Summer Road Trip to St. Augustine - Jupiter Magazine (2024)

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Pack up the car and hit the road for a history-filled weekend at America’s oldest metropolis, just a three-and-a-half hour drive from Jupiter

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Built in 1888, the perennially extraordinary Casa Monica Resort & Spa, Autograph Collection sits in the heart of St. Augustine’s Historic District. At check-in, patrons are treated to a glass of champagne before being escorted to one of the 138 guest rooms, including 14 multilevel Landmark Suites. No stranger to celebrities and dignitaries—like Spanish royals King Felipe VI and Queen Letizia, who visited in 2001—this grande dame carefully keeps one foot in the past and the other in the present. Last year, the AAA Four Diamond–rated property replaced its tapas-style restaurant with the Cordova Coastal Chophouse & Bar, whose cuisine reflects the flavors of southern Spain and Morocco. Part of an estimated $3 million renovation, a lobby refresh and makeovers to the guest rooms are also in the works.

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Once the home of the Dow Museum of Historic Houses, The Collector Luxury Inn & Gardens features nine historic buildings including the Dow House, which was built in 1839 and later purchased by Charles Dow. Guest rooms mix vintage touches with modern amenities like kitchenettes and walk-in showers with rainwater showerheads. The property also boasts a pool and gardens with lawn games, as well as one of the friendliest bars in town—The Well. The century-old bar serves light bites and well-crafted co*cktails made with liquors infused with herbs from the kitchen’s on-site garden. After a complimentary continental breakfast, guests can walk or bicycle to nearby attractions like the Colonial Quarter, which recently welcomed the Gallegos House, a historic home built in 1720 with materials made from oyster shells, sand, and lime that showcases colonial life in St. Augustine.

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Take a guided tour and see the cobblestone-festooned city through the eyes of a local expert. Old Town Trolley Toursfeatures one of the best modes of transport and simplifies the process of navigating the first city of postcolonial America. Filled with interesting and thought-provoking narration, these daily tours visit more than 100 points of interest including Flagler College and the seventeenth-century Spanish fort Castillo de San Marcos. In addition to unlimited on-off boarding, tickets include admission to St. Augustine’s History Museum and free shuttle service to Alligator Farm and other exciting points of interest.

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For a history tour with a Jazz Age vibe, book a 90-minute sightseeing odyssey with Pastime Tours, where you’ll ride around town in a Model T–inspired vehicle commandeered by history-savvy guides clad in Jazz Age–style regalia.

Indulge your last night in paradise with a spectacular sunset sail aboard the Freedom, St. Augustine’s only tall ship. Owners John and Sarah Zaruba, who also host daily sails and midnight sojourns aboard the stunning 76-foot, gaff-rigged topsail schooner, do not follow a set sailing path but are sticklers for finding the best spots to watch the final moments of the golden hour with their guests. Tickets include complimentary champagne and refreshments, lively musical entertainment, and possible dolphin and other marine life sightings.

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Eat & Drink

Many of St. Auggie’s top culinary destinations are located within heritage buildings and other historic landmark settings. The Old City House Inn & Restaurant, which specializes in Latin American and Mediterranean- style staples like pork osso bucco and chicken Milanese with chimichurri, is ensconced in a former stable house that once served Henry Flagler’s hotels. And a half-mile northeast, Meehan’s Irish Pub & Seafood House serves standout pub fare inside a former Gilded Age mansion that commands breathtaking views of the Matanzas River, Anastasia Island, and beyond. At one time, the site also served as a repository for construction materials used to build the Castillo de San Marcos, located 150 feet away.

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A locals’ favorite, Ice Plant Baris an upscale co*cktail den set inside an Art Deco building where ice was once made and cut for the local shrimping industry. Bartenders hand-carve ice for the delicious co*cktails, crafted mostly with house-made ingredients and spirits from small producers like the adjacent St. Augustine Distillery. After a long day of exploring, cool down with a Cool Runnings, made with orange juice, rum blend Licor 43, rose hips, strawberry, and Jamaican bitters and topped with a scoop of shaved ice.


Take a drive over the Bridge of Lions to the barrier island and visit the St. Augustine Alligator Farm Zoological, a must-visit for wildlife lovers. Founded in 1893, the attraction houses hundreds of reptiles, mammals, and birds including 24 crocodilian species ranging from the albino alligator to the critically endangered Indian gharial. Don’t forget to say hello to the zoo’s largest resident, a 15-foot, 1,250-pound saltwater crocodile named “Maximo.” And if you’re feeling adventurous, take the 45- to 90-minute Crocodile Crossing zipline tour and soar over lemurs, crocs, and more.

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Summer Road Trip to St. Augustine - Jupiter Magazine (2024)


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