Key West Comes Home

Something about Key West stays with you long after the sounds of ocean waves and

rollicking tiki bars dissipate into everyday hustle and bustle.

It’s a feeling, a state of mind that you absorb like rays of sunshine – osmosis for the soul.

If you’re lucky it dawdles deep into post-vacation, which is appropriate because nothing

and no one in Key West moves quickly.

The lingering effects of the Conch Republic are also tangible. I don’t mean souvenirs,

although I’ve brought home some extraordinary tropic wines from the Key West Winery,

white vintages from the Keys flavored with pineapple and mango. I mean the kind of

thing you look at every day, or invite people to enjoy with you so that they, too, can

indulge in the relaxation and rejuvenation that come so readily in the Florida Keys.

My love of Key West began in 2006 when my then-girlfriend (now wife) Danielle and I

made our first visit. We didn’t know what to expect, other than the stories from friends

who swore by the romance and fun that awaited us at the end of Route 1.

Falling in love was easy. We both were infatuated from the start. It began with our hotel,

Southernmost, which sits at the southern end of Duval Street, Key West’s main drag. The

opposite end of Duval Street, packed with bars and bands, can get rowdy and loud, but

Southernmost was far enough away with a private beach and tiki bar, to let the relaxation

seep in; but close enough that a quick walk put you mid-excitement.

On that first trip we explored the island tip to tail: we ate conch fritters and key lime pie;

absorbed the famous sunsets; drank with Captain Tony, God rest his ebullient soul; and

held hands atop the Key West Lighthouse, my single favorite spot in the world.

Key West became a part of us, a part of our relationship, which I later galvanized.

In 2008, we made a return trip, joined by my cousin, Ryan and his then-girlfriend (now

wife), Amanda. I had more than vacation in mind that weekend, and only Amanda and

Ryan were in on the secret – after all, I needed someone to carry the engagement ring so

Danielle didn’t find it in my suitcase.

My cousin took his job seriously, but it is worth noting that one should always ensure

they’re following TSA guidelines while carrying an engagement ring. He was stopped

and his bags searched because he had an oversized bottle of mouthwash in his carry on. I

give him credit, he talked his way out of that one by whispering that he had an

engagement ring, but it was close.

Our first day was a Saturday, and only in the background did we hear the warnings about

Tropical Storm Fay bearing down on the region.

That evening we were going to walk to the far end of Duval Street to our favorite

restaurant, Hot Tin Roof. Ryan and Amanda, per previous arrangement, ran late so

Danielle and I conveniently had to kill time by taking a stroll.

We accidentally-on-purpose happened by the Key West Lighthouse, which was closing

for the evening. Bob the lighthouse keeper was sweeping up at the front gate. In the

months prior, I had worked with The Key West Historical Society, proprietor of the Key

West Lighthouse, to set a secret plan in motion, complete with a secret code word.

Bob very nicely explained that the lighthouse was closed, but he’d let us take a walk up

while he finished cleaning.

I trembled climbing the stairs. Danielle was ahead of me and burst out onto the

observation deck before me.

At the top of the lighthouse, as the whole island sunk into a deep red sunset, I knelt and

asked her to marry me (she said yes).

Ryan and Amanda arrived shortly thereafter and joined us atop the lighthouse to soak in

the unforgettable view.

The next morning, with Tropical Storm Fay biting at our heels, we evacuated the Keys

after an abbreviated stay. But Key West, and the special memories we shared, have

remained with all of us since. Sharing a life milestone with family made Danielle and I’s

engagement that much more poignant, and the four of us frequently talk about a return

trip.

Return has not yet materialized, but I know the flavor of Key West took deep root in

Ryan and Amanda. Ryan’s love for the Keys has manifested in a building project. Over

the summer he began renovating his family’s backyard shed, turning it from lawn mower

storage into Key West tiki bar. His vision, he says, is straight out of the Conch Republic.

Once it’s finished, the story of our trip to Key West and Tropical Storm Fay will

undoubtedly be recounted numerous times.

In his song, “Magic” musician Kenny Chesney sings, “I believe there is magic here.”

Key West’s allure is otherworldly. It is intoxicating and everlasting. Once you’re there,

you never really leave. It could only be supernatural.

My wife and I made sure “Magic” was played during our wedding reception.

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Halfway Between Cape Cod and Key West

The following appeared in the January 2014 issue of Destinations Travel Magazine

St. Michaels, Maryland is just about halfway between Cape Cod, Massachusetts and Key West, Florida, in every possible way.

This waterfront vacation town situated on the Eastern Shore of the Chesapeake Bay mingles the Florida Keys’ laid back vibe with the Cape’s sailboats and seersucker shorts. Art galleries, wine shops and boutique restaurants lounge beside souvenir stores and old-time ice cream parlors. Tiki bar bartenders sling fruity rum cocktails to partying tourists, while at the same time a couple exchanges vows in a quaint, waterfront wedding ceremony at the upscale resort across the harbor. 

Located about an hour and a half drive from either Baltimore or Washington, D.C., St. Michaels is a go-to destination for regional vacationers. The look and feel resembles a tropical version of a New England coastal town, seamlessly melding together aspects of both locales into a mid-Atlantic waterfront respite.

For Cape and Keys frequenters, the similarities begin before you even arrive. Weekend summer traffic on the Chesapeake Bay Bridge would make anyone who has ever crossed onto Cape Cod – or any other beach destination – shudder. The sheer size of the bridge makes it as much a modern engineering marvel as the Seven Mile Bridge the traverses the Florida Keys.

In culinary terms, Maryland is known for crabs in the same way that New England is for lobster and the Florida Keys are for fresh fish. There is no better way to get a flare for the Eastern Shore than to partake in a crab feast along the water, and there is no shortage of quality establishments. For years St. Michaels Crab Claw restaurant and St. Michaels Crab and Steak House – located directly across the harbor from one another – have been serving up local seafood and the hallmark Maryland blue crabs.

For the uninitiated, a crab feast is similar to a lobster bake in that work is involved. One typically begins with a table wrapped in paper, which is promptly covered with the cooked crustaceans. Steamed and covered in mounds of Old Bay seasoning, they are simply prepared. A small mallet, paring knife and placemat instructions will get you to the best bits. The sweet, familiar shellfish flavor skews unique with the abundance of salty seasoning.

The culinary delights don’t necessarily require waterfront dining. Tasty wood-fired pizzas sizzle when dropped on your table at Ava’s. You’ll find perfectly executed entrees, from local seafood to twists on comfort food classics at 208 Talbot. Both of these spots are located right on the town’s main thoroughfare, Talbot Street, which is home to everything a seaside village might need – restaurants, cafes, ice cream parlors, art galleries, souvenir and antique shops and even a brewery.

For a taste of the Eastern Shore that requires much less work than shelling a crab, visit St. Michaels Winery (www.st-michaels-winery.com). The tasting room, located right on Talbot Street, is an informal chance to sip some unique wines, like the Chocolate Zin, a luscious and tasty dessert wine. As with many of the mid-Atlantic vineyards, St. Michaels makes excellent, crisp and dry whites, perfectly paired with a seafood dinner or better yet, a sunset.

Where St. Michaels hovers in between its northern and southern cousins, it ascertains one aspect of seaside living that sets it apart from anywhere else – its sunsets.

Perching along the right Massachusetts inlet or cove will provide a spectacular view of the setting sun. In Key West there is an entire pavilion at the end of the town’s famed Duval Street dedicated to street performers celebrating the stunning sunset view each night. St. Michaels may just outdo them both.

A few minutes out of the town center, Wades Point Inn on the Bay (www.wadespoint.com) guards the elbow of this L-shaped peninsula. A tree-lined gravel road opens into a sprawling green lawn stretching in almost all directions to the water’s edge. At the center stands a grand, whimsical 1819 Georgian-style manor house wrapped in multi-level porches. The main house offers three floors of quaint, bed and breakfast rooms while an adjacent building constructed in the 1990s has more family-friendly accommodations.

Waking up at Wades Point means homemade breakfast made from local ingredients, like scrapple or eggs from down the road. But day’s end is the Inn’s best selling point, and one of St. Michael’s best treasures.

The savvy visitor will have filled a hammock, staked out a lawn chair or a spot on the dock well before dusk, perhaps with a bottle of wine from the St. Michael’s Winery. Wades Point staff will happily provide wine glasses and a corkscrew.

Any spot affords a breathtaking panorama of the bay. The sun sets straight on, sinking down behind a wisp of land across the Chesapeake just large enough to mark the split between sea and sky. It washes the entire yard in surreal colors: orange, pink and purple light, reflecting off the water and the manor house’s white exterior. Serenity and scenery are one in the same.

St. Michael’s may resemble the best of the Cape and the tropics, but it certainly has a charm all its own.