Key West Itinerary for Adventurous Solo Travelers

key west itinerary solo travel

The Florida Keys are truly a world away and a visit to Key West is a must at least once in your life, even if you have to visit solo. I had an amazing visit to the Florida Keys this year and I can’t wait to share some of my favorite moments with you to help you plan your own solo Key West vacation.

I was hosted by the Florida Keys destination for my hotel stay, some excursions, and some meals. This post does contain some affiliate links that compensate me if a purchase is made. See full disclosures.

While I’m sharing things that work well for solo travelers visiting Key West, this Key West itinerary is still great for all types of travelers.

Where to Stay In Key West

key west itinerary barbary beach house

On my solo trip to Key West I stayed at the Barbary Beach House Key West. This property is absolutely divine and they greet you at check in with a yummy welcome cocktail!

The spacious apartment style suites are appointed with a clean modern decor but you still feel at home. The bathroom is massive and bright and the shower is roomy.

I loved the kitchenette with a sink and having the most adorable retro-chic refrigerator and microwave.

I had an ocean view from my patio that overlooked the beach across the street. They also provide a beach bag with beach towels.

key west itinerary

I loved the pool area and waterfall feature and it had late closing hours. Winning! There’s nothing worse than a gorgeous pool that closes early so you don’t get a chance to enjoy it if you’re out all day exploring. The outdoor patio of the onsite restaurant overlooks so it’s a fab choice to sit outside for your meals.

The grounds are lush and tropical with peaceful nooks and inviting hammocks and Adirondack chairs. It feels like a true escape.

The Barbary Beach House is a great escape that works well for solo travelers visiting Key West.

Adventurous Things to Do in Key West

  • Go Snorkeling. Snorkel in a sponge garden with marine biologists and observe and learn about dolphins in their behavior in the wild aboard a solar power & electric eco friendly catamaran with Honest Eco tours. It was a small group and having our crew in the water with us made it perfectly safe and fun to snorkel as a solo traveler.
key west itinerary

  • Take a sunset cruise. There are many tour operators offering a sunset cruise. I did the Champagne Cruise with Sebago. They offered an open bar and the sunset was spectacular. Even though I went solo, I made friends during the trip.
key west itinerary

  • Explore Fort Zachary Taylor Historic State Park. This park offers sunset views, a beach with lots of shaded areas to sit and picnic, and hiking trails around the fort. While I enjoyed my hike at the fort, I wish I had gotten there early enough to tour the fort. Be sure to check the hours when you plan your visit. Also expect to see giant iguanas on your hike. They are harmless but definitely a little intimidating if you aren’t expecting it. While the water at the beach was gorgeous, you should prepare for a very rocky shore and bottom. You absolutely need water shoes for this beach.
key west itinerary
  • Kayak at Smathers Beach. Smathers Beach is a public beach just across the street from the Barbary. They have chairs and umbrellas as well as kayaks and paddle boards for use by resort guests for free.
key west itinerary

What to Eat in Key West

There’s no shortage of amazing places to eat in Key West but here are my favorites from my Key West itinerary:

Half Shell Raw Bar

This dockside restaurant offers water views and casual atmosphere with amazing food. The lobster egg rolls are an absolute must when you visit the Half Shell Raw Bar. I also enjoyed the conch chowder. You really can’t go wrong with any of the seafood options but I especially enjoyed the trio with blackened shrimp, scallops, and Mahi. Make room for dessert because the bread pudding made with Cuban bread in a bourbon sauce is stupid good!

key west itinerary

Bo’s Fish Wagon

Don’t judge this shack by its rugged looks. You may question yourself as you venture into this make shift shanty of a restaurant in a parking lot but you’re making a decision your taste buds will thank you for. Bo’s Fish Wagon is a historic Key West gem that many probably walk right past. I only found it because the boat captain at Honest Eco gave me his local favorite recommendation. The conch fritters and cracked conch sandwich was perfection.

key west itinerary

Blue Heaven

key west itinerary

This slice of paradise is in the hustle and bustle of it all just 2 blocks from Duval Street. It’s a century-old building with a fun shaded courtyard and live music where roosters roam the grounds freely. I went for brunch and the meal was divine. They are known for the Benedict but I opted for a traditional breakfast of homemade pancakes and sausage and home fries and freshly made banana bread. It was a fantastic meal.

Additional Things to do in Key West:

  • The Key West Butterfly & Nature Conservatory
  • Mallory Square
  • The Southern Most Point photo op
  • Kermit’s Key Lime Pie

Adventurous Things to Do in Key West

Key West, Florida is a beautiful respite and worth planning a visit. Use this Key West Itinerary to plan the perfect visit for a solo traveler in Key West.

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1 Comment

  • Reply
    Tanya Raedeke
    April 8, 2022 at 12:44 pm

    We spent a week in Marathon, Florida but did not make it down to Key West. We plan to go back and go all the way to the tip next time!

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