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Explore the Oldest European-Established Outpost in the U.S. - Old San Juan, Puerto Rico

Home of the Pina Colada

By
Meeghan
Truelove

Is the icy chill of winter setting in, prompting you to dream of balmy breezes and tropical climes? Are you ready to trade in all those snowy driveways and bare-limbed trees for sunny beaches and swaying palms? look no further than San Juan, Puerto Rico. The tropical destination of your dreams awaits. Best of all? No passports or money exchange required. Just grab your regular ATM and credit cards and go!

San Juan was established in 1521. It's the oldest European-established outpost in the U.S., and a feast for the senses, a complicated and engrossing patchwork of neighborhoods that will enchant you however long you decide to linger. And there's no better neighborhood to start in than Old San Juan.

This barrio occupies a thin spit of land that juts out into the Atlantic Ocean and forms a narrow, natural port. There are trinket shops and touristy outposts galore, but it takes nothing to scratch the surface and dive into the genuinely rich cultural treasures that the gorgeous colonial borough has in store.

The streets of Old San Juan are lined with cobblestones made of iron slag, carried as ballast in the ships that sailed from Europe. The stones have a mesmerizing blue cast that adds to the ethereal quality of Old San Juan's streetscape. Colonial buildings are festooned with wrought iron balconies and embellishments and splashed with sherbet hues, meaning that even if you do nothing more than meander from one tree-shaded plaza to the next, you will be transported to a place that feels deliciously unlike home.

So, first things first: Old San Juan claims to be the home of the piña colada. And, lucky for us boaters, there's not just one place that lays claim to this infamy, but two. The first spot, Barrachina, has a lovely leafy courtyard and lubricates its creamy, frothy concoctions with Ron del Barrilito, one of Puerto Rico's longstanding, homegrown premiere rums. The second place that insists they deserve the title is the Caribe Hilton, on the outskirts of Old San Juan. There they lace their potion with a healthy dollop of Bacardi Superior. It might be your duty as an upstanding member of the cruising community to sample both versions and decide for yourself which one is best -- if not the "first."

After you've properly embarked on your Old San Juan escapade with a piña colada (or two), soak up some of the many historic sights. Don't miss Castillo San Felipe del Morro, known colloquially to locals simply as El Morro. Construction of the massive fortified site began in 1539, and you can pass a fascinating afternoon exploring its many nooks and crannies. You can also blissfully while away the time simply lolling on El Morro's enormous lawn, where locals gather regularly to picnic and fly bright, soaring kites.

The Catedral de San Juan Bautista is at the very heart of Old San Juan, a graceful 1540 structure where Ponce de Leon is interred in his eternal rest. There's also the wax-covered reliquary of St. Pio, a Roman martyr whose presence in the church speaks to Old San Juan's prominence as a colonial crossroads.

Next to the cathedral is El Convento, a 17th-century Carmelite convent that's now Old San Juan's premiere luxury hotel. The stunning arcaded passageways are themselves worth the stroll alone, but if you find yourself in need at this point of another piña colada, there's no better place to indulge than the hotel's tranquil courtyard.

To pick up something to take home, avoid the shops hawking shot glasses and refrigerator magnets, and head to La Calle, where you can find a selection of caretas, the vividly painted and delightfully gruesome masks traditionally worn by revelers during the pre-Lenten bacchanal of carnival. The shop Eklektika is an excellent source for all manner of authentic handcrafts, including the hand-carved figures of saints traditionally known as santos. Hecho a Mano is a stand-out boutique for one-of-a-kind accessories and clothing.

For dinner, Calle Fortaleza is a must. The street has emerged as the go-to spot in Old San Juan for unbeatably hip and enticing restaurants. Marmalade is helmed by a New York City-trained chef and popular for its cutting-edge dishes and sleek, candy-colored decor. Dragonfly has become a standby for its small-plates menu and sexy, atmospheric interiors.

If you only have the time -- or the energy -- to hit one nightlife spot, make it the Nuyorican Cafe, hands down the most consistently reliable spot to catch the island's irresistible and exploding salsa scene. The entrance is nestled into one of San Juan's back streets, and the sound of congas, cowbells and horns explodes through the doorway. It's a resolutely locals' place that embraces any wandering turistos who might stop by. Sip a cocktail and take in the scene, or hit the dance floor to try out your moves. Things don't really get going until around 11 p.m., so be patient -- you won't be disappointed.

Old San Juan is just the tip of the tropical iceberg when it comes to greater San Juan's enormous allure. So tell us what you think. If enough of you want to head back to the destination for further adventures, we'll cover the best of the rest that the contemporary city of San Juan has to offer in a future article.

For now, happy cruising, and buen viaje!

Where to Dock

  • Club Nautico de San Juan (787-722-0177) is a European-style yacht club offers 117 slips for vessels up to 250 feet along with in-slip diesel services. It's located just across from Old San Juan.
  • San Juan Bay Marina (787-721-8062) is located in San Juan at the entrance to Old San Juan and right next to Isla Grande Airport. This marina offers 200 slips, satellite TV, 24-hour security and 10% off transient dockage to Cruising Club members.
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OUTER SPACE. RACE CARS. ANIMAL SAFARIS. PIRATES.

These experiences are all part of a dream vacation to one of Florida’s famous theme parks. But the cool thing is that the Sunshine State offers these same topics as real, hands-on, family-friendly adventures. Here’s a Top 10 to try.

1. St. Augustine Alligator Farm & Zoological Park

Kids who love dinosaurs will love this park. Founded in 1893, some of the oldest and largest alligators are in captivity here. Plus, the Land of Crocodiles exhibit features 24 global species including the African dwarf, rare Nile and familiar North American crocodile.

Beyond crocodiles, “Some visitors like the colorful parrots, others prefer our python cave, the nesting wading birds in our rookery, or our wildlife shows,” says John Brueggen, director.“The more adventurous enjoy zip lining over the animals.”

Where to Dock: Camachee Cove Yacht Harbor

2 .Daytona International Speedway

race cars on the Daytona International Speedway
Daytona International Speedway | Credit DIS

The NASCAR season kicks off on February 19, 2023, with The Great American Race – the Daytona 500. However, any day is perfect for a speedway tour. The hour-long tram ride hits the highlights from an infield stop at the start/finish line to a view from high atop the tower seating. At a stop at the Motorsports Hall of Fame of America, kids can enjoy a wow moment looking at Michael McDowell’s 2021 Daytona 500 victory car.

“The Magic of Lights returns to the Speedway’s World Center of Racing in November through Jan. 1. It’s a dazzling display of more than 1 million sparkling lights and magical scenes, all viewed from the comfort of the guest’s vehicles,” says Russell Branham, Southeast Region director of track communications.

Where to Dock: Daytona Beach Marina

3. Kennedy Space Center Visitors Complex

Chat with a real astronaut. Train on high-tech simulators inside the Space Shuttle Atlantis. Go behind the gates of a working spaceflight facility. Experience microgravity like inside the International Space Station. The 42-acre complex on Merritt Island brings to life the U.S. space program’s epic story in an up-close, hands-on way.

“Kennedy Space Center is best known for rocket launches like the historic Apollo and Space Shuttle programs. Now, it’s known for the commercial companies with rocket launches happening almost every other week,” says Rebecca Burgman, senior manager for public relations and communications. The Visitors Complex offers some of the closest public launch viewing locations in the area.  

Where to Dock: Titusville Marina

4. Mel Fisher Treasure Museum

Lift a real gold bar at the famed treasure hunter’s museum in Sebastian, on the Indian River waterfront. “Kids especially like to look, touch and feel the weight of a solid gold bar from the Nuestra Senora de Atocha, the most famous and valuable shipwreck to ever be recovered,” says Nichole Johanson, the museum’s director and Fisher’s granddaughter.

“The bar weighs about five pounds, and you can still see the markings that tell its story like ownership, tax, purity, assayer and weight.” Kids get a fun and educational treasure hunt game to do while exploring the exhibits, with scavenger hunt items and riddles.  

Where to Dock: Sebastian Inlet Marina

5. Countryside Citrus

Children jumping on a "jumping pillow" on a bright sunny day
Courtesy of Countryside Citrus

Oranges are Florida’s top agricultural product, and its freshly squeezed orange juice, soft-serve orange ice cream and orange slushies are some of the kid-friendly draws at this Vero Beach farm. Another is the Fall Festival and Corn Maze in October.

“There are activities such as a jumping pillow, kiddie zip line and air cannon, not to mention the maze and great food offerings,” says Cheryl Roseland, owner-manager. Kids and parents can U-Pick strawberries from the farm’s patch from December to February. Countryside operates its El Sid Taqueria on Ocean Drive in Vero Beach, a more convenient location to marinas for fresh citrus ice cream and slushies.

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6. Everglades Safari Park

To ride on the wild side, travel less than an hour west of downtown Miami on Route 41, the Tamiami Trail. The chance to take an airboat tour through the Everglades National Park is well worth the time!

An airboat is a flat-bottomed open-air boat with an aircraft-like propeller in the back and a car engine for power that can glide over the waterways and sawgrass of the glades at speeds up to 40 miles per hour. On a half-hour tour, see wildlife, alligators and anhinga birds. Guides make stops to talk about natural and human history, such as how Native Americans used cat tails to make natural gauze.

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7. John Pennekamp Coral Reef State Park

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“The snorkel tour is an excellent way for families to experience the Park,” says Tim Linafelt, communications manager for the Florida Department of Environmental Protection’s Division of Recreation and Parks. “After a 10-minute coaching session, swimmers can get up close and personal with coral reefs and marine wildlife.” Plan ahead by checking out the park’s new 360-degree coral cam that streams a live feed. Lemon sharks, parrotfish and angelfish have made on-camera appearances.

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children snorkeling the shoreline at the Dry Tortugas with crystal clear blue watersu
Dry Tortugas | Credit Yankee Freedom III

8. Dry Tortugas National Park

Play in a 19th century fort in this seven-island park located in the Gulf of Mexico. To get there, book a ride on the Yankee Freedom III, a high-speed catamaran that departs from Key West for the two-hour, one-way trip. Then, have kids watch for Fort Jefferson on approach.

“The enormity of the fort is indescribable. It’s the largest masonry structure in the Western Hemisphere – made with 16 million bricks. It’s fun to explore with its endless halls,” says Piper Smith, VP of marketing for Historic Tours of America. Beside exploring the fort, it’s fun to swim or snorkel around the outside of the moat. The waters are filled with tropical fish, lobster, turtles and game fish.

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9. Mote Marine Laboratory & Aquarium

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10. Air Force Armament Museum

Florida’s northwest panhandle is a national center for military aviation. Pensacola is called the “Cradle of Naval Aviation” and is the official home of the Blue Angels. One hour east, this museum sits across from Elgin Air Force Base.

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THREE MUST-PLAY WATERFRONT PUTT-PUTT GOLF COURSES

palm trees on a minigolf course surrounded by turquoise waters
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Playing putt-putt Mini Golf is a ‘must- do’ shore thing on a Florida vacation. Best of all, many courses are near the beach. Lighthouse Cove Mini Golf in Jupiter is one block from the white sands. The two 18-hole courses weave around sea life, waterfalls and boats in a tropical fishing village theme. Play both! A new app lets golfers order drinks without leaving the greens.

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Two dark grey mega-yachts docked on the water at the boat show
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The twin sets of upward sloping on the superyacht, Thunder, looked to me like stairways to heaven. To say these were only a small part of the eye-candy features of this 164-foot Oceanfast, one of the largest yachts for sale on display at this year’s Miami International Boat Show, says a lot.

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Visitors walking the docks at the boat show surrounded by multiple mega-yachts
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Second to Alaska, Florida boasts the most coastline of any U.S. state at 1,350 miles. Add a year-round climate conducive to boating, and it’s easy to see why the marine scene is big here. Each year, the state hosts close to two dozen boat shows. The calendar runs from September to April, corresponding to the top tourism months for visitors from the north.

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“Record-setting attendance at the St. Petersburg and Sarasota shows in the past year now rivals the big shows in Fort Lauderdale, Palm Beach and Miami. In fact, the annual boat show held in downtown St. Petersburg’s waterfront is the second largest event in the city, behind the Firestone Grand Prix in terms of attendance, revenue and logistics,” says Cindy Dobyns, president and owner of AboveWater Public Relations & Marketing, who handles press for the show.

What’s Happening under the Tents?

Exhibitor for "Electrosea" discussing the product with a customer

Beyond boats for sale, you can discover so many things to see, do, eat and drink, toe-tap and clap for at Florida’s boat shows.

One of the most fun sights at the Miami Boat Show was watching a professional flyboarder in action at Pride Park in AquaZone. Standing on a skateboard-size board attached by a hose to a jet ski below that powered the water toy, dual jet streams of water propelled the rider some 15 feet in the air above the 40,000-gallon freshwater pool.

Pros also gave the public a wakeboard experience via a simulator. Crystal Kayaks, Seabobs and Hobie Cats were brands featured for a demo at the Fort Lauderdale Show. In Palm Beach, the intercoastal waterway served as the natural aqua zone. eFoil electric surfboards were an especially big hit.

New last year, the St. Petersburg Boat Show partnered with the Annapolis School of Seamanship to offer one-hour on-water training sessions held multiple times daily. Topics included Women at the Wheel, Basic Boat Operator and a Junior Captains Program. All were free. The only catch is buying tickets ahead of time and pre-registering for the sessions.

Seminars are a sought-out reason to attend boat shows. Every show offers them, and many shows invite local celebrity speakers. A good example is the Jacksonville Show, where last year Captain Tim Altman of HooDoo Sportfishing Charters and founder of the Wahoo Junkies brand gave two talks on wahoo trolling with bait and high-speed trolling.

One of the best-known seminar presenters on Florida’s boat show circuit is Captain Don Dingman, star of the Hook the Future TV show. Dingman hosts interactive fishing clinics full of demos for kids ages four to 16. At the Fort Lauderdale Show, each kid received a free Hook the Future/Carolina Skiff custom rod and reel combo. It shows how boat show seminars can hook the whole family.

Fred’s Shed is worth the cost of admission if you’re a DIY fan. Launched over a decade ago by the Chicago- headquartered National Marine Manufacturers Association, this up close and personal educational experience is held at NMMA events like the Miami Boat Show. Topics range from installing marine electronics to detailing and service and maintenance tips.

Food and entertainment make shows extra festive. There’s no need to leave the fun. On-site at the St. Petersburg show, for example, you can gobble up everything from stone crab claws to Greek gyros, street tacos and wood-fired picanha steak.

The Windward VIP Experience at several shows includes an open bar, wine and spirit tastings, gourmet food such as oysters on the half shell, as well as early access to the show and a shady air-conditioned oasis to sit and relax. Most shows feature live bands with oldies, classic rock and top 40 hits on tap.

View the Boats

A center console passing by a big yacht in front of a house on a canal in Florida

Of course, it’s the boats that float these shows. “All types of watercraft are featured, including fishing boats, cruisers, ski boats, pontoons, inflatables, personal watercraft, and more,” says Erin Johnson, administrative director of the North Florida Marine Association that puts on the annual Jacksonville Show.

Vendors, from national brands to local shops, exhibit and sell all the boating go-withs. There are nearly 100 of these at the Suncoast Boat Show, and more than 1,000 at shows such as in Fort Lauderdale.

Mega and superyachts are here too, just like Thunder. You’ll find the bulk of the 100- to 200-foot-plus vessels at the Palm Beach, Fort Lauderdale and Miami shows. All it takes is the price of a show ticket to walk the docks and dream.

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Sea Turtle | Credit Matt Botha

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The answer is rather simple. From beaches and coral reefs to everglades and tropical islands, Florida is home to a diverse array of ecosystems. Toss in a balmy year-round climate, and it’s got habitats that spawn a dazzling display of marine life.

These amazing creatures are so beloved by Floridians that they’ve been integrated into the local pop culture in celebration of the state’s indigenous beasts. Native aquatic creatures are elevated into iconic symbols, reflecting the region’s diversity, unique groove and reverence for the water.

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You’ll discover many of them on sports teams’ logos or mascots, bar napkins, restaurant menus, clothing (shirt, hat, etc.), pool floaties, ads for products, road signs, products in stores, souvenir shop merchandise, glassware, food and beverage labels, boats, flags and more.

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