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#EscapeMore: St. Augustine, Florida Travel Guide

#EscapeMore: St. Augustine, Florida Travel Guide

Image provided by Dream Finders Homes

 Our new Nautical Collection was inspired by our love for the ocean blue and sailing away to paradise. Looking for a destination known for its rich history and beautiful scenery? St. Augustine, Florida is the place to go. We’ve put together a travel guide to help you find your next adventure in the oldest city in the United States!

Where to Stay

The Casa Monica Resort and Spa pool.

Image provided by Kessler Collection

The Moroccan-themed Casa Monica Resort and Spa is located in the heart of downtown St. Augustine. Built in 1888, this ornately decorated hotel shows off its great history with elegant rooms and a beautiful art gallery. The hotel includes a high-end restaurant, rooftop pool, cafe and lounge. 

The Casablanca Inn on the Bay.

Image provided by Casablanca Inn on the Bay

Looking for a place to stay with a fantastic view? Look no further than the Casablanca Inn on the Bay. This inn has a Waterfront Cafe overlooking the beautiful glistening bay in downtown St. Augustine and the popular Tini Martini Bar. Each guest stays in a unique Mediterranean style room and receives two drink vouchers and a standard breakfast voucher.

Where to Eat & Drink

The O.C. White's Restaurant in Downtown, St. Augustine.Image provided by O.C. White’s Restaurant

O.C. White’s Restaurant is the perfect place to go if you are craving some delicious seafood. Located in the historic Worth House, this restaurant offers fresh local catch, lobster and crab legs, chicken, pasta and more! It offers indoor and outdoor seating where you can enjoy the beautiful Florida weather.


The Casa Reina Taqueria & Tequila Restaurant overlooking the St. Augustine harbor.

Image provided by by Visit St. Augustine

Casa Reina Taqueria & Tequila offers some of the best Mexican and Latin cuisine you can get in the city. The best part? You can enjoy the tasty meal on the rooftop overlooking the beautiful city and waterfront. 

 With our headquarters located in nearby Ponte Vedra Beach, our crew loves visiting this historic city. Other amazing restaurants we couldn’t leave out of our list:

  • River & Fort Restaurant & Rooftop Lounge
  • Columbia Restaurant
  • The Floridian 
  • St Augustine Fish Camp
  • The Ice Plant
  • Cousteau’s Waffle and Milkshake Bar
  • Peace Pie
  • Kilwins
  • Mayday Ice Cream
  • Hyppo Gourmet Ice Pops


What to Do  

St. George street in St. Augustine, Florida.

Image provided by Visit St. Augustine

A must in St. Augustine is to stroll down the pedestrian-only St. George Street. This historic road is lined with restaurants, shops, art galleries and other attractions. Some fun & stylish St. Augustine boutiques to walk in are the Red Pineapple, Two Sparrows and H.W. Davis Clothing and Shoes. The Red Trolley Tours are also available to take you to all the scenic sights while enjoying a sit down ride with tour guide leading the way. 

 The Castillo de San Marcos in St. Augustine.

Image provided by Visit St. Augustine

If you love learning about history, take a self-guided tour of the Castillo de San Marcos, the oldest masonry fort in the continental United States! 

 The St. Augustine Distillery.

Image provided by The St. Augustine Distillery

Get a free tour (and tasting!) when you visit the St. Augustine Distillery. Owned & operated by a local family, this distillery is committed to making world-class spirits using local agriculture. They work with farming partners throughout Florida to then distill and bottle their own spirits. See the barreling and aging process from start to finish before enjoying some more drinks at the Ice Plant Bar (located inside distillery).

 People having brunch on a St. Augustine Sailing Company boat.

Image provided by St. Augustine Sailing

Hit the seas on a unique experience with your travel pals! The St. Augustine Sailing Company offers a variety of sailing experiences to help you get the full tour of the historic city. They offer Brunch on the High Seas, Dinner Cruises, Sip N Sail Saturdays and many more experiences! We had the lovely opportunity to work with the sailing company for our Nautical photoshoot. Enter the voucher code “Cabana” when booking online to get a free bottle of wine with your sail.  If you call to book, just mention Cabana Life!


We loved being able to visit nearby St. Augustine for our photoshoot and can’t wait to go back! Inspired to visit the historic paradise and need help packing? Check out our new Nautical sun protective styles that keep you looking fabulous and sun safe while exploring the amazing city of St. Augustine! Learn more about the Nautical Collection on our Behind the Design blog. Embark on any adventure under the sun with Cabana Life’s UPF 50+ styles!

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