Planning your next weekend escape? Key West, FL, is a destination that has something for everyone—beach lovers, adventure seekers, and history enthusiasts alike. This sun-soaked paradise at the southern tip of Florida combines vibrant culture, iconic landmarks, and breathtaking natural beauty. After my weekend exploring Key West, I’m convinced there’s no better spot for the ultimate Florida vacation.
Read on for my personal guide detailing how to get to Key West, my stay at the Southernmost Inn, iconic landmarks like the Hemingway House, delicious dining options, and even where you can swim with dolphins in the Key West area.
Getting to Key West
Key West is unique—not just because of its laid-back vibe but also because getting there is part of the adventure. Here are two options for planning your trip:
Traveling to Key West by Car
The drive to Key West is legendary, especially if you take the Overseas Highway. This 113-mile stretch of road bridges the sparkling waters of the Florida Keys, offering stunning views the entire way. For road trip lovers, this is an experience of a lifetime. Driving also gives you the flexibility to stop at other nearby islands like Islamorada or Marathon to soak in more of what the Keys have to offer.
Pro Tip: The Seven Mile Bridge, located about 50 miles from Key West, offers one of the best spots for photo ops. Plan time for a quick pit stop!
Getting to Key West by Plane
If you’re short on time, flying is the quickest way to get to Key West. Key West International Airport (EYW) is small but perfectly functional, with direct flights from cities like Miami, Fort Lauderdale, Atlanta, and more. As soon as you step off the plane, you’ll be just a short taxi ride away from downtown Key West.
Both travel options lead you straight to the wonders of Key West, but having a car can make exploring the full island experience more accessible.
Where I Stayed: Southernmost Inn Key West
For accommodations, I opted to stay at the Southernmost Inn Key West, a charming adults-only boutique hotel nestled in a prime location. The vibe here is quintessential Key West—bright colors, plenty of sunshine, and an inviting atmosphere.
Highlights of the Southernmost Inn
- Cozy Rooms: The rooms were clean, comfortable, and tastefully designed, perfect for a relaxing getaway.
- Two Pools & a Hot Tub: Great for unwinding after a long day of sightseeing.
- Proximity to Attractions: Located just a short walk from iconic landmarks like Southernmost Point and Duval Street.
- The Southernmost Inn is located at 525 United Street, Key West, FL 33040. For reservations or inquiries, you can call 888-525-0037
- For Rates and Hotel Information <Southernmost Inn – Click Here >
If you’re looking for convenience and character, this hotel is a prime choice for your Key West vacation.
Unforgettable Adventures in Key West: Exploring, Dining, and Island Fun
Key West is packed with unique experiences. Each adventure offered something completely different, from history to wildlife to mouthwatering food.
1. Southernmost Point Buoy
You can’t visit Key West without taking a photo at the Southernmost Point Buoy, one of the island’s most famous landmarks. Located at the corner of South Street and Whitehead Street, the buoy represents the southernmost point of the continental United States. The line for photos can get long, but it’s worth a stop to capture this iconic moment. This located at Whitehead Street & South Street, Key West, FL 33040. The crowds get huge here, so get there early if you can.
2. The Hemingway House and Museum
Literature buffs, rejoice! A visit to Ernest Hemingway’s former home is a must. The Hemingway House and Museum gave me a glimpse into the life of the literary legend, complete with six-toed cats wandering the property. Don’t miss the writing studio—it’s a fascinating peek into where Hemingway penned some of his most famous works. The address is 907 Whitehead Street, Key West, FL 33040 and walking distance from the Southernmost Bouy. Here is ticket information for Hemingway House.
3. Dolphin Safari Key
One of the top highlights of my trip was an unforgettable dolphin safari excursion. Seeing these incredible creatures playful and free in their natural habitat was magical. Key West offers several dolphin tours, and I highly recommend adding one to your itinerary for a day filled with wonder and pure joy. To book Dolphin Safari, click here.
For those specifically interested in swimming with dolphins, consider heading slightly north to the Dolphin Swim in Duck Key, about an hour and twenty mintues from Key West. This facility focuses on ethical, interactive dolphin experiences, letting you swim alongside these gentle creatures in the most respectful way possible. Swimming with dolphins in the Key West area is an experience like no other!
Savoring the Flavors of Key West: A Culinary Adventure
Key West offers a culinary scene as colorful as its sunsets. Two spots thoroughly impressed me during my visit.
DJ Clam Shack
If you’re craving fresh, local seafood, this spot is non-negotiable. The lobster rolls here were loaded with fresh chunks of lobster (and no filler!), and the laid-back atmosphere added to the experience. The place is small in the front but walk to the back and there is more seating back there. There usually is a line at DJ’s but it is worth the wait. The address is 629 Duval Street, Key West, FL 33040
El Siboney Cuban Restaurant
Dive into bold, authentic Cuban flavors at El Siboney. The roast pork with plantains stole the show, but the black beans and rice were the perfect accompaniment. It’s hearty, comforting, and a must-try for fans of Cuban cuisine. It is reasonable priced, so this place is great for large parties and those on a budget. El Siboney Restaurant is located at 900 Catherine Street, Key West, FL 33040. You can contact them by phone at (305) 296-4184.
Other Suggested Key West Activities
Want to extend your trip? Here are 4 more Key West activities to consider adding to your itinerary:
- Explore Fort Zachary Taylor Historic State Park – Beautiful beaches, shaded picnic areas, and a bit of history combined.
- Snorkeling at Dry Tortugas National Park – Adventure awaits in these pristine waters filled with coral reefs and marine life.
- Sunset Sailing – Hop aboard a boat and witness one of Key West’s legendary sunsets—the ultimate way to end your day.
- Duval Street Bar Hopping – From lively bars to quaint shops, there’s plenty to explore on this iconic street.
Other Recommended Key West Hotels
If the Southernmost Inn doesn’t suit your style or availability, here are four other great options to consider:
- Casa Marina Key West – Luxurious and historic, located right by the water.
- The Marker Key West Harbor Resort – Close to the marina, this modern hotel boasts stylish rooms and fantastic amenities.
- Eden House – A cozy, affordable option with a relaxing garden area.
- Pier House Resort & Spa – Perfect for those seeking waterfront views and an upscale experience.
Why Choose Key West for Your Next Vacation?
A Key West vacation is about more than just beautiful beaches—although the beaches are incredible. The island captures the imagination with its rich history, lively culture, and endless opportunities for adventure and relaxation.
Whether you’re discovering Hemingway’s stories, feasting on fresh seafood, or fulfilling your dream to swim with dolphins in the Key West area, this sunny paradise offers something special for every kind of traveler.
Start crafting your perfect weekend getaway itinerary now. Don’t wait—Key West is calling!
