Key West

Florida

Featured Key West Activities

Sailing

Snorkeling Tours

Sunset Cruises

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 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,...

Great property, great staff, overall awesome experience. Appreciate the great hospitality on my first trip to Key West.

Super Dope!!!

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

Sunset Watersports

Destin

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TripShock Gift Card

Give the gift of lasting memories with a TripShock gift card! Able to be used on any activity anywhere in any TripShock...

TripShock Gift Cards

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...

The boat takes off from Key West at an easy to find and free parking location which cannot be said for many other activities in Key West. 
The  boat was clean, the equipment was a little worn but serviceable. The crew was friendly, helpful and available to help with removing landed fish.  
They filleted our catch nicely to take  home and cook that evening.

Simple Fun

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

Gulfstream Fishing, Inc.

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 in the sky! Fly high,  have the time of your life, and float like an eagle on the wind. Take in the scenery, look out for marine wildlife, or simply enjoy the ocean air as you soar. So what are you waiting for?! Spread your wings and get ready for liftoff. Book your experience today!

Smathers Beach Parasailing Adventure

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...

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

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...

The crew was extremely knowledgeable, very professional, personable great fun!!

Amazing Experience

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

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...

Well organized, on time, fun cruise! The crew, the boat, and the music were terrific. We thoroughly enjoyed it!

Great sunset cruise

Sunset sail

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

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

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

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

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

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.

Commotion cruise

Take a train ride through time and learn the legacy of Old Town from the Conch's themselves on this Hop On Hop Off Conch Tour Train in Key West. Be taken back in history where you'll discover the most famous sights. Your native tour guide will delight and enlighten you with interesting tales of yesteryears. All Aboard! It's time for you to learn about the magic and charm of Key West, get your seat on the Conch Tour Train today!

Hop On Hop Off Conch Tour Train Key West

Take a train ride through time and learn the legacy of Old Town from the Conch's themselves on this Hop On Hop Off Conch...

Traveler

This tour and our guide was awesome and I highly recommend it. However, we pre-booked our tickets and the lady at the desk was extremely rude, unprofessional and condescending. She took the gloss out of it and, quite frankly after a long journey to get there, annoyed us. Other than her, it was a great way to see the sights. Our guide saved the day.

Great tour to soak up the history

Great guides and wonderful fun for families!

Awesome family fun

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

Begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. First, you’ll sail seven miles off Key West’s majestic coast to the shallow Caribbean water of the Florida Keys Reef. Imagine yourself swimming in warm tropical waters with swarms of vibrant colorful fish all around you. Set off on an adventure and book your Morning Reef Snorkel with Sebago Watersports today.

Morning Reef Snorkel and Sail in Key West

Begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. First, you’ll sail...

My husband and I really enjoyed this little snorkeling jaunt! It was so fun and relaxing!

Even Old People Like Us Enjoyed It!

Captain Brett and his crew were great - is was a fun trip.

Great Trip

The crew was fantastic.it was our first time snorkeling with an ocean swell and none if us felt comfortable. It was murky the day we went as well.

Snorkeling

Treat yourself to an action-packed, 28-mile Jet Ski tour among the sparkling waters of Key West and beyond. Join entertaining and experienced guides as they lead you on a scenic tour around the island that includes a slew of fantastic sights like the Southern Most Point, Key West Harbor and a local sandbar where you’ll have a chance to take a dip! Choose the last trip of the day and take in the beautiful sunset! Don't miss out on this fast-paced adventure, book yours today.

Jet Ski Island Tour of Key West from Cow Key Marina

Treat yourself to an action-packed, 28-mile Jet Ski tour among the sparkling waters of Key West and beyond. Join...

This was so cool to tour around the island and also we took a dip in the water.

Amazing

Nice jetskis, Key West water and views and the best guides on the Island! We had a blast! This is a must do while in Key West!

Jetski Tour Keywest is awesome!

Paulie was an awesome guide. We had a blast and will definitely do it again. Thanks Paulie and sunset watersports!

Best tour and guide. Great experience!

Sunset Watersports Key West Waverunners

Get out early and experience nature at its finest with a half-day island adventure complete with sailing, kayaking, and snorkeling all in one. You'll see an incredible array of birds, fish, and other regional wildlife while you explore Key West's backcountry and take in all the natural beauty around you. Live the island dream as you set sail in a 65-foot schooner, then kayak through the mangrove forests and snorkel the blue waters. Book today and let your adventure begin!

Morning Half Day Sail, Snorkel, and Kayak Excursion

Get out early and experience nature at its finest with a half-day island adventure complete with sailing, kayaking, and...

What a great way to spend the morning in paradise! The crew was fantastic, blending history, ecology, and fun in a 55 foot sailboat adventure. Loved going through the mangrove hideout in a kayak!

Danger Charters Sail, Snorkel, Kayak Tour

The crew was super friendly, the boat accommodated the tourists nicely and the gear was clean and well cared for.  We both like to learn about the area in which we are traveling and Dan, Maryann and Bronit(sp?) we’re exemplary!  Great service all day- from info, cold drinks flowing, appetizers and getting everyone in their equipment.  Absolutely recommend this his!

Great day on the water!

My family and I had an absolute wonderful time! The only regret was it was only a 1/2 day trip instead of a full day. The crew (Braza, Brad and Gannon) were so professional and knowledgeable and made an extra effort to make sure everyone was comfortable, safe and having an awesome time with each activity. The boat was in ship shape order, as were the kayaks and other equipment. One of the highlights of our trip to Key West! Hope to get back down to the Conch Republic and Danger Charters again sooner than later!

Danger Charters was great!

Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s dream of sailing around the world “When and If” he was able, is available to the public for the first time in the yacht's lifetime. Sit back and experience the beautiful Key West sunset in style as the wooden schooner glides through the water driven by wind power alone. Meet the crew as they serve up a beautiful array of gourmet cheeses and share their stories of old Key West and the sea.

Sunset Sail Aboard the Historic When and If

Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s...

Great Sailing experience.  The crew was friendly and engaging and provided a full sail ship experience.  All of the guests were friendly and made the whole experience even that much better!  Will definitely do it again!

Great Sunset Sail

Fantastic trip

Loved getting a taste of real sailing on this amazing schooner. Captain and crew were skilled and attentive. A perfect way to enjoy the wind and sunset while in Key West. Would love to take a long trip on the When and If!

Sunset Sail Key West

Come along on this Champagne Sunset Sail and step into luxury. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline waters to landmark sites while sampling a wide variety of complimentary drinks. Come toast to an idyllic Key West sunset on the schooner cruise that is sure to become your favorite new Key West tradition. Book yours today!

Schooner Champagne Sunset Sail

Come along on this Champagne Sunset Sail and step into luxury. Sip, relax, and unwind aboard a gorgeous wooden schooner....

From the point of booking through to the end of the trip everything that was in was within the control of the crew was very nice  
Jamie, Bradley & Capt Mario were excellent.

everything was exceptional and all the crew were very accommodating

Top Key West Attractions, Tours & Rentals