The Best Romantic Things To Do in Saint Augustine

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When you’re in Saint Augustine for a Romantic Getaway, Valentine’s Day or a surprise engagement weekend, the most asked question is where are the most Romantic Places in Saint Augustine. We have compiled a Top 5 List of the Best Romantic Things in St Augustine.

The very first thing that you’ll need is a Romantic Hotel or a Romantic Bed and Breakfast. Well, we are going to tell you that you’re best bet is a Bed & Breakfast.


Now, it’s time to plan your stay. We’ll do what we can to help you out. Follow the links in our list below for more information on each place. Now for the Top 5 List!


There are so many wonderful places in Saint Augustine that it was hard for us to pick just 5. You’ll love every one of these places. Be sure to call each restaurant to make reservations or to see if they offer call-ahead service.

La Pentola Restaurant outdoor dining.LA PENTONLA – Specializing in Mediterranean and Latin cuisine, La Pentola has a relaxing and intimate courtyard for dining under the stars. If it’s a bit chilly for outdoor dining, their dining room is remarkably elegant. Fabulous food! Reservations accepted.

THE TASTING ROOM – Spanish Tapas at it’s finest. Order anything from small plates to full entrees with an award winning wine list. Beautiful ambiance in their indoor dining room and a romantic outdoor courtyard as well. Reservations accepted.

COLLAGE – If you are looking for the first-class dining experience, you’ll love Collage. Sitting next to the cozy fire when it’s a bit chilly with your sweetheart and sipping a sensational wine will warm your heart.  The food is scrumptious. Reservations accepted.

RAINTREE – More outstanding outdoor dining is offered as well as intimate indoor dining in their dining room. Their menu blends Mediterranean, American and Asian cuisine.  You will love the selection and the romance of this one. Reservations accepted.

O.C. WHITES – They have a menu that boasts everything from seafood, to pasta. Sit on their romantic patio, which overlooks the city marina as you sip one of their frozen specialty drinks. The building has unique history to go with your fabulous meal. Reservations accepted.


There is nothing quite as romantic as a setting sun. Here in St. Augustine we have quite a few locations,  and ways to watch and experience a magnificent sunset in the Oldest City.

The Schooner Freedom sunet sail.THE SCHOONER FREEDOM – Watch the sun setting behind the fabulous Saint Augustine skyline as you cuddle with your honey aboard this charming schooner. It’s a perfect way to start a romantic evening in the city. Reservations required.

THE ST AUGUSTINE LIGHTHOUSE SUNSET/MOONRISE – Sorry, but this only happens once a month, during the full moon, but it’s a very fun and romantic way to see the sun set and the full moon rise. The tour includes a champagne toast and light hors d’oeuvres. Reservations Required.

ST. AUGUSTINE ECOTOURS SUNSET SAIL – This is the perfect solution for an unforgettable proposal or just a very intimate sail with your sweetheart. You can book a private sail but even if you don’t they only take 6 people on this sailboat. Reservations required.

BEACHES AT VILANO – Order your favorite beverage and find a seat out on the deck that overlooks the inter-coastal waterway and the city of St Augustine, as you watch the sun slowly sink behind the city.

MATANZAS INLET – You have a couple of options here. Take your sweetie, a picnic and a blanket and walk down to the inlet beaches to watch the sunset. This is a state park at this area so no alcoholic beverages. But, you can go across the inlet to Matanzas Inlet Restaurant and sit outside by the water and watch a fabulous sunset there.


These are some of the secret locations and also some of the fun places that mostly just the locals know about.

THE GIFTED CORK – This is a delectible way start to your stroll around St. Augustine. Stop in for a wine tasting and you get to keep the glass. Don't miss their sister store, the Gifted Gourmet for a cheese tasting. It's fantastic! Click here for a discount coupon.

SAINT AUGUSTINE ART GLASS BACK GARDEN – A fabulous gallery with all kinds of incredible art. Unique jewelry and more. BUT the back garden is phenomenal and romantic. Be sure to check them out.St. Augustine Art Glass - the secret garden.

CLAUDES CHOCOLATES – If you like chocolate, you’ll love Claude’s! These Gourmet chocolates are heavenly. Go in and grab a sampler that will include bonbons and bark.

MISSION NOMBRE DE DIOS – The mission traces it’s origins back to the beginning of Saint Augustine. It was here that Pedro Menendez first set foot on land. The grounds are beautiful and magnificentally romantic.

CAFÉ ALCAZAR – A romantic lunch stop. (Because they are only open for lunch.) The Café Alcazar is located in the original swimming pool of the Alcazar Hotel, now the Lightner Museum.  Wonderful relaxing atmosphere and fabulous food paired with a lovely glass of wine is a perfect stop while you visit the old town.

There are many other romantic things to do in Saint Augustine, but we don’t have enough room here to list them all. Here are just a few more ideas. You can take a St. Augustine Pedicab Tour or just use them as a taxi in the Old Town area, take a Romantic Carriage Ride, a hand in hand walk on our beautiful beaches, or a stroll down Aviles Street, the oldest street in the country. If you need more ideas, be sure to talk to your Innkeeper at your St Augustine Bed and Breakfast. They know all of the wonderful things to do in town.

Jerry Houman
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