Key West Trip Planner Are you planning a trip to Key West? Start planning your itinerary on GAFFL. Here’s how:

Pick A Trip Type

Click on “Start A Trip” and pick your Trip Type

Choose Your Destination

Choose Key West as your destination and select how long your trip in Key West will be

Input Your Trip Details

Create a title for your trip and describe it by including things you will do and places you will visit in Key West

Start Your Trip

Select a meet up point and if other users on GAFFL like your trip itinerary, they can request to connect and meet up with you in Key West
Kevin
Bicycle Florida Keys
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Join Kevin for this road trip to Key West
Key West
Feb 1, 2026 - Feb 21, 2026 (Flexible)
I'll pick you up. Drive to Florida Keys and ride bikes and explore!!!! Very simple!!
Anthony
Key West music tour
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Explore Key West with Anthony
Key West
Feb 22, 2026 - Feb 26, 2026
Going to Key West to see a musician friend of mine and lots of other venues.
Graham
Planning Vacation
Explore Florida Keys with Graham
Florida Keys
May 31, 2026 - Jun 14, 2026 (Flexible)
Open for dates and places. Just need to go out and do something and explore. 

Andrew
Andrew
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Key West
I live in a beautiful small town and would love to show you around or give you advice on where to...
Scotty
Scotty
Connect with Scotty to meet up for coffee or drink
Connect and stay in Scotty's home
Key West, FL 33040, USA
Florida Keys are wonderful any time of the year.

Alexis
Alexis
Hollywood
Female, Age 29
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Hello! I'm Alexis, I'm from Olympia, WA (right outside of Seattle). I'm currently a Miami based f...
Kenton
Kenton
South Miami
Male, Age 30
Verified by
Hey, I'm a 28-year-old traveler based in New Britain, Connecticut. 🌍 I'm all about exploring new ...
Arianna
Arianna
Orlando
Female, Age 27
Verified by
Sold the city life and built out my jeep. Going for the long haul with my girlfriend from Miami t...
Vivek
Vivek
Vero Beach
Male, Age 42
Verified by
Newbie solo traveller... Want to start knocking off places off my bucket list one country at a ti...
Cari
Cari
Sarasota
Female, Age 33
Verified by
Hi, im Cari ☺️ I travel to different cities in the US currently and I run half marathons 🏃‍♀️💨 Th...
Gina
Gina
Tampa
Female, Age 54
Verified by
I have a love of water, fishing, swimming, boating, outdoors, architecture, history, museums. Re...
Skip
Skip
South Miami
Male, Age 61
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I'm a film & video producer formally from Angeles, living in Belize for the last 18 years. where ...
Loretta
Loretta
Cancún
Female, Age 37
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Scuba diving instructor from Singapore, currently in New Zealand on a working holiday. Looking fo...

FAQ

Why is GAFFL the best website/app for planning a trip to Key West ?

It is completely free to start planning your trip to Key West on GAFFL. You can keep all of your trip details in one place, including things you’ll do, places you’ll visit, where you’ll stay, and when you’ll fly. Also, after you’ve planned your trip, GAFFL helps you connect with other like-minded travelers planning a similar trip at the same time as you.

How do I plan a trip to explore different cities on GAFFL?

Planning a trip to explore cities on GAFFL is entirely free and very easy. Click on ‘Start A Trip’ and select ‘Explore Cities’ as your trip type. Then after providing your current location, select the city you want to plan your trip to. Create a title for your city exploration trip and describe things you’ll want to do and places you will want to visit. Then select a public place as a meetup point before or during your trip. You can also book hotels in that city and flights to that city and keep the information stored within your trip itinerary. Someone planning a similar trip can request to connect, meet up, share costs, and explore the city with you.

How can I plan a road trip to Key West on GAFFL?

Planning a road trip to Key West is completely free on GAFFL. Click on ‘Start A Trip’ and select ‘Road Trip’ as your trip type. Then choose where you’re planning to start your road trip and where you want to finish it. Create a title for your road trip and describe things you’ll do and places you want to visit while on the road. Then select a public place as a meetup point before or during your trip. Someone planning a similar road trip can request to connect with and together you can split costs for things like rental cars and lodging.

How do I plan a backpacking or hiking trip on GAFFL?

Planning a backpacking/hiking trip is absolutely free on GAFFL. Click on ‘Start A Trip’ and select ‘Adventure Travel’ as your trip type. Then choose your specific destination or a hiking trail and select the duration of your trip. Name your upcoming backpacking/hiking trip with a title and let others know the details of the trip in the description. Then select a meetup point in a public place. If other adventurers like your trip, they can request to connect and meetup with you.
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