Key West for Couples – Most Romantic Things To Do
Is the Winter getting you down? Why not enjoy a couples romantic getaway in Key West, Florida? Key West for Couples is the way to go. Key West is the westernmost key in the Florida Keys. South Florida is warm year round, so anytime is a good time to go. However, having been there in August, I can tell you that it is very hot and steamy in the summer.
One way to enjoy a trip to Key West for Couples is to do it with a large group of couples. We did such a trip in January, 2024 with a group of seven couples, better known as the ” Gang of 14.” The male side of the “gang” were all fraternity brothers who lived together fifty years ago. Not only did I get to see some friends whom I get to see on a regular basis, but I also got to see Coops and Duker and their partners, whom I hadn’t seen in many years. Coops was with his fiance, Margie, who we met for the first time.
By rhapsodyinbooks | Published 11/28/2013
Key West for Couples – Getting There
If there is one downside to having a romantic getaway for couples in Key West it is the challenge of getting there. As the map shows, Key West is somewhat at the end of the world. We have three suggestions that might work for you:
Fly to Key West
Fortunately, there are 30 direct destinations to Key West International Airport (EYW) from various cities in the United States and Canada. Some of the airlines that offer non-stop flights to Key West are American Airlines, United Airlines, Delta, Allegiant, Silver Airways, and JetBlue.
For more information about these airlines, please see our Airlines Choices Post. Or you can read our United vs American and Delta Airlines Post.
The most popular and frequently departed flights to Key West are from Charlotte (CLT), Atlanta (ATL), Miami (MIA), Tampa (TPA), and Orlando (MCO). You can also find direct flights from other cities such as Boston (BOS), Philadelphia (PHL), Dallas-Fort Worth (DFW), Chicago (ORD), New York (LGA and EWR), and Washington DC (DCA).
Separately, another alternative is to fly to Miami and drive to Key West. The one caution is that Miami is a difficult airport to traverse. It make take a while to find baggage claim, the rental cars and depart the airport.
Drive to Key West
If you are adventurous, like us, and you live in Florida, you may just want to drive. Besides the fact it is a beautiful drive, it gives you plenty of alone time for swooning over the color of the water. Or stopping at a just-can’t miss roadside shop. Or deciding it’s time for a little refreshment. Take as long as you want…the beauty of a flexible schedule!
The drive to Key West from Miami is 165 miles long and will take roughly 3 1/2 to 4 hours. US 1, the road from Florida City and Key Largo to Key West is a straight shot. You will not get lost. This is the southernmost section of US 1 which runs all the way up the east coast of the US from Key West to Fort Kent, Maine.
While you may want to drive from Miami to Key West non-stop, we recommend taking a break or two to enjoy some of the Keys and the beautiful scenery that you will pass on your journey. For information about our recommend stops see below in our section Couples Romantic Road Trip Miami To Key West.
Take Key West Express Ferry
Lastly, you might want to take a ferry from Fort Myers or Marco Island.
Similarly, just like the drive from Miami to Key West, the ferry ride will be a 3 1/2- 4 hour journey. Traveling via the Key West Express is truly the best way to get to Key West. You’ll enjoy air-conditioned interiors, exterior sun decks, plus a variety of seating options. There’s even a full-service galley, bar, and flat screen TVs with satellite television to watch during the duration of the ride. What a great way to gear up for a vacation! Plus the hassle of airline travel and the frustration of driving on a two lane highway is avoided by taking the ferry!
Enjoy Key West’s Romantic Breathtaking Sunsets 4 Couples
One of the best things for couples to do in Key West is to enjoy the sunsets. Given Key West’s southwestern location it is a beautiful place to take in the setting sun. Here are two ways to do it.
Sunset Cruise Boat Ride
There are a large number of sunset cruises that you and your partner may wish to take for a wonderful view of Key West and the sunset. Weather permitting, it will be one of the best sunsets you will see anywhere.
As previously mentioned, on our recent January, 2024 visit to Key West we were with twelve of our best friends, better known as the ” Gang of 14″. We booked ourselves on Barefoot Billy’s Sunset Cruise . Led by Barney, who arranged our boat ride, we had a great time. Barefoot Billy provided us with “all you can drink” and free hors d’oeuvres. He has a large pontoon style boat that can handle up to 35 guests comfortably. We had a pretty full crowd. But, it was still a great time. And those unfortunate souls who found themselves surrounded by 70-year old frat brothers and spouses adapted pretty quickly.
There are plenty of other sunset options to choose from. Especially, if you like sail boats. Specifically, we recommend taking a look at Trip Advisor which has some of the best sailing and other water activities to choose from.
Read reviews, compare prices, and find the best Hotels, Restaurants, Attractions and more. Compare prices & save money with Tripadvisor® (World's largest travel website).
Mallory Square
Just in case you easily get seasick when you are on a boat, or you would like to see the sunset without the drinks and hors d’oeuvres, we also have a land-based option for you. And, the best news is that it is free.
Mallory Square is near the historic district and is one of the western most points on Key West. It is renown for being a great place to take in the sunset. It is a fantastic family place as well as a beautiful romantic place in Key West for couples. If you still want access to adult beverages, there is also a very popular bar on the square with live music.
Key West for Couples: Visit Famous Places
Key West has some extremely famous places to visit. Especially if you are history buffs like Robin and I, you will love to visit the historic homes. Key West is famous for the Presidents who have visited here and it’s most famous person of all time. No, not Jimmy Buffet. I am talking about Ernest Hemingway, a man who was bigger than life. You might even want to get a souvenir picture of the famous man from Amazon. Before we went, we immersed ourselves in the PBS series on Ernest Hemingway by Ken Burns. Watching that before we went was an important part of our preparation for the trip!
However, the one spot (other than his home) we wanted to see was his hangout, “Sloppy Joe’s”. After Capt. Tony’s, who claims to be the first and original “Sloppy Joe’s”, and the place called “Sloppy Joe’s”, it turns out neither was right. In truth, the Castro-led Cuban government shutdown the original “Sloppy Joe’s” in 1965. But in 2013, it was restored and reopened. Meanwhile, in Key West, Hemingway’s friend Joe Russell purchased the old city morgue on Greene Street, turning it into a bar he named “Sloppy Joe’s”, essentially stealing the name of the original establishment in Havana. A true urban legend. That said, we mention both below.
Hemingway House
The Ernest Hemingway Home in Key West is an historic landmark and museum that showcases the life and work of Ernest Hemingway. He lived there from 1931 to 1939 with his wife Pauline and their six-toed cats.
A marine architect and salvager named Asa Tift built the house. It is located at 907 Whitehead Street, across from the Key West Lighthouse. It has a French Colonial style and is one of the highest points on the island.
Hemingway wrote some of his best-known works in this house, such as Green Hills of Africa, The Snows of Kilimanjaro, and To Have and Have Not. He also enjoyed fishing, boxing, and drinking with his friends in Key West.
The house is now open to the public as a museum, where visitors can see Hemingway’s personal belongings, his writing studio, and his famous polydactyl cats. The cats are descendants of Snow White, a white six-toed cat that Hemingway received as a gift from a ship’s captain.
You can visit the Hemingway Home & Museum website for more information. You can also find some tips and reviews from other travelers who have visited the house.
Harry S. Truman’s Little White House
The Winter White House is worth a visit. It was built in 1890. This beautiful structure was initially the command headquarters of the naval station during the Spanish-American War. However, It wasn’t until 1946 that it was converted into the winter residence of the 33rd President Harry Truman.
Harry S. Truman made 12 visits to the Little White House throughout his presidency. Between 1946 and 1952, Truman spent a total of 175 days residing and working at the Little White House. Step back into the era of Harry Truman and explore his personal belongings, including the living quarters where he and Bess resided, original furnishings, personal effects, and much more. Additionally, you’ll have the opportunity to see the rooms where Truman held meetings with the Joint Chiefs of Staff, worked on the Marshall Plan, and penned the Truman Doctrine.
Other well-known politicians and celebrities also made their way to Key West to visit the house. Among them were former Presidents Franklin Roosevelt, and Dwight D. Eisenhower, and British Prime Minister Winston Churchill.
William Howard Taft, the 27th President of the United States, made use of the Little White House when he visited in 1912. He’d arrived to inspect the world-renowned Panama Canal, built during his presidency.
The Little White House was also used when President John F. Kennedy chose it as his Winter White House in 1961. Kennedy was looking for an escape to the Florida Keys. The president spent a whopping 45 days in the House before he had to attend to important matters in Washington. In the 1980s, Key West underwent a transformation and became a tourist destination, where President Jimmy Carter and President Bill Clinton sought relaxation.
Southernmost Point Buoy
The Southernmost Point Buoy is a real landmark in Key West. Unfortunately, during our January 2024 visit to Key West, Robin and I never made it to the Southernmost Point in the Continental US. I had been there on previous visits to Key West, so I was fine passing on the visit this time. Nevertheless, some of the “Gang of 14” that we traveled with (January, 2024) made it down there. Unquestionably, if they send me photos, I will post them here.
The Southernmost Point is also well known as Milepost Zero for US 1. Well worth the visit and the Instagram pictures if you get there.
Go Diving, Fishing or Other Fun Activities on the Water
In addition to going out on the water for the Sunset Cruise, there are plenty of other fun things you can do out on the water. Key West is literally surrounded by the Atlantic Ocean and the Gulf of Mexico. Taking a Jet Ski Tour is very popular. As is going diving or snorkeling and searching for lobsters. The shallow waters on the Gulf side are ideal for lobster fishing which you can do by snorkeling or scuba diving. Even more popular is going fishing. It is a short trip to where you can do deep-sea fishing. The are plenty of fishing charters that can be easily reserved on Viator or other tour agencies.
Enjoy an Adult Beverage at a Famous Bar
It is said, by my good friend Ed, that there are two things to do in Key West, fish and drink. Hemingway also wrote some books and Jimmy Buffet wrote some songs, but we will get back to fishing and drinking. We are talking about having a good time.
Duval Street, which is the heart of old town Key West, runs from the Southern end of Key West to the Northern end. Here you find some of our and Hemingway’s favorite watering holes in all of the world. While they may not make the cut for romantic things to do in Key West, here you will have a good time. These places have live music, they are fun and have been known to create romantic evenings. these are our favorites:
- Sloppy Joe’s – Considered Hemingway’s favorite place, it is perhaps the classiest of this collection of our favorite top three watering holes in Key West. However, we must admit that is a low bar. (No pun intended.) If you only have time to visit one of these famous bars, this is the one we recommend.
- Capt. Tony’s Saloon- Formerly, the home of Sloppy Joe’s this bar is at the low-end of our three famous bars to visit. Definitely, the dive bar, you will be impressed by the money on the ceiling.
- Hog’s Breath Saloon – A nice outdoor place to get a drink with some good music, our favorite.
Key West for Couples – Recommended Restaurants
Unfortunately, since we were well feed on our sunset cruise, and spent excessive time at the bars, we didn’t get a chance to visit any of the fine restaurants in Key West. We did have lunch at the Alfonso’s which has a good selection of seafood. Mumbler, one of the “Gang of 14”. splurged and bought us the seafood tower. However, Alfonso’s, in general, was a little too touristy for our taste. So, it didn’t make our top 50 restaurant listing. Please see our Bib Gourmand vs Michelin Star Restaurant Post if you are interested in our top 50 worldwide restaurants.
We also had dinner at our hotel, the Key West Marriott Beachside. Their restaurant is a nice place to eat if you are staying there. HJ, one of the “Gang of 14” is in the top level rewards tier at Marriott. He hosted us one evening for after dinner drinks in his premier suite which he earned for his elevated status. If you are interested in learning more about benefits of being in the top tier at Marriott and other hotels, please see our post Marriott vs Hilton: Whose Reward Points are Better.
However, we definitely recommend that where ever you decide to eat for a nice dinner, make sure they have Key Lime Pie. Key Lime Pie is famous in this part of Florida and you will enjoy every bite. Kermit’s Key Lime Pie Shop on Elizabeth Street sells every version of this treat, from Key Lime Pie on a Stick, to Key Lime Salsa even to gluten free Key Lime Pie.
Getting Around Key West
Parking in and moving around Key West can be a challenge. Therefore, it is best to take shuttles when offered. Another alternative is to take the hop-on hop-off Old Town Trolley. Of course, you could also put on your walking shoes. In any case, don’t expect to be parking in one place, then moving the car to another place. You will either not find parking, or you will go broke.
Couples Special: Key West for Couples Romantic Cruise to Dry Tortuga National Park
The first time I went to Key West, I decided to do the all-day fast catamaran trip out to the Dry Tortugas. While the catamaran admittedly was fast, it was still an all-day affair.
The Dry Tortugas are a small archipelago of coral islands about 70 miles west of Key West in Florida. They are part of the Dry Tortugas National Park, which preserves the natural and historic resources of the area. The park is known for its crystal clear water, coral reefs, marine life, and bird life.
It is also home to Fort Jefferson, a 19th century coastal fortress that covers most of Garden Key. Fort Jefferson was built to protect the southern coastline of the United States and the shipping lane to the Mississippi River. It was also used as a prison during the Civil War. The Fort’s most famous prisoner was Dr. Samuel Mudd, who was involved in the assassination of President Abraham Lincoln. Fort Jefferson is the largest brick masonry structure in the Americas, made with over 16 million bricks. It is considered an unfinished fortress, as it was never fully armed or completed.
If you are interested in learning more about the Dry Tortugas and Fort Jefferson, you can visit the park’s official website. You can also explore the fort’s history and architecture with a guided tour or snorkel around the coral reefs and shipwrecks. The Dry Tortugas are a unique and beautiful destination that offer a glimpse into the past and the present of the Florida Keys.
Couples Romantic Road Trip: Miami to Key West
As the adventurous types, who have either flown to Miami or a Florida Resident who decided to drive from Miami out to Key West, you will be in for a lengthy 3/1/2 – 4 hour journey. That is if you don’t stop. But, we highly recommend that you do stop.
Known as the Florida Scenic Highway, the route is well marked with green mileage markers starting at mile zero in Key west. They are helpful to indicate specific locations and places to stop. There is some very nice scenery to see before you get to Key West. The Seven Mile Bridge along with other segments of the trip provide some fantastic views of the beautiful waters surrounding the Keys.
There are also some highly unusual sights, such as the largest lobster you have ever seen. Located at Marker 80. However, we don’t recommend eating here as this place is very much in the spirit of Key West Dive Restaurants.
Nevertheless, we did make two restaurant stops, one on the way in to Key West and one on the way out. We highly recommend both. On the way to Key West, we stopped at Robbie’s. In addition, to the pirate feeling, Robbie’s had a nice Key West style with dollar bills hanging all around. According to the bartender, there could be as much as $30,000 or $50,000 in bills and growing. The only two downsides and both are concerning: theft or fire!
And they had some decent seafood, Robbie’s also hosts Tarpon feeding. This is a favorite of young people looking to get their hands bit. Also, the pelicans are very popular and they will steal your bait. Robbies is at Marker 77 1/2.
Returning Back to Miami
The second restaurant we stopped at, on the way home, is Marker 88. It has a great water view and its own beach. The Mexican food that we had was excellent. All three of these places are located in Islamorada, which is the second most popular Key after Key West.
After our visit to Key West and Islamorada, we stayed overnight in Miami. Miami, of course, is the largest city in Florida. While in Miami we visited the famous Wynwood Design Area where we got some great pictures of the street art. To read more about Miami and Florida please see our Florida Hidden Gems Post. To see more about our love for Street Art, please see our Love Graffiti Art Post.