johns River trail, earning the nickname of the Waterfront Gateway City. Sanford and its surrounding areas were originally home to Florida’s Indigenous tribes for thousands of years before being incorporated in 1877. The culture of the city has massively evolved over the past centuries to integrate a spectrum of diversified cultures and communities that have molded the local neighborhoods into the stimulating city it is today.

Esteemed as an emerging trade center for local goods, historic downtown Sanford boasts an impressive marriage of artistic ingenuity with small-business craftsmanship that attracts visitors from all over the state. The charming city is well-known for its preserved streets that reveal a glimpse of eras past through the exhibition of historical architecture. As the neighborhood continues to expand with new galleries, antique shops, restaurants, and craft stores, it continues to make a name for itself as one of Central Florida’s liveliest spots.

When you’re looking for a new place to explore, it can be easy to get caught up in the allure of tourist spots and miss out on all the unique experiences the neighborhood has to offer. If you have a few hours to spare and want to escape the humdrum of bustling cities and attractions, head toward Lake Monroe and indulge in an exciting evening in downtown Sanford.

Boba Babes

Photo by Boba Babes Facebook

Lunch at Boba Babes Gourmet Tea & Waffles 

Saying it gets HOT in Florida is an understatement. When the sun is going down and that final heat wave hits like a brick, you’ll want to get in line at Boba Babes Gourmet Tea & Waffle Bar to cool things down. This sweet haven is a new addition to Sanford’s main street that combines a passion for crafted tea drinks with gourmet dessert waffles and wraps it all up in a pastel dream. Boba Babes’ menu is inspired by the milky tea-based drink Bubble Tea that originated in Taiwan, and their menu showcases a tantalizing variety of mouthwatering flavors to quench your thirst. Try the classic drink with traditional honey boba, or try adventurous combinations with popping pearls in lychee, mango, and pomegranate flavors to customize your treat. With loose-leaf tea options like white peach oolong, elderflower, and vanilla chai, you’ll make every excuse to take a detour through Sanford and try a new flavor.

You’ll find yourself needing something to munch on while you marvel over the countless tea options, and Boba Babes certainly does not disappoint. Offering gourmet organic waffles made with homemade sugar, organic milks, and local honey, these sinful snacks are not your everyday toaster waffle. Try a flight of waffle bites with your choice of assorted flavors like fruity pebbles and chocolate chip or take a dozen home to share with your friends. Since there’s plenty more places to see in Sanford, you might opt for the opulent Unicorn Waffle on a stick for an outrageously cute snack to grab on the go.


Photo by Magpies Facebook

Shopping at Magpies Modern General Store

Now that you’ve had your sugar fix, you’ll need to burn off some of that energy. There’s no better way to walk off those waffles than a few trips around Magpies Modern General Store. This delightful emporium is nestled into one of Sanford’s main street architectural beauties and supplies everything from apothecary goods to hand-crafted housewares. The store is designed to flow like an expertly placed art installation and will inspire you to envision each item in your home. You won’t often find the same merchandise twice, as the owners often travel to markets and craft festivals all over the country to procure and curate the uncommon finds they offer. Included in the myriad of oddities available are small-batch local goods created by Florida crafters, reinforcing the shop’s motto that “supporting local isn’t just an idea, but a way of life.”

Take a leisurely stroll around the store to peruse handmade fine jewelry, organic skincare products, woven clothing, and accessories made from natural Florida gemstones. Discover rare and elegant perfumes and oils, fragrant hand-carved soaps, and exfoliating facial incense to #treatyourself just for fun. Browse for your new favorite pantry staples like elderflower syrup and locally-made bitters for cocktail hour or pick out a pair of zodiac oven mitts to perk your kitchen up. No matter what you’re looking for, Magpies is the perfect place to find an atypical gift for that family member who is difficult to shop for, or to find that quirky gift for the White Elephant party at work. If all this shopping has you working up a sweat, be sure to swing by the cooler and grab an all-natural Hyppo Ice Pop made with care right here in Florida. Once you’ve shopped to your heart’s content, we’re ready to move on to our next stop on main street.

The Breezeway

Photo by The Breezeway Facebook

Dinner at The Breezeway Restaurant & Bar

When all those shopping bags get heavy and you need to take a load off, grab a seat in The Breezeway’s courtyard and enjoy a cocktail from the outdoor bar. Sit back and bask in the cool evening air under the stars while absorbing the bustling Sanford night scene. On the weekends, you’re likely to find lively karaoke singers fearlessly belting out their favorite hits for their adoring fans. Weeknights in the courtyard host an assortment of live musicians from Sanford and neighboring cities playing everything from soulful rock and roll to groovy 70’s disco classics. If karaoke is not your style, The Breezeway also offers a more intimate setting at their indoor bar where you can order a glass of wine and unwind. While many people stay for the drinks, most natives return for the knowledgeable and friendly staff that are always happy to welcome familiar faces.

Don’t leave the Breezeway without trying one of the locally famous dishes aptly named after the great city of Sanford itself. If you’ve worked up an appetite, try hearty favorites like the Sanford Special, a pork tenderloin sandwich piled high on a Kaiser roll, or the 1st Street sandwich made with ham, pepperoni, bacon, and mozzarella. The restaurant is also well-known for its Mile-High sandwich, their take on a savory Rueben sandwich that earned the restaurant its right as a staple for Sanford natives. With an impressive American-style menu including sizzling steaks, freshly-caught seafood, and savory pasta, you’ll find it hard to leave The Breezeway hungry.


Dessert at Wondermade

Hope you saved some room after dinner, because the heavenly scent of roasted marshmallows is calling your name next door at Wondermade. The dessert café stands out as one of Sanford’s unique sweet eateries, offering a modern twist on how we think of dessert. Marshmallows are no longer just a topping; the shop offers tons of ways to enjoy their freshly made marshmallows: roasted on a stick, packed into a gooey s’mores sandwich, dunked in a steamy cup of hot chocolate, or beautifully balanced in your favorite ice cream.

Did we mention that these are no ordinary marshmallows? Try not to buy them all when you see incredible creations like churro, lavender, and salted honey marshmallows. If you’re interested in something with a bit more bite, opt for the Boozy Set filled with beer, bourbon, gin, and Fireball marshmallows. If you’re not in the mood for sticky marshmallows, the café also serves handcrafted ice cream in adventurous varieties like avocado, cornbread, and maple bacon flavors. To add the cherry on top, Wondermade also shares incredible recipes incorporating their marshmallows on the café’s website to inspire you to make your own whacky creations. Life is too short to settle for any ordinary dessert. Indulge and lose yourself in a sumptuous Wondermade dessert.

Bitters & Brass

Photo by Bitters & Brass Facebook

Cocktails at Bitters & Brass

Bitters & Brass is the definitive Sanford bar and guarantees a singular imbibing experience like no other. The first bar in Florida to be owned and operated by bartenders, the 30’s era lounge is home to some of the most experienced bartenders in Orlando. With over 20 years of spirited experience combined, the owners make it their mission to perfect their craft with every drink they pour. The quality of their cocktails is unparalleled, showcasing a maddening array of classic drinks executed with new age flare. At Bitters & Brass you’ll find the essentials such as Side Cars, Tom Collins, Old Fashions, and my personal favorite, the Bee’s Knees. Try any of these cocktails shaken with an egg white for an otherworldly flavor or give your bartender the reigns to see what new concoction they can create.

The lounge is also known for their wildly experimental seasonal drinks crafted from the minds of the bartenders themselves. Using everything from absinthe and brandy to corn whiskey and Demerara rum, you’ll never sip the same drink twice. For the full experience, sit front row and center at the bar to watch the bartenders make every drink from scratch. The construction of each drink is like a moving portrait being executed by a skilled master, no gesture or ingredient without purpose or place. The result is a perfectly crafted cocktail that is as exciting to drink as it is to admire. Make sure to grab a few snaps of these masterpieces to commemorate the #bestnightever. If you like what you see, why not get in on the fun? Bitters & Brass hosts themed cocktail classes to give you the opportunity to become a pro behind the bar. Classes can be reserved every 2nd Saturday of the month for up to 12 people and includes everything you need to know to master the classics and start shaking things up with creations of your own.

Take a break from your mundane routine and enjoy the scenic route for a change! When you need to treat yourself to an evening of pure indulgence, main street in historic downtown Sanford has it all.