Florida – A Complete Guide to Visiting the Oldest U.S. City

Quick Intro: This post is kind of long so I put in some quick links. Check out what you need while visiting St. Augustine and make sure to leave us a comment for any other suggestions! If you’re just getting to know us, visit our About Us Page or take a look at the sailboat we live on – S/V Tipsy Gypsy 

Travel Accommodations
Anchoring, Moorings & Marinas
Transportation
Restaurant, Bars & Nightlife
Entertainment
Special Events
Sailor Amenities
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St. Augustine is the oldest city in the United States and one of the coolest ones you’ll ever make time for.  In 1565, Spanish explorers discovered this beautiful, bustling city in Florida and is now one of the most-exciting places to vacation for local Floridians and people from all over the world. Whether you come in by car or sail in by boat, you’ll be sure to have an incredible time. 

In this blog post, you will discover many of the attractions as well as necessities for experiencing the city of St. Augustine. You may not need everything but this will be a decent guide for you to plan your visit properly. We’ve been here multiple times via sailboat and is our favorite stop in Northern Florida. Enjoy our recommendations and be sure to leave us a comment with your own favorite stops for us to make time for along our next visit. 

Travel Accommodations

First of all, you’ll need to get here. There are plenty of areas to check flights but we almost always find the best prices on booking.com. In addition to getting here, you’ll also need to make sure you have a spot to put your things and lay your head at night. We typically use Airbnb to find an affordable, cute place close to the city. There’s also Anastasia State Park for anyone coming in to go camping!

If you’re like us and come in by boat, then you’re already set! 

Booking.com

Anchoring, Moorings & Marinas

We always do a mixture of anchoring, being on a mooring ball, or having a slip at a marina. Here are a few options for you to look through! If you’re not coming in by boat, you can skip this part. 

Anchoring 

The current rips through this area of the ICW because of the inlet being so close. For a very smooth anchorage, check out Salt Run. You’ll also have a dinghy dock close by. If you’re looking to be close to downtown there are also areas to anchor North and South of the Bridge of Lions. North of the bridge on the east side is the best area to anchor closest to downtown but can be loud with the frequent bridge openings and commotion from other tourists. If you’re looking for a quieter downtown experience, anchoring South of the mooring field is the best option but is a long dinghy ride to the dinghy dock at the Municipal Marina. You’ll need permission to dock there by purchasing a $12/day pass. 

Moorings

St. Augustine Municipal Marina takes care of the moorings on both sides of the bridge and the ones near the lighthouse at Salt Run. We prefer the ones South of the bridge because it is much smoother being further from the inlet but still close to downtown. There is a one week limit on the moorings and fill up fast so be sure to make a reservation. 

Marinas

St. Augustine Municipal Marina has multiple slips available as well. Alongside a one week limit on moorings, you can also get a reservation at the marina for one week. For longer stays, we suggest making a reservation at Marker 8 Hotel and Marina. 

For more suggestions on where to park your boat or work on your boat, visit Waterway Guides. We’re also a fan of making slip reservations at Snag-A-Slip. 

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Transportation

Once you’re here, there are plenty of ways around the city. Here are some options, we like ’em all.

Waxi Taxi – Water Taxi Service for up to 6 people.
Uber / Lyft – Always a great option for getting from place to place. 
Bike & Scooter Rentals – These scooters look like SO much fun. Bikes are always a good time too!
Old Town Trolley Tours – Environmentally friendly sightseeing tours 
Horse Drawn Carriage – Always a fun way to see the city.
Sunshine Bus Company – $1-$2 Bus rides to surrounding amenities

There are also rental cars available nearby. Around this city, we prefer to walk 🙂 

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Restaurants, Bars, & Nightlife

One of the best parts of travel is trying out new food and beverage. In this city, you really can’t go wrong but here are a few suggestions from us, tried and true.

Cellar 6 – Try the Baked Brie, yum. Great Happy Hour too!
Prohibition Kitchen – Live music & specialty cocktails. Vintage style. 
The Floridian – Innovative Southern Fare for Omnivores, Herbivores and Locavores.
OC Whites – Great place to sit outside and have a good meal.
Stogies – Late night bonfires, live music, great beer, and of course stogies.
Scarlett O’Hara’s – Sangria, great menu, and trivia on Tuesdays! 
Dolce Cafe – Good WiFi, delicious crepes. Great place to work remotely.
Tini Martini Bar – Somewhat pricey but the martinis are actually quite large.
Bog Brewing – Great service, awesome logo. Next door to Sailor’s Exchange!
Old Coast Ales – Fun games, good atmosphere, decent selection. Next to Osprey Tacos!
Ancient City Brewing – Two locations. Their tap room is conveniently located downtown. 
Dog Rose Brewing – Their Pale Ale is delicious. 
Rendezvous Imported Bottles – Great bottle selection. 
A1A Ale Works – Lots of Florida beers plus a couple Michigan Favorites! 

For more favorites, visit our Travel Map. Follow us on Untappd for Beer Reviews. If you’re coming in by boat, listen to the St. Augustine Cruiser’s Net for meet-ups and suggestions too!

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Entertainment

Besides all the yummy food and beverage, there are so many activities to enjoy during your visit!

Water Enthusiasts

We love being on the water and figure you might too. Close to downtown, there are multiple ways you can get on the water. Taking a scenic cruise on one of the local ferries is the easiest way. Kayaks, boards, and boats can be rented here and here. There are also plenty of private sailing charters and fishing charters too. We like Always for Sail but have yet to try out a fishing charter here. For a themed cruise, we recommend checking out the Black Raven Pirate Ship.

There are also multiple beaches to enjoy near St. Augustine including Vilano Beach and Crescent Beach. Who doesn’t love a beach day!? 

Mystery Fanatics

This ancient city is filled with mystery and paranormal activity. There are multiple ghost tours available throughout the city including Dark of the Moon at the St. Augustine Lighthouse and Ghosts and Gravestones on the Old Town Trolley. All other information for ghost tours can be found here.

Some other fun stops for oddities are Wolf’s Museum of Mystery and Ripley’s Believe it or Not!

History Buffs

This city has an impressive past being the oldest city in the United States. As you walk the streets, you’ll love the old architecture mixed in with new Spanish colonial homes. The Old City Gates still stand near the Castillo de San Marcos but the walls that once surrounded the city are no longer up. Ponce de Leon’s Fountain of Youth is nearby and other historical buildings are scattered throughout the city. We loved seeing the Old Jail and the Oldest House along our long dog walks.  There are plenty of museums to enjoy but we’d highly recommend checking out the St. Augustine Lighthouse + Maritime Museum and the Lightner Museum.

You can do a self-guided walking tour around the city to experience more history with plenty of signs to keep you on track and informed or take a trolley to skip the reading and hear from a professional. 

Animal Lovers

Walking the pier provides a spectacular view of the city. Dolphins are spotted frequently playing around the Bridge of Lions and at low tide you’ll see beds of oysters that cover the river’s bottom. Ospreys fly above the highest mast while pelicans, gulls, cranes, and herons cover the docks. There’s great fishing all over the place and if you’re lucky, you’ll even see a manatee. 

If you’re coming to St. Augustine, you need to visit the Alligator Farm. There are tons of alligators, every species of crocodile, plenty of tropical birds, monkeys, and lemurs. It’s so much fun! We especially loved feeding the Alligators and watching the Cassowary run around. 

Music + Theatre Admirers

Live Music is everywhere in St. Augustine! In alleys and bars you’ll hear local musicians playing their favorite songs and singing their hearts out. In addition to big names being scheduled at the St. Augustine Ampitheatre, you can find daily scheduled music here. 

If you enjoy musicals and plays, check out the schedule at the Limelight Theatre.

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Special Events

Lots of events are always happening here. From weddings to concerts to holiday celebrations. Here are a few major ones that always stand out to us!

Sing Out Loud Festival – We always like live music 🙂 
Florida Tiny House Festival – Different variations of tiny homes and space-saving accessories.
St. Augustine Art & Crafts Festival – Hundreds of crafters sharing their artwork.
Holiday Regatta of Lights Boat Parade – After sunset, the boats light up for this unique parade!
Nights of Lights – Millions of tiny white lights all throughout the city. 
Nights of Pints – In sync with Nights of Lights, local breweries come together for a fun beer tour.
Beach Blast Off – New Years Eve Celebration!

For a complete list of Festivals and Events in St. Augustine, go here. 

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Sailor Amenities

If you’re a sailor like us, you may need to catch up on some errands. Here are some nearby amenities.

Groceries – You’ll need a car for provisioning. Publix is a few miles away and the Old City Farmer’s Market is open on Saturdays at the Ampitheatre. For alcohol provisions, ABC Liquors is a good option.
Boat Supplies – You’ll need a car for West Marine but Sailor’s Exchange is in walking distance.
Post Office – About 1 mile away. You can send/receive mail out of the Munipal Marina too. 
Propane Fills – Amerigas is nearby as well as St. Augustine Gas Co. Both will refill propane tanks.
Diesel/Gas – Munipal Marina Fuel Dock has both
Water Fills – Munipal Marina Fuel Dock 
Pump-Outs – Munipal Marina has a pump-out boat that will come to you!
Salon/Spa – Small Indulgences Salon and Spa has great service and a wide variety of services. 
Library – Flagler College has a nice library and a beautiful campus. 
Movie Theater – Epic Theaters of St. Augustine but you’d need a car. 

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We really love St. Augustine and will always be a place we visit <3 Cheers & thanks for reading!