Explore Uptown St. Augustine: San Marco Avenue and Beyond

Spinster Abbott’s in a former Indian River Fruit building on San Marco Avenue under a sunset sky in St. Augustine

Explore historic attractions, browse independent shops and discover local restaurants along San Marco Avenue in St. Augustine’s Uptown neighborhood.

Just north of downtown, Uptown brings together some of St. Augustine’s best-known historic sites and a neighborhood filled with places to eat, shop and linger. San Marco Avenue connects much of the experience, while nearby side streets lead to a community theatre, local art and scenic walks. Spend an afternoon browsing, build a day around the attractions or settle in for dinner and an evening out.

Explore Uptown’s Historic Attractions

Mission Nombre de Dios and the National Shrine of Our Lady of La Leche

Visit the grounds of Mission Nombre de Dios and the National Shrine of Our Lady of La Leche at 101 San Marco Avenue. The Great Cross rises above this historic waterfront setting, where visitors can explore the historic chapel, museum and spaces for quiet reflection. Walk through the grounds to discover the Rosary Garden and other sites that connect the Mission’s history with its continuing role as a place of pilgrimage.

Ivy-covered chapel at the National Shrine of Our Lady of La Leche on the Mission Nombre de Dios grounds in St. Augustine

PicturedMission Nombre de Dios and the National Shrine of Our Lady of La Leche

Fountain of Youth Archaeological Park

Turn onto Magnolia Avenue to visit the Fountain of Youth Archaeological Park at 11 Magnolia Avenue. The 15-acre attraction offers another opportunity to explore St. Augustine’s past, with exhibits and the Spring House among its features. Allow time for the park as its own stop before continuing through Uptown.

PicturedFountain of Youth Archaeological Park

Old Jail

Explore a different chapter of local history at the Old Jail, located at 167 San Marco Avenue. Built in 1891, the jail offers guided tours through its cells and living quarters, with costumed interpreters sharing stories of incarceration and law enforcement in St. Augustine. Its imposing cells provide a memorable contrast to the building’s decorative exterior.

Magnolia Avenue and the Old Senator

Make room for a scenic detour along Magnolia Avenue, where arching oaks frame one of the neighborhood’s distinctive streets. Nearby, the Old Senator Live Oak offers another opportunity to appreciate the mature trees that help shape Uptown’s landscape.

Iron cells inside the historic 1891 Old Jail on San Marco Avenue in St. Augustine

PicturedOld Jail Museum

Browse Local Shops and Art

Leave time between attractions to explore Uptown’s independent shops. Browse jewelry at Anchor Boutique, hunt for vintage discoveries at Antiques & Things and Cool and Collected, or explore furnishings, clothing and artwork at Coastal Traders. Crafts Without Borders adds handmade and fair trade goods from artisans around the world.

For a connection to St. Augustine’s creative community, visit Jenna Alexander’s studio at 73 San Marco Avenue, where fine art and artist-designed merchandise offer a locally inspired keepsake. At Spinster Abbott’s, Snake Bird Vintage adds another browsing opportunity with vintage clothing, accessories and home finds.

Stop for Coffee, Lunch and Something Sweet

Spinster Abbott’s

Combine a coffee break with a little shopping at Spinster Abbott’s. Its espresso bar, taproom and bodega bring several experiences together in one neighborhood gathering place. Stop for a drink, explore the shelves or take a break before heading to the next shop. The business draws inspiration from its building’s earlier life as an Indian River fruit stand, giving the space an Old Florida connection.

Juniper Market

Plan a breakfast or lunch stop at Juniper Market, located at 48 San Marco Avenue. Coffee, sandwiches and baked treats make it a convenient place to refuel during an afternoon of exploring. Choose a seat inside or enjoy the neighborhood from an outdoor table.

Alms + Fare

Visit Alms + Fare at 154 San Marco Avenue for naturally sweetened baked goods, coffee drinks, toast and smoothies. The wellness-focused bakery offers another option for a morning stop or an afternoon treat.

The Witty Whisker Cat Cafe

Pair a coffee break with some feline company at The Witty Whisker Cat Cafe, located at 7 Old Mission Avenue near Raintree Restaurant and next door to Limelight Theatre. The cafe serves coffee, wine and sweet treats, while the cat lounge offers time with adoptable cats from Feline Canopy of Care, a local rescue nonprofit. Reservations are suggested for the cat lounge and for special events like yoga with cats.

Crème de la Cocoa

Continue farther north to Crème de la Cocoa, located at 299 San Marco Avenue. The bakery’s selection includes cakes, pies, cookies, chocolates and other desserts, making it a sweet addition to an Uptown outing. Pick up something to enjoy during the visit or bring a few treats back to share.

Discover The Pickle Factory

Add a flavorful stop at The Pickle Factory, located farther north at 239 San Marco Avenue. Housed in a former Coca-Cola bottling facility, this specialty shop brings together pickles, pantry finds and pickle-themed merchandise. It’s an opportunity to browse an unusual selection of edible souvenirs while discovering another historic building along the avenue.

Stay for Dinner and Drinks

Raintree Restaurant

Make dinner part of the itinerary at Raintree Restaurant, located at 102 San Marco Avenue. Set in a restored Victorian home, the restaurant combines historic surroundings with a menu drawing on Mediterranean, American and Asian influences. Indoor dining and a spacious courtyard provide options for a relaxed meal, with desserts offering a reason to linger.

PicturedRaintree Restaurant Pation Dining

Boat Drinks

Find a taste of the tropics at Boat Drinks, located at 123 San Marco Avenue. The Uptown restaurant and bar serves seafood, island-inspired dishes and tropical cocktails in a setting that celebrates Florida’s coastal character. Outdoor seating adds another option for enjoying an evening in the neighborhood.

Cortesse’s Bistro and Flamingo Room Piano Bar

Continue to Cortesse’s Bistro at 172 San Marco Avenue for Mediterranean-inspired dining and patio seating. The Flamingo Room Piano Bar brings live piano music and cocktails into the experience, making this a natural choice for visitors looking to pair dinner with evening entertainment.

Carrera Wine Cellar

Enjoy a glass of wine or browse bottles at Carrera Wine Cellar, located at 35 San Marco Avenue. Visitors can also check the schedule for wine classes, adding a tasting-and-learning experience to a neighborhood outing.

Catch a Show at Limelight Theatre

Build an evening around a performance at Limelight Theatre, located just off San Marco Avenue at 11 Old Mission Avenue. St. Augustine’s community theatre presents plays and musicals throughout the year. Pair a performance with an Uptown dinner reservation for an evening that brings together local dining and the performing arts.

Two costumed actors perform on an Egyptian-themed set during a community theatre production in St. Augustine

Plan an Uptown Outing

Choose a few stops to explore at an easy pace, leaving time to browse and take a break along the way. Combine the Mission grounds with shopping and lunch, devote a day to the historic attractions or arrive later for dinner and a show.

Many shops and cafés cluster along San Marco Avenue, while attractions and additional businesses extend onto neighboring streets and farther north. Check the distance between planned stops, use designated crossings and review individual websites for current hours, tickets and reservations before heading out.