St. Augustine stands out prominently from other communities in Florida, and throughout the United States for that matter. The ancient city on the Matanzas River, which is part of the Intracoastal Waterway, has just about 14,000 residents, but it's been continuously inhabited since its founding by Spanish admiral Pedro Menendez de Aviles since 1565, making it the oldest European-established city in the United States. It's also a bit unusual among Florida's most gay-popular vacation destinations, in that it's not a beach town (although it's on the Matanzas River, which is part of the Intracoastal Waterway, and it's a short drive from St. Augustine Beach and Vilano Beach, on neighboring barrier islands). And it's in a relatively conservative area of northeastern Florida, far from the state's main tropical LGBT playgrounds a few hundred miles south. The city of Jacksonville, however, which does have a sizable gay scene, is a mere 40 miles up the coast.
Abundant with both quaintly cozy and grandly imposing buildings that date back, in some cases, hundreds of years, St. Augustine contains the best collection of Spanish Colonial buildings in the state, as well as a good many structures in other styles, from wood-frame Victorians to Mediterranean Revival structures from the era of railroad magnate and developer Henry Flagler, who built the fanciful, turreted Ponce de Leon Hotel (now part of Flagler College) in 1888. An inviting city for strolling, St. Augustine has a compact downtown that's rife with cafes, restaurants, wine bars, and lounges as well as both typical tourist shops and attractions and more sophisticated galleries, boutiques, and historic sites.
The downtown area also contains several large mainstream hotels—including notable upscale properties like the historic Casa Monica Resort & Spa and the Hilton St. Augustine Historic Bayfront. But arguably the greatest draw for romance-seeking gay travelers is the city's significant supply of charming B&Bs and inns, a few of them LGBT-owned and several others quite popular with gay travelers. Romance is the key word here: St. Augustine isn't overly trendy and certainly doesn't boast a sizable club scene—head up to Jacksonville if it's a night of gay-bar-hopping you're after. But for couples looking for a charming, richly historic destination, or even to plan a same-sex wedding or honeymoon, the self-proclaimed "Ancient City" anchoring Florida's "First Coast" makes for a memorable gay getaway.
Here are some favorite GLBT-welcoming lodgings in St. Augustine. Have a look at the St. Augustine, Ponte Vedra & The Beaches Visitors and Convention Bureau website for more information on what to see and do in the area. If you're combining your visit with trips nearby, check out the Jacksonville Gay Hotels Guide and Amelia Island Gay Hotels Guide, both of which list plenty of inviting options in those areas.
Just a couple of blocks from the historic heart of St. Augustine, including Flagler College and Castillo de San Marcos, the LGBT-owned At Journey's End B&B (89 Cedar St.) is a charming and peaceful hideaway with a helpful staff and all sorts of much-appreciated amenities, including complimentary beer and wine, afternoon snacks, full breakfast, and Wi-Fi. In this late-19th-century wood-frame Victorian, guests can choose from among five rooms, including the tropically furnished Key West Suite (which has its own private entrance) and the ultra-romantic Howard Carter Room—formerly the Egypt Room—with its two-person steam shower and private veranda. Rates are moderate considering the level of service and comfort.
If it's a beachfront getaway you're after, consider staying at the gay-friendly Beacher's Lodge (6970 A1A South, St. Augustine Beach) in St. Augustine Beach. The 95-room, mid-priced hotel overlooking the sandy sweep of Crescent Beach is just 10 miles south of historic downtown St. Augustine and is right by several casual restaurants and pubs. It's a great compromise if you're wanting to soak up the history of the region but still prefer a larger property rather than a B&B, and you want to be on the beach or by the pool, which is one of this property's best amenities. Rooms have casual resort furnishings and are quite spacious, with the largest suites at 550 square feet; all units have kitchenettes or full kitchens. The property is pet-friendly, too.
A mere five-minute walk to the historic buildings flanking Plaza de la Constitucion and Ponce de Leon Circle as well as St. Augustine Marina, the old-world Casa de Solana (21 Aviles St.) inn is among the oldest standing structures in this venerable Spanish Colonial city—it was built in 1763. The meticulously restored, LGBT-owned house now contains 10 guest rooms, the majority of them with gas fireplace and deep whirlpool tubs as well as balconies. Each afternoon, wine and cheese are served—it's a nice time to get to know your fellow guests or relax after a day of exploring the area. Guests also start off each morning with a full hot breakfast, perhaps broccoli-cheddar quiche or ham-and-egg-stuffed crepes with topped with Hollandaise sauce. Although this is an ancient building, the rooms—with tile or hardwood floors—feel cheerful and light, thanks to the tasteful decorating
Situated just a block from the Matanzas River waterfront and a couple of blocks north of the Cathedral Basilica of St. Augustine and the stately Plaza de la Constitucion, the gay-owned Inn on Charlotte (52 Charlotte St.) has eight richly appointed rooms, and its next-door sister property, the Hemingway House B&B (54 Charlotte St.) offers another six rooms. Both properties exude charm, and include such amenities as hearty gourmet breakfasts in the morning, off-street parking, and afternoon wine social hours. The Inn on Charlotte dates to 1918 and has been furnished with fine antiques. Some rooms have private balconies, Jacuzzi tubs, and fireplaces.
The gay-owned Saragossa Inn (34 Saragossa St.) is on a quiet block in downtown St. Augustine, just a quick and pleasant stroll from countless restaurants and attractions. This handsome 1920s Arts and Crafts home with six handsomely furnished rooms—each with a private bath and wet bar—is upscale but not unreasonably priced. Guests are treated to a three-course breakfast each morning, and the innkeepers can help to arrange a variety of activities in the area, from in-room couples massage to historic carriage rides. Romantic touches in some rooms include four-poster canopy beds and fireplaces. You'll also find refrigerators, microwaves, coffeemakers, hairdryers, Wi-Fi, and other contemporary conveniences in each room.