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The Fabulous Florida Keys: An Itinerary for a Couple's Trip

Join me & my husband as we celebrate our anniversary in the Florida Keys. We found some great places to stay, play and eat!

TL;DR? Check out our itinerary summary here.

Happy 10th Anniversary (+2)

My husband and I missed out on celebrating our 10th anniversary two years ago because of COVID. We had booked a cruise to Cuba for May 2020 but it was cancelled, as was permission for Americans to travel to Cuba for tourism. For our 12th anniversary we got as close to Cuba as possible: the Florida Keys! Follow along with our trip and check out some of these awesome places when you're there.

Day 1: Fly to Miami, Rent Convertible, Visit South Beach

We recommend splurging on a convertible for your trip to the Keys. It's well worth the extra money! We put the top down, blasted some old school hip hop and explored downtown Miami and South Beach. We had some delicious Cuban food for lunch, dipped our toes in the beautiful turquoise water, and walked by the Versace Mansion which is now a boutique hotel and restaurant.

If we had flown in earlier, we would've liked to explore John Pennekamp Coral Reef State Park in Key Largo. It's America's first undersea park and offers swimming, snorkeling, fishing, camping and more. Maybe next time.

Next stop was our hotel: Hawks Cay Resort on Duck Key (101 miles south of Miami International Airport).

Day 2: Explore Resort, Dolphin Connection's Trainer for a Day Program, Visit Robbie's Marina in Islamorada

Hawks Cay Resort Lagoon

We'd checked into the hotel after dark so when we woke up the next day we were pleasantly surprised by the beauty of our surroundings. Hawks Cay Resort has luxurious pools, two of which overlook a saltwater lagoon and tidal river. The resort has well-kept grounds with lots of palm trees, flowering plants and tropical bushes. We loved seeing the iguanas and curly tailed lizards scampering around.

The highlight of the whole trip for me was the Trainer for a Day program through Dolphin Connection at Hawks Cay. The resort is the only one in the mainland United States that offers dolphin interaction on site. I've been a dolphin fanatic since I was a little girl so this was my dream come true.

I spent about three hours working with a trainer named Gabriela. I shadowed her and learned all about dolphin behavior, health, anatomy and the training process. I was able to spend a considerable amount of time swimming with, cuddling, touching and even painting a canvas with the dolphins. It was super expensive (around $500) but something I'd always wanted to do. The price tag includes a photographer and 150+ digital photo package. Checked off my bucket list!

Me & my dolphriend

In the afternoon we traveled 17 miles north to Islamorada, FL to visit Robbie's Marina, a well known spot for good food, good drinks and feeding tarpon. Tarpon are huge fish that beg for fish scraps at marinas all down the Keys. Nurse sharks like to get in on the fish scrap action, too. Our visit to Robbie's was extra special because a family of six manatees happened by the dock and my husband got to pet one on the nose for the first time. So exciting!

Hint: For a less congested tarpon feeding experience, check out Lazy Days Oceanfront Dining in Islamorada. We bought a bag of fish chunks at their seafood market for $3 and fed the tarpon - just the two of us - from their dock. The food was pretty good, too.

Dining in Duck Key

  • Angler & Ale overlooks the marina and serves tasty mahi mahi tacos and cheeseburgers, among other offerings. My husband enjoyed the local beer flight.

Day 3: Reef Snorkeling, Sandbar Swimming, Sunset from Seven Mile Bridge in Marathon

My husband and I booked an excursion with Solé Watersports, another entity on site at Hawks Cay Resort. We chose the group snorkel and sandbar trip on their 45 foot catamaran for $95 each. Ten of us, plus the captain and first mate, motored to a reef about a half hour away from the resort. They provided all of the snorkeling equipment plus unlimited adult beverages. Hurrah!

We had a great time exploring the reef and seeing all of the beautiful, brightly colored fish and coral. I'm glad I brought my Akaso camera (thriftier version of a GoPro) to capture some underwater shots.

After snorkeling we boated a short distance to a pristine sandbar. We had the best time walking along the sandy white bottom and swimming in the turquoise water. I even caught a horseshoe crab that was wandering by. It was completely relaxing and felt like we were in paradise.

Once back on dry land, we headed ten miles south to Marathon. We bought a slice of key lime pie at Sweet Savannah's and watched the sunset from the north end of the Seven Mile Bridge. It was a romantic end to a perfect day.

Dining in Marathon

  • Treat yourself to a delicious Italian feast at Frank's Grill. We had the eggplant parm and chicken française. Delizioso! There's no view - it's in a strip mall - but the inside feels cozy like an Italian restaurant should. The food's so good you won't miss the water view.

  • If you're in the mood for seafood and dockside dining with a party vibe, try Island Fish Company. The crab stuffed shrimp was awesome!

Day 4: Bahia Honda State Park

We put the convertible's top down and cruised the bridges to Bahia Honda State Park, 23 miles south. The drive through this part of the keys is idyllic - ocean water the color of Windex, sailboats on the horizon, and palm trees swaying in the breeze. My husband and I couldn't believe we were still in the United States as it felt more Bahamian.

We decided to rent a tandem kayak ($18/hour) to explore the shores of the state park ($9 per car entrance fee). It was an easy paddle from beach to beach. At one point we jumped out of the kayak and waded through the warm, shallow, crystal clear water because it was just too beautiful not to. Once again, we felt like we were in paradise.

Hint: Get lunch at the park's snack bar within the gift shop. My husband ordered a ham sub and it was the best one he'd ever had and super affordable, too. The snack bar also has key lime pie from the Key Lime Pie Company which wins our award for #1 best KLP. (We're pretty much experts as we tried a total of seven different slices on our trip!)

Dining in Marathon:

  • Florida Keys Steak & Lobster House doesn't look like much from the outside, but inside it's nice and the food is fantastic. I had tempura lobster sushi and the presentation was amazing. My husband had a perfectly cooked medium rare filet mignon.

  • We developed an insatiable addiction to Cuban coffee on our trip. We had an especially good one at Isla Latte. Check it out.

Day 5: Key West, Part I

The Artist House

We drove from Duck Key south to Key West, 60 miles worth of beautiful ocean views. After checking into our bed & breakfast, The Artist House, my husband and I enjoyed a bottle of champagne he had arranged for our arrival. He's the best!

The Artist House is a purple seven-room Victorian guesthouse a block from Duval Street, the happening spot in Key West. It is eclectically decorated and has a storied past - it's the original home of Robert the Doll. Robert the Doll inspired the creation of Chucky from the freaky Child's Play movies as he's considered "the most haunted doll in the world". Yikes! But The Artist House doesn't feel creepy at all and Robert lives elsewhere now. If you'd like to visit him, he resides at the Fort East Martello Museum.

Once we were settled in, we decided to check out Key West. Here are the highlights:

  • Explored Duval Street. Lots of bars, restaurants, shopping, key lime pie spots and souvenir shops. It's considered the main drag of downtown. So much fun.

  • Conch Tour Train. This adorable train with live narration has been chugging tourists around Key West since 1958. We went on it first thing "to get a lay of the land". It brought us by some of the most popular sites in Key West.

  • Sloppy Joe's Bar. Ernest Hemingway was known to have frequented this saloon back in the day. We had some delicious sloppy joe nachos and enjoyed some live music and drinks.

  • Mallory Square. This waterfront location is a party every night starting two hours before sunset. There's live music, street performers, food and drink vendors, and artisan stands. We loved Reidiculous Reid's stunt show. The view of the sunset from Mallory Square is perfect and something special to witness with loads of strangers.

  • Comedy Key West. We went to a Saturday night comedy show and laughed our @$$es off. This club is one block off of Duval Street and features local comedians as well as national acts.

  • The Chickens. OMG. My favorite thing about Key West is all of the loose chickens walking around the streets. There's loud cock-a-doodle-do-ing roosters and mamas with their little chicks and black ones and white ones and friendly ones and skittish ones. I've never seen anything like it!

Day 6: Key West, Part II

For some bizarre reason, I woke up before sunrise. I don't think I've ever done this in my life. I love to sleep in, especially on vacation. Perhaps I was too excited to sleep knowing I was in Key West and it was officially our anniversary!

I woke up my husband (sorry Hunny) and we walked down a deserted Duval Street to the coastline. We visited the Southernmost Point at Whitehead and South Streets and had our photo taken with the famous black, red, yellow and white buoy that marks the spot.

Being from Maine, we've been to the Easternmost Point in the continental US (West Quoddy Head, ME) and the northern terminus of Route One (Calais, ME). The southern terminus is this very buoy!

We found a spot facing the Atlantic Ocean and watched the sun come up over the horizon. Then we took a meandering stroll back to our bed & breakfast. It was so cool to be out on the street before the city was awake. It was very quiet and peaceful aside from all of the roosters crowing.

The emptiness of the streets allowed us to really take in our surroundings and appreciate the unique architecture of Key West with its brightly painted houses, intricately carved gingerbread trim and decorative shutters.

We swung by Ernest Hemingway's Home and said hi to some of his famous six-toed cats from outside the gate.

We stopped by Cuban Coffee Queen for a nice strong Cortadito. Mmmmm. We wondered how we'd ever go back to drinking our drip brew at home after having been spoiled by this good stuff. Love their motto: "Drink more Cuban coffee and do stupid things faster". LOL.

Once it warmed up we went for a dip in the ocean next to the AIDS Memorial at Edward B. Knight Pier. I wish we had masks and snorkels with us because the water was crystal clear. Some of the folks fishing on the pier up above narrated what they could see swimming in the water near us: lobsters, lots of fish and even a shark!

On the evening of our anniversary my husband booked us a dolphin watch and sunset sail through Sebago Watersports. This particular sail was 2.5 hours long and included unlimited beer, wine, champagne and tapas on a catamaran for about $80 each. The sunset was gorgeous, as expected, and we saw a number of dolphins; one even breached all the way out of the water for us!

Dining in Key West

  • We were craving some more Cuban food so our friend who lives in Key West suggested his favorite spot, El Siboney. It's a bit outside the confines of the city but definitely worth the drive. The prices are affordable, the portions are huge and the food is authentic and delicious. The roast pork with yuca and tamale was especially good.

  • We met our friend at the Boathouse Bar & Grill for happy hour. We were glad to drink half priced cocktails over good conversation in a lively place. We tried the conch fritters, fried shrimp and fish bites - all tasty and bargain priced from 4:30 to 6:00 PM.

  • Mary Ellen's Bar was just what we needed after a few too many drinks on Duval Street. We ordered some late night tater tots with curry sauce, a patty melt and a buffalo chicken wrap to share in this Christmas-light covered dive. We loved the risqué decor and posters advertising their vibrator races for charity!

Day 7: Drive Back Up the Keys, More Cuban Coffee (of course), Air Boat Ride at Everglades Alligator Farm, Return the Convertible and Fly Home

On the last day of our vacation we checked out of the bed & breakfast, said goodbye to lovely Key West and headed north on Route One to Miami. Along the way we stopped a few times to dunk our feet in the ocean and grab one last glorious Cuban coffee.

The last stop before Miami International Airport was the Everglades Alligator Farm in Homestead (42 miles from the airport). We went on a 30 minute airboat ride and saw a few gators in the wild. Then we explored the farm and saw thousands of gators of all different sizes, from inches long to twelve feet long, in a variety of different habitats. Price of admission also included a gator wrangling show and the chance to hold a small gator.

Our trip to the Florida Keys was one we'll never forget. I hope you get to experience it for yourself and check out some of the awesome spots we loved.

XO, Snark Mom


Our Itinerary & Suggestions for Your Trip

Day 1

  • Explore downtown Miami and South Beach. Splurge on a convertible!

  • Go snorkeling at John Pennekamp Coral Reef State Park in Key Largo.

  • Explore your hotel or resort's amenities. We highly recommend Hawks Cay Resort in Duck Key.

Day 2

  • Meet some dolphins at the Dolphin Connection in Duck Key or Dolphin Research Center in Grassy Key. If you prefer sea turtle, visit the Turtle Hospital in Marathon.

  • Explore Islamorada: Robbie's Marina & Lazy Days for feeding tarpon, seeing manatees and nurse sharks.

Day 3

  • Book a sandbar swimming and/or reef snorkeling boat excursion. We recommend Solé Watersports in Duck Key.

  • Watch the sunset from Seven Mile Bridge with a slice of key lime pie and a cocktail.

Day 4

  • Visit Bahia Honda State Park for swimming, fishing, and kayaking.

  • Enjoy your hotel or resort's pool.

  • Take a leisurely nap.

Day 5

  • Head to Key West

  • Take a Conch Tour Train ride for an overview of the city.

  • Explore Duval Street's bars, restaurants and shops.

  • Visit Mallory Square before sunset to see the street performers and vendors.

  • Watch the sunset from Mallory Square.

  • Enjoy the nightlife: comedy club, live music, dancing at da club.

Day 6

  • Stop by the Southernmost Point buoy and take a selfie.

  • Visit the Hemingway House.

  • Walk the streets and check out the beautiful homes and gardens.

  • Swim beside the Edward B. Knight Pier.

  • Take a romantic sunset cruise with your partner.

Day 7

  • Enjoy the sights as you drive north to Miami.

  • Visit the Everglades Alligator Farm in Homestead.

Day 8+

  • Daydream about the amazing time you had in the Florida Keys!

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