The Ultimate 6-Day Guide to Key West, Florida

At the southernmost point of The Florida Keys, the archipelago of Key West is known as “America’s Caribbean”.

Here, the sun shines 260 days of the the year. It’s also home to the third largest barrier coral reef in the world.

In November 2020, I spent 6 days in this tropical paradise to explore its lively streets, white sand beaches, and world renowned culinary scene (hello, Key Lime Pie!)


Read on below for my full day-by-day itinerary to plan your own warm weather getaway to Key West, Florida!

Day 1 Itinerary::

Getting there

With numerous big name airlines operating into Key West International Airport, traveling by plane is the most convenient.

If for some reason a direct flight is not available from your airport, Key West is a short drive from Miami Dade airport by rental car or bus.

I flew American Airlines from Evansville, Indiana with a stopover in Dallas, Texas in late October 2021.

Total cost for round-trip flight was $203.

A Slice of Old Havana

While the island of Key West is home to dozens of top rated hotels, there are a couple that stand out from the rest. I meet up with my friend Joy, a food and travel blogger from DC, and head to our first lodging destination: is the Cuban-inspired oasis of Havana Cabana Key West hotel.

Havana Cabana Waterfront Hotel in Key West. Photo Cred: East Coast Contessa

Ranked the best among the Top 25 Most Saved Hotels in the World on Trip Advisor, this dog-friendly resort is deeply steeped in southern charm and an authentic Caribbean flair.

Home to two distinct classic 1957 Chevy’s out front and some of the best Cuban food North of Havana, Havana Cabana Resort is a destination of relaxation and nostalgia — but it doesn’t stop there.

Vintage 57 Chevy’s in front of Havana Cabana Hotel in Key West. Photo Cred: East Coast Contessa

Cuban Inspired Amenities

Upon arriving, we check our luggage at the front desk and head to the resort’s on-site bar, Mojitos Pool Bar. Here, we use our tickets for complimentary welcome drinks.

Unique mixed drinks such as the “Grapefruit Negroni” and the “Hibiscus Rum Punch” grace the menu, and all can be enjoyed next to the largest hotel pool in Key West!

The pool at Havana Cabana Hotel in Key West, Florida. Photo Cred: East Coast Contessa

After soaking up some sun and sipping our way to happiness, we head to our suite. 

With views of the Salt Pond Keys, the Vista Mar Two Queen Gulf View Balcony is cozy and vibrant — like a tropical getaway should be. 

Modern accent walls add flair while traditional oak furniture and finishes add comfort and class. 

We take in the views on the balcony, pour a whiskey and rum from a bottle of complimentary Bacardi Black, and get ready for an evening downtown.


Hotel Transportation

Out of all of the perks at Havana Cabana Key West, one of the best is most certainly the free shuttle. Every hour on the hour until 10:30pm, hotel cheffuers take guests from the hotel lobby to the drop off point: the historic Seaport downtown. 

The multi-seat vans are spacious and clean, and a great alternative to Ubers and taxi cabs. 

The drop off location makes it convenient to explore Duval Street and downtown Key West by foot 7 days a week.  Don’t forget to tip your driver!

Sloppy Joe’s Bar

The island of Key West is home to nearly 400 restaurants in just over four square miles, so we begin our island food tour immediately. 

Our first stop is Sloppy Joe’s Bar, an island staple and former hang out spot for Ernest Hemingway. Here, we order a smorgasbord of must-haves:

  • Sloppy Joe’s Famous Sloppy Joe Sandwich with ground beef, peppers, onions, and sweet tomato sauce; 
  • Creamy White Fish Dip made with fish, Old Bay, hot pepper sauce, mayo, and sour cream;
  • The Cuban sandwich with ham, cheese, and mustard, on baguette; and
  • Two traditional margaritas over ice with salt rim.
Conch Republic Seafood Company

It’s the last night of the island’s famous Fantasy Fest, so live music, laughs, and drinks cheering to better days fill the air. The atmosphere is lively and energized as people of all ages celebrate great weather and strong cocktails. 

Many of the island’s top-rated restaurants are within walking distance from each other downtown. We make our way to our next foodie destination: Conch Republic Seafood Company.

One of the most well-known spots for late night bites and strong cocktails, Conch Republic sits adjacent to Mallory Square. 

We sit down at the bar and order a frozen “Key Lime Pie Colada” and an “Island Cosmopolitan“. Their top-rated “Lobster Bisque” and “Conch Chowder” with local seafood are also easy choices.

After our night caps, we catch the last free shuttle back to Havana Cabana for a comfortable nights sleep before our next day of adventure.

Cost: Conch Chowder: $11; Lobster Bisque: $11; Key Lime Pie Colada; $15

Address: 631 Greene Street, Key West, FL 33040


Day 2 itinerary:

Poolside Mornings in Key West 

We start our morning poolside with a hearty Cuban breakfast at Floridita Food Truck.

 The “Palomilla Steak and Eggs” with onion and peppers and the “Cuban Sandwich” with cheese croquettes are the choices of the morning — both delicious.

Cuban food at the Floridita Food Truck at Havana Cabana Key West. Photo Cred: East Coast Contessa

After breakfast, we take in the tropical vibes at the Havana Cabana’s pool with fresh guava juice and a morning mojito. Here, guests enjoy pool parties with a local DJ every Saturday and Sunday, and mermaid tail rentals are provided to those wishing to partake in professional “Mermaid classes”. 

A couple hours of sun rays later, we make our way back to our room to freshen up and shower before catching the 10am shuttle downtown. 

Fort Zachary Taylor Historic State Park 

The state of Florida is home to some of the nation’s most beautiful state and national parks, and Key West is no exception.

On the southern edge of the island sits Fort Zachary Taylor Historic State Park. This 87-acre fort pre-dates Civil War times, and lies at the meeting point of where the Atlantic Ocean flows into the Gulf of Mexico.

Sparkling turquoise waters glisten just off the park’s coastline, and white sand beaches call visitors from near and far. 

Getting to Fort Zachary Taylor

We took an Uber from downtown’s Duval Street to the park for $10USD, then paid the park guide at the gate. The driver drops us off in the parking lot for the Fort Zachary Taylor State Park Beach. 

Consistently voted as one of Key West’s best beaches, you can rent a chair, beach umbrella, and towel for an hourly fee. There are also grab- and-go snacks and beverages on the beach at the Cayo Hueso Café. Here, there are plenty of picnic tables to relax and enjoy.

It is open from 10am to 6pm daily.

What to See and Do at Fort Zachary Taylor

Fort Zachary Taylor Beach is unarguably one of the best places to snorkel or swim on Key West. However, there are plenty of other activities you can partake in even if you don’t want to get your feet wet.

The most notable area on the island is the old fort itself. As a National Historic Landmark, it was built in the 1840’s and played a significant role in Florida’s early development. One of the few forts to never experience hostility or war, it’s still home to many Civil War cannons and war gear.

You can take a narrated tour with a guide, stroll the grounds at your own leisure (like me), or bike the shaded paths alongside the fort. 

The two-tiered seaward fort wall itself also has some very Instagrammable spots for great photos. See below!

Old Civil War Cannons at Fort Zachary Taylor State Park. Photo Cred: East Coast Contessa.

Cost: $7 per vehicle/ $.50 cents per additional vehicle’ $2.50 pedestrian or bike.

Address: 601 Howard England Way, Key West, FL, 33040

Visit the Southern Most Point Buoy

Although a tourist spot, a can’t miss sight during a visit to Key West is The Southernmost Point of the Continental U.S. Representing the lowest latitude in the continental U.S., the landmark is an anchored concrete buoy that attracts millions of visitors each year. We make a quick stop here to get a picture for the gram (because if I didn’t have a picture did I really even go to Key West?)

While the location is free to visit, the wait time for photos is 15-20 minutes.

Cost: Free.

Address: Corner of Whitehead Street & South St, Key West, FL 33040


The Southernmost House

A half-mile walk from the Southernmost Point Buoy, we came to one of the most colorful houses in Key West: The Southernmost House.

Also known as The Mansion, the Southernmost House is a historic Victorian Inn thay sits at the “quiet end” of Duval Street.

While it offers upscale rooms, a heated pool, and beautiful ocean views, it’s most known for something even more unique. 

World Famous Lobster Pizza at Seaside Cafe

We walk through the lobby of the mansion and make our way around to the back. The smell of salt water and wood fire pizzas hit our noses immediately. 

This is the Seaside Cafe at the Mansion, known for island classics such as mojitos, key lime coladas, and wood fire pizzas — but not just any pizza. 

Seaside Cafe is reveled for its world-famous wood-fired “Lobster Pizza” with fresh lobster meat, cream sauce, fontina cheese, garlic puree, and fresh parsley. 

World Famous Lobster Pizza at the Southernmost House in Key West, Florida. Photo Cred: East Coast Contessa.

A must-have if visiting the island, other menu items worth trying are the “Lobster Honey Biscuits” with spicy honey, deep fried waffle biscuits and cold lobster salad, and the “Conch Fritters“.

Cost: Conch Fritters (5): $13; Lobster Pizza: $23; Honey Butter Lobster Biscuits (2): $21.

Address: 1400 Duval Street, Key West, FL 33040

An Evening at Mojitos Pool Bar

We explore more of Duval Street to admire the murals and scope out the restaurants and bars. We pass by the Wyland Mural and the former Strand Theater that is now the most beautiful Walgreens pharmacy in the U.S.. Both are great spots for an Instagrammable photo!

The Wyland Mural in Key West. Photo Cred: East Coast Contessa

After dark, we decide to head back to the Havana Cabana property for some down time in the hot tub and cocktails at the Mojitos Pool Bar.

On this evening, it’s the perfect spot to enjoy another mojito night cap under the twinkle of the string lights in the palm trees above. 

We grab some light bar snacks to-go in the form of coconut shrimp and chicken wings covered in guava BBQ sauce to enjoy while watching a movie in the room!

Day 3 Itinerary:

A Taste of Key West’s Best

If there’s one thing that will get me up early (other than a flight), it’s the promise of good food.

On this day, we make our way downtown via Uber back to Duval Street for none other than more food. After all, Key West has no shortage of it!

Today is different than the usual restaurant visit for lunch or today. Instead, we are taking a guided tour to explore the very best in Key West cuisine — the known and the best kept secrets.

Led by top-rated Key West Food Tours via small group walking tours, we taste and drink our way through the island on foot!

El Siboney Restaurant

We first stop at a budget-friendly local favorite: El Siboney. It’s 10am, but that doesn’t mean it’s too early for a drink. 

We are served homemade red sangria alongside a traditional Cuban lunch of Ropa Vieja, sweet plantains, white rice, and black beans. Cost: Cost of food and drinks included in tour.

Address: 900 Catherine Street, Key West, FL 33040

The Rum Bar

Fifteen minutes away from El Siboney back towards Duval Street, we head to our next location. This time, it’s not for food but for one of Key West’s most popular — and potent — cocktails: the Rum Runner.

We are told there is clearly no better place to enjoy this cocktail than the Rum Bar itself. 

Featuring a vast rum menu, The Rum Bar sits on the ground floor of the Speakeasy Inn at the upper end of Duval Street.

We sip the potent concoction made of two types of rum, grenadine, and pineapple juice al fresco on the bar’s patio. After good conversation and a bit too much alcohol, we head to our next destination.

Address: 1115 Duval Street, Key West, FL 33040

Kaya Island Eats

To get a taste of the Hawaiian Islands in Key West, one only needs to go to Kaya Island Eats. 

This outdoors outpost dishes up some of the most flavorful island-inspired fare such as tacos, salads, and rice bowls.

We cozy up at one of the outdoor picnic tables and order a plate of Kaya’s  Macadamia / Coconut Catch. It’s a bed of jasmine rice topped with seared white fish, Thai peanut sauce, and Hoisin Accent Mango Salsa. 

It’s slightly spicy with a sweet undertone from the mango — and it’s to die for.

Address: 628 Duval Street Rear, Key West, FL 33040

Mangoes Key West

It’s not a trip to Key West without trying a conch fritter or two (or three).

We are told the best ones the island can be found at Mangoes Restaurant, a fish-focused eatery and bar.

Sitting on a bustling corner on Duval Street, Mangoes in a secret hideaway for seafood lovers. We grab a seat in their indoor private seating area to enjoy a plate of their homemade conch fritters with key lime caper aioli. 

When they say they are the best in the city, it’s no joke.

Address: 700 Duval Street, Key West, FL 33040

Cuban Coffee Queen 

For our last and final stop on the walking tour, we make a stop for something sweet.

The Cuban Coffee Queen is a counter-serve coffee stand that has become a local favorite. Offering traditional Cuban sandwiches and plates, brew, and smoothies, it’s the perfect place to wrap up a delicious day.

We sip a hot Cortado and savor a slice of chocolate covered Key Lime Pie from Kermits before saying our goodbyes.


Address: 5 Key Lime Square, Key West, FL 33040

To book this tour with Key West Food tours, visit and select “The Southernmost Food Tour”. Pro Tip: choose the “add on” option for additional drinks — you won’t regret it!

Waterfront Luxury at Parrot Key Hotel

Ready for relaxation after our walking tour, we check out of our first hotel and make our way to the second property of the trip — another of Key West’s waterfront gems.

Just off of the main strip of N Roosevelt Boulevard, the Parrot Key Hotel & Villas sits tucked away from the hustle and bustle. 

We arrive at the property on a warm and sunny day, and it’s a good thing: a relaxing pool day awaits.


An Independent Collection property, we quickly realize why the Parrot Key Hotel ranks as one of Conde Nast Traveler’s Top Resorts.

Lounging at The Grove

After check in, we first head to Parrot Key’s main pool, which is home to it’s on-site bar and restaurant, The Grove.

Some of the best poolside dining in Key West, we each grab a hand crafted cocktail (the “Very Berry Mojito” and an OG Mojito).

For bites, we order two of The Grove’s most popular dishes: The Key West “Shrimp Scampi Pizza” and “Blackened Mahi Tacos

The Shrimp Scampi pizza is a quick favorite as it’s topped with fresh Gulf shrimp and plenty of garlic.

While we ate, hotel staff were happily mingling with guests.  They began handing out fresh slices of pineapple and watermelon and complimentary water — a great tropical touch.

It’s warm and sunny, so we find some poolside chairs and finish our drinks over good conversation.

Key West Luxury

The Parrot Key Hotel & Villas are home to 148 impeccably designed guest rooms.

We step into one of their 375 square ft Waterfront Double Queen guest rooms, which offers some of the best views of the Gulf of Mexico. 

Featuring high-end amenities such as a full service drink and snack bar, the L’Occitan toiletries are an added bonus. 

We notice a door that leads to a back deck, so we open the blinds and twist the doorknob. 

Outside is one of the most surprising and unbelievable hotel amenities: a private beach!

Two Adirondack chairs claim a place on the desk. Comfy lounge chairs and umbrellas line the sand, and oversized hammocks hang from every other palm tree. 

A pier leading out onto the Gulf of Mexico extends off the beach behind a row of Bay Cedar trees. We take some time to explore it and enjoy the views before heading on out next foodie adventure downtown.

Address: 2801 N Roosevelt Blvd, Key West, FL 33040


Round 2 at Kaya Island Eats

We decide to take a second round at Kaya Island Eats after trying it on our tour with Key West Food Tours.

After a round of cocktails with a “Key West Colada” and the “Pina Rita” with Cream of Coconut, it’s time for food! 

We order a starter of “Hawaiian Pork Sliders” topped with mango Key Lime slaw and Guava Lava sauce. All menu items at Kaya Island Eats perfectly blend Polynesian cuisine with a local Key West flair.

For main dishes, we order two plates:

The “Legendary Rasta Pasta” with jerk seasoned chicken, macadamia nut, garlic and basil; and 

A bowl of “No Worries Coconut Curry Rice Bowl” with yellow curry, shrimp, and fresh vegetables. 

We finish off the meal with a Hawaiian favorite: “Hula Girl Pie”! A generous serving of Tahitian Vanilla ice cream is topped with toasted coconut, macadamia nuts, and whipped cream.

It is the sweetest ending to our third day in Key West!

Cost: Hawaiian Pork Sliders: $13; No Worries Coconut Curry Rice Bowl: $20; The Legendary Pasta Rasta: $24;


Day 4 Itinerary:

Cafe con Leche at Koffie House

To start our fourth day in Key West off the right way, we decide to visit an adorable coffee shop off Duval on Greene Street.

The night before, we were admiring the beautiful Bali-like decor from the street and knew we had to try it out.


Finding its home in one of the oldest and most historic brick buildings in Key West, The Koffie House is a unique gem. It offers health-conscious food and beverages like vegan and vegetarian options, cold pressed juices, and tapas style bites.

We sit down at their swing bench bar and order two cold Cafe con Leches. They both come with cold brew, almond milk, a splash of lavender syrup, and coffee ice cubes. 

For breakfast, we split a plate of the “Of Course…An Avocado Toast!” with smashed avocado, pepita seeds, hard boiled egg, and crisp radish on multi grain bread.

This spot absolutely can’t be missed during a trip to Key West! It is open from 8am to 4pm daily. 

Cost: Of Course…An Avocado Toast!”: $11; Iced Coffee: $6.

Address: 602 Greene Street, Key West, FL 33040


The End of the Road at the Mile Marker 0

From The Koffie House, we decide to get our daily exercise in and walk to our next stop: the famous Mile Marker 0.

It’s a short four minute walk to our destination, which is the corner of Greene Street and Whitehead Street.

Here marks the official end of U.S. Highway 1. It is the longest north-south road in the country spanning 2,370 miles from Fort Kent, Maine. 

An official sign marks the exact spot that is now a souvenir shop, but remains one of the most photographed spots on the island. 

It’s a must-see if on the island as it’s not far from downtown. Make sure to pick up an adorable magnet from the shop before you leave!

Address: 501 Whitehead Street, Suite 1, Key West, FL 33040


Hemingway’s Key West

Continuing on our walk, we made our way down Whitehead Street towards another well known sight in Key West: the dwellings of famous writer Ernest Hemingway himself.

We first pass the intersection of Petronia Street and Duval and lay eyes on the colorful four-way rainbow crosswalks.


This area is known for its lively bar and LGBTQ scene, so the rainbow decor is only fitting. We stop for a quick photo (ok, a photo shoot), before we continue towards our final destination.

Polydactyl Cats

Upon arriving at the Hemingway Home & Museum, we are greeted by a beautiful orange tabby cat with green eyes. “That’s Lucy. She likes to pose for photos” says one of the groundskeepers. They all know the cats by name — and personality — it seems. 

You see, Hemingway loved Key West. In fact, he loved it so much, that his father in law bought him a Spanish colonial home on Whitehead Street in 1931.

He also loved cats — polydactyl cats more specifically. He bought his first one named Snowball, and more of these six-clawed felines followed. Together, they lived side-by-side for nearly a decade.


The Grounds 

We walk into the two-level colonial home, viewing snippets of the author’s life on the walls: his fishing conquests and many of his best literary works. 

Cats lazily lounge in nearly every corner: on the beds, on the window sills. They clearly have free range of this home.

Outside, a beautiful veranda overlooks a giant swimming pool — the first one ever built in Key West. Surrounding the house is a lush tropical garden where Hemingway would read manuscripts and fist fight with friends after a long night at the bars.

Just behind the main home lies the bungalow. Here, Hemingway kept his prized animal heads and stuffed fish while he wrote long form. 

We take our own tour (though guided tours are also available). After a couple of hours, we make our way out of the house to spend more time with our newfound feline friends. 

Visiting Hemingway’s Home

The Hemingway House is open daily for walk-in visits from 9am to 5pm 365 days of the year. 

Visitors can reserve their tickets online, or buy at the ticket booth on property. Visitors can enjoy the property for as long as they like as there are no time limits.


While petting the cats is allowed, feeding them is not.

Cost: General admission is $17 for adults, and $7 for children 6-years-old and older. Children under 5-years-old are free.

Dinner Al Fresco @ The Grove

We call an Uber to head back to the Parrot Key Hotel. It’s nearly sunset and we want to catch the colors dancing across the sky from our private beach before dinner.

Dinner reservations are at 7pm at The Grove, and we hear their local caught Mahi Mahi is one of the best on the island. 

We start the meal with cocktails: a rich and chocolatey mudslide and a Key Lime Pie frozen martini with a graham cracker crust rim.


For main courses, we decide to stick with seafood and try two of the most popular dishes: 

  • Local Caught Grilled Mahi Mahi” with a side of rice pilaf and parmesan Brussel sprouts; and 
  • Key West Pink Shrimp Scampi” with grilled asparagus and rice pilaf.

We order one more round of drinks and bring them back to our waterfront suite after dinner. 

We open up the door to the patio and let the warm breeze flow through the room before turning in for the evening.

Day 5 Itinerary:

Flapjacks at The Breakfast Club, Too

Breakfast is a popular meal in Key West. And if I’m being really honest, food in general is popular in Key West.

The culinary scene is one of the most impressive I have yet to see, so coming hungry to the island is definitely a requirement.

We start our fifth day out at a local eatery and popular brunch spot: The Breakfast Club, Too.

Next to Kermits Key Lime Pie, this bustling breakfast spot is busy for many reasons, but we will start with their Bloody Mary — all 11  varieties of them! One, dubbed the “Monster Mary” has both bacon and a chicken wing on it!

However, it’s not just the Bloody Mary’s that bring the crowds, it’s the grub, too.

Bendicts, Waffles & Pancakes, Oh My!

Serving popular plates like their variety of Egg Benedicts (read: Lobster Benedict) and breakfast sandwiches, it’s a true gem.

We opt for a sweet over savory option on this day, and order the coveted “Pancake Charcuterie Board”. 


This dish is not for the faint of heart. Featuring 14 mini pancakes, a variety of fresh fruit, peanut butter, Nutella, homemade pastry cream, and jam, it can feed a crowd. 

Just for clarification, there were only two of us. Don’t judge.

The Breakfast Club too is open daily from 8am to 2pm.

Cost: Pancake Charcuterie Board: $30; Watermelon Peach Mimosa: $9

Address: 610 Greene Street, Key West, FL 33040


Catching Rays at Smather’s Beach

Known as one of Key West’s most popular beaches, Smather’s Beach, while man made, is great for snorkeling and swimming.

On Key West’s Southern Shore, this 1-mile long beach is a great place to come to snorkel the reef and take in the crystal blue waters.


As guests of Parrot Key Hotel & Villas, we made reservations for an afternoon at Smather’s Beach, where our beach chairs and towels were complimentary.

We enjoy two hours on the sand until a major lightening storm rolled in, but were able to walk the entire length of the beach and back while a nice couple watched our belongings (the South is the best, y’all). 

Pro Tips: Smather’s is close to the airport, so if you want to take in some last minute rays before hopping on your flight, this is the spot.


It’s also a great alternative to snorkeling Dry Tortugas if you are unable to secure tickets on the Yankee Freedom Ferry.

The Lobster Shack

It’s not a visit to Key West without a meal at The Lobster Shack.

Known for their succulent lobster rolls, rich and creamy soups, and chill vibes, this small seafood eatery packs a serious punch.

Following beach time, we hail an Uber the 20 minutes back to Duval to snag a late lunch here, ordering two of the most popular rolls on the menu.

The “Key West Lobster Roll” (buttered lobster with a hint of key lime juice) and the “Traditional Lobster Roll” (lobster roll with a touch of mayo).


We pair it with a bowl of the “Best Lobster Bisque” and a Michelob Ultra with a lime wedge. Chef’s Kiss.

Cost: Traditional Key Lime Roll: $25; Key West Lobster Roll: $25; Lobster Bisque: $11.50; Michelob Ultra: $6.


Day 6 Itinerary:

Sipping Wine on Key West Time

It wasn’t dubbed “The Prettiest Hotel in Key West” by the New York Times for nothing. 

In fact, The Gardens Hotel boasts anything but ordinary lodging. 

On this day, we aren’t staying on the property. On this day, we’re only there for the vino.

In the rear of the hotel, lies the d’Vine Wine Gallery — an impressive collection of more than 36 wines from around the world. (Heaven, anyone?)

Sip Your Way Around the World

First, we buy a pre-paid “wine card” at the hotel’s front desk. We can load any amount of our choosing, so we go with $15. The price of each wine depends on the brand and the size of the pour (2, 4 or 6 ounces). We can sip until the funds on our cards run out!

Believe it or not, $15 goes a very long way when a 2 ounce pour costs $1.60!

We were able to try 8 different international wines from France, Spain, and Italy before our funds were depleted. 

And the best part? Guests can sample the wine as early as 10am. I know this because I did it, no shame. 

Before making our exit, we made our way around the exterior gardens. The grounds were full of lush greenery and Asian inspired art work.

The hotel is even home to two giant Galapagos turtles that tend to put on an occasional show, if you know what I mean.

This is a definite must-see for wine connoisseurs. It’s also an affordable activity for solo travelers, bachelorette parties, or couples.

Pool Days = Best Days

After Joy left to go to the airport,  I decided to pass the time poolside at The Grove until my flight back home.

The fresh fruit infused water and complimentary watermelon slices were the perfect poolside snack while I made edits to my photos and collected my thoughts from the past week in paradise.

Using the table side QR code, I put in an order for a tossed caprese salad with a bottled water to-go. 

I took in the final moments of the warm breeze, packed up my carry on luggage, and said “until next time” to paradise.


Visiting Key West, Florida 

Key West is an ideal getaway not just for those who enjoy warmer weather, but for those who enjoy history, the arts, great beaches, and even better food.

It’s for travelers who enjoy water sports of all kinds, or for those who simply enjoy planting their butt in the sand with a cocktail in hand.

Regardless of why one might find themselves in Key West, the point is to just get there. 

This 2-mile-by-4-mile slice of heaven is a rare gem that we are so lucky to have here in the U.S. And the best part? It’s only a flight (or bus ride) away.

Know before you go:

  • Book early. Hotels and activities book up fast, so don’t wait until the last minute.
  • Hotels and food are above “normal” Florida prices, especially with   inflation. Plan accordingly.
  • Reserve a seaplane or ferry ride for Dry Tortugas at least two months in advance. These are the only two modes of transportation to access the park.
  • Try all of the Key Lime food and drinks! It’s a huge part of the culinary culture on the island — from martinis to lobster rolls to pies, creamy dips, and more!
  • Be nice to the roosters and chickens! They are protected by the city and have free range of the island.
  • Enjoy your time! Experience the island’s vibrant night life. Go out for a drink at one of the many outdoor bars on Duval Street.

If you are planning a warm weather getaway to Florida this winter season, check out my other blog posts about all things Sunshine State here and here. Happy Travels!

This blog post was created in sponsorship with Havana Cabana Resort and Parrot Key Hotel.

28 replies to “The Ultimate 6-Day Guide to Key West, Florida”

  1. Great post! I recently went to Florida as well and this post was spot on. Although I was in Miami instead of Key West, it’s great to learn about things to do in different areas of Florida. I really liked how you included pictures throughout your post and also included cost in your Key West guide. All of your pictures were beautiful and really gave a great representation of the different places you visited while in Florida. After viewing your guide, I would defnitely add Key West to my list of desired locations to travel to!

    1. Hi Lindsay! Thank you so so much for reading my Key West blog and for your kind words about my piece! Florida truly is such a diverse place with different cuisine and culture in every region. We are so lucky to have it here in the U.S. I hope you get to visit Key West soon!

  2. At last, some detail about Key West. I know many people who have holidayed there but fail to mention the tropical fabulousness of the region. Looks like a great place to chill. So thank you, Alexandra, for sharing this.

  3. For someone who lives in GA, it seems crazy that I still have not made it to Key West! This post contains so much helpful info and I will be sure to use your suggestions when we plan a trip down there. Thanks!

  4. I haven’t tried a lobster pizza before but it looks lush. Key West looks like the perfect place to visit to get away from the winter weather up north.

  5. Visiting Florida is on my bucket list. Key West sounds and looks spectacular particularly the food – conch fritters and the pizza – WOW. I’m looking forward to trying these!

  6. Thank you for this amazing travel guide to Key West. I´m actually planning on visiting Miami at the end of the month and couldn’t decide if I should also do a road trip to Key West. Your blog post really helped me to decide and now I definitely want to add Key West to my list and visit after Miami. I think the food convinced me 😀 especially the famous lobster pizza. Can´t wait to try!

  7. Wow the photos on here are really lovely – I’ve always had a dream to go to Key West, my family would go to Florida growing up but usually Miami or Orlando area, this post reminded me there are so many amazing places I haven’t discovered yet in FL!

  8. Which hotel did you like better Havana Cabana or Parrot Key—I am having a hard time deciding which one to book! Thank you for sharing your trip –looks amazing!

    1. I personally liked Parrot Key more, but it depends on what you are looking for! I have heard Havana Cabana is now more of a party hotel verses when I stayed, so if you’re looking for more of a lively scene, maybe go with that one. Parrot Key is more quiet and secluded in another part of the town and has multiple pools and a secluded beach for certain suites. If you book a stay at either, let them know you learned of them through my site! I hope this helps and thank you for reading 🙂

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𝐓𝐡𝐢𝐬 𝐢𝐬 𝐭𝐡𝐞 𝐭𝐲𝐩𝐞 𝐨𝐟 𝐩𝐥𝐚𝐜𝐞 𝐲𝐨𝐮 𝐤𝐞𝐞𝐩 𝐲𝐨𝐮𝐫 𝐩𝐡𝐨𝐧𝐞 𝐨𝐧 𝐀𝐢𝐫𝐩𝐥𝐚𝐧𝐞 𝐌𝐨𝐝𝐞 𝐨𝐧 𝐩𝐮𝐫𝐩𝐨𝐬𝐞 👌🏻😮‍💨

The 5-star luxury @sunscapecoco resort in Punta Cana @dominicanrepublic is nothing short of a dream stay. The @hyatt property offers 24 different on-site restaurants and bars My favorites were DaMario’s for Italian cuisine and Blue Water Grill steakhouse!

It also provides 24-hour room service (late night pizza + fries yes please!), a full service spa, daily activities and family-friendly entertainment on-property, six pools, access to a stunning white sand beach, beach lounge chairs and cabanas (for rent), gift shops, a casino (if that’s your thing), and an on-site medical clinic. 

For those visiting with kids, a section of the property contains the Explorer's Club for kids ages 3-12 which offers a large playground, pool, arts and crafts, and movie nights. A kid approved snack + food truck is also nearby.

Want to explore beyond the resort? You can easily book private transport or a tour at the @amstardmc desk in the front lobby or before your arrival.

It really has everything you could want or need! 

What’s a place you keep your phone on airplane mode to truly enjoy the experience? Let me know below!
#UnlmitedFun #SunscapeResorts #SunscapeCoco #DominicanRepublic #Caribbeantraveler #Caribbeantravels
𝐇𝐨𝐰 𝐭𝐨 𝐬𝐩𝐞𝐧𝐝 𝟒 𝐚𝐦𝐚𝐳𝐢𝐧𝐠 𝐝𝐚𝐲𝐬 𝐢𝐧 ::

(You’ll want to SAVE this for your next trip!)📌

𝐃𝐚𝐲 𝟏:
- Check into the @hvicharleston. Here you can enjoy a complimentary wine and cheese reception, milk + cookies at night, and a made to order breakfast in the mornings!
- Grab a sweet pick me up at @tintoycrema next door 
- Stop for pics at Rainbow Row
- Walk to White Point Garden + The Battery
- Visit Old Exchange and Provost Dungeon
- Have a late seafood lunch at @fleetlanding 

𝐃𝐚𝐲 𝟐:
- enjoy complimentary breakfast at @hvicharleston (order the ham + cheese quiche or croissant!)
- take the free DASH bus from the hotel to Liberty Square to visit the @southcarolinaaquarium. They have an amazing Sea Turtle Rescue Center! 
- eat lunch at @browndogdeli (I recommend ordering The Folly Beach Turkey Crunch Wrap or the Fried Green Tomato BLT) 
- tour the Nathaniel Russell House and/or the Edmondston-Alston House (it survived hurricanes, the earthquake of 1888, and the Civil W*r!)
- eat dinner at @magnoliaschs. Order the fried green tomatoes and southern egg roll!

𝐃𝐚𝐲 𝟑:
- enjoy another breakfast at @hvicharleston! You can order it as early as 6am.
- Board a boat to @ftsumternps. This historic Fort is marked as the spot where the first battle of the Civil W*r was fought. Reservations required. 
- take an Uber to @fireflydistillery to try their Sweet Tea Vodka, Banana Pudding Moonshine, and their Chocolate Pecan Whiskey. Dont pass up a boozy moonshine milkshake (for 21+) and a Rocket Burger from @rocket_burger_chs food truck!

𝐃𝐚𝐲 𝟒:
- enjoy an iced coffee and a breakfast sandwich at @carmellasdessertbar (just a few blocks from @hvicharleston)
- stroll through the @charlestoncitymarket. It’s been around since the mid 1800’s!
- eat late lunch at @hymans_seafood. Don’t pass up their hush puppies and crab cakes. They were voted Best in Charleston for a reason! 

Click on the link in my bio to read my full “4 Days in Charleston” guide (yes, there’s more!) on my blog to help you plan the ultimate Charleston vacation.
𝐌𝐢𝐧𝐢 𝐆𝐮𝐢𝐝𝐞 𝐭𝐨 @puntacana 𝐃𝐨𝐦𝐢𝐧𝐢𝐜𝐚𝐧 𝐑𝐞𝐩𝐮𝐛𝐥𝐢𝐜 ✨

I had 4 full days to spend in the eastern region of the @dominicanrepublic (which was definitely not enough time to see everything!) but made for a great intro to the DR. 

Here are just a few must-do activities to check out when you visit!

✨ Stay at the newly updated @sunscapecoco by @hyatt. This 5-star all inclusive @sunscaperesorts property offers *24*on-site restaurants, bars, and cafes for unlimited food + drinks. It also has a spa, multiple pools, and beach access.
✨ Visit the Basilica Nuestra Señora De La Altagracia in Higuey. It’s one of the most important religious sites in the country!
✨ Spend a few hours at Playa Macao. It’s a beautiful white sand beach with bright turquoise waters!
✨ Try traditional food such as Dominican fried chicken, Bandera Dominicana (rice, beans, and stewed chicken), and Sancocho (a hearty stew).
✨ Spend a day exploring the islands of Cotubanamá National Park with @amstardmc 🌴 

Do you have plans to visit the @dominicanrepublic soon? You can see more from my time there in my IG stories and my “Dominican” highlight! 
#DominicanRepublic #puntacana #puntacanaexcursions #dominicana #UnlimitedFun #sunscaperesorts #SunscapeCoCo #caribbeantravel #caribbeanvibes #amstarwelcomesyou #dominicanrepublic🇩🇴
Looking to sell, buy, or trade your car from the comfort of your home? You’ll want to check out @driveway_hq! makes it easy to find the value of your current vehicle through a convenient evaluation process that only takes a few minutes. Instant offers are valid for 7 days.

When you’re ready to buy, its inventory of more than 30,000 new and used cars makes finding the perfect one a breeze. Simply search inventory by year, make, model, color, gas milage, and more. Driveway will even pick up your old car or deliver your new one right to your doorstep!

As someone with a busy travel schedule, Driveway takes the stress and hassle out of searching for a new car so I can explore on my own time. From road trips in the mountains to quick spins around the city, wherever I’m going it helps me get there.

Driveway. The way better way to buy and sell your car online. # AD
If there’s one thing I’ve learned from years of traveling, it’s that sometimes less is more — especially when it comes to packing. {ad}

These days, I’ve definitely been utilizing carry on’s rather than checking a bag but, I’m not exactly the lightest packer 🤭 so I’ve had to master the art of maximizing less space.

This is where Pebbler packing cubes come in! 🫶🏻

Pebbler’s chic five piece set includes a convenient laundry bag and comes in sleek colors like black and sand. Let me tell you — they make packing, unpacking, and organizing clothes a breeze. Made of water-resistant material, double zippers for easy access, and breathable mesh, they help keep clothes wrinkle free, save space, and make for a smoother travel experience. They are the ultimate travel and packing essential!

Tap the link in my bio and use code “𝐀𝐋𝐄𝐗𝐀𝐍𝐃𝐑𝐀𝟏𝟓” for 15% off your Pebbler order to enjoy a smoother, lighter journey on your next adventure!

#PebblerPartner #Amazontravelfinds #travelhack #packinghack #Pebblerpackingcubes #packwithme
𝟓 𝐏𝐥𝐚𝐜𝐞𝐬 𝐲𝐨𝐮 𝐜𝐚𝐧’𝐭 𝐦𝐢𝐬𝐬 𝐢𝐧 𝐂𝐡𝐚𝐭𝐭𝐚𝐧𝐨𝐨𝐠𝐚, 𝐓𝐍: 𝐏𝐚𝐫𝐭 𝟑! @visitchatt 

1. @lodgecastiron Museum + @sopitt_bigbadbreakfast. Located in the heart of cast iron’s hometown of South Pittsburg, Tennessee, this museum is a must for those who love cooking, history, food culture, and very large skillets! After the museum, grab brunch at Big Bad Breakfast (the chicken + waffles and cornbread omelet are 😍)
2. @rembrandtscoffeehouse. This cozy European style cafe serves unique coffee drinks and teas, fresh-baked breads, breakfast sandwiches, and beautiful pastries. Try a raspberry vanilla iced brew with an Egg + cheese biscuit sammy ♥️
3. @huntermuseum of American Art. Built in 1905, it became an art museum in 1952. It’s collection spans the history of American art from the colonial period to the present day and includes paintings, sculptures, contemporary studio glass, and crafts. The views of the Tennessee River from here aren’t shabby either!
4. @hellomontyonmain. This chill Southside hang out serves amazing beer, craft cocktails, and shareable plates. Order the Cast Iron Cheese Dip, the Fried Brussel Sprouts, and the Cast Iron Caramel Apple Crisp.
5. @meanmugcoffeehouse. Established in 2011, this quirky, lively coffeehouse boasts reclaimed wood & brick accents and serves unique coffees and light bites. Order a Mean Mug Nitro Cold Brew with Peach cold foam, and an egg + avocado toast! *don’t forget to check out the @kelseymontagueart mural next door for a fun photo opp!*

Are you planning to visit Chattanooga, Tennessee soon? 🇺🇸 #hosted
#VisitChatt #ChattanoogaTN #Chattanooga #tnvacation • Southeast USA • Visit the USA • USA roadtrip • summer road trip •
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