Miami and The Florida Keys – How To Do It All in Under a Week
Beaches and Bridges
We headed down to Florida for the Daytona 500 race and took some extra time to enjoy Miami and the Florida Keys. My elderly parents joined us which made this a special time. Taking my parents on a trip meant factoring in short walking distances, avoiding overly spicy foods, and navigating the little quirks that come with traveling with seniors. (Basically the same energy as traveling with toddlers—just swap the juice boxes for wine).
Florida greeted us with its signature mood swings—warm and sunny one day, windy and cold the next. Daytona even threw in a full-on rainstorm just to keep us on our toes during the race. But even with the unpredictable weather, we packed a whole lot of good food, and memorable moments into this trip. If we did it again? We’d add an extra day in Miami and extend our stay in the Keys. Our hotel in Miami and the one is Islamorada both deserved more time.
Landing in Fort Lauderdale & Straight to Little Havana
We didn’t waste a second. Right off the plane, we made a beeline for Little Havana. If there’s one thing you should always prioritize after landing, it’s a great meal. Our target? Café La Trova.
Cafe La Trova
This spot is flagged on multiple foodie lists—Eater, Michelin Guide; you name it. It is a James Beard Award Winner and is listed on the World’s Best Bar List. And it did not disappoint. From the moment we walked in, the place felt like a party. Live Cuban music fills the air, bartenders shake up cocktails with impressive theatrics, and the entire space just buzzes with an energy that makes you want to settle in for the night.
We started with empanadas and croquettes— If you’re in Little Havana, you don’t just casually glance at the appetizer section; you order everything you can knowing it will be delicious. Both were crispy, golden, and oozing with flavor. But just when we thought we could stop there, curiosity (and our complete lack of self-control) got the best of us. The waitress described this great special for 2-4 people and we couldn’t resist. However it surely could have fed 4-6. There was some shame in how much we left on our plates.
This hot platter arrived sizzling, piled high with a carnivore’s dream lineup—succulent sausage, juicy chicken, perfectly grilled steak, and crispy potatoes tucked into every available space. It was the kind of meal that demands a deep breath before diving in. I would love to say we made a dent but mostly it was just a gallant effort to eat as much as we could. Every bite I took was covered in chimichurri sauce. Really fresh and vibrant.
DON’T MISS – The Cafe La Trova old fashioned, made with rum instead of bourbon. Pair with the ham croquettes.
Stuffed but happy, we danced our way out of Café La Trova and made our way to our first hotel.
The Palms Hotel & Spa
After an epic start in Little Havana, we finally made our way to our hotel for the night—The Palms Hotel & Spa, a beachfront retreat in Miami Beach that gave us just the right mix of relaxation and luxury.
But first, we took the iconic drive down Ocean Drive—because if you’re in Miami and don’t cruise through this neon-lit stretch at night, did you even go to Miami?.
Located a little further up Miami Beach, The Palms Hotel & Spa was a perfect escape from the energy of South Beach. It’s quieter, a bit more upscale, and has direct access to the beach—basically, exactly where you want to be if you love the ocean but also love sleeping.
First Impressions & Arrival- The hotel’s lush, tropical aesthetic immediately sets the tone—palm trees everywhere, warm terracotta tones, and a Cuban-inspired outdoor lounge that makes you want to settle in with a mojito (or three).
The room? Spacious, ocean-and-pool-view perfection. We could see the hotel’s private beach area, which comes with full service (meaning someone will bring you snacks while you stare at the waves).
Miami in Style: Sightseeing, Champagne Toasts and a Luxurious Dinner
The next morning we started our day with breakfast on the terrace overlooking the pool. I’m convinced that food just tastes better when eaten outside, near water, with a light breeze—but maybe that’s just vacation brain talking. We then made our way to start our touring.
Miami’s Hop-On, Hop-Off Bus
Our go-to low-effort, high-reward way to see a new city. The stop was conveniently located near the hotel. This made it a senior-friendly, minimal-walking option (a major win). We started in South Beach, and our first area was Wynwood Walls. This neighbourhood is covered in cool street art and sitting on the top deck of the bus was a great way to see it. The headphones are easy listening and reference what you are seeing. An hour in and we were in Little Havana where we had decide we would stop for lunch.
It covers the major attractions with lots of flexibility. You can get off and spend time in the areas, checking out art, restaurants or shopping or if you have some mobility restrictions you still get a really great over view of the city as you ride along.
The main areas you’ll get to experience are
South Beach – famous for its Art Deco architecture and the fun Ocean Drive. Experience the pristine beaches here and great dining options.
Wynwood Walls – a dynamic neighbourhood known for its colorful street art and murals. It is a must get off for art enthusiasts and has so many unique photo opportunities that your young Instagrammers would find lots of beautiful content.
Little Havana – Full of Cuban culture. The ideal place to have lunch and experience authentic Cuban cuisine, music and a bustling atmosphere.
Downtown Miami – The urban core is where you’ll find the Bayside Market place – a waterfront shopping and entertainment complex as well as the historic Freedom Tower.
Design District – This neighbourhood is famous for its high-end fashion boutiques, art galleries and architecture. This is stylish stop.
Ball and Chain – A taste of Old Miami
One of our favorite stops was Little Havana (again!), where we grabbed lunch at The Ball & Chain—a Miami institution that’s been around since 1935.
The vibe? Vintage Cuban charm, live music, and a lively atmosphere. This is a fun place to spend some time before and after lunch.
The food and cocktails? A perfectly crispy, melty, traditional Cubano sandwich and some top notch cocktails.
The secret weapon? A quiet, tree-enclosed patio out back, ideal for when you love the energy of a place but also want to actually hear the people you’re eating with.
Cigars and Churro Mania
We checked out a cigar store next door, hoping to snag some authentic Cuban cigars… only to be reminded that you still can’t buy them in the U.S. (a major letdown).
Just down the street, we grabbed some churros at Churro Mania—good, but not life-changing. Fried dough is always a pretty delicious way to end a meal but these weren’t anything special.
Miami In Style
The Four Seasons Champagne Bar & The Surf Club
There are a number of great dining options in Miami Beach and the culinary scene in this city is worth the trip. For dinner, we chose to do something upscale so we got dressed up and headed farther up the beach to the Four Seasons Hotel. Here you will find a gorgeous champagne bar and the stunning Surf Club
Champagne Bar at The Four Seasons
We started with pre-dinner drinks at the Champagne Bar, where I had a glass of Blanc de Blanc champagne. A top notch old fashioned was enjoyed by the gentlemen and my mom had a very pretty vodka cocktail. There is something for everyone on the menu and the high ceilings and elegant furniture match their menu. You can order food here if you aren’t up for a full meal.
The Surf Club – A Michelin -Starred Experience
Dinner was at The Surf Club, a Michelin-starred restaurant helmed by the acclaimed chef Thomas Keller (of Napa’s French Laundry fame). If you love food that’s both comforting and wildly elegant, this is your spot. The menu is classic continental cuisine. This is truly sophisticated dining. The restaurant has a historical charm atmosphere. You’ll also find it in the Four Season’s Hotel.
DON’T MISS – The Buns: I don’t know what kind of sorcery was used, but these were the softest, airiest buns I’ve ever eaten. It’s like they injected them with clouds. The entire menu is incredible so it seems I’m undervaluing the rest of our meal but these buns were truly that incredible. Also consider the Dover Sole Meuniere; delicate with a browned butter, lemon and capers. It was perfectly executed.
The Service: Impeccable. The kind of place where you never have to ask for anything—because someone has already anticipated your every need. However I’d like to note that the wait staff was not pretentious. They were warm and welcoming and the formality was secondary to a very kind reception. The Food: Rich, refined, and worth every bite. The kind of experience where the food is part of the entertainment. It’s exactly what you would expect from Keller.
Although we didn’t do a nightcap after supper; our seniors were done for the evening, I would highly recommend you take advantage the great ambiance and top-tier drinks Miami has to offer.
Rooftop Nightcaps
The Living Room at the W South Beach is chic, lounge stye with craft cocktails and often has live music. You’ll settle into plush seating and a buzzing atmosphere. DON’T MISS – South Beach Sling; gin, fresh citrus cherry liquor and herbal notes.
St. Regis Bal Harbour Bar and Wine Vault is elegant and offers fine wines, signature cocktails, and a refined atmosphere. DON’T MISS – The St. Regis signature Bloody Mary. However they have an extensive selection of rare wines and champagnes.
Makoto’s Bar; which has a Japanese twist so you’ll have a great cocktail and dessert pairing here. The chocolate hazelnut lava cake is going to be your DON’T MISS – This is also a sleek and stylish Japanese restaurant in case you’re interested in an All in One Excellent evening.
Sugar at EAST Miami is a top rated rooftop bar with stunning panoramic views, a lush garden terrace and Asian influenced flavours on the cocktail menu It is located on the 40th floor and their DON’T MISS – the Tom Yum; a tequila cocktail with Thai chili and ginger.
Florida Keys – Our Escape to Islamorada
Heading south and leaving Miami in our rearview mirror quickly becomes a new adventure. The palm trees sway a little looser and life immediately slowed down. The keys are a state of mind. On our way down to Islamorada we made a couple of stops.
Robert Is Here – Smoothie Heaven
This pit stop is early into your trip and its a legendary fruit stand in Homestead. This place is part petting zoo, part roadside market, part tropical oasis and 100% Florida. They are famous for their smoothies – blended magic made from whatever exotic fruit is in season. And if you’re an old guy you can just have a banana milkshake because the fun smoothies were to new age for him. The options are a little overwhelming and rightly so when they have a market full of fun tropical fruits like guanabana, passionfruit and mango.
Snook’s Bay – Key Largo
Key Largo is known for diving, snorkeling, and Key Lime Pie. It should be creamy, tart and have just the right amount of sweetness. Here you’ll sit at their tiki bar on a waterfront deck to enjoy. You might order a second slice before you’ve finished the first. We tried them continuously through out our vacation and we each had a favourite which I will share. Snooks Bayside is famous for the Key lime Pie. DON’T MISS – Add a Frozen Key Lime Colada for real commitment.
Robbie’s – Lunch at Islamorada
This is not the same Robbie as Smoothie Robbie’s but apparently there are a few Robbie’s in the Keys. This is a cool beachside restaurant where the “real” locals – aka the giant tarpon and the feisty pelicans – run the show. We ate a great lunch; exactly what you would expect to eat on a dock with overlooking silly tourists feeding the tarpon and fighting off the pelicans. Cold beer and some fish tacos. The atmosphere is laid-back. colorful, and a little chaotic. The staff keep it fun and the seafood is fresh. We had one waitress who told us we should feed the tarpon although she hadn’t done it yet and we had another one who thought we were crazy if we did it. You’ll need to decide.
DON’T MISS – Conch Fritters; a true Florida Keys staple; and add a Key Lime Mojito to make sure you know you’re in the Keys.
Picture this: You pay $5 to get your bucket of big minnows? (I don’t know fish they actually are); you fight your way to the end of the dock so a pelican doesn’t get the minnows and then you’re ready. You lean over the dock with a fish in your hand, a massive tarpon launches itself out of the water, and BOOM – its gone in one gulp. Then you fight off another pelican and do it all over again. My tarpon were lazy. The tarpon did not jump until the minnow was let go and just about to land in the water. Perhaps just as well as some people claim the tarpon put half of their arm in its mouth to get the measly minnow.
Tiki Bar – Sunset Drinks in the Keys
I would recommend Lorelei’s for the best sunset views as it faces the other side of the keys or some spectacular views. However the Tiki Bar is a great place for happy hour and is the home of the original Rum Runner. Be warned – it is a Rum PUNCH. Although we couldn’t see the sun slip into the ocean we were still treated to ocean views and a masterpiece of pinks, oranges and purples. It was also located at our hotel so the convenience was perfect. DON’T MISS – The Rum Runner but also try a Mai Tai. It is their signature drink.
Pierre’s
Pierre’s is a stunning restaurant housed in a colonial style mansion right on the water. IT is romantic, eclectic and effortlessly cool. Candle lit tables, cozy lounge areas and intricate architectural details fill this space. Menu is French fusion and full of seafood. This is where I had my FAVOURITE KEY LIME PIE. It is all the things its is supposed to be but just a little more on the sweet side than the others I have tried. This is your restaurant to celebrate a birthday or anniversary; it is for your fancy night out. DON’T MISS – Seared Jumbo Scallops with a saffron linguine.
After a day of driving, eating and narrowly escaping pelican attacks, we were excited to unwind in the Keys paradise. We stayed at the Three Waters Resort and Marina – a hidden gem with incredible views and a relaxed, boutique feel. An hour and a half from Miami; (if you’re in a hurry and want to drive straight there), it is a destination in itself.
This resort is sprawled across 15 oceanfront acres, and is a freshly reimagined oasis. The rooms are island inspired and they offer 9 different dining options.
The resort excels at bringing a balance of barefoot luxury and modern hospitality. As a member of the Marriott portfolio you are able to access you Marriott membership perks and also have some assurance of the standard of hospitality you are going to experience.
We ate breakfast every morning out on the dock of their main dining restaurant. The sun was warm and a gentle breeze was a great way to start each day. In the evenings there are great cozy nooks with firepits and comfortable chairs along the property; making it a great way to end your day here as well.
Day Trip to Key West
A day trip to Key West is a classic Florida adventure; guaranteed ocean views, quirky history, great eats and and tropical drinks. Since we’re coming from Islamorada you want to get an early start.
Midway Cafe
A solid caffeine fix is a how you’ll want to start your day and Midway Cafe and Coffee Bar is the perfect place to fuel up. The cafe is charming, colourful and known for its locally roasted, coffees, fresh-baked pastries and hearty breakfast options. Either grab something to go or sit down and settle in. DON’T MISS – Key Lime Muffin with a Coconut Cold brew will equal the ideal refresher for a warm Florida morning.
Seven Mile Bridge
As you make your way south, one of the most breathtaking parts of the drive is the Seven Mile Bridge, connecting the town of Marathon to the Lower Keys. A great stop is the park at the entrance to the Old Seven Mile Bridge (by Pigeon Key); get out and walk part of the bridge and enjoy the really unique views. This restored section of the old bridge gives you uninterrupted ocean views and it absolutely the best way to appreciate the stunning blue waters of the Keys. After your little walk and break the drive over the new Seven Mile Bridge is cool, and engaging.
Bahia Honda State Park
A bathroom break is always a good excuse for a stretch of the legs, a chance to explore and an ice cream break. This gorgeous beach park is known for its clear water, sandy shores and and a creepy cool remnants of of the old railroad bridge. There’s a small concession stand and ice cream next to the water during warm day was a highlight.
However it got better; as we watched people gather down next to the water in the marina area we were curious to know what they were checking out. Cameras were out and people walked along side the water edge so we knew there was something in the water. We were thrilled to find a manatee floating his handsome self around the edge of the marina. They are big gentle looking creatures. This turned out to be more than just a quick bathroom stop for us.
Duval Street
This street is not what I expected although I wasn’t disappointed. I was expecting posh boutiques and thought I’d be purchasing some chic linen seashell napkins to bring home as a souvenir. That is not what is going on down at Duval Street. Come ready for a party. The street is lined with fun restaurants and bars.
Sloppy Joe’s
No visit to Key West is even relevant unless you step into the legendary Sloppy Joe’s Bar. It is an iconic water hole and is known for being the fabourite haunt of of THE ERNEST HEMINGWAY, who spent much of his time writing and drinking in Key West. The bar, established in 1933 is always packed with lively crowds but also with history. There is live music all day long and the drinks are the attraction. DON’T MISS – The Original Sloppy Joe, a messy mix of ground beef, tomato sauce and spices served over a bun. Have it along side a Papa Dobles (Hemingway Daiquiri)
Salute
After the energy of Sloppy Joe’s, lunch at Salute offered a quiet, quaint and more relaxed beachfront escape. This is a hidden gem that sits right on Higgs Beach, which is strong contradiction of beach views instead of the tourist crowds of Duval Street. The menu has a Caribbean – Italian fusion theme. We enjoyed a flavourful lunch and then a nice beach walk before heading to our next stop. DON’T MISS – Grilled Fish sandwich washed down with a Mojito. however if the crab claws are in season they are a MUST. This was obviously a late lunch when you see all that we squeezed in before we filled our bellies.
Southernmost Point Buoy
Although I feel this is a must we chose to just drive by. Our seniors weren’t up to standing in line for the photo op. This is a Buoy landmark that marks the southernmost spot int eh continental U.S. and is just 90 miles from Cuba. The line appeared to move quickly and I think it would be worth snapping a pic of. This is where you’re going to want to check the cruise schedule for a smoother experience.
Sunset Grille and Raw Bar
As you make your way back to Islamorada, a sunset stop at Sunset Grille and Raw bar in Marathon is a great half way mark and if timed properly the sunset will cooperate. This is an open-air bar that sits at the foot of the Seven Mile Bridge so the views of the sunset are unbeatable. While the atmosphere and scenery are top notch the food is not the main attraction. Come for the tropical drinks, live music and the view of the sun dipping below the horizon. Our waitress was phenomenal but our food was average. DON’T MISS – the sunset.
Latitudes
We unfortunately were unable to get reservations to this restaurant and it will be one of the first things I do the next time we visit. It is the ultimate in Key West dining. It is beachfront and ahs a private island ambiance. You take a short ferry ride from downtown Key West to Opal Key Resort and Marina to a tropical paradise with tables right on the beach. DON’T MISS – This; don’t miss this. You’re going to have to book a reservation; I won’t make the same mistake twice.
Final Thoughts on Islamorada and the Keys – Magical
Miami is is fun but the Florida Keys are a different world. You feel like you have left the United States. The Overseas Highway brings a new feeling with it. Life slows down, the stress melts away and suddenly you are focused on good food, drinks and vibes. The Keys are full of scenery, history and energy. We will add a couple of days to our itinerary next time we come to visit; one extra day in Islamorada to enjoy the beaches and our stunning hotel and another day in Key West to make some new friends and memories along Duval Street
