St. Augustine is a great place to visit solo thanks to lots of tours, a fantastic winery, a multitude of fun restaurants, plenty of unique shopping and several historically significant landmarks that link America’s oldest city to its Spanish roots. A three day stay in this beautiful, quirky town will keep you busy yet give you time to experience a lot of what St. Augustine has to offer.
Where to Stay
Ideally, travelers would check in the night before so they are rested and have a full next day to get an overview of the city. St. Augustine has some traditional lodging options like the Hilton and Holiday Inn. However, there are some historically interesting and cozier options for the solo traveler like the 1791 built St. Francis Inn, with the claim to fame of being the oldest inn in St. Augustine. Here, customers are lavishly accommodated with a full breakfast buffet that includes free mimosas and Bloody Marys on Saturdays and Sundays, an evening social hour daily from 5:30-6:30 p.m. with free appetizers and drinks, and nightly desserts for all guests from 7:30-9:00 p.m. In addition guests get free use of hotel bicycles, a free glass of sherry and fresh flowers in your room upon arrival, internet access, and a heated pool. In addition, guests enjoy free use of nearby gym facilities and free entrance into the St. Augustine lighthouse plus 50% off admission at Oldest House, a historic museum that traces Florida’s history. These wonderful amenities are all housed within walking distance to all the great attractions of St. Augustine for a great deal.
St. Francis Inn
279 St. George Street, St. Augustine, Florida 32084
Check-in after 3 p.m./Check-out 11:00 a.m.
If you would rather stay waterfront, Bayfront Inn is a prime location. With a view of the beautiful Bridge of Lions, it also boasts of its age with one of the seven oldest buildings in St. Augustine on their property. It too provides complimentary breakfast, has a hotel on the Matanzas Bay side, and necessities that will make your stay comfortable for a lower price.
138 Avenida Menendez St. Augustine, FL 32084
Check-in after 3 p.m./Check-out 11 a.m.
After eating breakfast, jump on a trolley from Old Town Trolley Tours to see most of St. Augustine in just a few hours with knowledgeable tour guides. Buying one ticket gives you unlimited use of the trolley for three days and with over 22 stops, you can break up the sights. These trolley rides give you an overview of the city, squeezing down narrow streets while you note places that pique your interest to return to later. Stay on board and do the whole ride at once, and then you can start round two and jump on and off where you want.
Old Town Trolley Tours
201 Front Street , Key West, Florida 33040
8:30 a.m. to 4:30 p.m.
After trolley time, take a stroll down St. George Street, the pedestrian-only shopping haven for quirky gifts, some wine tastings, and to grab a bite for lunch. One great lunch option is Mill Top Tavern, which looks like a tree house and has good pub grub and drink prices. They often have live music playing too. Also, stop in at the Vino del Grotto Winery store to get a few samples of their delicious fruit infused wines.
Mill Top Tavern
19 1/2 St. George St. St. Augustine, FL 32084
11:30 a.m. until 12:30 p.m. most nights
Vino del Grotto Winery
53 St. George St. St Augustine FL 32084
Opens 10 a.m. daily, closes 6 p.m. Monday-Thursday and 9 p.m. Friday-Sunday
After being re-energized with food and drink, hop back on the trolley and head to the Castillo de San Marcos, the fort built first in 1672 by the Spaniards. Touring this fort is a quick adventure but standing on these historic 300+ year old grounds is a must. If you have the energy and time, pop over on the trolley to the fun, infamous and albeit touristy Fountain of Youth.
Castillo de San Marcos NM
1 South Castillo Drive St. Augustine, FL 32084
8:45 a.m. to 5:15 p.m.
Fountain of Youth
11 Magnolia Avenue St. Augustine, FL 32084
9 a.m. to 5 p.m.
For dinner, you have many choices such as O.C. White’s with outdoor waterfront dining. Try some of their signature dishes like the Gouda Crab-Stuffed Portabella Mushroom appetizer followed by the Shrimp Abaco made with sauteed garlic, mushrooms, tomatoes, artichokes and a creamy sauce.
118 Avenida Menendez St. Augustine, Florida 32084
Monday-Thursday 11 a.m.-10 p.m., Friday-Saturday 11 a.m.-11 p.m., Sunday 9:30 a.m. – 10 p.m.
Use this morning to see some of the sights slightly outside the historic district. Hop on the beach shuttle and head to the St. Augustine Lighthouse for great views. Continue on and spend some time at the Alligator Farm before relaxing a few hours on the St. Augustine Beach. After you’ve had your fun in the sun, grab some lunch at South Beach Grill with classic seafood choices like grilled fish tacos or blackened fish wraps.
South Beach Grill
45 Cubbedge Road St. Augustine , FL. 32080
Breakfast 7:30-10:30 a.m., Lunch/Dinner 11 a.m. – 9 p.m.
Head back into town and visit some more shops on St. George. Stop for a pre-dinner drink at one of the many local bars such as Rendezvous World of Beer Bar with over 150 beers from around the world. It’s part of a shopping plaza, so from St. George Street you have to keep walking down a long hallway in order to reach this beer lover’s paradise.
Rendevous World of Beer Bar
106 St. George St. St. Augustine Florida
11 a.m. – 2 a.m. (most nights)
For dinner, A1A AleWorks is a popular choice, and it will keep the beer theme going as they brew their own beers such as their King Street Light Lager, Porpoise Point IPA, Bridges of Lions Brown Ale, Red Brick Ale, and A. Strange Stout. Choosing just one might be problematic, but that can be remedied if you order their beer sampler. On one of the busiest streets in St. Augustine, this place is always happening and they have great meal choices with a seafood focus like their Mango Barbeque Shrimp Skewer or their Lobster and Shrimp Tacos.
1 King St. St Augustine , FL 32084
Sunday-Thursday 11 a.m.- 11:30 p.m., Friday-Saturday 11 p.m. – midnight
Time to get some last minute sightseeing in this morning. Consider touring Flagler College, which began as Hotel Ponce de Leon. History and architecture merge to create a breathtaking, luxurious building that transports visitors back to old Europe.
59 St. George Street St. Augustine, Florida 32084
Tours 10 a.m. – 3 p.m.
For lunch, perhaps stop at the nearby Casa Monica Hotel, a 5-star luxury hotel in the heart of St. Augustine right across from Flagler. They have an indoor/outdoor cafe with gourmet sandwiches, soups, and salads and a view of the beautiful grounds of Flagler for a prime people-watching location. After lunch, peek inside the hotel lobby for a glimpse of the award-winning accommodations. Then, walk or hop on the trolley and head to the nearby San Sebastian Winery. Sure to be one of the highlights of your trip, the winery does a free, full tour of their production area with tastings provided throughout. They have outstanding wine and great gifts and souvenirs. After the tour, head upstairs to The Cellar Upstairs, their rooftop jazz and wine bar with live music on Fridays and Saturdays until 11pm and Sundays until 5pm. They have been voted “Best Live Music” in St. Augustine and bring in musicians who put a blues and/or jazz slant on classics as well as contemporary tunes. They also have great cheese and meat platters as well as other light fare.
Casa Monica Hotel
95 Cordova St St. Augustine, FL 32084
Open daily for breakfast, lunch, and dinner
San Sebastian Winery
157 King Street, St. Augustine, Florida
Monday – Saturday 10 a.m. – 6 p.m., Sunday 11 a.m. – 6 p.m.
For your last dinner, try some authentic dishes at the well-known Spanish-focused Columbia Restaurant, Cuban-centered Habana Village, or Mediterranean-minded La Pentola. Each has a vibrant atmosphere and fun dishes to enjoy. For a list of restaurant choices, visit www.therestauranttimes.net.
To wrap up your visit, consider a Ghost Tour of ancient St. Augustine since it is considered to be one of the most haunted cities in America. Choose from riding in a hearse, sailing, or walking (with some operating as pub crawls) for your thrills and chills. One option is the Travel and Discovery channel featured Ghost Tours. Or stop by for a nightcap at the Tini Martini Bar, featuring ever-evolving martini specials and live music most weekends.
A Ghostly Experience
2 St. George Street St. Augustine, Florida 32084
8 p.m. Sunday-Thursday, 8 and 9:30 p.m. Friday and Saturday
The Tini Martini Bar
24 Avenida Menendez, St. Augustine, Florida USA 32084
Noon until 11:30 p.m. or later
I hope you enjoy St. Augustine as much as I have. Happy travels!