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Most families think of Orlando when planning a family vacation to Florida.  But they are missing out on a real gem, only 90 minutes up the Atlantic coast in America’s oldest city: St. Augustine.  It was founded in 1565 by Pedro Menéndez de Avilés, a Spanish conquistador, and owned in turn by the Spanish, the British, the Spanish again, and finally the United States in 1819.  The city boasts Spanish colonial architecture, historic sites, a hopping art and nightlife scene and gorgeous beaches.

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We love St. Augustine and had the pleasure of living in the area for a few months.  It’s an amazing city for families. Here is a sample of the fabulous things to see, eat and do when visiting.

Cathedral Basilica of St. Augustine

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Established in 1565 and later re-built in the 18th century, the Cathedral Basilica is the oldest church in Florida.  The architecture is beautiful and it’s worth a peek as you pass by on the main street.

Castillo de San Marcos National Monument

This was our favorite spot in St Augustine: Castillo de San Marcos, the oldest masonry fort in the continental United States.  It’s an amazing historical site and you can read all about it in our recent post.  They have excellent exhibits and a group of historical re-enactors loads and fires cannons from the roof every hour Friday through Sunday.  Adult tickets are $10 and good for 3 consecutive days.  Kids 15 and under are free.

St. Augustine Hop-On Hop-Off Trolleys

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A great way to see the sights of St. Augustine and learn its history is to take one of the two hop-on hop-off trolley tours in town.  There are two companies: the Red Train and Old Town Trolley Tours, and they both offer a tour of the city with live commentary, but you can jump on and off at each stop to see most of the sites in St. Augustine.

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St. Augustine Pirate & Treasure Museum

Our boys loved the St. Augustine Pirate & Treasure Museum.  It’s a wonderful place full of real pirate artifacts, hands-on displays and animatronics!  Young explorers are given a treasure map and search for clues while learning the fascinating history of pirates!  Some of the displays can be a bit scary for younger kids.  Adults $13.99, 5 to 12 $6.99 and kids 4 and under are free.

St. George Street

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Starting at the City Gates and running through the middle of downtown is St. George Street.  Walk through the streets of the old city and soak in the beautiful architecture and rich history.  The streets are lined with quaint little shops, museums, historical buildings and cafes.

Schooner Freedom

St. Augustine is beautiful from the water and there is no better way to see it than by boat.  We had a wonderful time on the Schooner Freedom.  Our 2 hour boat ride included wine and hot chocolate and lots of conversation with the friendly crew.  They even let our boys help hoist the sails.   We took the Day Sail but they also offer a Family Day Sail and a Sunset Sail.  Our tickets cost $40 per adult and and $30 per child (16 and under).

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Maple Street Biscuit Company

Maple Street Biscuit Company is a fun place to grab a quick bite.  They specialize in fried chicken and biscuits and have some fun combinations.  They also serve salads and sides.  We devoured Squawking Goat Fried chicken on a biscuit with goat cheese and pepper jelly.  The fried green tomatoes and sweet potato fries were yummy.  They also have several vegetarian options.

Gas – a Full Service Restaurant

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Want a thick, juicy burger?  This is your place.  It’s just over the Bridge of Lions from downtown towards St. Augustine beach.  Gas serves up fantastic burgers, milkshakes and fries in a fun retro atmosphere.  The menu is full of American favorites from homemade potato chips to meatloaf and apple pie.  The food is locally sourced and they have a large selection of craft beers.  The Reuben Roll appetizer is a favorite and the burgers are fantastic.  They also make a delicious veggie burger and offer GF buns.  We eat at Gas every time we visit St. Augustine.

Whetstone Chocolates

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Try to save some room after your meal because no visit to St. Augustine is complete without a stop at Whetstone Chocolates.  Conveniently located next door to Gas, for your after-dinner enjoyment, they also have a shop back across the bridge in the old town.  Whetstone specializes in fabulous chocolates and amazing fudge, but they have some great gelato.

The dark salted caramel fudge is one of the best things we have ever tasted and the boys go nuts over the chocolate alligators.  They offer daily tasting tours of their factory at 139 King Street.  The tour is $8 per adults, $5.50 per child, but children 5 and under are free and each adult ticket comes with a $2 coupon towards purchase.  Did I mention that you get to taste the chocolate?

Cousteau’s Waffle and Milkshake Bar

Need an afternoon pick me up?  Visit Cousteau’s Waffle and Milkshake Bar for thick creamy milkshakes and delicious homemade waffles topped with decadent treats.  I still dream about the waffle topped with Nutella and strawberries!

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Right near the St. Augustine Visitor Center (a blissfully air conditioned place to rest your heels and get some maps!), we found this odd concrete sphere in the garden with a plaque on it.  It is the “Zero Milestone” of the Old Spanish Trail, a series of roads and highways built from 1915-1929 that linked St. Augustine, New Orleans, Houston, San Antonio and San Diego, over 2375 miles.  It was mostly replaced by US Interstates in the 1950s, but pieces of it are still visible, and St. Augustine was the eastern terminus.

No trip to Florida is complete without spending time on its beautiful beaches.  The coast of St. Augustine is gorgeous!

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A Day Trip to St. Augustine A Day Trip to St. Augustine