Introducing the Magic City
The city’s growth was like magic.
That’s how Miami’s early visitors felt when they came down to escape the winter each year, only to find the city had dramatically changed from the year prior.
Since the Great Freeze of 1895 that first put Miami on the map as a freeze-proof settlement, the Magic City’s continuous transformation has earned it status as a global destination and one of North America’s most unique cities.
From its Latin American culture to its Caribbean flair, Miami is bursting with character.
It’s a city for art lovers, beach dwellers, club-goers, and foodies.
Whether you’re looking to relax near beautiful blue waters, bask in Hispanic culture, explore thriving art and architectural scenes, or party the night away at world-famous clubs, Miami offers many reasons to visit.
It’s also a city of many sides, and each of its neighborhoods provide visitors with a different experience.
A well-executed trip to Miami should give you a glimpse into the ‘305’ from every angle, which is what this “Four Memorable Days in Miami” itinerary aims to do!
Day One: Coconut Grove, Coral Gables, and Little Havana
The Coconut Grove and Coral Gables neighborhoods offer the perfect introduction to Miami. Each area offers plenty to see and do, yet neither feels as congested as other parts of the city.
Coral Gables
Coral Gables, home to the University of Miami, is a well-manicured community full of Mediterranean architecture and giant banyan trees looming over the streets.
The downtown area is very walkable, with dozens of restaurants and shops spanning multiple blocks.
Start with a walk down the half-mile stretch of Coral Way known as the Miracle Mile, or soak in the European vibes of Giralda Avenue, a pedestrian plaza with at least a dozen outdoor dining options.
For your first sunshine and water combo of the trip, the Venetian Pool, a historic swimming hole featuring waterfalls and caves, is just a few blocks away.
If Brunch is on your radar, check out Tap 42, one of Miami’s top brunch spots that makes for a hip hangout at any hour.
Just down the street, Bulla Gastrobar is a superb dinner choice that serves up phenomenal tapas and delicious sangrias.
Coconut Grove
When you’re ready to explore beautiful Coconut Grove, consider using the free Coral Gables Trolley, which will get you within walking distance of the neighborhood’s main drag.
Nestled up against Biscayne Bay, Coconut Grove is a picturesque neighborhood with a zen, tropical vibe.
In addition to its eclectic shops and eateries, the area is known for its historic homes, beautiful marinas, and impeccable green spaces.
For a bite and beverage, consider stopping in to Jaguar, an establishment known for its delectable ceviche.
Once you’ve had the chance to wander up and down Grand Avenue and its surrounding blocks, enjoy a walk along the scenic waterfront until you reach Monty’s, a hoppin’ bayside hangout featuring live music and plenty of tropical vibes.
Little Havana
After spending the better part of the day in two largely-affluent areas, it’s time to immerse yourself in the Latin American culture that makes Miami so unique.
Little Havana showcases all the best parts of Cuban culture, and any trip to the Magic City should include a stop there.
The heart of the Cuban district is 8th Street, also known as Calle Ocho. The most popular stretch is between 13th and 17th Avenue, and that’s where I’d recommend starting your exploration of the area.
Within this four-block radius, you’ll pass several Cuban memorials, Domino Park- where Cubans play endless rounds of dominoes each day, and the Cuban Walk of Fame.
You’ll also find markets, cafes, hand-rolled cigar shops, and walk-up food windows lining the streets.
There’s no shortage of classic Cuban options for dinner, but if you have to choose just one, Old’s Havana Bar and Cocina has my vote.
The retro-themed eatery is well-known for serving up delicious, massive portions, which I experienced firsthand.
When my wife and I grabbed dinner there, I ordered the ham, and I swear they brought me an entire pig!
After dinner, grab an inventive scoop of ice cream or sorbet at the renowned Azucar Ice Cream then finish the night with a Mojito at Ball & Chain, an iconic music venue and bar. The performers are incredible, and the energy is off the charts.
Seriously, this place is a Miami must!
Day Two: South Beach
When most people picture Miami, South Beach is usually the first place that comes to mind.
Located across Biscayne Bay from downtown Miami, colorful South Beach is best known for its high-end retail and dining, see-or-be-seen culture, and over-the-top party scene.
But even if you prefer to keep a lower profile, South Beach’s stunning beaches, art-deco architecture, and fantastic walkability will make your visit there worthwhile.
Brunch and Beach
Start your day with a meal at the cozy Sunny Side Cafe & Eatery or the always-lively Limonada Bar + Brunch.
After you’ve satisfied your AM cravings, head to South Pointe Park for a beautiful walk on the south side of the barrier island. The park offers incredible views of Fisher Island, Key Biscayne, and downtown Miami.
Nearby, you can soak up the sun at South Pointe Beach, or head north until you find a beachfront environment that suits you.
Once you’ve got all the direct sunlight you can handle, walk across the street to Ocean Drive, one of South Beach’s main drags.
Here, you’ll have a chance to admire the famous Art Deco buildings as you survey dozens of street-side lunch options. From quaint cafes to energetic eateries that feel more like day clubs, you’ll find just about every type of atmosphere along this famed stretch.
Bike and Shop
Follow up lunch by renting bikes from Citi Bike, South Beach’s bike-sharing rental system. Rental stations are scattered up and down the beach, and the rates are surprisingly cheap.
The boardwalk that runs along the ocean is perfect for biking. I’d recommend taking it to North Beach, where the mood is much more chill. On the way, you’ll pass plenty of bumpin’ day clubs, pocket parks, and beach access points.
For many visitors, shopping is an important part of the South Beach experience. If that sounds like you, head to Lincoln Road, one of the most famous retail districts in the U.S.
The district has a long list of exclusive and eclectic shops, with some of South Beach’s premier dining options sprinkled between them.
Dine and Drink
Come evening, take a walk down Espanola Way. The area, built 100 years ago to resemble a Mediterranean village, is filled with romance, charm, and top-notch dinner choices ranging from French to Cuban to Italian and Mexican.
If you’re looking to party the night away South Beach-style, you’ll have endless options such as LIV and Do Not Sit On The Furniture.
Looking to keep things on the classier side? Check out Sweet Liberty Drinks & Supply Company’s upbeat environment or Swizzle Rum Bar & Drinkery’s intimate speakeasy setting.
Day Three: Everglades and Wynnwood
Everglades National Park
After spending two days soaking in urban culture, a quick getaway to the subtropical wilderness of Everglades National Park is the perfect respite.
Everglades is one of the largest wetlands in the world and plays home to some of the most fascinating plant and animal life in the U.S., including endangered species like the Florida panther and Leatherback sea turtle.
Though you could easily spend the entire day exploring the park, two to three hours will give you enough time to see and experience the fascinating subtropical wilderness.
If you’ve only got time for a single activity, consider hiking the 0.8-mile Anhinga Trail. This boardwalk trail can be accessed just a few miles beyond the northern entrance and makes an ideal activity for visitors of all ages.
When I completed this hike, I saw exotic birds, a variety of fish, massive turtles, and at least ten alligators. For wildlife viewing, this trail is hard to beat.
If you decide to spend an entire day exploring the park, drive further south for a chance at spotting the alligator’s largest cousin, the crocodile. Who knew there were crocs in Florida?!
On your way back from the park, stop at Robert is Here, a fruit stand and farm popular with tourists and locals. Grab one of their world-famous shakes and a fresh batch of guacamole before you head back to the city.
Vizcaya Museum & Gardens
The Vizcaya Museum & Gardens is another great way to spend the day if you’d prefer to stay closer to the city. The stunning property was built as an estate in the early 20th century and modeled after a historic Italian villa.
Today, most of the grounds are open to visitors who can tour the massive home featuring 500-year-old art and ten acres of Eden-like gardens that provide a remarkable setting for photos.
Wynnwood
Once you’ve had the chance to regroup, start your evening at the Wynnwood Walls, a captivating outdoor art museum in the vibrant Wynnwood neighborhood.
In 2009, real estate developer Tony Goldman saw the warehouse walls that dominated the Wynwood neighborhood as an opportunity to transform the area into one big art canvas. Today, the Wynwood Walls are the focal point of that realized vision featuring creative masterpieces from some of the world’s top muralists and graffiti artists.
The detail in each piece is incredible, and many of the walls are redone two or three times a year, so there’s always something new to admire.
Spend some time exploring the rest of the neighborhood on foot and you’ll see many more impressive artistic displays. As you roam the area, you’ll find plenty of restaurants, breweries, and bars to spend the remainder of the evening.
Veza Sur Brewing has an excellent indoor/outdoor space and pours some of the best beers in the city.
For dinner, you can’t go wrong with Le Chick Miami, a fried chicken hot spot with a great ambiance and even better cocktails.
To finish the night, head to Astra’s rooftop, a chic space that offers sweeping views of the Miami skyline.
Day Four: Key Biscayne, Downtown, and Brickell
On your final day in the Magic City, a trip back to the beach seems like an appropriate start.
Rather than going back to South Beach, take the Rickenbacker Causeway, which connects the Miami mainland to Virginia Key and Key Biscayne.
The views alone are worth the drive, with spectacular vantage points of the Miami skyline and the turquoise bay dotted with watercrafts big and small.
Beach Options
Hobie Island Beach, located on a thin strip of Virginia Key, is the first beach you’ll pass, and it’s Miami’s most dog-friendly. The beach’s proximity to downtown keeps it busy at all times of the day, and big shady palm trees, skyline views, and nearby food trucks add to its appeal.
Those continuing to Key Biscayne will have several other beaches to choose from. Crandon Beach is a local favorite where you can rent kayaks and paddle boards, while the beach at Bill Baggs Cape Florida State Park is known for its peaceful environment as well as the Cape Florida Lighthouse, Miami’s oldest standing structure.
On you way back across the Causeway, consider a stop at Whiskey Joe’s, a casual beach bar, or Rusty Pelican, a stylish seafood restaurant. The neighboring establishments sit on the northern tip of Virginia Key and boast waterfront views worthy of a postcard.
Downtown & Brickell
Begin your last evening out with a trip to Bayside Marketplace located downtown. Whether you want to eat, shop, take a boat tour, or ride in the Miami Observation Wheel, there are plenty of ways to spend a few hours at the lively marketplace.
Grab one final meal at La Cañita, a highly-rated Cuban joint, or walk a couple blocks over to indulge in the award-winning Peruvian fare at CVI.CHE 105.
Stay out past your self-imposed curfew to enjoy Miami’s nightlife one last time in the downtown-adjacent Brickell neighborhood.
Brickell has plenty of bumpin’ hot spots at street level, but the real magic happens hundreds of feet up at mesmerizing rooftop bars like Rosa Sky and Sugar.
No matter which rooftop you choose, the panoramic views of the lit-up skyline will blow you away, and I think you’ll agree it’s the perfect way to end four memorable days in Miami.
Four Day Itinerary
Day 1
- Explore downtown Coral Gables including Miracle Mile
- Grab brunch at Tap 42 or dine outside at one of the Giralda Avenue’s restaurants
- Take the free Trolley to Coconut Grove
- Spend an hour shopping and strolling the area around Grand Avenue
- Walk north along the bayside parks and stop at Monty’s for a beverage and live music
- Start the evening taking in the Cuban culture in Little Havana
- Dine at Old’s Havana Bar and Cocina or one of the other nearby Cuban restaurants
- Drink and dance at iconic Ball and Chain
Day 2
- Start the day with brunch in South Beach
- Take a walk around South Pointe
- Soak up the sun at South Pointe Beach
- Grab lunch along Ocean Drive
- Rent Citi Bikes and ride the boardwalk up to North Beach and back
- Spend the evening on Lincoln Road or Esponala Way
- End the night with a cocktail at Sweet Liberty Drinks & Supply Co. or Swizzle Rum Bar & Drinkery
Day 3
- Make the hour drive down to Everglades National Park
- Experience the unique ecosystem and diverse plant and animal life on the Anhinga Trail.
- Stop at Robert Is Here for their famous shakes and fresh goods after leaving the park
- Start the evening by admiring the artwork and murals at Wynnwood Walls
- Stroll around the neighborhood and stop into Veza Sur Brewing.
- Grab dinner at Le Chick Miami or one of the other fine eateries in the neighborhood
- Finish the day with skyline views from Astra’s rooftop.
Day 4
- Head to one of the beaches off the Rickenbacker Causeway
- Stop at Whiskey Joe’s or Rusty Pelican for a bite and bayside views
- Wander around Bayside Marketplace and take a ride in the Miami Observation Wheel
- Indulge in one final meal at La Cañita or CVI.CHE 105.
- Wrap up the trip with more spectacular views from the rooftop of Brickell’s Sugar or Rosa Sky.