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Look past the cheesy tourist traps, and you’ll discover a blend of history, art, politics, and culture in Old San Juan.

With the boats tucked safely into slips at Palmas del Mar Yacht Club, we grabbed our overnight bags and hit the road, ready for 24 hours of something completely different.

Walkable. Cultured. Bustling. Historic. Food-centric. Old San Juan is the perfect city for lousy tourists like us. Ambling from one side of the city to the other, we took it all in, nibbling as we went. I was surprised by how good it felt to have sidewalks beneath my feet.

I’d be remiss to not mention another highlight of the trip; our glorious room at the Sharaton. Yes, we decided to take our first night off the boat (in over nine months) and between the king bed, the HOT shower, and the air conditioning, it was the stuff of dreams.

We rolled around like drunk toddlers on those crisp white sheets.

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Bo, navigating us around the city

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A turret in the massive wall that surrounds the northwest side of Old San Juan

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The city is paved in blue cobblestones, which are made from a byproduct of iron smelting. They crossed oceans as ballast aboard merchant ships hundreds of years ago.

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There was no shortage of refreshments to keep us cool

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Sampling a Mallorcan sandwich with cafe con leche. The sandwich is made on soft, slightly sweet bread, filled with jamon and queso (ham and cheese), grilled, and topped with powered sugar.

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Outside Barrachina, the birthplace of the pina colada. We kept meaning to go back to this place but somehow never made it.

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Brian and me

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Brian and I used to take Sunday afternoon strolls around NYC and wander into a wine bar for some charcuterie, cheese, and a glass of wine. Having this experience at La Boutique du Vin transported us back home.

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Part wine shop, part tasting bar, you select your wine from the retail shelves, pay a small corkage fee, and enjoy at one of their lovely polished stone tables.

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A selection of cheese and charcuterie from the US and Spain

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I’m on a mission to find a straw hat that doen’t make me look Amish. We dropped into the famous Ole Curiosidades, a habadashery that was featured in the travel section of the New York Times. Unfortunately, the Panama style is not flattering to my head shape.

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Bo and Brian, unable to resist the siren call of glass cases and heat lamps.

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Unique empanadilla flavors at Mavi Cafe.

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Allison and Bo

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At the Castillo San Felipe del Morro Lighthouse, a World Heritage Site. The Spanish originally built this fort during their occupation in 1539.

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Shaved ice cart. The vendors scrape ice shavings off of the giant block inside the glass, then pour flavored syrups over it.

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Cherry coconut piragua

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The state of New York Board of Tourism has a small gallery in Old San Juan to promote visiting our home state. Their current exhibit featured artisanal foods from NY, with a healthy nod to some of our favorites from Brooklyn.

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Refreshing, well made artisanal popsicles

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It was difficult to choose but we decided to go with dulce de leche and tamarind.

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Brian demonstrates the proper stance for eating a paleta on a hot day to avoid dripping on your shorts.

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Drinks and dinner at La Factoria, a popular bar for the bohemian set in Old San Juan. It’s one establishment comprised of a series of connected rooms, each with it’s own theme.  We were there on a Wednesday and only two of the rooms were open – the classic cocktail room (pictured) and the wine bar. They had pork buns on the menu (a New York favorite of ours) along with a dozen other sharable plates and some respectable pizzas. Obviously, we loved this place.

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Brunch at Caficultura. Cosmopolitan, casual, and delicious.

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Cafe con leche. We ordered Mallorca bread with guava butter, french toast with pineapple compote, huevos rancheros, and a fabulous pressed turkey sandwich with an egg on top.

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Back at the Palmas del Mar marina in Humaco, PR, we’re making the usual preparations and keeping cool at the pool.

Following our fun interlude in the city, we’re back at the marina making preparations for the coming months. We’ve been to Costco and Walmart and have refreshed our stocks of everything from cheese to paper towels. We’ve refilled diesel and water, fixed a few broken things, and given the boat a good scrub down. Today, we’ll cast off the dock lines, en route to the Virgin Islands, the birthplace of this adventure.