Group

Key West

Florida

Featured Group in Key West

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

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...

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

As time went by the fishing spots got better and exciting ... If you are not use to being out on the water please  take a Motion Stickiness Pill 

Gulf Stream Fishing

Gulfstream Fishing, Inc.

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

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 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

Service spectacular, captain friendly and very knowledgeable! Food was great, drinks were good and atmosphere awesome! Enjoyed and highly recommend

Excellent Sunset Cruise

Sunset Watersports

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...

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

Jet Ski adventure

Barefoot Billy's

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 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

Enjoyed the excursion, operators were very good.

Snorkeling

The Captain & Crew wete terrific, equipment was newer and clean, the drinks were the best! Thanks!!

Great Time!!

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

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

Excellent

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

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

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

Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your journey takes you away from commonly charted boat paths to unobstructed views and miles of turquoise waters, while snacking on delicious sushi and snacks. Travel to where the Gulf meets the Atlantic and on to the Southernmost Point of the United States. For an intimate and romantic evening that is sure to help you unwind, book a Sunset Harbor Cruise and toast to life!

Seabreeze Sunset Harbor Cruise with Wine and Beer

Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your...

Our sunset cruise far exceeded our expectations!  The food was better than described. The Sushi was made at restaurant next door and the Prosecco did not disappoint but the real highlight of this trip was the outstanding service delivered by Marta!  Not only was she attentive to us but she anticipated everyone’s needs.  She and the captain were fun and committed to making it a memorable experience!  Do not miss this trip!

Amazing Night!

The sunset cruise was beautiful! Lots of fun! The food and drinks were great too!

Beautiful

The captain and first mate were so accommodating and very professional. Truly they are one reason we come back to Key West. We thank you.

Second time

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...

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

It’s a really nice boat ride,really nice place where they took us to snorkel. 
Really nice experience!

Best boat ride!

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

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

What better way to spend your day than with a shared sandbar experience? Travel the crystal clear water of Key West, Florida with family and friends to the backcountry sandbars of Key West. Feel the sun and the salty breeze on your skin. Take a moment and admire the natural beauty this part of Florida has to offer. Your captain knows the best spots to make your experience one to remember. Once at the sandbar, get out in the water! Relax on floats while the water gently rocks you or dive under the water as you snorkel. Make lifelong memories, book your Shared Sandbar Experience today!

Shared Sandbar Experience

What better way to spend your day than with a shared sandbar experience? Travel the crystal clear water of 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...

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

Everything was fantastic except we saw no need for the music and the experience would 
 have been so much better without it it is hard to talk over it

Sun set sail

Enjoy this Rum Runner Bar Boat Castaway Cruise and get out on the water for some fun to last the summer through. Cruise the gorgeous water on the best value bar boat in Key West and give a cheers for every gorgeous sight. Perfect for you and up to 5 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 today!

Rum Runner Bar Boat Castaway Cruise

Enjoy this Rum Runner Bar Boat Castaway Cruise and get out on the water for some fun to last the summer through. Cruise...

We had an incredible time with Captain Brian…truly enjoyed the cruise. Thank you so much, we will definitely be back!

Best time ever!

Excellent ! Captain very friendly. Excellent trip.

Exceillent

Had the best captain this is a must trip.

WOW THE RUM RUNNER!

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

You are invited to take an exclusive cocktail & food tasting tour on the Waterfront in Downtown Key West! Step into the colorful streets with a local guide and indulge in cocktails and bites and learn about how Old Fisherman’s Wharf has transformed into Yacht Harbor! Sit at the bar Mel Fisher did while his treasures sat out front on display. Open your ears to live music and island vibes as you cocktail your way to Mallory Square’s Sunset Celebration! Book your tickets today!

Key West Sunset Celebration Walking Tour with Cocktails

You are invited to take an exclusive cocktail & food tasting tour on the Waterfront in Downtown Key West! Step into the...

Guide was great and made for an enjoyable evening

Salty Seaweed

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....

everything was exceptional and all the crew were very accommodating

sunset cruise

If you're looking for one of the best sunset cruise experiences in Key West, this is it. My wife and I booked this cruise without knowing much about it, but we knew that we wanted to be on a boat that had fewer people than the big boats, and a more intimate experience. That's exactly what we got. The crew consisting of Russ the Captain, Isaac the First Mate, and Laura (her second day on the job) were the absolute best. They were fun, funny, willing to answer our silly questions, and went above and beyond to serve us first class snacks and excellent, top shelf drinks. They played music that added to the ambience. We made great friends on the boat and enjoyed the sail. The evening was perfect, the sea was calm, the sunset was spectacular, and there was a full moon that rose immediately after the sunset. This cruise was worth every penny we paid for it. We would do it again in a heartbeat. Don't miss it!

An Amazing Experience

Awesome cruise! The crew was the best! Lots of fun!

Sunset Cruise on the Appledore Star

Schooner Appledore

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...

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

Fun!

Strike out and explore Key West on a double rider scooter rental. Soak up the sun and delight in the breeze as you travel around the island. Navigate the narrow streets with ease and get to those hidden local gems. Discover why travel by scooter is the best way to get around in Key West and rent your scooter today!

Key West Double Rider Scooter Rentals

Strike out and explore Key West on a double rider scooter rental. Soak up the sun and delight in the breeze as you...

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

Hang out like the locals! The shallow, clear backcountry waters of the Florida Keys sets it apart from anywhere else in the country. Just a short boat ride will transport you to what feels like a world away! Explore secluded sandbars, shallow reef patches, and tropical wildlife at your own pace during this private charter. Pack up your favorite refreshments and snacks and cruise into Paradise! Book today!

Private Tritoon Charter on the Barefoot One

Hang out like the locals! The shallow, clear backcountry waters of the Florida Keys sets it apart from anywhere else in...

Snorkel, dolphin watching and sandbars. Captain Zach was the best.

Perfect Chill Day

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...

Scuba

Great time ! Great crew!

This sunset sail was great! The crew were all amazing!

Sunset sail

Be your own guide as you explore the sapphire blue waters of Key West in a kayak rental from Barefoot Billy's. With beauty surrounding you in all directions, you can take it all in at your own pace while spending quality time with family and friends. Set out on a journey to explore the inshore and backcountry waters of Key West with a Barefoot Billy's Kayak Rental and book today!

Kayak Rental at the Reach Resort

Be your own guide as you explore the sapphire blue waters of Key West in a kayak rental from Barefoot Billy's. With...