Miami to Miami Itinerary | Exploring South Beach

Miami, Florida, has always been a go-to vacation spot for people worldwide. It’s famous for its luxurious hotels, the lively nightlife of South Beach, and the vibrant culture of Little Havana. But Miami offers much more than that, including exceptional dining, thrilling sports activities, and exciting boating adventures. On this Miami to Miami itinerary, you will start in Miami, travel south to the Florida Keys, then return to Miami.

Day 1 | Miami

The starting point for your Miami to Miami itinerary is vibrant Miami. This city is modern and diverse. From sun-kissed South Beach to vibrant Little Havana, Miami offers something for everyone.

Spend some time exploring before heading out on your Miami to Miami itinerary. Here are a few ideas of what to see and do in and near Miami:

Venetian Pool, Coral Gables

Dive into the beautiful Venetian Pool in Coral Gables, a historic pool filled with spring water, coral caves, and lush landscapes. It was once a rock quarry, but now it is a unique spot to cool off and relax.

Art Deco District

Explore the vibrant Art Deco District by taking a walking tour. Admire the iconic Art Deco architecture and pastel-colored Art Deco buildings that make this area distinctive.

Ocean Drive

Cruise along Ocean Drive, a bustling street parallel to the beach. Enjoy the endless rows of palm trees and take in the vibrant atmosphere of Miami’s famous strip.

Bayside Market

Stroll through Bayside Marketplace, a waterfront shopping and entertainment complex. Enjoy shopping, dining, and live music with stunning views of Biscayne Bay.

Lincoln Road

Visit Lincoln Road, a pedestrian mall in the heart of South Beach. Explore shops, dine in trendy restaurants, and take in the palm-lined boulevard.

Calle Ocho

Immerse yourself in the culture of Little Havana by taking a trip to Miami’s Calle Ocho. Savor authentic Cuban cuisine, explore the art scene, and soak in the lively atmosphere.

Downtown Miami

Head to Downtown Miami for a taste of the city’s bustling core. Here, you’ll find skyscrapers that offer amazing views of the Miami skyline. It’s the perfect spot to take in the city’s modern charm. Visit the iconic Ball & Chain Club while in Miami.

Live Music

Enjoy live music at various venues throughout the city. Miami’s diverse music scene offers a range of genres. You’ll find everything from Latin beats to jazz, making it a great destination for music enthusiasts.

Wynwood Walls

Dive into the world of street art at Wynwood Walls. This outdoor museum is a feast for the eyes with colorful murals and graffiti.

Bayside Marketplace

Explore Bayside Marketplace once more for its combination of shopping and entertainment. Take a relaxing stroll along the bay and savor the picturesque views of Biscayne Bay as you enjoy your day.

Day 2 | Boca Chita and Elliott Key

On the second day of your Miami to Miami itinerary, you’ll set sail for the enchanting Boca Chita and Elliott Key. Both are within the breathtaking Biscayne National Park.

Boca Chita Island: Start your day on Boca Chita Island, a hidden gem that boasts pristine landscapes and a captivating history. Relax at this island paradise. Sink your toes in the soft sandy shores and swim in crystal-clear waters.

Snorkeling Paradise: Boca Chita’s surrounding waters are an underwater Eden. Don your snorkeling gear, and dip beneath the surface to uncover a mesmerizing world of colorful coral reefs.

Historic Lighthouse: One of the highlights of Boca Chita Island is its iconic lighthouse. Learn about its rich maritime past and even venture inside for a closer look. The lighthouse’s summit offers panoramic views of the surrounding seascape.

Elliott Key – After exploring Boca Chita’s underwater world and historical charm, continue your journey to Elliott Key. This is the largest island in the park.

Days 3 and 4 | Key Largo, Florida Keys

Your next stop is Key Largo, the first of the Florida Keys. This island is a haven for outdoor enthusiasts.

Underwater Wonderland: Key Largo’s underwater realm is a haven for snorkeling and diving enthusiasts. Put on your snorkel gear and explore the coral gardens.

Wildlife Encounters: Key Largo is not only about underwater marvels; it’s also a sanctuary for native wildlife. For nature lovers, the island is a perfect spot for birdwatching.

Fishing Adventures: Fishing enthusiasts will love Key Largo. Fish the inland waters or venture offshore for impressive sportfish.

Tranquil Retreat: Key Largo also offers moments of tranquil serenity. Sink your toes into the soft sands, savor the balmy breeze, and unwind with a good book.

Day 5 | John Pennekamp, Rodriguez Key

Day five transports you to the enchanting John Pennekamp Coral Reef State Park, the first undersea park in the United States. Encompassing approximately 70 nautical square miles, this protected marine wonderland invites you to explore. It is home to intricate coral reefs and vibrant marine ecosystems.

Indeed, you can go diving or snorkeling. Unveil the kaleidoscope of colors beneath the water’s surface. Or opt for a dry adventure aboard a glass-bottom boat tour to observe the mesmerizing marine world without getting wet.

Day 6 | Indian Key and Islamorada

Here, you can embark on a journey as you explore Indian Key. It’s a Historic State Park that once served as the first county seat for Dade County in 1836. This island also holds a rich history as a hub for cargo salvage businesses. In fact, there was once a town on the Key for the salvage workers and their families.

Fish, snorkel, picnic, and explore fascinating ruins. Following Indian Key, your journey continues to Islamorada.

Miami to Miami itinerary | Islamorada

Islamorada is the Sport Fishing Capital of the World. However, this tropical village has more to offer, such as eco-tours, dolphin encounters, luxury spas, and waterfront dining,

Eco-Tours: Eco-tours let you explore the unique ecosystem of the Florida Keys. Kayak through the serene backwaters or hike through lush forests. You’ll have opportunities to spot local birds, colorful butterflies, and perhaps even elusive wildlife, such as the Key Deer.

Dolphin Encounters: Adults and children will enjoy the Dolphin Research Center. Learn about these fascinating creatures and their natural habitat.

Luxury Spas: To complete your relaxation, rejuvenate your body and soul at the luxury spas in Islamorada. The Spa at Cheeca Lodge is among the best in the Florida Keys.

Waterfront Dining: There are many waterfront restaurants in the Florida Keys, and Islamorada has several. Savor fresh seafood and Caribbean-inspired dishes while taking in the scenery. The Islamorada Fish Company offers fantastic views of Florida Bay.

Day 7 | End of Your Miami to Miami Itinerary

Enjoy a day sailing back to Miami from the Florida Keys. End of your Miami to Miami itinerary until next time. Of course, you can stay in Miami and explore for additional days.

Best Time to Travel on a Miami to Miami Itinerary

The best time to embark on a Miami to Miami itinerary depends on your personal preferences and the type of experience you desire. Miami and the Florida Keys’ climate and tourism patterns vary yearly. So, consider these factors when planning your journey.

Here’s a breakdown of the different seasons and their pros and cons:

Winter (December to February):

Pros: Miami’s winter is pleasant, with warm temperatures and lower humidity. This season is ideal for those who want to escape colder climates.
Cons: It’s also the peak tourist season, so expect larger crowds and higher prices for hotels and activities. Be sure to book well in advance.

Spring (March to May):

Pros: Spring is a delightful time to visit. The weather remains pleasant, and the crowds begin to thin out as the peak season winds down. You can enjoy the beach, outdoor activities, and cultural events more easily.
Cons: While the weather is excellent, prices may still be relatively high, and it’s advisable to make reservations in advance for popular attractions.

Summer (June to August):

Pros: Summer is perfect if you love hot weather and love water activities. Miami’s beaches and waterways are inviting, and there are numerous summer events and festivals to enjoy.
Cons: The summer months are hot and humid, with occasional heavy rain and possible hurricanes. You may encounter more thunderstorms.

Fall (September to November):

Pros: Fall is an excellent time to visit Miami if you prefer lower prices and more manageable crowds. The weather remains warm and pleasant, making it suitable for outdoor activities.
Cons: The fall season overlaps with hurricane season, so there’s a slight risk of encountering adverse weather. But it’s good to know that hurricanes rarely happen in Miami.

Ultimately, the best time for your Miami to Miami itinerary depends on your priorities. Winter and spring are your best bets if you desire perfect weather and don’t mind the crowds. On the other hand, if you prefer cost-effective travel with a slight risk of rain, fall is a solid choice. Summer is perfect for those who love the sun and water activities but can tolerate the heat and occasional rain.

Best Boats for a Miami to Miami Itinerary

Selecting the best boat for a Miami to Miami itinerary is important to ensure a comfortable and safe journey. The choice of boat largely depends on your preferences, budget, and the size of your group.

Here are some of the best types of boats to consider for this adventure:

Sailing Catamarans: Sailing catamarans combine stability, space, and the thrill of sailing. They are excellent for a more relaxed and eco-friendly experience, offering spacious sunbathing and open-air dining decks. Catamarans are great for those who want to enjoy the sea breeze and take their time exploring the numerous anchorages and coves in the Florida Keys.

Power Catamarans: Power catamarans are famous for their speed, stability, and efficiency. They offer a luxurious and comfortable cruising experience with multiple cabins and all the necessary amenities. These boats are perfect for travelers who want to see more of the Florida Keys in less time.

Sailboats: For those who appreciate the grace and serenity of sailing, a sailboat offers a unique experience. These vessels are ideal for those who want to embrace the traditional art of sailing.

Motor Yachts: Motor yachts provide a blend of luxury and speed, allowing you to reach your destinations quickly while enjoying comfortable amenities.

We will work with you to find the best boat for your Miami to Miami itinerary. We’ll take into account your group size, what you like to do, and your budget when planning the trip.