Ready to Embark on Your Next Adventure?
Whether you’re a seasoned traveler or planning your very first trip, a well-crafted itinerary can make all the difference. An unforgettable journey always starts with a thoughtful plan.
In this post, we’ll explore inspiring itinerary ideas that might spark your wanderlust and have you packing your bags in no time.
Picture this: you’re cruising down a breathtaking coastal road, the ocean stretching endlessly on one side and dramatic cliffs rising on the other. Along the way, you’ll discover hidden coves, charming beach towns, and local spots that turn a simple drive into a memory you’ll never forget.
Suggested Route: US Route 1 from Miami to Key West
- Day 1: Miami
Start your journey in Miami. Start your day early with a walk along Ocean Drive and watch the sunrise over South Beach. One of the most iconic Miami experiences! Next, enjoy a leisurely breakfast at Big Pink, a casual spot known for generous portions and authentic Miami vibes! Perfect spot to fuel up for some exploring! Next, head to the Wynwood Arts District to explore the many galleries, shops and colorful street murals. Grab a casual bite for lunch while soaking in the creative atmosphere! Head over to Little Havana and walk Calle Ocho where you can grab a Cuban coffee, relax and sightsee in Domino Park and enjoy the music filled vibe! As the evening rolls around, venture to Bayside Marketplace or Brickell Key where you can stroll the waterfront and watch the sunset over Biscayne Baye. Dinner at Kiki on the River or Joe’s Stone Crab are both highly recommended! No visit to South Beach is complete without experiencing the nightlife that Miami is famous for! Grab rooftop drinks at Sugar and enjoy the panoramic view then go dancing at the many clubs in South Beach for the full Miami experience!
- Day 2: Islamorada
Head down US 1 to Islamorada. Book a half-day charter to explore Alligator Reef, one of the most famous reefs in the Keys, full of tropical fish and clear turquoise water. After a fun filled morning, head over to Lorelie Restaurant and Cabana Bar for a bite to eat. This waterfront spot is known for fresh seafood, island cocktails and a laid-back tiki vibe. After, head to Robbie’s Marina to feed the giant tarpon right off the dock and spend some time browsing the local art stalls and shops! Finish the day with a breathtaking sunset cruise in the Gulf as the sun dips below the horizon. If you still have energy, end the day with dinner at Lazy Days or Islamorada Brewery & Distillery and end the day with a local beer, craft cocktail or slice of Key lime pie.
- Day 3: Marathon and Big Pine Key, end the day in Key West
Head out of Islamorada after enjoying a sunrise at Anne’s beach and breakfast at the Midway Cafe & Coffee Bar – a local favorite offering fresh pastries, hearty breakfasts and excellent coffee options. A must do for any trip to the Keys is the Turtle Hospital in Marathon. Located halfway between Islamorada and Key West, this educational, heartwarming adventure offers short tours where you can see rescued sea turtles up close and learn about their rehabilitation. Before continuing south, grab the fixings for a picnic at the Key Fisheries, famous for their lobster Reuben where the staff is happy to pack up to go meals! Enjoy your lunch at Bahia Honda State Park in Big Pine Key. Known for some of the best beaches in the Keys, plus views of the old Bahia Honda Rail Bridge. This is the perfect spot to swim, snorkel or relax on the sand! After a relaxing afternoon enjoying the scenery and beaches, continue the journey to your final destination, Key West!
- Day 4-6: Key West
Start your first day with breakfast at the iconic Blue Heaven. A must-visit spot for pancakes, delicious beverages and coffee and enjoy the roosters roaming around within a tropical courtyard vibe! Head over after filling up to the Southernmost Point and grab a picture at the buoy. Tip: go early to avoid long waiting lines! Next, check out the many shops, galleries, bars and eateries along the famous Duval Street in the heart of Old Town. For lunch, check out the Conch Republic Seafood Company where you can enjoy fresh seafood and dockside views in the Historic Seaport. Finish your afternoon at the Key West Lighthouse & Keeper’s Quarters where it is worth the climb to enjoy panoramic views of the beautiful island! A must do in the evening is the Sunset Celebration at Mallory Square which happens daily. Here you will find street performers, food stalls and a lively crowd gathered to watch the sun dip below the Gulf. Finish your day at the El Meson de Pepe where you can enjoy authentic Cuban food and live music!
Begin Day 2 with breakfast at Cuban Coffee Queen where you can grab a coffee and pressed sandwich to go. Book a half-day trip to explore the coral reefs, sandbars and marine life that make Key West famous! Fury Water Adventures and Honest Eco are popular, reputable tour providers. Upon your return to land, head to Schooner Wharf Bar for lunch. This spot is a rustic, open air restaurant near the marina. To end the day, head to Fort Zachary Taylor Historic State Park where you can swim, snorkel or just relax at one of the best beaches in Key West. For dinner, enjoy the upscale seafood options with gorgeous views of the Marina at A & B Lobster House. Before heading back to rest, check out a few of the lively bars that make Key West famous! Enjoy live music and refreshing drinks at Irish Kevin’s, Green Parrot, Captain Tony’s or my personal favorite, Hog’s Breath!
Day 3 is all about relaxation and nature. Begin with a leisurely brunch on Duval at Bagatelle where you can enjoy one of their fabulous mimosas. Then head on over to the Key West Butterfly & Nature Conservatory where you can walk among the colorful butterflies, flamingos and the beautiful tropical flower landscape. You can’t visit Key West without a tour of the mangroves, I recommend either a kayak or paddleboard tour. This is a peaceful way to see local wildlife up close and personal. Start your afternoon with a bite at Eaton Street Seafood Market where you can order a fresh catch or a famous lobster roll, all their seafood is locally sourced from native fishermen. After lunch, stroll over to the Truman Little White House where you can explore President Truman’s historic vacation retreat. The rest of your afternoon can be spent shopping in the many unique galleries and shops that Key West has to offer or enjoy your hotel’s pool! A great way to end your last evening in Key West is on a sunset sail aboard a catamaran cruise-many include champagne, live music or food! Finish the day at Louie’s Backyard-iconic Key West dining with unforgettable oceanfront views!
- Day 7: Head back to Miami for your journey home!
Crafting Your Own Unforgettable Itinerary
Now that you’ve explored different itinerary ideas, it’s time to create your own unforgettable adventure! Whether you’re dreaming of tranquil beaches, bustling cities, or off-the-beaten-path escapes, a well-crafted itinerary will help make your journey smooth and memorable.
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Travel by Kelly 