St Augustine Sailing - Nights of Lights - St Augustine downtown - winter time - Sailboats

Nights of Lights – Dinner

There’s no better time to wander the historic streets of St. Augustine, Florida than Nights of Lights, when millions of white twinkle lights dance above, below and all around. After a cozy sail aboard one of our luxury yachts, we have some favorite spots to grab a bite and view the spectacular lights.

Catch 27

We love Catch 27’s commitment to serving fresh, locally-caught seafood. In a way, we share the waters with them! This cozy space is on one of St. Augustine, Florida’s oldest cobbled roads, Charlotte Street, which shines with festive lights – you’ll enjoy the walk there as much as you will the food. Dine in the restored home or enjoy a meal under the stars on their patio. Start with the Deviled Egg BLT with Southern Fried Oyster or Stuffed Piquillo Peppers, warm up the local specialty Minorcan Clam Chowder and don’t miss the Fall Risotto, served with your choice of protein.

Click here for their website:  Catch 27

Catch 27 Restaurant

Meehan’s Irish Pub

Meehan’s is a traditional Irish Pub located right on the waterfront. Snag a patio or balcony table for a perfect view of the illuminated yachts and waterfront. They boast the largest whiskey collection around, with many specialty bottles and limited vintages. You won’t want to miss their famous Reuben Rolls and Hand-Cut Irish Chips (French Fries to us Americans), dusted with garlic and parmesan – hot tip, dip them in the creamy chive dressing! Head up to Johnny’s Oyster Bar for a flight of the freshest oysters, or keep it homey with comforting Bangers and Mash or a Tommy Dolan prime burger.

Click here for their website: Meehan’s Irish Pub

Casa Reina Taqueria & Tequilla

One of St. Augustine’s newest restaurants, Casa Reina Taqueria & Tequila, is more than just tacos. They take traditional Mexican and Latin American cuisine and fuse it with coastal Florida flavors for a dynamite combination. Be sure to hit the rooftop for a crafted cocktail and an expansive view of the illuminated Plaza de la Constitución and the waterfront. Classics like the Jalapeno Rellenos, Queso and Chimichangas anchor the menu, while their more quirky dishes, like the Ancient City Ribeye with chimichurri and truffled hot sauce, Nashville Hot Chicken Tacos and Mexican Sushi, add a global twist.

Click here for their website: Casa Reina Taqueria & Tequila


This nationally recognized local staple since 2007 will make you feel like you’ve stepped out of colonial Spain and into a chic French haute cuisine. Perfect for an anniversary, birthday or indulgent night out, Collage has made a name for themselves through the recipes they’ve perfected. Escargot, Beef Tenderloin Au Poivre, Veal Orleans and tender Shrimp and Lobster Fettuccini will have you booking your next reservation before you’ve even finished your appetizers. And be sure to leave room for their signature dessert, The Bougainvillea, named after the flowers circling the entrance. Be sure to head to the right when leaving to stroll by the majestic architecture of Flagler College, lit from bollards to turrets.

Click here for their website: Collage


Follow the twinkly waterfront lights down to the tiny, bricked Cuna Street, and you’ll find Michael’s, where they’re all about good food, great wine and even better company. This casually elegant eatery has been widely feted, with its wine list receiving accolades from The Wine Spectator for over a decade. Order the Sunday Bread Plate to see how sumptuous the humble bread and butter basket can be, with freshly baked sourdough and miso furikake butter. The menu is a global exploration, with Blistered Shishitos, Lyonnaise Potatoes, La Chamba Chicken, Australian Wagyu Striploin and Criollo Shrimp Mofongo vying for a place on your table. Headed by restauranteur Chef Michael Lugo, Michael’s wine list is meticulously curated, and their highly trained staff can help select the perfect vintage.

Click here for their website: Michael’s

Koolaburra Coffee

The Plaza de la Constitución is the shining center of downtown St. Augustine and is a don’t-miss location. As the weather gets chillier, make a stop by The Kookaburra Coffee. This Aussie-American espresso bar serves a cornucopia of delicious hot beverages guaranteed to warm you up. Purists can enjoy an expertly-roasted short black or flat white, but locals also love their signature lattes, the Honeybadger and the Lavender. And, of course, there’s rich Hot Chocolate made with creamy Dutch cocoa.

Click here for their website: The Kookaburra Coffee

Gaufre’s and Goods

Take the road less traveled and head south of the Bridge of Lions and down the tiniest path towards this jewel hidden away on Charlotte Street. Many of the homes and businesses in this historic part of town join the festivities and drape their buildings in white lights. Gaufre’s is the perfect stop while exploring the area. You’ve never had a better pierogi outside of Poland – try the potato and cheese one sauteed with bacon and onion. They also specialize in Greek delicacies like Saganaki and Grape Leaves. And don’t miss the gaufres – a crisp, sugar waffle dusted with powdered sugar and you’re choice of toppings.

Click here for their website: Gaufre’s and Goods

St Augustine Sailing


There’s no denying the magic of this beautiful port city in the winter season. Make it an unforgettable night on the town during Nights of Lights with a sail on one of our luxury sailing yachts and dinner out.

Or enjoy one of our private chef experiences on board and save dinner out for another evening! For more information on our available excursions, visit our website here.