Skip to content
AIRBNB EXPERIENCES

Unique things to do in Key West

Book unforgettable activities hosted by locals on Airbnb.

Top-rated activities

Biologist Guided Dolphin Watch & Snorkel
You will meet me at my electric catamaran, Squid, under my HONEST ECO sign. We will depart from the dock located at the Historic Seaport. We will head out on the water to an area which provides a year round home for about 200 wild Bottlenose Dolphins. This is my moment to share the wonders of these marine mammals with you, while always operating my vessel in a manner that is safe and respectful of the dolphins and their need for space. With the right know-how I can usually find dolphins in under an hour and in calm waters. After observing the dolphins many different behaviors from the boat we will head to one of my favorite spots to snorkel with sponges, coral heads or a patch reef. I will take you to the best place with the best visibility that day. My mate will be your guide, leading you around a calm snorkeling spot and point out animals that make our ecosystem unique and answer any questions that you have. Check in at the HONEST ECO boat Squid. If you are driving down the keys the day of the trip just remember it is a road that is only one way in and one way out. One accident on that road can hold you up for the day. We do not issue refunds if you miss the boat. It is best to ride a bike in Key West or take a cab. Lastly, the marina parking lot is around $20 to $30 for the day. It can fill up in the afternoons please plan accordingly! Thank you!
Snorkel, Kayak, Dolphins, Sail, & Organic Lunch- Six hours
Check in is at the boat at 9:10 am This is a 6 hour trip on the water! We will begin this HONEST ECO experience on a spacious 42' sailing catamaran. With 1,092 Square Feet of deck space, plenty of room to relax. We will depart from the dock located at the Historic Seaport. Sail out to a mangrove island that we can only reach in a shallow draft boat. You will learn about our Key West ecosystem as you Kayak through Mangrove Islands. We will explore the distinct habitats of the Key West National Wildlife Refuge and learn about our diverse animals and plants We will head to another one of my favorite spots to snorkel on the reef, coral heads or a sponge garden. I will take you to the best spot with the best visibility that day. My mate will be your guide, leading you around a calm snorkeling spot. I will point out animals that make our ecosystem unique and answer any questions. I will provide a lunch spread from our favorite organic cafe Date and Thyme. If you are driving down the keys the day of the trip just remember it is a road that is only one way in and one way out. One accident on that road can hold you up for the day. I can not issue refunds if you miss the boat. It is best to ride a bike in Key West or take a cab. The marinas parking lot is around $20 to $30 for the day. It can fill up in the afternoons please plan accordingly! Thank you!
Sunset Sail and Dolphin Search aboard a Sailing Catamaran
Boarding is 20 minutes before we depart. You will meet me at HONEST ECO 42' Sailing Catamaran. I am docked by the Dock Masters Office at the Historic Seaport Key West Bight Marina. Enjoy a beautiful Key West sunset while sailing on a spacious 42' Sailing Catamaran. It has over 1000 square feet of deck space. I will provide light snacks, water and a cooler. It is BYOB (Bring your own Adult Beverages) We will be searching for dolphins as we enjoy the sail. We watch dolphins by day so we are pretty good at finding them. If you are driving down the keys the day of the trip just remember it is a road that is only one way in and one way out. One accident on that road can hold you up for the day. I can not issue refunds if you miss the boat. It is best to ride a bike in Key West or take a cab. The marinas parking lot is around $20 to $30 for the day. It can fill up in the afternoons please plan accordingly! Thank you!
Mangrove Maze Tour
Welcome to Blue Moon Kayak Key West! Once you are checked in each person will get instruction on how to kayak and we will go over the layout of our route for the experience. Once we are ready we will launch from Floating docks. Our Kayaks are very stable with nice back rests to support you through out the trip. We cross Cow Key Channel and go West into the Center of Key West where we will show you how to navigate the Mangrove Mazes into the Salt ponds. All the while you will get to see Iguanas, Parrot Fish, Barracuda, Small Sharks, Night Crown Herons, Great Blue Herons, White Herons, Green Herons and more! Learn about the history and culture of Key West while we take in all the nature. We will end at our starting location. Other things to note: If there are high winds or Lightning the trip may be delayed or rescheduled. Your guide will determine safety for the trip. We will still go if there is just rain. We also provide alternate routes along the North side of Stock Island if necessary to avoid the elements.
Sunset Sail on Historic Schooner Yacht in Key West
Experience true classic sailing on Key West’s most elegant and historic schooner for a gorgeous open sunset sail. Our sunset sail includes complimentary wine and beer with optional onboard premium beverage upgrade. We board 15min prior to departure from the Perry Hotel and Marina 7009 Shrimp Rd. Key West for a 2hr sunset trip which allows guests to help raise sail, take a turn at the helm or relax and enjoy your trip. Once off the dock, we motor out of the harbor, point the ship into the wind and set sails. Our guests are welcome to lend a hand or sit back and take in the experience of a traditional classic yacht from the best view! Enjoy as the schooner turns with the wind and the engine is turned off! You're sailing now! Once the sails are up and the crew has adjusted them to the wind, your talented crew will serve up some delicious house wine that even has the When And If on the logo! We invite you to ask any questions about how the boat operates and what it takes to sail a Schooner. Each one of our crew loves to share their stories of what brought them to the sea. The ship also has her own unique history as the once private yacht built in 1939 for General George Patton, we love to share all that we know about the vessel, as well as local knowledge of Key West waters and ocean-life. Sailing on the Schooner When And If is an experience not to be forgotten!

Discover Key West by the sea

Local Musician playing live on a spacious sailing catamarn
Come sail with me while we enjoy a Key West Sunset Sail on a 42 foot sailing catamaran with over 1000 sq ft of deck space to spread out and relax. This sunset sail has a unique local musical touch. Any town, as it welcomes and caters to its visitors can wind up with homogenized offerings in order to appeal to most people. We can see this at restaurants with their conch fritters and mahi sandwiches, bars with their cover bands, and booze cruise sunset sails with their jimmy Buffet covers. And don’t get us wrong, None of these things are bad! But sometimes you want to take a risk and see if you can find the reward of a real, unique experience! To kick off this trip, we will be giving over the creative reigns to Turner Harrison. Turner is a professional musician in town and is also responsible for all designs, scores, videos and basically all that is visually and audibly appealing.
The Rum Runner, the Bar Boat of Key West
The waters of downtown Key West have great history surrounding them. You can still hear echoes of past parties and festivals on our turquoise waters. The Rum Runner shares these stories for you when you ask, or just enjoy the views without any work. On the Rum Runner you depart from the only downtown public beach. Simonton Beach. Our great departure location offers a beach, lounge chair, and a awesome Restaurant and Bar. The Rum Runner allows you to bring Key West with you on the water. A crazy local captain with even crazier stories if you ask, all true by the way. No work with bar seats on the water, built in coolers to bring your ice cold drinks with you. Music, lights, waters stops during the day trips. On the Crystal clear waters you will see downtown, historic harbor, great sunset viewing areas, Mallary Square, Sunset Key, the dolphin playground, and a 120 year old shipwreck next to Christmas Tree Island. You can see anything on our waters and on Christmas Tree. Meet the local wildlife and not just the people. The Rum Runner is your Key West Bar Boat Boat or (party boat). Very safe, very stable and with room to walk around, dance to your favorite music, or enjoy a drink and even a sunset. The Rum Runner is your Good Times and Tan lines in Key West
Reef Snorkel & Sunset Sail
We will snorkel the reef and enjoy the sunset while sailing on a spacious and fun sailing catamaran. You will also get to enjoy fresh organic fruit, veggies and hummus from our favorite local organic cafe, Date and Thyme. Florida’s Barrier Reef is right off the coast of Key West. We only provide this trip during a limited time, June through September, because we want to snorkel the reef when the weather is just right. Explore the wondrous wildlife of the reef with one of our biologists. It truly is one of the most beautiful places you need to see while in the keys. Sailing, the original form of renewable energy transportation! I am on a mission to spread the value of conservation and I think amazing nature experiences with a knowledgeable biologist is the best way to do that! But sometimes all you need to do to appreciate nature is go sailing and watch a sunset! Other things to note Meet at the boat 15 minutes before departure. Call or text my wife Jen with any questions. 305-294-6306.
Sunset Kayak Cruise on the Gulf
Blue Moon Kayak Key West is the only Kayak Company on the North Side of Stock Island in Key West. This gives us a unique location for a Sunset experience. Meet me at our Sunset Marina Ship Store at our launch time (typically 45 min- 1hr before sunset). Please note the marina has no guest parking, so please take an uber or rideshare. If you have a car, parking is available on College Rd. You will have a chance to use the restroom before we hit the water. Once we are on the water we will paddle East towards Key Haven and turn around to watch the sunset over Fleming Key. We may also here the cruise ships horns blow as they leave port too! Feel Free to bring a small cooler if you want to have a drink or snack while we watch the sun dip down. As the sun goes down we will start to look in the water for our glowing jellies! When we get back it will be dark, but we will have lights on our kayaks for a safe journey back to the Marina. This is our easiest and shortest tour we offer in Key West and is great for all ages. Water is typically only 2-4 feet deep depending on the tides. Other things to note Kayaking is a watersport! So please come prepared to get wet. You may leave your shoes on our dock, but we have no secure place for valuables or gifts you may have bought throughout the day. Please leave them at home/in the hotel. We will have a dry bags for small items (keys, wallets, phones).
Private sunset cruise, harbor tour and wildlife viewing
Jump on board our Nautic Star Legacy to view one of nature's grandest spectacles, the famous Key West sun setting over our crystal clear turquoise waters. First we will cruise around the island, viewing several points of interest, the Historical Key West harbor, various wildlife and some beautiful islands. We will listen to your choice of music and enjoy some cold beverages. Once the sun starts to set the and magnificent colors start to emerge we will go to our prime sunset viewing location. Enjoy the boat ride back to the dock as your captain continues to share stories with you. Please note that this is a private tour! The price for the tour is $395 for up to 6 passengers.

Activities near top attractions

Photo of Fort Zachary Taylor Historic State Park
Fort Zachary Taylor Historic State Park47 locals recommend
Photo of Harry S. Truman Little White House
Harry S. Truman Little White House27 locals recommend
Photo of Sloppy Joe's Bar
Sloppy Joe's Bar45 locals recommend
Photo of Southernmost Point of the Continental US
Southernmost Point of the Continental US64 locals recommend
Photo of Key West Aquarium
Key West Aquarium27 locals recommend
Photo of Blue Heaven
Blue Heaven53 locals recommend

All activities near Key West

Biologist Guided Dolphin Watch & Snorkel
You will meet me at my electric catamaran, Squid, under my HONEST ECO sign. We will depart from the dock located at the Historic Seaport. We will head out on the water to an area which provides a year round home for about 200 wild Bottlenose Dolphins. This is my moment to share the wonders of these marine mammals with you, while always operating my vessel in a manner that is safe and respectful of the dolphins and their need for space. With the right know-how I can usually find dolphins in under an hour and in calm waters. After observing the dolphins many different behaviors from the boat we will head to one of my favorite spots to snorkel with sponges, coral heads or a patch reef. I will take you to the best place with the best visibility that day. My mate will be your guide, leading you around a calm snorkeling spot and point out animals that make our ecosystem unique and answer any questions that you have. Check in at the HONEST ECO boat Squid. If you are driving down the keys the day of the trip just remember it is a road that is only one way in and one way out. One accident on that road can hold you up for the day. We do not issue refunds if you miss the boat. It is best to ride a bike in Key West or take a cab. Lastly, the marina parking lot is around $20 to $30 for the day. It can fill up in the afternoons please plan accordingly! Thank you!
Snorkel, Kayak, Dolphins, Sail, & Organic Lunch- Six hours
Check in is at the boat at 9:10 am This is a 6 hour trip on the water! We will begin this HONEST ECO experience on a spacious 42' sailing catamaran. With 1,092 Square Feet of deck space, plenty of room to relax. We will depart from the dock located at the Historic Seaport. Sail out to a mangrove island that we can only reach in a shallow draft boat. You will learn about our Key West ecosystem as you Kayak through Mangrove Islands. We will explore the distinct habitats of the Key West National Wildlife Refuge and learn about our diverse animals and plants We will head to another one of my favorite spots to snorkel on the reef, coral heads or a sponge garden. I will take you to the best spot with the best visibility that day. My mate will be your guide, leading you around a calm snorkeling spot. I will point out animals that make our ecosystem unique and answer any questions. I will provide a lunch spread from our favorite organic cafe Date and Thyme. If you are driving down the keys the day of the trip just remember it is a road that is only one way in and one way out. One accident on that road can hold you up for the day. I can not issue refunds if you miss the boat. It is best to ride a bike in Key West or take a cab. The marinas parking lot is around $20 to $30 for the day. It can fill up in the afternoons please plan accordingly! Thank you!
Sunset Sail and Dolphin Search aboard a Sailing Catamaran
Boarding is 20 minutes before we depart. You will meet me at HONEST ECO 42' Sailing Catamaran. I am docked by the Dock Masters Office at the Historic Seaport Key West Bight Marina. Enjoy a beautiful Key West sunset while sailing on a spacious 42' Sailing Catamaran. It has over 1000 square feet of deck space. I will provide light snacks, water and a cooler. It is BYOB (Bring your own Adult Beverages) We will be searching for dolphins as we enjoy the sail. We watch dolphins by day so we are pretty good at finding them. If you are driving down the keys the day of the trip just remember it is a road that is only one way in and one way out. One accident on that road can hold you up for the day. I can not issue refunds if you miss the boat. It is best to ride a bike in Key West or take a cab. The marinas parking lot is around $20 to $30 for the day. It can fill up in the afternoons please plan accordingly! Thank you!
Whiskey's Welcome Walkabout
Your DOTCOM info tour to help yawl get to know Key West. Nothing says vacation like starting a tour with a cocktail at a hidden gem in town. This hour long stroll will take you along the longest mile in the world -- from the Atlantic Ocean to the Gulf of Mexico. Can do early in the morning or if you dare late at night.... . We will go on and off Duvall St as I point out cool places to explore and give you ideas to how and maximize your time on the island: hint that the biggest is making sure you rest, relax, and enjoy the tropics. We may even stop at some spots that aren't the generic trip advisor recommended places. You will see and learn about the Historic Seaport, Mallory Square, and the charm of old town Key West. This is a small group to private tour experience so that it is personalized to you and your questions. With my knowledge of the island and contacts you can get some unique opportunities by walking with Whiskey Rick!!
Key Whiskey Trail
We are going to start our whiskey tour off with a rum... yes a rum... if you are a Whiskey lover this tour is for you. If you are a rum lover, wine, ice cream, craft beer, Key Lime pie, or any other special item please book this as a private tour and we will cater to you area of interest. We will stroll around the seaport and old town and I will take you to hidden gems off the beaten path. You will be welcome to get a beverage to go from any or all the of the places we visit (with that said based on current work force situation in this town I can't guarantee places will be open everyday and if too crowded will respect staff and not add more business than they can handle with my tour and timing). Stories will be shared of the history of the island and places wreckers, shrimpers, poets, authors, musicians, and others hung out. I have access to a couple private patio's and we will try to enjoy a sampling of whiskey or other special request item in that local. We will end the tour on Duval street and you will be steps from the infamous bars that made this town legend -- with you hearing the back story on them and your ability to then go and enjoy.
Local Musician playing live on a spacious sailing catamarn
Come sail with me while we enjoy a Key West Sunset Sail on a 42 foot sailing catamaran with over 1000 sq ft of deck space to spread out and relax. This sunset sail has a unique local musical touch. Any town, as it welcomes and caters to its visitors can wind up with homogenized offerings in order to appeal to most people. We can see this at restaurants with their conch fritters and mahi sandwiches, bars with their cover bands, and booze cruise sunset sails with their jimmy Buffet covers. And don’t get us wrong, None of these things are bad! But sometimes you want to take a risk and see if you can find the reward of a real, unique experience! To kick off this trip, we will be giving over the creative reigns to Turner Harrison. Turner is a professional musician in town and is also responsible for all designs, scores, videos and basically all that is visually and audibly appealing.
The Rum Runner, the Bar Boat of Key West
The waters of downtown Key West have great history surrounding them. You can still hear echoes of past parties and festivals on our turquoise waters. The Rum Runner shares these stories for you when you ask, or just enjoy the views without any work. On the Rum Runner you depart from the only downtown public beach. Simonton Beach. Our great departure location offers a beach, lounge chair, and a awesome Restaurant and Bar. The Rum Runner allows you to bring Key West with you on the water. A crazy local captain with even crazier stories if you ask, all true by the way. No work with bar seats on the water, built in coolers to bring your ice cold drinks with you. Music, lights, waters stops during the day trips. On the Crystal clear waters you will see downtown, historic harbor, great sunset viewing areas, Mallary Square, Sunset Key, the dolphin playground, and a 120 year old shipwreck next to Christmas Tree Island. You can see anything on our waters and on Christmas Tree. Meet the local wildlife and not just the people. The Rum Runner is your Key West Bar Boat Boat or (party boat). Very safe, very stable and with room to walk around, dance to your favorite music, or enjoy a drink and even a sunset. The Rum Runner is your Good Times and Tan lines in Key West
Key West Private Sail Adventure on a Beautiful Catamaran
Our adventure begins at 9am departing from the popular Key West historic seaport and setting sail towards a beautiful snorkel spot on the 3rd largest reef in the world. You are welcome to bring any snack, adult beverage or we can provide you the concierge information and she'll take care of it for you. After a super fun day of snorkeling we will return you back to the dock by 1:00 pm with plenty of time for you to head to your next adventure! Other things to note Just bring sunscreen, sunglasses a camera and a smile!
Whiskey Rick's Twisted Tales
Small group or private experience to maximize the ability to focus on the stories you want to hear. I will take you on a path that will lead to strange tales of the paranormal, weird locations, unknown experiences and have you learn, laugh, and love the adventure. I have access to a place that very few can enter after hours. I will start with an overview of the trip at watering hole with some ghost occurrences of it's own and then we will set off on our journey. You will be able to ask questions and explore to the level of detail you want to hear of the bizarre and creepy stories I tell. As we walk around old town we can go in or stay outside depending on your comfort level. The places we pass will leave you wanting to learn more and I will provide links/ books you can get to take that passion if time doesn't allow the depth you crave. We will end up in a pirate hideaway that you can hang out in or depart as quickly as possible (lol), but when you do -- you will have my contact info for future treks to go more in depth and/or share with friends so they can learn/enjoy/experience what you will be telling others about in photos and other mediums with maybe some orbs or other mysterious items in those images and memories. This experience is limited in size to ensure interaction between host and participants.
Whiskey Rick's Whimsical Beach Adventure
We will enjoy fun in the sun in the Southernmost City. Our afternoon will consist of a couple of spots to cool off in the water (pool and/ or ocean). Enjoy some live music. Sip some beverages and maybe try out some tasty treats this town is known for. This tour is one that at the end -- you can linger and enjoy where we are, go back to a spot along the path, or I can point you in a direction to continue the fun -- heck I might join too!! It is all about enjoying the Seas, the Sun, having some Sips, and learning the unique history of our island, the landmarks, the people while exploring and enjoying.
Date tour for one or two with Whiskey Rick on a private tour
This is YOUR tour... ignore start time and location. For one or two people (more than that please book/ request a private tour). I do a hybrid of my tours for YOU. This is a couples so that you can relax and enjoy Key West that can also be a tour for one. I will coordinate with you and adjust my tours while throwing in a few special extras that fluctuate based on timing and tour design. We can and will flex on start time and location -- even blend a few tours. The magic of Key West will be shared and enjoyed as we walk thru old town and the seaport telling stories and enjoying things that you might otherwise walk right by. Those hidden gems will be brought to your attention and the history behind the various places shared. Did you say Ghost tour by day? A Historic Happy Hour? Seaport at dawn? A Welcome tour at night? We can do this and more -- YOUR private tour is customizable and tailored to one or two people. Book the 6am tour and we will adjust to what time you want to start or request your start time and I will create that booking for you. The further in advance the easier to work that specialization into the tour.
Reef Snorkel & Sunset Sail
We will snorkel the reef and enjoy the sunset while sailing on a spacious and fun sailing catamaran. You will also get to enjoy fresh organic fruit, veggies and hummus from our favorite local organic cafe, Date and Thyme. Florida’s Barrier Reef is right off the coast of Key West. We only provide this trip during a limited time, June through September, because we want to snorkel the reef when the weather is just right. Explore the wondrous wildlife of the reef with one of our biologists. It truly is one of the most beautiful places you need to see while in the keys. Sailing, the original form of renewable energy transportation! I am on a mission to spread the value of conservation and I think amazing nature experiences with a knowledgeable biologist is the best way to do that! But sometimes all you need to do to appreciate nature is go sailing and watch a sunset! Other things to note Meet at the boat 15 minutes before departure. Call or text my wife Jen with any questions. 305-294-6306.
Harry Truman Historic Stroll
Walk in Harry's footsteps. President Truman spent 6 months of his presidency in Key West. We will walk and talk about his impact then and today. Stopping to explore spots and go into detail on his legacy. It is recommended you do the Little White House tour prior to this so you can get a baseline knowledge on his 11 trips and the importance of Key West. On this trek we can dive into depth on the issues, offer unique insight into the man and his family, cover a wide range of topics and discuss in detail. For history nerds this a tour that you can ask questions and have a conversation. All of us can learn as we share knowledge and explore.
Mangrove Maze Tour
Welcome to Blue Moon Kayak Key West! Once you are checked in each person will get instruction on how to kayak and we will go over the layout of our route for the experience. Once we are ready we will launch from Floating docks. Our Kayaks are very stable with nice back rests to support you through out the trip. We cross Cow Key Channel and go West into the Center of Key West where we will show you how to navigate the Mangrove Mazes into the Salt ponds. All the while you will get to see Iguanas, Parrot Fish, Barracuda, Small Sharks, Night Crown Herons, Great Blue Herons, White Herons, Green Herons and more! Learn about the history and culture of Key West while we take in all the nature. We will end at our starting location. Other things to note: If there are high winds or Lightning the trip may be delayed or rescheduled. Your guide will determine safety for the trip. We will still go if there is just rain. We also provide alternate routes along the North side of Stock Island if necessary to avoid the elements.
Key West Old Town Secret Food Tour
On our Secret Food Tour: Key West Old Town, we'll walk off the main tourist traps of Duval to show you the real city and its best food. After our 2 first delicious bites we take a leisurely walk and explore the history and culture of the city. Enjoy tropical soups, mouth-watering appetizers, gourmet tacos, exclusive island sweet treats and lots more. Plus there’s our amazing SECRET DISH! Please let us know of any allergy/dietary requirements beforehand so we can try to accommodate!
  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West