Key West

Florida

Featured Key West Activities

Snorkeling Tours

Sunset Cruises

Dinner Cruises

Sailing Charters

Deep Sea Fishing Charters

Boat Tours

Parasailing

Jet Ski/Waverunner Rentals

Dolphin Cruises & Tours

An eclectic artists community, Key West is the perfect spot to relax, and take-in South Florida vibes. Many of the top things to do in Key West involve the picturesque coastline. This includes sunset cruises, dolphin tours, and deep sea fishing excursions. Explore the exotic reefs while scuba diving, or simply stick to the shore for pristine beaches and some old-Florida culture. There is something for everyone in Key West and the Florida Keys.

Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted sunset fade into dark as the stars give an encore unlike any other. Stretch out and enjoy a pampering of complimentary drinks with family or a special someone. Come feel the ocean breeze blow through your hair and dance across your skin as the sun sets over Key West, book your Champagne Sunset Sail today!

Champagne Sunset Catamaran Cruise

Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted...

We loved this relaxing experience. Bring sunglasses for before the sun sets. Fantastic staff.

Beautiful!

No issues, super easy and crew easy going and professional, very safe

Excellent cruise

The sunset cruise was amazing! The boat was clean and crew was awesome. There were other boats and the captain did great job of keeping us where we could see the sunset and get pictures. The crew were friendly and helpful. It was a relaxing trip with an amazing view!

Sunset cruise

Sebago Key West

Hop aboard for an adventure through the most diverse underwater ecosystem in the United States with the Glass Bottom Boat Reef & Eco Tour. Enjoy traveling the tropical and sun-kissed waters of the Florida Keys on a sleek and comfortable catamaran as you scope stunning seascapes through a glass bottom. Take an underwater adventure in North America’s only living coral reef without even getting wet. See the home to elkhorn, brain coral, and hundreds of diverse fish species. Come along on a fun and informative tour of the Florida Keys on Key West's only window to the sea! Book now!

Glass Bottom Boat Reef & Eco Tour

Hop aboard for an adventure through the most diverse underwater ecosystem in the United States with the Glass Bottom...

Reef Tour

Amazing experience . The guide was very knowledgeable about the marine life and reefs . Had a good view of the under water marine life including fish and turtles

Excellent

My husband & I went on the Glass Bottom Tour in Key West & it was so wonderful to learn about the Coral Reef which is quite large & important to the Ecosystem m! Our guide, Keith explained that the coral reef was a living organism & not a plant. He told us about the different types of coral which was very interesting @ informative. Great tour & I recommend it!

Very informative tour

Fury Water Adventures

If you're looking for the best angling adventure in Key West, then this 6 hour Party Boat Fishing Trip is the one for you! Cruise brilliant blue waters as your expert captain and crew put you on the fish! Enjoy the thrill of the catch as you reel in a shot at record-breaking snapper, grouper, cobia, amberjack, and more. Learn expert tips and tricks, as well as local secrets that will ensure you have the trip of a lifetime! Book today!

Key West Party Boat Fishing Trip (6 Hour)

If you're looking for the best angling adventure in Key West, then this 6 hour Party Boat Fishing Trip is the one for...

My husband and son had a great time fishing.  They loved the boat and the vibe.  Would definitely do it again!!

Great trip caught plenty just wish they were bigger! Great captain and crew, will go again next time I am in Keywest

Fishing

Had excellent time on party boat. Crew was great

Happy customer

Gulfstream Fishing, Inc.

If you are looking to make memories on a glorious Key West sunset as you dine and enjoy drinks with your loved ones, then this is the perfect cruise for you. This Key West Sunset Dinner Cruise allows you to have it all. Experience a delectable dinner and drinks out at sea with a friendly crew and dine on tropical-inspired featured dishes like Roast Pork with heavenly Cuban Bread followed by fried plantains. Your meal is prepared fresh on board and your catamaran features a fully stocked bar and comfortable seating in a climate-controlled cabin. So get out on the water and dine, drink, and dance away the day on this classic Key West Sunset Dinner Cruise. Reserve your spot today!

Key West Sunset Dinner Cruise

If you are looking to make memories on a glorious Key West sunset as you dine and enjoy drinks with your loved ones,...

It was a wonderful time and the staff was great and very welcoming

Great

Great experience, I would definitely recommend, over the top hospitality

Sunset dinner cruise

Rachel was exceptional and very outgoing...food was great and other staff were very helpful taking pictures for people and mixing drinks

Captain

Sunset Watersports

Come parasail the ocean blue skies of Key West where you’ll get a bird's eye view of Key West and Smathers Beach from 300 feet up! One of the best things about parasailing is that anyone can have the time of their lives floating like an eagle on the wind. Take in the scenery, look out for marine wildlife, or simply enjoy the ocean air as you fly. So what are you waiting for?! Spread your wings and get ready for liftoff by booking today!

Smathers Beach Parasailing Adventure

Come parasail the ocean blue skies of Key West where you’ll get a bird's eye view of Key West and Smathers Beach from...

This was by far the most awesome experience ever!!  The staff was friendly.  Captain Ty and his mesmerizing eyes was beyond friendly awesome amazing wonderful.  And the first mate was so helpful funny. Even though there is construction in front of their place please don’t pass this one by.  We did a lot on our trip including swimming with dolphins, snorkeling the Christ of the Abyss.  But the parasailing by far blew everything else out of the water.  I honestly can’t say enough great things about this place.  Please take the time, get through the construction.  It will be worth it!   I wish I could give this place 10 stars.

AWESOME!   MUST DO!!

Parasail

Take an adventure into the depths to explore Florida's best reef on a snorkeling experience you will never forget! The Sandie Cat is Key West's newest and fastest snorkeling catamaran, which means less time wasted and more time for exploring the deep blue sea! Join the crew as they hoist the sail and get you and your family and friends out for a true Key West experience. Enjoy a complimentary breakfast, as well as unlimited mimosas (mango, strawberry & orange) & unlimited draft beer, in this all-inclusive snorkel experience. Reserve your spot today!

Rise & Reef Snorkeling Trip With Breakfast & Unlimited Mimosas

Take an adventure into the depths to explore Florida's best reef on a snorkeling experience you will never forget! The...

The crew was fantastic! Knowledgeable, personable and made sure everyone had a great time. This activity is great for everyone whether you enjoy snorkeling or not. So much fun and I would definitely do it again.

Great Experience

If you only do one thing in Key West, this is it.  It’s fun, relaxing, and always a great time.  The trip was beautiful and the staff was amazing!

Key West must!

The absolute best time to take a snorkeling trip in the Keys is Sunday morning.
 Our boat, which will often carry over a 100 people, had about 20 making this a phenomenal experience.
Great crew
 Very knowledgeable and engaging.

Best time to snorkel

Adventure out and join this Guided Backcountry Paddle Tour of Key West's lush island mangroves. Choose from a paddleboard or kayak and enjoy the sheltered, calm water of the mangrove ecosystem. See the wonders of this unique habitat as your experienced nature guide highlights the plants, animals, and marine-life it contains. If you seek a relaxing and authentic retreat, book this unique paddle adventure today.

Guided Backcountry Paddle Tour

Adventure out and join this Guided Backcountry Paddle Tour of Key West's lush island mangroves. Choose from a...

My husband and I went kayaking in the mangroves in Key West for our honeymoon. This was such a relaxing activity and it was nice to learn about Key West from a “Conch.” I highly recommend!

Kayak the Mangroves

Wonderful experience with a very knowledgeable guide. Thank you for the opportunity to be taught about the echoes system. Would recommend this tour to anyone! Well worth the two hours and the cost was very reasonable.

Wonderful experience

Guide was fantastic - very knowledgeable and friendly. Would definitely recommend!

Great experience

Key West Eco Tours

Enjoy this Rum Runner Downtown & Island Tour and get out on the water for some fun in the sun. Cruise the gorgeous water on the best value bar boat in Key West and give a cheer for every gorgeous sight you see. Perfect for you and up to 15 of your crew to kick back and chill or snorkel and swim at the stop at Wisteria Beach. See Sunset Key, Wisteria Island, a 100-year-old shipwreck, and more. You can BYOB and/or sample rum on board. So, don't miss the boat! Book this experience today!

Rum Runner Downtown & Island Tour

Enjoy this Rum Runner Downtown & Island Tour and get out on the water for some fun in the sun. Cruise the gorgeous water...

Lagerheads Watersports

Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green Flash." Experience the magic and romance of sailing at dusk as you sip champagne and watch for dolphins and other marine wildlife in the surf. Your friendly captain and crew will teach you the basics of sailing and even let you take the wheel. So, take a turn at the helm of one of the fastest schooners in the United States, book today!

Key West Sunset Sail on America 2.0

Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green...

Everything was perfect!  The crew, the weather, the water and sunset all made for a great experience.  Highly recommend!

Everything was perfect!

Had a wonderful time! Great crew took good care of us and gave my husband a turn at the wheel

Sunset Sail

Superb activity and totally recommended.
Not a party boat but great fun and real sailing.

Schoonerful

Classic Harbor Line Key West

Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local landmarks and sail past Sunset Key and historic Fort Zachary Taylor as you dine on a tasty selection of varied hors d'oeuvres. Watch the sunset with your favorite drink in your hand and your loved ones by your side. Enjoy live music from local musicians! These are moments you’ll savor long after you leave town! Don't miss the boat. Book your spot today!

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local...

Nice sail out of harbor, staff very nice and helpful.  More variety on premium beers would be nice.  Toilet wouldn't flush and smelled aweful!

Nice evening

Captain and crew made the sunset cruise seamless. Plenty of room to move around and enjoy the views. Bartenders did a great job with the cocktails!  We would do this cruise again.

Excellent service, relaxing ride, amazing sunset

Fantastic!  Great crew and drinks and food.  My wife and I had a very romantic time even with lots of other guests on board.  Highly recommend this one!

Sunset Cruise out of Key West FL

Old Town Trolley Tours allows you to get off at any of its convenient stops. When you're ready, just re-board and it's on with the tour!
Find out where to dine, shop, and just relax and have a good time. The Old Town Trolley Tours are Key West's most comprehensive tours, covering over 100 points of interest. The guides have been extensively trained and are proud to share the history, lore, and legends of Key West. Don't miss out, book your spot today!

Old Town Trolley Tours Key West

Old Town Trolley Tours allows you to get off at any of its convenient stops. When you're ready, just re-board and it's...

I started to buy these tickets from Carnival Cruises but decided to look for them at a cheaper price and that when a came across Tripshock. After some research to make sure this company was legit, I called customer service with a few questions and then purchased the tickets online for about $15 less per ticket. The only problem I encountered was on Key West itself. The day we arrived the entire city was having internet and cellular issues so I could not pull the voucher up on my phone. After about 30 minutes trolley company somehow figured out how to see my confirmation and voucher numbers and I went on my merry way.

Found cheaper tickets

Good; fast, professional and true, thanks

All drivers were very knowledgeable.  Trolley was very dependable when needed. Great way to experience Key West

Very dependable

Historic Tours of America Inc. Key West

Don't miss your chance to “Do it All” with a day-long Watersport Adventure Package in Key West. This all-inclusive experience gives you full access to a variety of awesome activities like kayaks, paddleboards, snorkeling, jet skis, floatables, water trampolines, and banana boat rides. Choose your activities and have your day your way with this Do It All Water Sports Adventure Package. Book today!

Do It All Water Sports Adventure Package

Don't miss your chance to “Do it All” with a day-long Watersport Adventure Package in Key West. This all-inclusive...

Great crew! Great time! Really outstanding!

Best time ever

Was a truly great experience. We had roughly 70-90 people on our party boat. The crew was amazing at making sure not only everyone was having a great time but safe as well. We were in two rainstorms they did a great job of getting us out and back in the water and continuing our tour with exceeding expectations. Highly recommend anyone, couple, or family to attend this great experience. Also parasailing was amazing and the photos they capture are 100% worth purchasing. Even a six year old little man wanted to go again the moment his feet touched the boat. Thank you all for the amazing time.

Also loved knowing this company is family owned !

Highly recommended!

My son and I had an great time. There is plenty to do throughout the day. Don't forget your sunsun. I would definitely do this again.

Awesome Deal

Join a Private Tiki Boat Party in Key West, Florida with your own custom Beachcat Tiki Boat. Glide through the gorgeous, clear Florida Keys water and take in the stunning scenery of the area around you while listening to some of your favorite tunes on an 8-speaker Bluetooth stereo system. Bring your favorite cocktail, a couple of snacks, and your most fun-loving friends for an adventure everyone will remember! Book this 2 hour Tiki Boat Party today!

2 Hour Private Tiki Boat Party

Join a Private Tiki Boat Party in Key West, Florida with your own custom Beachcat Tiki Boat. Glide through the gorgeous,...

Key West Promotions

Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset Sail. Enjoy superbly crafted tapas like tuna poke and shrimp cocktail along with champagne, select premium wines including LaCrema, beer, and sangria as you journey to view majestic dolphins, landmark sights and the world famous Key West sunset. Get an authentic sailing experience as the captain and crew raise the sails on your luxurious catamaran and set out to find dolphins playing and frolicking in the surf and often near the boat! Book yours today!

Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset...

We loved the dolphin sunset cruise! We were in the right spot and saw about 20 dolphins. It’s August so it was very hot when the cruise started. An hour in it was much more comfortable!

So many dolphins!

It was super fun. The sangria was fabulous, the staff was very nice. We saw a family of dolphins. The sunset was out of this world. I totally recommend it. It was definitely worth the money.

The experience was wonderful! Saw so many dolfins! Food and drinks were good. And the sunset was amazing!!! Crew was great.  Friendly and ready with drinks. And the music was really good too. Would highly recommend!!!

Couldn't have gone better!

Take an afternoon and plunge into the depths of Florida's coral reef for an amazing snorkeling experience. The Sandie Cat is Key West's newest snorkeling catamaran, which allows you to get to the reef with speed, comfort, and some serious style. Join the captain and crew, round up your group, and hit the waves for an unforgettable Key West experience packed with fun, sun, and tasty spirits. This all-inclusive trip boasts an open well bar including unlimited mimosas (mango, strawberry & orange) & a variety of soft drinks! Book your spot today!

Dip and Sip Afternoon Snorkel with Open Bar

Take an afternoon and plunge into the depths of Florida's coral reef for an amazing snorkeling experience. The Sandie...

Great trip, crew was super nice and ready to answer any question you may have,. Drinks were 

Wonderful experience. The crew was very friendly and knowledgeable. Beautiful boat ride. Fun snorkeling experience! Would do again.

We had a awesome time. The crew was great. Very informative and fun.

Dip and sip

Race around the tropical waters of beautiful Key West on a Jet Ski Island Tour. An exciting, high-speed tour around the Island, this 27 mile ride will amaze you with all of the sights and sounds of the island. Take in the sun, scope notable landmarks, and learn interesting facts and history about America's southernmost city along the way. Conveniently departing from the Marriott Beachside, this is one ride you do not want to miss! Book today!

Jet Ski Tour of Key West from Marriott Beachside

Race around the tropical waters of beautiful Key West on a Jet Ski Island Tour. An exciting, high-speed tour around the...

The guide was amazing and very informative. The ride was so fun and beautiful looking out onto both the Gulf of Mexico and the Atlantic Ocean. Jet skis felt very safe and handle rough waves well. Definitely will be back!

Disappointed we didn’t get to do the whole trip. We were with members of a group that was too scared to keep up. 

Clark two

We had a wonderful time!! We rented 2 skis for one adult and two teens. Loved that this company allowed 17yr olds to drive a ski solo. Very hard to find that in Key West. 

The guides were informative and attentive. My 17yr old struggled to get going at the beginning so one guide hung back and helped her along until she got the hang of things. The tour was very safe and provided for plenty of speed and even offered “free play time” at the end. Very fun and one of the cheaper establishments on the island. If we come back and rent skis again, we will definitely use this company! Thank you!!

Yippie Ski-ppie

Barefoot Billy's

Discover the beauty of Key West, Florida while enjoying an adrenaline rush on this Freestyle Jet Ski Adventure!Your action-packed fun combines the powerful jet ski's exhilarating speed with an unforgettable experience. Under the supervision of a guide, travel to safe open water for you to enjoy your freestyle ride! Keep your eyes peeled for abundant sea life like  dolphins, turtles, and other marine creatures. Whether you're a nature enthusiast, adventure lover, or simply seeking an unforgettable experience, this Key West Jet Ski Adventure is the perfect choice. Take to Key West's waterways and have some fun in the sun. Book your ski today!

Key West 1 Hour Freestyle Jet Ski Adventure

Discover the beauty of Key West, Florida while enjoying an adrenaline rush on this Freestyle Jet Ski Adventure!Your...

Key West Boat & Jet Ski Adventures

Join a clear kayaking adventure through Sugarloaf Key, pure untouched  Florida beauty in the Keys National Marine Sanctuary. Enjoy this tropical paradise with unique marine habitats and a knowledgeable ecotour guide that will lead you across open seagrass flats, through a secluded maze of mangrove tunnels, and around mangrove islands and sand flats! Along the way get a chance to see wildlife like turtles, jellyfish, tropical fish, and more, as the guide shares their knowledge of these unique ecosystems and their inhabitants. Create memories to last a lifetime and book your Florida Keys Clear Kayak Tour at Sugarloaf Key today!

The Florida Keys Clear Kayak Tour at Sugarloaf Key

Join a clear kayaking adventure through Sugarloaf Key, pure untouched  Florida beauty in the Keys National Marine...

Get Up and Go Kayaking - Florida Keys

Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around the world. Rated one of the top two sunset tours in all of North America by Coastal Living Magazine, this luxurious Wind and Wine Sunset Sail on a historic Schooner will not disappoint. Make some new friends, enjoy tropical music, and delight your palate as you watch the sun melt into the water. Book your spot today!

Wind and Wine Sunset Sail

Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around...

A wind and sail

A perfect 2 hour smooth sunset sail on a beautiful boat with experienced captain and crew! Plenty of a variety of wines to go around paired with tasty hors d’oeuvres. Would highly recommend!

Wind and Wine Sunset Cruise

Danger Charters

Experience tropical diving or snorkeling and swim with abundant marine life on a thrilling excursion to two different reef locations. Whether you are a certified diver or beginner snorkeler, this is the best way to enjoy the beauty of the only barrier reef in North America. Glide through the shimmering waters in search of coral, tropical fish, sea turtles, and more! Just a short boat ride away from shore, this tour delivers unmatched natural beauty in a small group atmosphere.

Reef Dive or Snorkel Excursion

Experience tropical diving or snorkeling and swim with abundant marine life on a thrilling excursion to two different...

It was an interesting trip, crew was awesome!

Pretty cool

Stormy was very friendly, and we enjoyed her talking with us. At the second spot, we saw five dolphins; it was awesome!

Dolphins!

My family and I really enjoyed the trip. The crew went the extra mile to help my 12-year-old daughter get over her fear of snorkeling. By the end of the trip she was asking me how to get scuba certified because she loved snorkeling so much.

Great trip with fantastic folks

Lost Reef Adventures

Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this nightlife experience. You can dance the night away to live music while you sail the calm waters. Enjoy the best seat in the house with all of the good time essentials like draft beer, live music, open well bar, and appetizers. Book your spot now!

Sunset Sip and Sail with Open Bar and Live Music

Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this...

Fun singing with the steel drummer and grooving to his music.

Perfect length of time, enjoyed sunset.

Great Time

Sunset and sip

Good laid back time. Boat was very clean. Crew was personable.

Simple but Fun

Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Miss Valyn Catamaran. A twilight experience unlike any other, this is your opportunity to enjoy the nightlife while having the option to plunge into the depths by Florida's best reef! Take in the fleeting Key West sunset while indulging in an ambiance that only the cat delivers. Enjoy reef snorkeling, draft beer & wine on this snorkeling experience. Book your spot today!

Key West Sunset Snorkel Cruise

Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Miss Valyn...

The price was good and the crew was professional and fun.

Scuba

Great time ! Great crew!

This triple combo tour gives you three amazing experiences in one package. Watch pods of local dolphins playing in their natural habitat, snorkel at a tropical reef, and last but not least witness the famous Key West sunset! This action-packed, three-for-one adventure is sure to yield magic and memories to last a lifetime. Book now!

Triple Combo Snorkeling, Dolphin, and Sunset Cruise

This triple combo tour gives you three amazing experiences in one package. Watch pods of local dolphins playing in their...

So worth the money! Paige and Ellen are super helpful and kind and play good music. Good drinks, environment, and staff. Captain Owen stopped so we can look at the dolphins and admire the ocean, also a very smooth ride. Would definitely do it again

Amazing trip

We had a wonderful time & treated special by the workers.

Sunset cruise combo

Awesome boat cruise, we saw tons of dolphins, the crew members were super nice and played good music. Highly recommend this boat cruise and it made my trip to key west worth it!

Triple combo snorkeling dolphin and sunset cruise

Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise. Experience some of Key West’s best musicians as you dance to the backdrop of a gorgeous, tropical sunset. Eat, drink, and be merry aboard a spacious and comfortable catamaran and take in all of the stunning sights and sounds. For an evening you'll want to last forever, set sail on this Live Music Sunset Cruise! Book today!

Live Music Sunset Cruise with Cocktails Included

Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise. Experience...

My daughters and I had a really good time! Mathew and his crew were excellent! Thank you!

Sunset cruise 8/4/23

Both my wife and I had an amazing experience with your crew and cruise, food , and drinks were amazing!!!     Music was great , will definitely be seeing you again!!!

Cruise with cocktails

We had a fantastic time. The crew was great , thoroughly enjoyed the band. Would definitely recommend this cruise  to friends.

Top Key West Attractions, Tours & Rentals