Key West, Florida - Jim Flynn's BestWeekends

Key West, Florida

Key West, Florida Overview

At the southern tip of Florida and only 90 miles from Cuba sits the southern most U.S. city of Key West. Once the base for Caribbean pirates and later home to Ernest Hemingway and Tennessee Williams, Key West also served as the winter White House for President Truman and the inspiration for the drawings of John James Audubon.

Inhabitants are a colorful blend of eclectic artists, writers and others just escaping from everyday life. Everyone has a story and they’re more than willing to share it with you. No one seems to care about the rest of the world, only about enjoying life every single day. This is Jimmy Buffet’s headquarters and the site of the annual Parrot Head convention. Sunshine, tropical breezes, crystal clear water and a never ending party make this an ideal weekend getaway.

Where else would you find a restaurant that celebrates Thanksgiving every Thursday night or a town that sponsors bed races down its main street or a place where restaurant owners call the local jail first when employees don’t show up for work?

Unlike other parts of Florida dominated by fast food restaurants and neon signs, Key West is more like a tropical Caribbean island with tall palm trees, incessant sunshine, crystal blue waters, cascading bougainvillea and colorful hibiscus.

Duval Street, the center of most activity is lined with countless open air restaurants and bars, live music, souvenir shops, clubs and B&B’s. You could spend your whole weekend here just making (or drinking) your way from one end to the other.

Each day ends and evening begins in Mallory Square with the Celebration of Sunset. The Square is filled with hundreds of people, street vendors, and street performers and the sunset is the most glorious you will ever see.

When warm is what you want, there is no better weekend destination than Key West.

When To Go

Key West is a great weekend destination all year with the exception mid-summer when the heat can be oppressive and late summer/early fall which is hurricane season.

Getting There

You can reach Key West by air from anywhere in the country, usually with a stop in Atlanta or Miami first. Or, you can fly into Miami, rent a car and drive down through the keys to Key West. The trip is about 3 1⁄2 hours and is really an enjoyable ride with beautiful blue waters on each side of the highway. I like to stop half way down in Islamorada for lunch or to stay overnight at the delightful Cheeca Lodge (have one of their mangoritas) and then continue on to Key West. Islamorada is the bone fishing capital of the world, so if you are a fisherman, it’s not a place to miss.

Getting Around

The island measures only 4 by 2 miles so you will not need a car in Key West as most activities are within walking distance. Bikes and mopeds are the preferred methods of transportation and rentals are available everywhere. Taxis, pedicabs (rickshaw like cabs on bicycles) and Uber are also readily available.

Things To Do

Key West is a water sports haven offering everything from world class deep sea fishing to scuba and snorkeling in clear blue water to jet skiing, parasailing, challenging bone fishing and just about anything else you can think of relating to the water. Most accommodations have pools, but there are also wonderful beaches to enjoy.

The island is steeped in history and offers the opportunity to go back in time to the days of pirates, shipwrecks, Hemingway, Tennessee Williams and more through museums and island tours. Golf is nearby, there are two excellent theaters with road shows of top productions, excellent art galleries are scattered throughout the town and there is, of course, shopping everywhere. Sunsets here are legendary and merit their own festival each evening. The feel is very laid back. Every day seems like a celebration of life.


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

Water Sports

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.

Bikes, Mopeds, Etc…

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.


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.

Dont Miss

  • Sunset at Mallory Square (Gotta do it once)
  • Danger Sunset/Wine Cruise
  • Any meal at Louie’s Backyard
  • Breakfast at Blue Heaven and Pepe’s
  • Pub crawl on Duval
  • Snorkeling
  • Drag show at La Te Da
  • Butterfly Conservatory

The Best Of...

Food & Drink


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!


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.


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.


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

Special Things

Island Oasis

If you are not staying at Sunset Key, a day here is well spent. Take the launch outside the Hilton for the 10 minute ride to Sunset Key. For $20 per person you can enjoy their magnificent, uncrowded white sandy beach and infinity pool. Enjoy drinks at Flippers poolside bar and then have a wonderful lunch at the delightful outdoor Latitudes Beach Café. A perfect day

Fly Me To…….the Island

About 70 miles west of Key West lie seven undeveloped islands called the Dry Tortugas, Tortugas, Spanish for turtles and Dry because there is no fresh water on the islands. Fort Jefferson is one of the islands and was initially a lighthouse built to protect ports in the Gulf of Mexico region and to warn ships of the rocky shoals. Later it was used as a military prison during the Civil War. Today it is a national park.

Coral reefs, shipwrecks, beautiful sandy beaches, history and wildlife combine to make this a wonderfully romantic side trip.

Pack a lunch and take the first seaplane of the day to the island. The trip takes about 40 minutes and you’ll have about 2 1/2 hours on the island. Snorkeling equipment is provided and there are showers available before the trip back. This is great.

Where To Stay

Casa Marina Resort

OVERVIEW of the Casa Marina Resort

If a full service hotel is what you are seeking, The Casa Marina will fit the bill. Opened in 1920 it has the charm of an old world hotel with all the modern amenities. It is located just outside the heart of town on the largest private beach…

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La Mer/Dewey House


OVERVIEW of the La Mer/Dewey House

Staying here is getting the best of all worlds. La Mer and Dewey House are delightful, private and intimate oceanfront B&B’s, but are part of the adjacent Southernmost Hotel which has three pools, two outside bars and a fishing pier.  Also part of the complex is the Southernmost…

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Ocean Key Resort


OVERVIEW of the Ocean Key Resort

If location is everything, then the Ocean Key Resort has it all. Situated at the end of bustling Duval Street and right on the Gulf, the Resort stands next to Mallory Square the site of the nightly sundown festival.


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Parrot Key Resort


OVERVIEW of Parrot Key Resort

It is not often that a new resort is built in Key West, so Parrot Key, made the wait worthwhile. Located about two miles outside the center of town on North Roosevelt Blvd.(U.S. 1) this is the perfect places for families, couples traveling together or "girl's…

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Sunset Key Cottages

OVERVIEW of Sunset Key Cottages

Few choices are better for a truly special occasion than the Sunset Key Cottages located on a private 27 acre tropical island, just a 10 minute boat ride from the heart of Key West.

THE ROOMS at Sunset Key Cottages

The exquisite cottages, which make…

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The Gardens Hotel


OVERVIEW of the Gardens Hotel

Once the largest private estate on the island, the Gardens Hotel has been transformed into an exotic oasis just blocks from the action on Duval. The Main Building, which houses Reception, has a delightful living room with reading material, videos and…

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The Mermaid and The Alligator


OVERVIEW of The Mermaid and the Alligator

I stumbled upon this charming 1904 Victorian B&B as I was leaving town on a recent visit and made a point of staying there on a return trip. I am so glad I did because this is now one of my favorites in Key West. Staying at the…

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Where To Eat


The yellow flag on the white clapboard building above two bay windows on Duval means you have found one of the best Italian restaurants in Key West, Antonia's. Owners Antonio Berto and Phillip Smith (also the chef) have created a comfortable, yet sophisticated restaurant in a candlelit wood paneled room with a cozy bar, creative…

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Cafe Marquesa

Warm yellow/gold walls, accented by dark mahogany molding and large mahogany framed mirrors create an inviting atmosphere for Cafe Marquesa, an intimate 50 seat spot about two blocks from Duval. Add wide-paned windows with views to the street, shaded table lamps, crisp linens and you have the makings for a very romantic meal. The open…

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Cafe Sole

'A meal in Provence' is how Café Sole describes itself and that is a very apt description. The setting and the wonderfully prepared seafood with a French influence can transport you to the French countryside. Owners John and Judy Correa have created a very special place that is will be a highlight of your trip to Key…

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Little Pearl

When you come to Key West you are going to want some seafood and The Little Pearl is a wonderful neighborhood wine bar and seafood restaurant. Brought to you by the owners of sister restaurant Thirsty Mermaid, Little Pearl shines with creative cooking and a killer wine list. The small, intimate dining room has a…

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Louie’s Backyard

Picture white tablecloths, candlelight, tiny lights sparkling in the trees, the soft rush of the water hitting the dock and maybe a full moon and you begin to understand the lure of this perennial outdoor favorite. There is no more romantic setting in Key West. Ask just about anyone and they will tell you that…

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