Curator’s statement
This was my first time visiting Key West, a destination that had long been on my list. I love that it’s part of the continental US, yet feels like your own little island tucked away in the Caribbean. We spent a holiday weekend wandering the streets, indulging in local favorites, and soaking up the sun before setting off on the iconic Overseas Highway (US-1), a stunning 100+ mile drive over turquoise waters that connects the Florida Keys. This destination guide highlights the stops I personally saved along the way, along with tips for having the best experience, plus a few extra road trip favorites from Marathon, Islamorada, and Key Largo waiting for you at the end!
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Things to do in Key West
Final glimpse of the sun as it sets from Sunset Pier
Watch the sunset: You don’t want to miss sunset in the southernmost city of the continental United States, it is also a true Key West ritual. I recommend grabbing a spot at Sunset Pier or Sunset Tiki Bar for the best waterfront views and a lively atmosphere! Tip: Arrive 30–45 minutes before sunset to secure a seat along the bar at Sunset Pier, as seating is first-come, first-served.
Walk Duval Street: In my opinion, the best way to experience a new city is by walking and allowing yourself to get a little lost. Duval Street is the heart of Key West, offering the perfect starting point to wander in and out of shops, bars, and restaurants while exploring the surrounding side streets. The daytime vibe is relaxed and easygoing, while evenings are noticeably more lively and social.
Smathers Beach: One of Key West’s most popular beaches, it is ideal for lounging, swimming, and soaking up the sun. It’s also a hub for water sports and beachside walks with ocean views. Tip: Visit earlier in the day for calmer conditions and fewer crowds!
Visit Mile Marker 0 (Route 1): Stop by Mile Marker 0 and the nearby Southernmost Point to mark the official end of US Route 1. It’s a quick but iconic photo stop—especially meaningful if you’ve completed a long drive from outside of the Florida Keys!
Snorkeling: Key West offers great snorkeling both onshore and offshore. Snorkel directly from Smathers or Higgs Beach, or book a boat excursion to Dry Tortugas National Park or Sand Key Lighthouse for clearer water and vibrant marine life.
Key West Tropical Forest & Botanical Garden (Fort West Martello): A peaceful garden that offers a break from the bustle of downtown. Wander among lush tropical plants, shaded walking paths, and historic fort ruins scattered throughout the grounds. I would recommend stopping by Uva Wine Shop to pick up a few snacks and a bottle of wine for a relaxing picnic.
Places to eat & drink in Key West
Breakfast & a Bloody at Blue Heaven
Blue Heaven: Famous for breakfast with roosters roaming through the outdoor seating, Blue Heaven offers a colorful and easygoing island vibe. Don’t skip the banana pancake. It was truly unforgettable.
Mary Ellen’s Bar & Restaurant: A great dive-style spot, especially for sports lovers, with plenty of TVs! Must-try: The frozen Irish coffee topped with cookie crumbles.
General Horseplay: A playful nod to Bill Murray, this stylish cocktail bar serves creative drinks and small bites. Think of it as the speakeasy of the Keys, and live music on select nights
Little Pearl: Think date night... fresh seafood, a martini, and intimate ambiance. Ideal for a more elevated dining experience.
Durty Harry’s: We stumbled upon this small, tiki-style outdoor bar while walking down Duval Street. You’ll find locals and first-time visitors shoulder to shoulder at the bar, making it a great spot for casual drinks and people-watching.
Honorable Mentions:
Cuban Coffee Queen
Square Grouper Key West
Better Than Sex Dessert Restaurant
Need to know
As promised, my favorite stops along Route 1 on our way up to Key Largo!
Mangrove Mama’s Restaurant & Bar (Summerland Key)
Fred the Tree: You can not stop but give him a wave as you drive over the famous Seven Mile Bridge.
The Island Fish Co. Restaurant & Tiki Bar (Marathon)
Georgie’s Coffee Shop (Marathon)
Marker 88 (Islamorada)
Cafe Moka (Tavernier
Italian Food Company (Key Largo)
Snooks Bayside Restaurant & Tiki Bar (Key Largo)
Key West lived up to my expectations in the best way! It is easygoing, vibrant streets, and reminds you to slow down and enjoy the little moments. I hope this guide helps you plan thoughtfully, travel with ease, and experience the island the same way I did: with curiosity, flexibility, and plenty of time to enjoy the journey as much as the destination!
Travel Advisor
Taylor French
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For more inspiration and insider recommendations, visit our Key West page.