Key West, Florida

All of the beaches are on the south side of the island, the ocean side. Local favorite is South Beach at the end of Duval. There is a snack bar/restaurant on the beach with chair rentals and drink delivery. Fort Zachery Taylor State Park also has a great beach and it has restrooms, food and chair rentals. Smathers Beach on South Roosevelt has it all including all the water sports rentals.

Key West Golf Club is the only local choice. It’s a Rees Jones designed 6,500 yard course, just minutes from downtown Key West.

Public courts at Bay View Park, Truman and Leon Streets. Also availability at Key West Tennis, 811 Seminole Ave. by the Casa Marina Hotel.

You can walk/run just about anywhere in Key West and I find along the docks at the Waterfront or along beach as the sun is rising on S. Roosevelt to be most enjoyable

Key West Boat Rentals is the place for small 16′ and up boats. For all other water sports like jet skis, wave runners and parasailing contact Sunset Water Sports.

Keys fishing is an angler’s nirvana. Deep sea charters for big game fish cost $550-$650 1/2 day, $750-$850 full day for up to 6 people. Sharing a charter runs $125-$135 per person 1/2 day, $200 full day. Bone fishing (also known as flats fishing) is a Key’s favorite. A real challenge to hook and land these great fighting fish. Usually two man boats. 1/2 day @$375-$425. Full day, $575-$625. Off-shore/light tackle fishing costs @$450/$550 1/2 day and $650/$750 full day. Finally, there are party boats with pricing in the $35 to $40 range. Contact Key West Fishing Charters.

Another option is to go down to N. Roosevelt Blvd where all the charter and party boats are docked and make your own deal. Depending on how hungry they are, you can sometimes negotiate good rates.

There are any number of places to rent bikes and scooters. Many accommodations rent or provide bikes on their own. Tropical Bicycle and Scooter, 1300 Duval is one of the largest. Bike routes are marked on the street, throughout the island.

Southpoint Divers, 500 Truman Ave. Top Ten in North America and Highest Rated Dive Center in Key West, Scuba Diving Magazine. Best Dive Center, Key West People’s Choice Awards.

There are some 36 art galleries scattered throughout Key West. Wyland Gallery is a spectacular place that shouldn’t be missed. Gingerbread Square Gallery is another great choice. Florida Keys Council of the Arts produces a Gallery Guide which is available almost anywhere. Most of the galleries are clustered on Duval Street from Southard to United. You can stroll along Duval and just pop in and out. I particularly liked the Alan S. Maltz Gallery on Duval.

Audubon House and Tropical Gardens, 205 Whitehead a tribute to the naturalist. Period Antiques, original Audubon engravings, native and exotic plant gardens. Ernest Hemingway Home and Museum. 907 Whitehead Street  site where author wrote his greatest works. Key West Aquarium, 1 Whitehead Street  since 1934: sharks, turtles, tropical and game fish. Key West Butterfly and Nature Conservatory, 1316 Duval Street  walk through a tropical paradise of plants, flowers and hundreds of exotic butterflies.

Conch Train Tour. Board at Front and Duval or the Key West Welcome Center. 100 points of interest. Old Town Trolley Tours, available in many other cities, also operates in Key West.

You might want to take one of the above tours as an introduction to the island and then pick up a copy of Sharon Wells Walking and Biking Guide to Historic Key West. It is available for free around town or at the Visitors Center.

Sharon is a noted local historian, photographer and author. She has compiled 10 self-guided tours (walking or biking) that cover all the interesting points of interest.

Red Barn Theatre. 319 Duval. 20th year of professional theatre. Nov-June. The Tennessee Williams Fine Art Center. Florida Keys Community College. Broadway size stage presenting national and international productions. Nov.-April. Key West Theater features music and comedy acts.

From tacky to upscale, Key West has it all. The town could do with a few less t-shirt shops, but what can you do? Pretty much everything is on Duval, so you will stumble upon just about anything.  Besame Mucho, is several eclectic boutiques in one.

Sunset

Celebration of the daily sunset is a ritual here and it all revolves around Mallory Square where musicians and street performers congregate to celebrate the setting sun.

Breakfast

Blue Heaven, 729 Thomas Street. Off Duval. Fresh fruit, homemade breads including a delicious banana bread, farm fresh eggs and a seafood Benedict served in a dirt yard with baby chicks and roosters running under foot. Quite an experience. Bagatelle is a local’s favorite with cocktails! Try the Kim’s Watermelon Breeze to start, Ketel One cucumber mint vodka, muddled cucumbers & watermelon, mint, lime, juice, served on the rocks. Great eggs dishes (Lobster Omelette , three egg omelette, warm water lobster, applewood smoked bacon, swiss cheese, key lime hollandaise) and corned beef hash.  Banana Cafe is a little touch of Paris with a fantastic selection of crepes. Try the Inside Out French Benedict crepe, egg, ham, swiss, herbs, sweet caramelized onions, key lime hollandaise. Opens at 7:30am. Something faster, but equally delicious? Try Croissants de France, an incredible bakery, great coffee. Sit outside and watch the early morning action.

A little hair of the dog, perhaps? Pepe’s, Opened in 1909, it’s the oldest eating house in the Keys. Open for breakfast (and bloodies, mimosas etc.) at 6:30am except Sunday. Great selection and pricing of oysters. Thursday nights they serve a complete Thanksgiving dinner. soup to nuts. All drinks are made with freshly squeezed juices. Free pickles for pregnant women. This place is fun!

Lunch/Brunch

Louie’s Backyard, one of our dinner favorites is equally good for lunch and is the place for Sunday brunch. There’s no better setting. Cafe Sole, another dinner favorite, is also open for lunch. Try the Half Shell Raw Bar,  for great fresh oysters and other raw bar favorites, along with wonderful sandwiches, all right on the water. Turtle Kraals is a casual, waterfront restaurant with the best cerviche, peel & eat shrimp, conch fritters, burgers, fresh fish and more. Hot Tin Roof offers a fantastic waterfront setting, an elegant open air dining room and excellent food. Santiago’s Bodega has a great tapas menu, killer Sangria

Steak, Sushi and Ice Cream

Prime is considered the best steak on the island. Sushi lovers head to Origami’s and Flamingo Crossing’s ice cream is anyone’s choice for the best ice cream. 1105 Duval. Great tropical fruit sorbets and unusual ice creams like Cuban coffee, coconut piña colada and mangrove honey-walnut. Opens 11am.

Oyster Bar

Two favorites, both on the water; Half Shell Raw Bar and Alonzo’s Oyster Bar.

Wine Bar

Wine-O’s at the La Concha Hotel. 200+ wines. Bites and Chocolate menus to pair with wines. Lots of wine events. Happy Hour.

Cocktails

There’s always music and lots of tourists at the Hog’s Breath and Sloppy Joe’s, but our current favorites include a relatively new place, Santiago’s Bodega, right off Duval. Small bar, good wines and a wonderful tapas menu. Sunset Pier at the Ocean Key Resort has delicious spring rolls and steamers and chorizo. Half Shell Raw Bar, offers the obvious. It’s ice cold beer, pool tables and great drinks at The Green Parrot.

The poolside Sunset Tiki Bar is open from 10 AM – 10 PM every day of the week.  Live music in the evening, for their own sunset celebration, and 2 happy hours daily.  Rise and shine with the Morning Happy Hour from 10 AM – Noon and enjoy 2-4-1 Bloody Marys; or relax with the sunset, during Evening Happy Hour from 5 – 7 PM, with 2-4-1 well drinks, domestic beer, and our famous Margaritas!

Morning Paper

Vacation is one thing, but I can’t survive without the morning paper. Go to L. Valladares & Son, 1200 Duval Street. Opens 8am. New York and other out-of-town papers.

Sunset & Cocktails

El Mason de Pepe on Mallory Square has a salsa band every day at sunset, great chips and salsa and margaritas. Sunset Pier at the Ocean Key Resort is jumping at sunset and the upstairs bar at the Westin overlooks Mallory Square and has great views. A another alternative is the Wind & Wine cruise on Danger Charter’s Prize, a 65 foot replica of a wrecking schooner. You’ll enjoy a tasting of upscale wines, hors d’oeuvres and a magnificent sunset for $85 per person.

While Away a Rainy Day

Schooner Wharf at Schooner Wharf and William Street. Locals favorite and mine too! Voted Best bar and People’s Choice. Gravel outdoor courtyard with tables and umbrellas. Great raw bar. Get the Drunken Shrimp, shrimp and spices steamed in beer. Lots of wonderful apps. Live music all the time. Michael McCloud is fun during the day. You can buy his CD, “Greatest Tits”.

After Dinner Fun

Before heading out for the night, a stop at Better Than Sex Dessert Bar is a must. Nothing like it anywhere.

Once your sweet tooth has been satisfied, there are any number of things to do. The Duval Crawl. There are an infinite number of bars and cafes, many with music up and down Duval. You could spend an entire night and still not hit them all. Green Parrot Bar, Off  Duval so less touristy. Everyone’s favorite bar. Pool tables, darts, great live music, cheap drinks and dancing make this a hot spot for those in the know. La Trattoria, 524 Duval has an upscale, classy bar serving great espresso martini’s with big windows overlooking busy Duval. In the back, Virgilio’s has a covered garden patio and an air-conditioned inside bar with live jazz, bands or a DJ playing 70’s and 80’s music. One of my favorite places after dinner is La Te Da, on Duval. Sit at the lively piano bar and sing along or take in the fabulous drag show, it’s a riot and very entertaining. Last but not least, Afterdeck Bar at Louie’s Backyard. Can’t beat the setting, right on the water. The bar is lively, the drinks are good. Best place to just relax with a drink and talk.

Souvenir

Unique jewelry design with a nautical theme at Neptune Designs. For the gentleman; hand rolled cigars at Clinton Square.