Old Town Key West: Welcome Racers and Travelers

Strolling about Old Town Key West offers plenty of shopping options for the ladies and the lads.

Strolling about Old Town Key West offers plenty of shopping options for the ladies and the lads.

Appeared in Napa Register

In the last two years I’ve been lured by Key West’s turquoise waters and opportunity to create sailing photographs with backgrounds other than the Golden Gate Bridge, Alcatraz and San Francisco city front. Key West Race Week, held mid-January for the past 30 years, is a sailor’s bucket list item. In the United States this is the first major warm water regatta of the year, attracting a thousand or more sailors from around the globe. A highlight of the regatta--the TP25--a fleet of eleven 52-foot racing beauties that deemed Key West Race Week to be part of their official 2017 regatta circuit. Crews from Turkey, Russia, Italy, Great Britain, Sweden, the U.S. and more were present. Aside from shooting on the water I was there to cheer a few Bay Area sailors.

Sightseeing in Key West is easy in that the island is roughly only one mile wide and four miles long.  Accommodations are plentiful, but in-season stays can be costly. Last year I stayed in two northern end hotels (Note, ask about resort fees before you book. Some sites charge $25 and higher per day whether or not you sit by the pool). Getting around is simple: walk, cycle, bus, drive or take the mini Conch Train. Many hotels rent out bicycles by the day or week. A cycle ride from island-top to bottom is a breeze and walking the length is very possible too.

Wandering Through History and Architecture in the Neighborhoods
For locals and visitors alike, a most traveled route originates on the upper and west side of Key West, N. Roosevelt Boulevard. Many large chain hotels, grocery stores, fast food spots and dive shops are located along this street; the route is hardly charming until it becomes Truman Avenue. At the intersection of Truman and Jose Marti Boulevard is Bayview Park, home to many weekend craft, beer, wine and folklore events. Roughly seven blocks south on Truman, take a right hand turn at Frances Street (Bare Assets strip club is a landmark—a sailor’s favorite chill spot) and walk one block to reach the Key West Cemetery. Founded in 1847 following a hurricane that washed away the old cemetery and scattered the dead throughout a forest, this site roots relocated gravestones that date to 1829 and 1843, as well as more recent stones. Due to the high water table, many graves are above-ground vaults similar to what is seen in New Orleans. A prominent monument here honors the U.S.S. Maine, a vessel that was blown up in Havana Harbor in 1898, killing 260 American sailors.

From the cemetery, pick any adjacent street to wander past Old Town Conch houses, quaint pastel color homes, jungle yards and proper porches with pairs of chairs. Architectural hallmarks include Victorian-era asymmetrical facades, complex roof structures with turrets and widow’s walks, mixed surface treatments and “gingerbread” accents that include turned spindles, pillars, railings and the all-important tall slatted storm shutters. A favorite touch is the sky blue color paint at the underside of a second story overhang above the ground level veranda. Simply walking about with a camera or sketch pad may keep you entertained for a day. Cut through the neighborhoods and find corner convenience shops, small restaurants, surprising gift stores, plus gorgeous 100 plus year old estates converted to inns and resorts. Large three-story properties sit aside cheerful multi-color bungalows. Streets are narrow and many are one-way.

Duval Street, a Tourist’s Landmark
Head south and find east-to-west Duval Street, the main tourist drag with loads of bars, night clubs, restaurants and souvenir shops. Most dining here is al fresco and happy hour pricing reigns. In high-season these spots tend to be loud, crowded and filled with younger folk. It’s worth a stroll for people watching—particularly the Green Parrot, a local dive bar located one block south of Duval on Whitehead Street. Of note at 907 Whitehead is the Ernest Hemingway Home and Museum, at 205 is the Audubon House and Tropical Gardens, and at 1 is the Shipwreck Treasures Museum. Back up on Duval, consider visiting the oldest house and museum at 222, St. Paul’s Episcopal Church at 401. Numerous other venues worth visiting are within walking distance.

Ready for water’s edge? Head to the Galleon Harbor. This region is home to  myriad vendors promoting everything from dives to glides, fishing to a ferry ride to the Dry Tortugas National Park, and of course sunset cruises aboard replica historic yachts. Advance reservations seldom needed. Open air bars and restaurants can be found along the mini boardwalk, and there’s a short promenade of cottage vendors that dead-ends adjacent to the Waterfront Brewery. In front of the brewery is a top caffeine spot, Cuban Coffee Queen, where locals and tourists place their orders then sit on planter boxes while the one or two baristas prep.

Getting There
Direct flights to Key West exist, but if you’re looking to save a little money and don’t mind driving, consider winging into Miami or Fort Lauderdale. For my trip in January I flew to Miami and not only saved more than $300, my SFO-origination flight was non-stop. Line up a rental car before you depart. Vendors such as Hertz, Avis, Budget have desks at the airport; lesser known vendors have off-site locations accessible via courtesy shuttles.  

I play the online rental bidding game. What started off as rack rate $36 per day with one vendor, yielded to $9 from another vendor, Ace Rental, as booked five days before my departure. When at the rental office be prepared to pony up for a bridge tolls pass. I took the flat $10 per day pay-in-advance option, as opposed to the $16 rate assessed each time the car passed through. Know where tolls are located then determine which option is best per your route. I also returned the car with a full tank; there are plenty of 24-hour gas stations in the Miami airport area.

You can immediately make the three hour drive (or more, depending upon time of day) to Key West or rest in the area overnight. Alternatively, drive part way. I opted to stay in Marathon, roughly two hours from Miami. My hotel was affordable versus most January options in the Keys--$102 per night courtesy an accepted bid on a two-star hotel from a well-known travel Web site. Decent accommodations in Old Key West run a minimum twice that price, and if you book your stay during Key West Race Week the rates climb steeply. This is a venue to see by foot, and parking in the area is easy courtesy public lots that have flat rate all-day parking.

Being There
My trek this year had weather that was hot, logged no rain, offered mild winds and saw hardly a cloud in the sky—ideal for strolling about, which, if you are not on the water, should be a top activity for an Old Town holiday. The locals say those weather conditions are normal. However, fluke conditions can occur. Last year at the same time we experienced temps in the lower 70s, heavy rain, thunder and lightning, plus absolutely hurricane-like conditions.