Wine and Dine in St. Augustine this Holiday Season

Learn more about restaurants and activities to wine and dine at around St. Augustine during the holiday season!

Regardless of whether you've never stepped foot in St. Augustine, are a seasoned visitor, or maybe just recently moved here (like me), the holiday season is a magical time to experience the nation's oldest city.

Bright white lights in abundance, illuminating the night sky and casting a world famous sparkling sheen on every downtown street corner. What more could you ask for? And what better way to experience the city in all of its glitz and glory this holiday season, than by wining and dining?

What exactly do I mean by "wining and dining?" Although wining and dining can certainly be done lavishly, I like to think of it as simply eating, drinking, and being merry, all while partaking in the spirit of the season.

Here is a rundown of where to wine and dine in St. Augustine this holiday season. While the majority of these mentions are watering holes and eateries that have quickly been added to my own list of personal favorites, some are establishments I'm eager to visit for the very first time.

Sit & Sip

Looking for a place to sit and sip? The following locales invite you to do just that, and make great places to start (or finish) your evening out and about in St. Augustine. Each boasts its own unique appeal and represents a different part of the city, yet none are more than a short drive (or long walk) apart.

Downtown Bayfront

Tini Martini Bar: Because I'm a sucker for any place that has festive lights and holiday decor year-round, plus a water view, the Tini Martini Bar at the Casablanca Inn immediately caught my attention. Sitting on the charming porch of this historic inn, while sipping a Noveltini or Classy Tini makes you feel a little bit fancy. No matter which martini you choose, it will be shaken just right, and just for you. My first visit to the Tini was on a Saturday evening, which meant I got to enjoy live music while sipping on my cocktail. Not only is this spot suitable for a dressy date night, it's a great spot to take your family. Just ask my mom.


DOS Coffee and Wine Bar: If you're in the mood to relax and chat over a sizable glass of wine, in a locale that's removed from the downtown bustle, make a stop by DOS. Although regularly frequented for coffee by locals and tourists alike during the daytime hours, come the evening, DOS acts as a wine bar. My first wine sipping experience at DOS was during an Art Walk event. DOS was offering their specialty Sangria in a glass so large I felt I needed both hands. Along with coffee and wine selections, DOS is known for opening its doors to community events.

Historic Lincolnville

Ice Plant Bar: I've been a fan of the Ice Plant Bar since before moving to St. Augustine. Although still pretty new to town, I run into at least one person I know (if not five or six) whenever I go, which just makes me feel right at home. Adjoined to the St. Augustine Distillery, at the Ice Plant Bar, not only do you feel like you've traveled back in time, you can take advantage of trying out local flavors in the form of signature cocktails and grub. Or, you can always do what I do and go later in the evening and order a Horse & Buggy (shot of whiskey plus PBR, although I usually pass on the shot). Before you select a table to plant yourself at for the duration of the eve, stay put by the bar long enough, take a look at the fine-tuned methodology that goes into the making of your cocktail, all the way down to the ice. (What's so special about the ice? Just watch and you'll see).

Anastasia Island

The Conch House: Situated just minutes from downtown St. Augustine, over the Bridge of Lions on Anastasia Island is the Conch House. The Conch House lounge has quickly become my own post-work day island oasis on weekdays, thanks to happy hour from 4-7 p.m. If you walk all the way to the end of the dock, you'll find a quiet and removed place to sit, sip and see the sunset. If you have your stomach set on oysters or a full plate of seafood, back on land, the Conch House restaurant has an expansive dining deck with Tiki Hut booths suspended over the marshland, leaving little separation between you and nature.

Taste & Tour

There's something to be said for getting to taste and sightsee while moving about. Whether you prefer exploring on your own two feet or an open air ride, the following tour options provide you the opportunity to salute your taste buds while experiencing the holiday ambiance.

San Sebastian Winery: I don't know about your family, but my family's favorite type of group outing is the kind that involves generous amounts of wine. Thanks to San Sebastian, you don't have to pay a visit to the countryside for an authentic winery experience at what some consider to be the birthplace of American wine. San Sebastian Winery offers complimentary tours seven days a week. The best part of any winery visit (second only to the free samples), are the bottles you can purchase to take home and share with your friends, or keep to yourself and drink later while reminiscing about your trip. If you've ever been to town and driven by the winery on a weekend evening, you may have seen and heard the live music performances up on the roof at "The Cellar Upstairs," Wine, Jazz & Blues Bar.

St. Augustine Distillery: When I first stepped through the doors of the St. Augustine Distillery, I was pleased to learn the tours are free. Not only do you get to learn about the history of ice and distilling in Florida while touring this historic renovated ice manufacturing plant from 1917, you get to do some tasting in the process. The only reason I didn't go ahead and take a tour right then, is because I knew after sampling small batch spirits, I would never get my work done the rest of the day. Needless to say, this tour is at the top of my list this holiday season, on a day I don't have anything else planned.

Recently, the Distillery has been offering weekly classes on Saturdays, and there are still a couple left in the lineup. If you are a cocktail enthusiast looking to do some mixing and making of your own, consider signing up to take part in these upcoming classes. As a former Gin lover, I have to say, the first one sounds especially tempting.

  • Gin 101 & Gin Cocktails: Explore gin's history, taste the different categories and learn about the process of creating the Distillery's New World Gin. Plus, make your own classic gin cocktail creation with the help of bartenders. $35 per person. 6:15 p.m., Saturday Dec. 13.
  • DIY Bar - Party On!: This introductory crash course teaches you how to make your own craft cocktails at home. The best part? You go home with handcrafted party recipes and all the know-how to host your own successful cocktail party. $35 per person. 8 p.m., Saturday, Dec. 13.

"Nights of Lights" Wine and Carriage Tour: If you'd prefer to ride around the old fashioned way (horse and buggy) there's a festive wine and carriage option, just for you. During a 45-minute group tour, guests ride along in a horse-drawn carriage, taking in the historic sights and white lights, while sharing a bottle of wine (for two). Tours are $49 per person, and depart from the Tasting Tours Lounge. Other Tasting Tours include: Corks and Forks Tour (Food and Wine Tasting Experience), Wine About Town Tour (Wine Lovers Tour), and Beer About Town (Beer Lovers Tour). Personally, I've got my sights on the Wine About Town Tour. For a full listing of upcoming tasting tours, visit the Tasting Room's Tours & Adventures calendar.

Set Sail

Nights of Lights Sunset Sail: I must admit, I've been looking for an excuse to treat myself to a sailing excursion all season, and think I've finally found one—getting to experience Nights of Light from the water via Schooner Freedom Charters. Nightly sailing outings depart from the City Marina at 4:15 p.m. and last two hours. $45 includes complimentary soda, water, beer, wine and hot chocolate.

Regatta of Lights: If there's one event I've heard locals (and tourists) say they are sorry to have missed in year's past, it's the Regatta of Lights. For this reason, it's written in Sharpie on my calendar so I have no excuse to miss. The Regatta of Lights is a fancy name for a parade of boats of all shapes and sizes adorned in lights, cruising through the bay and competing for awards. This year's regatta takes place Saturday, Dec. 13 and kicks off at 6 p.m. It's recommended to arrive well in advance if you're hoping to take a seat along the bayfront for a view from one of downtown's eateries. You could always take in the experience with a martini in hand while sitting and sipping at the Tini Martini Bar.

Inventive Dining

From plant-based creations to multi-course spectaculars, the following options offer an inventive alternative to your typical dining experience this holiday season. The first is an eatery that I'm especially partial towards (for good reason), and the second, a gourmet garden cottage that I have been crushing on and am most eager to try.

Present Moment Cafe & Market: Perhaps you have an herbivore joining you, or maybe you are simply craving some health-filled, delicious vegan eats. Believe this vegan when she says, Present Moment Cafe rivals the vegan cuisine I've tasted in the Big Apple. Located on West King Street, just outside of historic downtown, the Present Moment Cafe offers you an upscale, yet peaceful raw vegan dining experience, and the best hummus I've ever tasted. Instead of a shot of liquor, consider pairing your entrée with an invigorating wellness shot that will take your breath away, in the best of ways. They even have dessert (as seen in the cover photo)!

The Gourmet Hut: Have you ever dreamt of dining in an enchanting courtyard on a European countryside and having the chef come to your table to discuss with you the evening's creations? Me too! Thanks to the Gourmet Hut, this dream can become a reality. Have dietary needs or preferences and curious what the evening's menu will be? Walk by and check out their chalkboard or simply call ahead before planning your dinner outing. This one's on my holiday date dining list, and I can't wait to see what kind of plant-based spectacular they whip up.  

Sweet Detours

I'm pretty sure it's been proven, no wining and dining experience is complete without dessert. Although I typically stick to vegan cheesecake from the Present Moment, or cupcakes from the Floridian, the following downtown establishments are dedicated to sweet treats that are sure to make any mouth water. The fact that these dessert stops are in walking distance of each other means you can double up if you're feeling up to some extra indulging.

The Chocolate Turtle: Every time I'm walking to dine at the Floridian, I am distracting by the overwhelming aroma of something I love—chocolate. The Chocolate Turtle dessert bar's menu includes cakes piled high, tortes for the sharing, mousse cups, s'mores, brownies, and more. Plus, you get to wash your selection down with coffee, wine, beer or even some chocolate specialty drinks if you're not chocolate-ed out.

Cousteau's Waffle & Milkshake Bar: Just a short walk from the bayfront on Hypolita Street is Cousteau's dessert novelty waffle and milkshake bar. As an alternative to ordering an entire milkshake or waffle, Cousteau's now offers doughnut bites by the dozen (or half dozen) you can take with you while you walk around downtown and view the lights. If you happen to have a red beanie with you, wear it inside. Not only will you match the employees, you'll receive 10 percent off.

  • Pop Quiz! What do "Matching Pajamas," "Life on Mars" and "Jaguar Shark" have in common? Not only are they menu items at Cousteau's, they are references to movies by a certain film director and screenwriter. Who is it?
    Answer: Although I'm the worst when it comes to pop culture reference, even I could figure this one out.
    Hint: His first name is three letters and rhymes with, "guess." (Give up? The answer is Wes Anderson).

Stay the Night

After all of your wining and dining, you'll need a place to sleep. And there's something inviting about resting your head in a place that feels like home. Perhaps that's why I've always been drawn to Bed and Breakfasts.

If you're seeking to stay somewhere that is festive, quaint and intimate, consider one of St. Augustine's many Bed and Breakfast options. Not sure which one to pick? What if I told you there was an event taking place this month that allows you to experience not just one, but countless bed and breakfasts and sample some original menu items in the process?

Photo courtesy of Bayfront Westcott House.
Photo courtesy of Bayfront Westcott House.

Photo courtesy of Bayfront Westcott House

Bed & Breakfast Holiday Tour: Signing up to participate in the Bed and Breakfast Holiday Tour is a great way to get in the spirit of the season, and feel like you're on HGTV without all the cameras and scripts involved.

This year's Annual Bed & Breakfast Holiday tour takes place Saturday Dec. 13 and Sunday Dec. 14 from 1-5 p.m. Tickets are $30 per person. Each Bed and Breakfast partners with a local restaurant for the event, to provide delicious treats for the occasion. 

If you aren't able to secure a stay at one of these Bed and Breakfasts this holiday season, this event gives you a chance to scope them out and decide which ones to add to your lists of "must stays" for 2015.

For a full list of St. Augustine Bed and Breakfast accommodations, check out our Bed & Breakfast Listings.

Looking for somewhere to stay last minute, or planning in advance but not sure where to begin your search? Take a look at our "Places to Stay" section for a full listing of area condos, hotels, motels, pet-friendly options and more.

Wine & Dine into the New Year

Not sure you'll be able to make it in town before the New Year? Fear not. Nights of Lights continues all the way to the beginning of February and there are nonstop events to experience between now and then. If you ask me, this sounds like the perfect excuse to extend your wining and dining well into 2015.