Key West, Florida: Our New Hawaii!

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By Mike DuBose and Debra DuBose with Blake DuBose

We have been to the Hawaiian Islands, our favorite vacation spot, about 30 times. Each of the islands has its own unique characteristics and offerings, but whichever we visit, we always have fun! However, traveling there can take 15 or more exhausting hours of flying time and airport connections. Combined with the major time zone difference from our home in Columbia, SC, the trip can wreak havoc on our mental and physical systems!

Recently, we began searching for a January travel destination that mimics many of Hawaii’s great qualities, but with shorter travel times. Notably, we were looking for a place with warm temperatures that was in (or close to) the Eastern Standard Time zone. This would enable us to experience minimal jet lag (versus traveling through a six-hour time difference to Hawaii, leaving one day and arriving the next when returning home).

Key West, Florida met our criteria! Located about 95 miles from Cuba and 160 miles from Miami, Key West is the southernmost point in the United States. About 25,000 people are permanent residents on the 2-mile by 4-mile island, which was nearly doubled in size over the years by a landfill. Key West is one of 1700 “Florida Keys,” an archipelago of islands spanning 137 miles. (Many are very small and uninhabited, however, and only 43 of the islands are connected by bridges.)

Key West has a tropical climate similar to that of many Caribbean nations, with high temperatures during the day in January averaging 74 degrees Fahrenheit and falling to the mid-to-high 60s at night. The air is slightly humid, which makes it feel warmer, and the chance of rainfall is less than 29% on most days in January. Thus, December to February is a great timeframe to visit Key West, with very pleasant weather!

In terms of personality, Key West is a laid-back, artistic, and scenic destination with a continuous “happy hour” spirit. It boasts more than 300 restaurants and bars, most of which serve fresh fish, and the food is excellent! For such a small island, there are many things to see and do.

Getting there: We flew to Key West on Delta Airlines directly from Atlanta, Georgia. The flight takes less than two hours, and unlike with other Caribbean islands, no passports or Customs checks are required. However, the runway in Key West is short, so you are limited to one piece of checked luggage per person, plus two carry-ons. (See our article on packing for tips on traveling light.) If you wish to carry more than one suitcase, you can gate-check another piece prior to boarding your flight. The Key West airport was small, but when we flew in and out, there were not a lot of passengers and clearing the TSA line did not take long. The airport does not have any mobile connector ramps to handle passengers boarding or disembarking the airplane, so be prepared to heft your carry-on luggage down the steep stairs from the airplane door to the tarmac and carry them into the terminal!

We interviewed other travelers who flew to Miami, Fort Lauderdale, or other nearby Florida cities, rented cars, and then drove on US Route 1 through all of the keys. It takes between 3-4 hours to drive this “Overseas Highway” from Miami to Key West. Most people we spoke to said the trip was enjoyable and beautiful. Some stopped along the way at various islands, ate at local restaurants, and/or visited sites. Others warned that traffic along the single-lane highway can be very unpredictable, since speed limits are low and traffic can be heavy (especially on Saturdays). If a wreck occurs, you could be stuck on the highway for hours! If you want to drive from Miami or Fort Lauderdale but don’t want to make the whole trip in one day, we recommend staying in Key Largo, which is an island about 100 miles from Key West.

While in Key West, we saw a lot of out-of-state non-rental cars, so other individuals traveled longer distances to get there. Some even drove down from the northeast! However, those we interviewed who drove the entire way said it was exhausting and they would not do it again. Another option is to fly into a city like Fort Myers, Florida and take a ferry to Key West.  

Where to stay: There are about 100 hotels in Key West. We checked in at the Marriott Beachside Hotel at 3841 North Roosevelt Boulevard (, which is about 1 mile from the airport. The hotel operates a complimentary shuttle to and from the airport until 11 PM, but our flight was delayed due to weather and we arrived in Key West at midnight. Since the shuttle was finished for the night, the hotel paid for our taxi, which impressed us!

The Marriott Beachside Hotel was excellent, and we plan to return. We used Marriott points for our stay, but if you can, splurge on a Presidential Suite (they have 68 of them, with one, two, or three bedrooms) with a gulf view on a high floor. These are large, fabulous rooms with full-sized kitchens, balconies, and great sunset views. The hotel is located in a quiet area about 3 miles from Duval Street, Key West’s bustling “main drag,” but they have large shuttles that run every hour to and from the hotel. The shuttles will drop you off in front of Jimmy Buffet’s Margaritaville restaurant and bar, which is located at 500 Duval Street, and return you to the hotel until 11 PM.

While we chose to stay a few miles from the beaten path, you may want to be situated closer to the action so you can literally walk out of your hotel to the nearby attractions. However, keep in mind that prices tend to increase as you approach the main tourist area. Other things you should consider are: where the hotel is located on the island, daily parking fees (if you plan to bring a car), if it provides a shuttle, and any resort fees (which can be hefty). provides many helpful reviews from other travelers that can help you plan your stay.

Getting around: The island is very small, so you can move around quickly by car, but parking is extremely limited. Taxis are very expensive, and Uber was not operating on the island when we visited in January 2017. Some visitors rent bicycles, which we will consider on our next visit. Large electric golf carts are also available for rent. However, if you stay at a hotel that has a shuttle, most main attractions, restaurants, shops, museums, and bars will be within walking distance from the shuttle drop-off point. You can also ride the fun, open-air hop-on hop-off Conch Tour Train (, which picked up near our hotel (or similar transportation offered by other tour programs). Ticketholders on some of these tours also receive discounted entry to major tourist sites.

Where to eat: With so many restaurants on this tiny island, deciding where to dine was our greatest challenge! Since Key West is near both the Atlantic Ocean and the Gulf of Mexico, fresh fish and seafood are prominently featured in its cuisine. (We recommend trying hogfish, a popular offering in many restaurants—it was delicious!) During our eight-day stay, we started each morning with a great, free buffet breakfast at the Marriott (ask for Karoly or Ben as your server), ate lunch between 2-3 PM, and dove into a delicious dinner around 8 PM. We walked 10,000 steps each day to ward off weight gain from all the food and drink we consumed!

Locals say that every time you visit, you will find a new restaurant, especially on the side streets. Another person we interviewed said that competition among restaurants is high, but that the best ones have survived over the years. We decided to eat at many different places to savor the local culinary delights, and from our experiences, we don’t think there are any bad restaurants on the island! Sometimes, it was fun just wandering around, looking at menus, and asking some customers about the quality of the food.

To save money, look for dining discount coupons at the airport, hotels, and tourist locations. Your hotel’s concierge will also be able to provide you with 10% off coupons for some restaurants. However, we did notice that the best restaurants and tourist attractions did not participate in these discounts, so you may want to take that into account when budgeting for your trip.

The following are some recommended restaurants based on our dining experiences and suggestions from Key West locals. Online reviews can also guide you based on your budget and food preferences. Note that the town’s relaxed vibe extends to dining: many of the restaurants do not take reservations!

Tavern N Town: reviewers rated this restaurant at the Marriott Beachside Hotel one of the top ten in all Key West, but we (and other couples we spoke to) found it expensive and not particularly outstanding. We did discover a new favorite wine there, however, and will give it another chance on our next trip. The restaurant also offers a five-star breakfast buffet for $20, but it is free for Marriott Gold and Platinum Elite members. In a good tradeoff, non-Elite Marriott members can also obtain a free breakfast if they eat dinner there. (See for menus and reservations.) 

Mangoes: This is an open-air restaurant founded in 1980 that serves a variety of American and Caribbean dishes. It is a neat place to have a drink, and although we didn’t eat there, other patrons said that the food was good. Located at 700 Duval Street, it’s in the central Old Town area of Key West. (See

Jimmy Buffet’s Margaritaville: Popular musician Jimmy Buffet’s “Caribbean rock’n’roll” music is exemplified in songs like “Margaritaville,” where he sings, “Wasted away again in Margaritaville, searchin’ for my lost shaker of salt.” It’s a type of music that many people associate with island living in places like Key West, where Buffett spent years working on a yacht while perfecting his musical style. Although Margaritaville is a chain, the Key West location ( is the original restaurant and bar, founded in 1985. While we did not eat there, everyone we talked with said the food was good, and it’s worth a visit. Margaritaville is located at 500 Duval Street.

El Siboney Restaurant: This small restaurant ( is located on the southern side of Key West at 900 Catherine Street, a few blocks away from the end of Duval Street. It serves really good Cuban food, as well as excellent homemade sangria (a wine drink with fruit juice).

Conch Republic Seafood Company: Located on the north side of the island, Conch Republic Seafood Company ( has an open-air setting on the wharf overlooking the water. The food, which includes fish and other seafood fresh off their boat, is great!

Grand Cafe: We stumbled on this nice restaurant, which has both indoor and outdoor seating, while walking around the popular Duval Street area. The food is good, and it is fun to sit at a table out front and watch people walk by. When we were there, the Hard Rock Cafe across the street had an excellent singer, so we visited The Grand Cafe twice to relax, watch the sidewalk crowds, and listen to the music. We particularly enjoyed their Key lime martini. (See for menu and reservations.)

Blue Heaven Restaurant: Many locals recommended Blue Heaven (, an open-air restaurant located near the Ernest Hemingway Home and Museum. We tried their Key lime pie, which is about 4” high and very delicious!

Caroline’s Cafe: Located at William and Duval streets, this excellent, reasonably-priced restaurant features salads, sandwiches, and seafood. Debra recommends the Tex-Mex Rolls appetizer! (Visit for more information.)

Schooner Wharf Bar: This is an open-air restaurant and bar right across from the place where some sunset cruises start in Key West Bight. It’s popular with the locals for the live music it offers, particularly that of Michael McCloud. He is an excellent singer, but beware: he uses some rough language! (See

Sloppy Joe’s: This famous restaurant and bar was named by author Ernest Hemingway, who was a regular. In fact, when Sloppy Joe’s was being moved from its original location to its current address at the corner of Duval and Green streets, Hemingway bought the old urinal, which can still be seen in the backyard of the Ernest Hemingway Home and Museum. His wife was embarrassed by the urinal, and decorated it with ornaments to disguise it! To this day, Sloppy Joe’s ( remains a vibrant bar with live music (and it even hosts a Hemingway look-alike contest each year in mid-July). Although we did not stop there on this visit ourselves, the patrons looked like they were having a good ol’ time when we passed by.

Kermit’s Key West Key Lime Shoppe: The main store and kitchen is located in Old Town at the corner of Greene and Elizabeth streets, and a second, smaller store is at 802 Duval Street. A friend recommended the business for its famous Key lime pie bars, which are Key lime pie slices with graham cracker crust that are covered in a thick layer of chocolate. It was our favorite treat on the island; we made two trips for it! In addition to sweets, the store also sells just about everything you can think of with Key lime in it, such as jellies, salsas, and sauces. Kermit’s Key lime pie has been lauded by the Food Network as the best you can buy! (See for locations, or even to order a pie delivered to you.)

Other recommended restaurants: We ran out of time to visit all the restaurants, but locals and online reviewers strongly suggested: Hogfish Bar and Grill (which requires a taxi or car to get to from central Key West), Louie’s Backyard, Cafe Sole, B.O.’s Fish Wagon, Deuces “Off the Hook” Grill, Garbo’s Grill, Santiago’s Bodega, Eaton Street Seafood Market, Hot Tin Roof, Seven Fish, Bagatelle, and La Trattoria. They are on our list for next time!

What to do: We found that just wandering around, watching people, getting lost, relaxing, eating a variety of foods, and enjoying the great weather were our favorite things to do in Key West! Wherever you choose to go, take a map with you. Most hotels will provide you with one if you ask, or grab one at the airport from stands in the luggage area. Here are some activities we particularly enjoyed on our trip:

Embark on a sunset cruise: There are many different companies offering sunset boat rides in Key West. We went on the America 2.0, a 105-foot sailboat that actually uses its sails (some just use motors) and was recommended by our Marriott concierge. A two-hour trip runs about $85 per person. It was a good cruise, and we saw a beautiful sunset. The boat was bigger than most, so everyone had seats (our captain pointed out nearby smaller boats where participants had to stand). However, the seats were wooden and very uncomfortable, so bring a seat cushion with you if you go! It was good sailing, with lots of wine, beer, bottled water, and non-alcoholic beverages included in the ticket price. Unlike the many sunset cruises we have experienced in Hawaii, the hors d’oeuvres were very disappointing—just a few small servings of vegetables and shrimp. If they were to step up the quality and quantity of hors d’oeuvres and add some seat cushions, it would be a five-star event!

Fly in a biplane: Mike grew up near his grandfather’s airport in Darlington, SC, where he would fly in a 1939 Piper Cub each day. In Key West, he recreated this fond memory by donning flight goggles again and taking to the air with Debra in a 1941 biplane piloted by Conch Republic Air Force tours. It was a fun and unique experience to see the beautiful water and reefs from above!

View beautiful butterflies at the Key West Butterfly and Nature Conservatory: This non-profit houses 50+ butterfly and 20 exotic bird species in a special glass-covered, climate-controlled habitat. One of the most interesting butterflies we saw had a design mimicking a snake’s head on the ends of its wings to scare off predators! Visitors can also see the life cycle of a butterfly at the Learning Center, where we learned that some species only live for ten days. While it cannot be compared to the Butterfly Conservatory we visited in New York City, it was worth the visit! (Tickets are $12 for adults, $9 for seniors and military, and $8.50 for children; see for hours and other information.)

Enjoy the sunset from Mallory Square: Each night, starting about an hour before the sun goes down, hundreds of people visit Mallory Square Dock to celebrate the beautiful sunset over the Gulf of Mexico. The Mallory Square area, which is located in the heart of Old Town at 400 Wall Street, is full of vendors, musicians, food and drink carts, and performers. There are also many shops, monuments, museums, and restaurants nearby.

Tour the Harry S. Truman Little White House: President Truman stayed here for 175 days over 11 visits, using it as his “Winter White House” and as a break from the stress of the presidency. In fact, he loved the area so much that he wrote to his wife, Bess, saying that he would like to move the US capital there! Now a museum, the home has been restored to its original décor and was a good 30-minute historical visit. (Buy tickets—prices are $15 for adults, $4.50 for children, and $13 for seniors—online at

See 17th-century treasure at the Mel Fisher Maritime Museum: If you are interested in history, this is a fascinating place to visit. Treasure hunter and Key West resident Mel Fisher spent many years looking for the wreck of the Nuestra Senora de Atocha, a Spanish galleon that was lost off the Florida Keys in 1622. He found it in 1985…packed with $450 million worth of gold and silver! Once he made the discovery, the state of Florida tried to claim the treasure, sparking a legal battle that went all the way to the US Supreme Court. The Court ruled in Fisher’s favor, and he got to keep all the treasure! Fisher founded the non-profit Mel Fisher Maritime Museum (see for tickets, which cost $15 for adults and $5 for children) to display some of the artifacts, including jewelry, gold and silver bars, swords, and tools. The museum is located at 200 Greene Street, at the corner of Greene and Whitehead streets.

Visit the Ernest Hemingway Home and Museum: Celebrated American author and Nobel Prize winner Ernest Hemingway wrote many classics in this house, residing there for over ten years. The home, which is situated at 907 Whitehead Street, opened as a museum in 1964 and has been restored to its original state. An interesting quirk of Hemingway Home is its polydactyl (six-toed) cats, roughly 50 of whom live on the estate. They are descended from a white polydactyl cat named Snowball, who was given to Ernest Hemingway by a ship's captain (the cats receive food and regular veterinary care). Thirty-minute tours of the home are offered 365 days a year at a cost of $14 for adults and $5 for children; visit for information.

Take a walk down Duval Street: About 1.25 miles in length, Duval Street runs north to south from the Gulf of Mexico to the Atlantic Ocean. The famous commercially-zoned street is located in downtown Key West and contains hundreds of shops, restaurants, and bars.

Feel the breeze along the Historic Seaport: Key West’s Historic Seaport stretches along the waterfront at the ends of Front, Greene, Elizabeth, William, and Grinnell streets. Hundreds of boats and many restaurants are located along this boardwalk. We enjoyed strolling around the area, especially in the afternoons when the fishing boats had returned and boat crews were cleaning their catch (you would also see about 20 pelicans floating in the water below the pier waiting for the leftovers!).

Other activities to try: There are hundreds of things to do and see in Key West, including: renting a jet ski, snorkeling, kayaking, scuba diving, deep sea fishing, parasailing, glass-bottom boat rides, skydiving, golfing, wine and food walking tours, and visiting the Key West Aquarium. It just depends on your interests and how much time you have! Check for ideas, or ask your hotel’s concierge for recommendations.

The bottom line: Key West is a great place to visit! The town is defined by its fun, relaxing atmosphere; excellent food and drink; and good weather—even when it’s cold back home. We plan to return next year!

About the Authors: Together, we have logged more than 2 million flight miles over the world in the last 40 years. Our corporate and personal purpose is to “create opportunities to improve lives” by sharing our knowledge, research, experiences, successes, and mistakes. You can e-mail us at

Mike DuBose received his graduate degree from the University of South Carolina and is the author of The Art of Building a Great Business. He has been in business since 1981 and is the owner of Research Associates, The Evaluation Group, Columbia Conference Center, and DuBose Fitness Center. Visit his nonprofit website for a free copy of his book and additional business, travel, health, and personal published articles.

Debra DuBose has been married to Mike for 45 years and co-writes articles with him. She holds bachelor and graduate degrees from Winthrop University and Francis Marion University.

Blake DuBose graduated from Newberry College’s Schools of Business and Psychology and is president of DuBose Web Group (

Katie Beck serves as Director of Communications for the DuBose family of companies. She graduated from the USC School of Journalism and Honors College.

© Copyright 2017 by Mike DuBose—All Rights Reserved. You have permission and we encourage you to forward the full article to friends or colleagues and/or distribute it as part of personal or professional use, providing that the authors are credited. However, no part of this article may be altered or published in any other manner without the written consent of the authors. If you would like written approval to post this information on an appropriate website or to publish this information, please contact Katie Beck at