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Ultimate Florida Keys Adventure

Written by Lee Ann Shobe

Sunset in the Florida Keys

For this month's blog, the “Adventure with Purpose” team chose from our “Top 10” places to visit in Florida, and the Florida Keys topped the list. If you are planning a trip to Southern Florida or are interested in learning more about the area, we provide links to many of our stops along the way.

Blog team contributors Bruce and Lindsey Underwood did the research, which resulted in this excellent and informative travel guide, “The Great Florida Keys Adventure.”

The guide targeted many of the best restaurants, bars, snorkeling areas, and historical sites throughout the Keys. Get ready to follow us as we take you on the Ultimate Florida Keys Adventure.

Day 1

We left before sunrise on a Sunday morning and drove so we could immerse ourselves in Florida’s ever-changing landscape. As we approached Hollywood, Florida, the rising sun illuminated the city with brilliant light, preparing for a new day. Then suddenly, this gigantic guitar that appeared to be ascending into the sky caught our attention, and we quickly snapped this picture of this unique landmark Guitar Hotel and Hard Rock Café downtown.

Our first stop was Key Largo, the first of the Keys and widely known for its outdoor adventures and the world’s largest artificial reef. We arrived at a perfect time to stretch our legs and enjoy a fabulous brunch at The Buzzards Roost.

The staff was friendly, the food and drinks were superb, and the live guitar music set the stage for a trip we are not likely to forget.

After brunch, we caught Highway 1, which follows the stunning Florida coast 100 miles from Key Largo to Key West, the southernmost point in the US.

One of our favorite sections of the drive was the Seven-Mile Bridge in Monroe County. It felt peculiar driving over a bridge surrounded by water as far as the eye could see. We marveled at how the sparse clouds on the horizon framed our view of the breathtaking blue hues that glistened across the water. The bridge parallels the famous Florida Keys Over-Sea Railroad, constructed by Henry Flagler in the early 1900s, and reminds us of Florida’s rich history.

Seven-Mile Bridge

Before heading to our VRBO, we stopped at the legendary No Name Pub, founded in 1936 on Big Pine Key. The Pub's sign tells the story; it’s hard to find but worth putting in the effort. As we entered the pub, we were instantly amused by the eccentric décor of using dollar bills as wallpaper placed there by patrons. We commented that the walls must be valued at several thousand dollars as Bruce and Lindsey added their names and dollar to the Pub’s wall. It was a unique place with excellent drinks, and we were glad we stopped.

As we left, we observed a small deer overseeing the activities from a close but safe distance, waiting for any leftovers.

The next stop was our condo at Venture Out Resort on Cudjoe Key and home for the next six days. It was a perfect two-bedroom, two-bath, sizable living and dining room and fully equipped kitchen. The best part of the condo was the deck that looked out over the marina basin, where we drank our morning coffee, made our plans for the day, and solved the world's problems. These fond memories will stay with us forever.

Condo on Cudjoe Key

View from the deck

Before calling it a day, we enjoyed a seafood dinner at Tonio’s Seafood Shack and Tiki Bar on the waterfront in Summerland Key. It was a quaint restaurant on the water, creating a perfect ending to the first day of our adventures.

Tonio's Seafood Shack


Day 2

We spent our second day getting into the unique vibe of Key West. We hit the shops, restaurants, bars, and historical sites. Key West is the southernmost point in the US and only 90 miles from Cuba, differentiating itself from the other Keys.

As we made our way down Duval Street, the main street in Key West, we were unprepared to see a mother hen and her chicks leisurely making their way to their next stopping point or a rooster holding court over his subjects. We found this fascinating and endearing to see tourists sharing the sidewalk with these protected residents.

Hemingway’s house is a must-see and the day's first stop. The home and museum are enchanting, complete with the descendants of Ernest Hemingway’s original six-toed cat, Snowball. An interesting fact is that the 50-plus cats living on the property have their own staff to care for them.

Ernest Hemingway, a respected novelist and Nobel prize recipient, lived in this home with his wife Pauline and two sons from 1931 to 1940. During the nine years he lived in Key West, he completed 90% of his works, including For Whom the Bell Tolls.

If you decide to visit the property, I recommend you consider a docent to guide your tour. They will provide the right balance of personal stories giving insight into Hemingway’s out-of-ordinary lifestyle and his growth as a writer.

Hemingway's Writing Studio

Three resident cats have decided to make Hemmingway's bed their home.

Staying in the spirit of Ernest Hemingway, we headed to Sloppy Joe's for lunch. Sloppy Joe’s was established in 1937, and its claim to fame is the creation of the original Sloppy Joe. The story is told that after visiting Cuba, Ernest Hemingway brought the sandwich concept back to Key West and suggested his favorite bar change its name to Sloppy Joe’s in honor of the Cuban original sandwich. They took his advice, and the restaurant serves thousands every year.

However, there is another version of the story; a diner cook in the midwest during the 20s or 30s named Joe introduced the sauce to the loose meat mix, but when you're in Key West, everyone believes it’s the first version.

I was the only one that didn’t order a sloppy joe, and in hindsight, I’m glad I didn’t because I didn’t hear any of our group give rave reviews--maybe the cook was having an off day.

The entertainer, Tim Hollohan, is a superb musician who had the crowd energized and people dancing, creating the out-of-the-mainstream Key West Vibe.

KINO Leather

The shopping and unique gifts were plentiful, and we brought several items for upcoming birthdays and Christmas.

After shopping, we cooled off at Hog’s Breath Saloon with a Key Lime Cocktail.

Lindsey and I loved the cocktail but be warned: you probably will only need one. The guys said it was good but too sweet for them.

After a long day, we returned to our condo just in time to put our feet up, play some cards, and watch the fisherman dock for the evening. We wanted to turn in early because we booked a snorkeling trip with Captain Hook's for the next day. Snorkeling was one of the reasons we came to the Keys but little did we know that our tour would not go as planned.


Day 3

We were up early, feeling like we were in our twenties again and looking forward to a day of snorkeling at the reef. Can you think of a time when you were so excited to participate in something you loved, then an unexpected event foils the plan and crushes your excitement? Well, that is just what happened during our snorkeling excursion.

We decided to write a stand-alone piece describing our snorkeling trip because a few words wouldn't do the story justice. No one tells the story better than Lindsey, so she will share our experience in a supplement blog that will be posted simultaneously with this one, so make sure you read it too--I promise it will provide some laughs. We did survive and lived to tell our story.

Despite the unforgettable snorkeling tour, we managed to recover and keep our dinner plans at SQ GR2. The food was delicious, the Florida décor was tasteful, the atmosphere was relaxed, the staff was top-notch, and we highly recommend this restaurant.

Sunset from Mallory Square

After dinner, we returned to Key West and took in the gorgeous sunset at the famed Mallory Square. Mallory Square has been a focal point of Key West’s social and commercial life since the city’s inception in the 1820s.

Today at the square, we found the nightly art festival to be a unique experience. We walked through the vendor's booths, visited with the arts and craft exhibitors, and found it enlightening. There were psychics, street performers, and food and beverages, but the sunset from the square was the main event. As the sun began to drop below the horizon, everyone in the square stopped what they were doing for a moment to take in this breathtaking view.

After sunset, we walked to the Hard Rock Café, where we met our tour guide from Key West Ghost and Mystery Tour.

Hard Rock Café was once the home of a prominent Key West resident and business owner. According to our guide, there have been numerous sightings from staff and patrons of the past owner wandering the halls and rooms of his house.

The 90-minute walking tour took us through Old Town Key West, home to many colorful characters over the years, and our guide made the ghost stories intriguing. The time was interactive, and I found the stories our guide told were at times chilling (Yes, Lee Ann, it is a ghost tour) but presented in a fascinating historical setting.

We made stops at:

Key West’s Oldest Graveyard.

The home of Robert the Doll (No creepy dolls for me)

Ernest Hemingway’s first home in Key West, where the “Watcher” waits

Former Club Chameleon


Days 4 and 5

The guys got up early on day four and decided to explore the waterways close to our condo; then, determined to get our snorkeling in, we headed to Fort Zackary Taylor State Park.

Before hitting the beach, we grabbed lunch at The Lobster Shack. It is a small cozy restaurant, but the lobster rolls were fantastic and made us long to eat more, but we contained ourselves.

The Fort Zachary Taylor State Park beach provides opportunities to picnic, swim, snorkel, paddle, and fish.

During the Civil War, the Union troops took over the Fort and maintained it during the war. It was strategically in a position to detain any ship trying to supply the Confederacy. Make sure you check out the Fort while you are there.

Day 5

We headed to Bahia Honda State Park for the day and immediately found it was our favorite spot for snorkeling and swimming. You can see the remnants of the Overseas Railroad from the beach, and the palm-lined shores, several species of birds, and clear water set the stage for a relaxing beach day.

Bahia Honda State Park

During our planning, we decided to dress up and experience fine dining in Key West one evening. The guys were not totally on board with the dressing-up thing, but they compromised. We chose One Duval where the food and view were terrific. While eating dinner, we watched an endless parade of sail and party boats skimming along the water as the sun slowly began to kiss the horizon.


Day 6

We woke up Friday morning and couldn’t believe it was our last day. We decided to visit beautiful Islamorada, the key where the movie I AM Number FOUR and the Netflix thriller Bloodline were filmed, to name only a few. If you are a fan of the Bloodline series, look closely; you will see some familiar places that will pull you right back into the drama. Hint: the Bait Shop.

Our first stop was the Florida Keys History and Discovery Center. We we extremely impressed with the storyboards detailing a comprehensive history of the area, starting with the Florida Keys' first people to the history of the Flagler’s Over-Sea Railroad and the 1935 Hurricane that destroyed Islamorada. The Center also has documentaries playing throughout the day if you want to learn more. The documentaries are excellent and worth the extra time spent at the center. We watched how the Over-Sea Railroad was built and the documentary on the aftermath of the devastating 1935 hurricane.

The key has some great shopping, where we picked up several souvenirs and had fun with the unique displays.

Our final stop was Lazy Days restaurant on the water, and we enjoyed something you don’t see every day. While eating, we watched the big fish come close to the dock, looking for food. Most of the fish were giant tarpons, but we also saw nurse sharks looking for the generosity of the patrons to share a bit of their lunch.

After our late lunch, we returned to our condo, where a beautiful sunset, a game of cards, and fond memories from our trip will be with us forever.


Lindsey Underwood - Editor and Contributor

Bruce Underwood - Photographer

Jim Shobe - Contributor



I enjoyed this so much. Armchair traveling! It looks like you all had a wonderful time and you've provided lots of good travel tips.

Lee Ann Shobe
Lee Ann Shobe

Thank you.


Cindy Arnold
Cindy Arnold

What a fabulous chronicle of your trip to the Keys…..the pictures are stunning and as I read I felt like I was right there with you…thanks for sharing your adventures!

Lee Ann Shobe
Lee Ann Shobe

Thank you 😎



What an awesome trip! Thanks for taking me to the Keys. Looks like lots of great memories.

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