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A Rainy Day in St. Augustine

It's been known to rain from time to time in the Sunshine state. While most showers are short-lived, there are days when there seem to be more showers than dry moments. What do you do in the oldest city in the United States when the weather doesn't cooperate? You stay inside. There are so many inside Old City attractions close enough together; if you don't mind getting damp you can see quite a few sights. I have five great ways to make the most out of a rainy day in St. Augustine.

History: Castillo De San Marcos

Location: On the waterfront. |  Website

This historic Spanish fort is a great spot to duck into when the sky starts turning gray. If it's raining already, run across the street from the main Old City. You'll dry up quickly. You can explore the fort and take shelter from the storm for hours. The fort has room after room that details the history of the fort. The rooms have exhibits with living quarters, information about the different periods (Spanish, British, and American), the construction of the fort, and artillery storage. You can examine the writing and pictures on the walls, walk through the halls, and climb up the stairs during a break in the weather. 

Tips: Catch a ranger tour if you can. They close at 5 PM.

Art Appreciation: Lightner Museum

Location: South of Flagler College | Website


This old Flagler hotel, Hotel Alcazar, houses an art collection that could keep you entertained for hours on a rainy day. You can really take the time to enjoy the paintings, statues, and furniture pieces all crowded into the rooms of this historic building. You can see the original architectural design as you walk through the ballroom, music room, and bedrooms. After you're done viewing the extensive collection, you can grab lunch at the CafĂ© Alcazar (open from 11 AM-3 PM). The dining area is in a space that once was hotel's large indoor swimming pool. The food is delicious and fresh. When they have a musician performing, the acoustics are amazing.

Tips: Take the time to really enjoy the collection. It's a bit crowded in spots, but it's worth the attention. Plan this as a morning/afternoon visit. The last admission is at 4 PM.

Sipping & Relaxing: Casa Blanca Inn

Location: On the waterfront, on the edge of the Old City. | Website


I like to sit on a covered patio and watch the waterfront when I can't be walking around. Casa Blanca Inn has an open, covered patio and an extensive martini list. They have decadent 'tinis, fruity 'tinis, tart 'tinis, and sparkling 'tinis. They have heaters on the patio to dry you up and warm you up on chillier days. If the patio is full, you can sit inside and chat with the bartender, read through the martini menu, and study the modern art hanging on the walls. It's not a cheap drink, but you get a full pour and a bit in the shaker to take with you. The view is great.

Tips: It's bar service only, and they don't have food. Go on a full stomach or plan on running to grab a snack after.

Tour & Drink: San Sebastian Winery

Location: East on King Street | Website


This winery is to the east of the Old City, so it's best to head out when the skies are just turning gray, unless you don't mind a bit of a walk in the rain. Climb up to the second floor to start the tour. You walk through various rooms where they give you a taste or two and tell you about the history of the winery and current operations. You get to see the barrels where they age the port and sherry. The tour ends with a view of the operations. Afterward, walk up to The Cellar Upstairs Bar and grab wine by the glass or bottle, or even a wine cocktail (like the delicious wine mojito). When it's not raining, they have a wonderful rooftop patio. During the storm you can sit at the bar or in the quiet seating area. If you're lucky, you might catch a band playing.

Tips: Head there for the afternoon; the shop closes and tours end at 6 PM. The rooftop bar is a great place to watch the sun set.

Dining: Taberna del Caballo

Location: Old City - Spanish Quarter | Website


When you can't get into the crowded Columbia for fresh-baked bread and ropa vieja, this spot will more than do. You might even catch a glimpse of a settler drinking a mug of ale after work. This quiet spot has great food and covered patio seating. You can enjoy the warm Florida weather, while being shielded from the rain. It's a good spot to share tapas or flatbread, or get a sandwich, salad, or bigger entree. You can enjoy sangria while listening to the relaxing sound of rain falling by candlelight. Not only is it more cozy than Columbia, the prices are great. We left full and satisfied.

Tip: Order a few small plates and share. You don't want to end up having to leave any on the table, if you can't take it on the road.

There are plenty of bars and restaurants in the Old City with live music and pub grub. There are sights that take no more than 15 minutes to see. This city is made for tired tourists. This list gives you an idea, but get out there and explore...if you don't mind getting wet!

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