Bucket List Dreams- Key West

When you are in Key West, you will notice how time slows down and you are now officially on island time. When I think of Key West, I think of The Ernest Hemingway Home, Mallory Square, Duval Street, perfect cotton-candy colored sunsets and of course, Key Lime pie! The Island community of Key West is filled with charming conch houses and is divided into two sections: Old Town and New Town. Key West has a rich historical significance, a vibrant art, and cultural scene, a multitude of kitschy and quirky places, entertainment venues and street performers and so much more.


Old Town is located downtown and is the historic heart of Key West. I love all of the sights of the quaint Old Town area. The renovated and preserved hotels and bed and breakfasts in Old Town are quite distinctive. Old Town offers charming cottages, bungalows, and b&bs.

New Town offers more modern and beach-style lodging. New Town consists of shopping centers, restaurants, and hotels. Many of the hotels are all lined up which provides the ease of selecting accommodations for guests. Key West is extremely pricey, and on holidays those prices skyrocket. I saw 2-star budget motels going for 300+ a night during a holiday. Many folks will drive out of Key West and get a room at one of the other neighboring islands.


Key Lime Square is a nice area to get lunch at one of the sidewalk cafes or enjoy eating curb-side. The Cuban Coffee Queen is a favorite spot to grab a coffee or a quick bite. Key Lime Square is great for people watching, spotting iguanas, and seeing chickens cross the road.


Duvall Street is the entertainment district of Key West. On Duvall Street, you will find all of the storefronts, restaurants, and boutiques. Many off-the-wall stores are offering unique novelties and gaudy souvenirs. There is live music, street parties, and festivities. Duvall Street can be sensory overload, and that’s really what makes it so much fun.

Mallory Square offers the most stunning sunset views of Key West. The sky and the waters are multi-colored splashes of pink, blue, yellow, and orange. The scenic, panoramic views are breathtaking. Everyone gathers here as night falls to witness the splendor of the sunset. We watched the sailboats and cruise boats roll by with tours as the sun went down in the evening. You’ll definitely want to bring your camera because the backdrop is tremendous.

Mallory Square is primarily a lively shopping district with boutiques, restaurants, and hotels. They have clean facilities here and paid parking in the garage. We spent an embarrassing amount of time watching this hilarious cat man put on a crazy cat show!

If you are visiting Key West, you must catch the famous Key West sunset here at Mallory Square then have a slice of the famous Key Lime pie of course.


The Cafe is a favorite vegetarian-friendly restaurant in Key West. The atmosphere here is really zen. We decided to get a slice of vegan Key Lime pie because you can’t go to Key West and not get a slice of their famous Key Lime pie. It was presented beautifully and tasted delicious. You’ve got to try their veggie burgers also.

The Ernest Hemingway Home and Museum is famous to Key West! Hemingway’s Home holds tours throughout the day. A visit to the Hemingway Home and Museum was definitely on my bucket list and is a great attraction for all. Avid book lovers, emerging authors and novelists and all those who appreciate great literary works will love this place.


Southernmost Point has a very iconic landmark, the giant red, black and yellow buoy. This massive marker signifies the southernmost point in the continental United States where the land and ocean meet. The land completely ends, and the Atlantic Ocean begins at this very marker. And we’re just 90 miles from Cuba!




Hwy 1, Mile marker 0 is quite literally the end of the road! Or is the beginning? You will also find this marker near the Southernmost Point monument. Interestingly we are at the very end and even the very beginning at the same time! This actually made me feel very accomplished.



And my bucket list dreams just keep coming true!

With All My Love,
The Vintage Gypsy

“She would be half a planet away, floating in a turquoise sea, dancing by moonlight to flamenco guitar.”

Bucketlist Travel

Bucket List Dreams- The Florida Keys

Bucket List Dreams Come True In The Florida Keys



The Florida Keys offers world-class attractions and entertainment among some of the most breathtaking natural scenery you’ve ever laid eyes on. The Keys consist of The Upper Keys, The Middle Keys, and The Lower Keys. The Florida Keys are made up of five major islands– Key Largo, Islamorada, Marathon, Big Pine Key, and Key West- totaling 1,700 neighboring islands in the vicinity. The Keys offer once in a lifetime snorkeling amongst living coral reefs, dive sites with tropical fish, glass-bottom boat tours, dolphin expeditions, sports fishing, marine animal encounters and so much more!

We began our trip in Florida City The Gateway to the Keys. We spent a couple nights in  Miami, a night in Florida city and a night in Homestead during this epic road trip adventure. We passed by the Everglades National Park and was then onward to the keys. We had a 4-hour drive across the open water with the Gulf on one side and the Atlantic Ocean on the other! Some of  Florida’s kitschiest and most peculiar things can be seen in The Keys!

The Overseas Hwy


Embarking on an exciting trip to the beautiful and tropical Florida Keys islands is a dream come true! The Keys are made up of 1700+ living coral and limestone islands across the scenic coastal Overseas Highway and you get to cross the famous 7-mile bridge! The Keys takes you through Key Largo to the Key West islands. There are 43 islands across the 113-mile chain of islands connected by 42 bridges that we have to cross! The Overseas Highway offers the most scenic drive straight through the magnificent ocean.

Upper Keys

Key Largo

(Mile Marker 108-90)

Key Largo has gorgeous pastel seascapes you can dream up. Key Largo is known for being the Diving Capital of the World. In Key Largo, there are world-famous diving and dive sites for snorkeling with the living coral reef.

Key Largo is the largest island on the keys. There are many fun attractions in Key Largo. A stop at the visitors center is a good starting point. They have coupons for hotels and local attractions, Florida Keys souvenirs, and Key Lime pie.

The islands, marine life, and living coral are all protected by the Florida Keys National Marine Sanctuary. The Florida Keys National Marine Sanctuary also protects the remains of shipwrecks.

That swoon-worthy feeling when you’ve left the mainland and officially reached the first island! *le sigh* We began on the Overseas Hwy and through the famous 7-mile bridge which is 35,867 feet long. I loved being able to see the Gulf of Mexico and the Atlantic Ocean at the same time! We’re officially on island time. You will definitely want to stop off to explore each major island city on the keys.

Florida Keys Overseas Heritage Trail

The Florida Keys Overseas Heritage Trail offers gorgeous, dreamy scenery.  The water is like a sunset and it is so beautiful- it’s aquamarine in color with hints of pink. You can fish off here, walk the little trail or just relax by the water. You must pull off the Overseas Hwy and stop off here to see this beautiful water. It is breathtaking!




The Laura Quinn Wild Bird Sanctuary

The Wild Bird Rehabilitation Center is near Key Largo, located Tavernier, is a safe-haven to hundreds of injured and endangered bird species. The sanctuary cares for injured, orphaned and rescue birds and rehabilitates them so they can be protected and gain strength at the same time.

The wild bird sanctuary is a natural habitat which includes birds of prey, tropical birds, and seabirds. There are many varieties of rescue birds that have been rehomed here. The Florida Keys Wild Bird Rehabilitation Center is an oasis for so many beautiful wild birds such as owls, hawks, pelicans and more.

There is also a little walkway behind the bird oasis that has beautiful grounds and views which highlights the Mangroves, scenic waters, and more little birds and ducks walking about. The center is free to visit but they do have a little donation box set up at the front. This is a great stop for all ages. We had a really enjoyable visit here.









Other things to do in Key Largo and The Upper Keys:

Everglades National Park is the perfect getaway for outdoor enthusiasts. Park visitors can explore the marshes, swamps, mangroves, and take air-boat rides through alligator and crocodile-infested waterways.

John Pennekamp Coral Reef State Park is an underwater park and affords visitors the perfect family trip.You can take a boat tour, snorkel, swim and more.

Florida Keys National Marine Sanctuary encompasses the Florida Bay, the Atlantic Ocean, and the Gulf of Mexico. Families can boat here and there is also a museum.

Dagny Johnson Key Largo Hammock Botanical State Park is great for outdoor lovers who enjoy nature walks and taking in all of the sights and sounds of nature.

Jules Undersea Lodge is the worlds only underwater hotel. They offer dive classes on site and an underwater hotel adventure where guests can stay a few hours or even overnight!


(Mile Marker 90-70)

Islamorada, or purple island, is made up of 6 islands and popular islands?? Islamorada is the Sports Fishing Capital of the Florida Keys. The major islands here are Windley Key, Upper Matecumbe Key, and Lower Matecumbe Key.

The Islamorada Visitors Center should be your first stop. We were road tripping through the Florida Keys and saw this bright and inviting visitors center and decided to stop in. The visitors center is located directly in front of the Founders park. Islamorada is known for its coral reefs.

Other things to do in Islamorada and The Upper Keys:

Theater of the Sea is perfect for families on vacation to visit together. The theater of the Sea offers sea lion and dolphin shows and marine life encounters.

History of Diving Museum takes visitors on an under the sea experience with mementos and artifacts dating back 4,000 years encompassing the history of diving, shipwrecks and deep sea treasures.

Windley Key Fossil Reef Geological State Park showcases unique fossilized coral and limestone formations. For the outdoor lovers, this is a nice park to visit for exploring trails and nature walks.

Middle Keys


(Mile Marker 70-35)

The Middle Keys consist of the islands of Marathon/ Key colony. The major islands located nearby are Marathon, Deer Keys, Long Pine and Grassy Keys and Pigeon Key.

Marathon and surrounding islands offer tons of tons of water activities and family-friendly attractions. Visitors can engage in sports fishing and can charter boats and fish either Gulf-side or Atlantic-side.

The 7 Mile Bridge

The world-famous 7 Mile Bridge connects the middle keys to the lower keys, from Knights Key to Little Duck Key. Driving across the ocean is a surreal and unforgettable experience.


I loved seeing all of the natural formations on our drive. There are a terrific amount of points of interest to discover and explore. I especially liked seeing island after island lined up. It is a true oasis.



Other things to do in Marathon and The Middle Keys:

 The Dolphin Research Center in Grassy Pine offers dolphin and sea lion shows. This is a great fun-filled and educational experience for all age groups.

The Turtle Hospital in Marathon cares for endangered and wounded sea turtles. The hospital offers tours and educational opportunities to learn about the sea turtles and nesting preservation projects.

Sombrero Beach is a public beach in Marathon. This beach is one of the more popular beaches in the Keys.

Long Key State Park offers campground sites for guests who wish to swim, snorkel, kayak or fish.

Lower Keys

Big Pine Key and the Lower Keys

(Mile Marker 35-25)

Big Pine Key offers more of the beautiful sights and points of interest you’ve come to love about the keys. In Big Pine Key you will likely see deer crossing the street! These spotted deer can usually be seen in plain sight and often darting across the roads.


Other things to do in Big Pine Key and The Lower Keys:

Key Deer Refuge is home to endangered Key Deer species. Visitors can walk the grounds and search for deer.

Bahia Honda State Park in Big Pine Key offers more water play with their public beach access. There are water sports rentals and leisure water activities including snorkeling, kayaking, and canoeing.

Now, once you reach the end of the lower Keys, you have made it to the tropical paradise of Key West!


Key West

(Mile Marker 25-0)

 Key West is the Southernmost city in the continental U.S.  Once you arrive in  Key West you are only 90 miles to Cuba! Key West is truly a beautiful destination with sunsets bright and vivid as an artists palette!


Key West is quirky and fun, also full of chickens from Cuba walking down the streets, huge iguanas crawling everywhere and restaurants boasting “the best key lime pie” ever served here. So yea, it’s pretty awesome.

Mallory Square is the place to be to catch one of those famous Key West sunsets. The views are spectacular as far as the eye can see. There are plenty of entertainment options, especially from the varying street performers. There are ample boutique shops and dining establishments. No trip to Key West is complete without a sunset evening spent at Mallory Square.



The Ernest Hemingway Home and Museum is one of the top reasons I just had to come to Key West. The home is in immaculate condition, the guided tours are informative and entertaining, and the grounds are inspiring! I love Hemingways’ writings so to visit his home was certainly one of my bucket list dreams. Hemingway Home and Museum is a must-see, must-visit.



Other things to do in Key West:

Duval Street is where it all happens. There are street performers, restaurants, bars, art stores and much much more. The liveliness on Duvall Street is infectious.

Key West Museum of Art and History, or Custom House, holds historical significance to the city of Key West. The bold red structure showcases unique sculptures in the front entrance. The Custom House was once operated as a government building and was both previously the courthouse and post office. The Custom House displays art and architecture.

Harry S Truman Little White House offers tours for history enthusiasts to visit the old Winter White House of the 33rd president of the United States.

With it’s South Florida climate and close proximity to Cuba, The Keys offer a tropical Caribbean atmosphere which is second to none. If you come to Key West for nothing more than a slice of Key Lime pie then do just that!


And my bucket list dreams just keep coming true!

With All My Love,
The Vintage Gypsy


“I was always an unusual girl. My mother told me I had a chameleon soul, no moral compass pointing due north, no fixed personality; just an inner indecisiveness that was as wide and as wavering as the ocean.”-Lana Del Rey