Boat Tours

Key West

Florida

Featured Boat Tours 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 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

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

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

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

Barefoot Billy's

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.

Great experience

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

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

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!

Get out early and experience nature at its finest with a half-day island adventure complete with sailing, kayaking, and snorkeling all in one awesome package. 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 beautiful 65-foot Schooner, then kayak through the mangrove forests, and snorkel in sky blue waters in search of tropical marine species. 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!

Danger Charters

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

Rise, shine, and hop aboard this Rum Runner Downtown Morning Cruise. Relax and start your day the right way as you sightsee, take photos, and search for marine life on this easy going morning cruise. Enjoy a worry free experience with your USCG licensed captain. Listen to stories of yesteryears and learn a little about Key West's colorful history. Don't miss this one, book your Rum Runner Morning adventure today!

Rum Runner Downtown Morning Cruise

Rise, shine, and hop aboard this Rum Runner Downtown Morning Cruise. Relax and start your day the right way as you...

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...

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!

We were very skeptical about a booze cruise, but this turned out to be a high point of our stay.  Fantastic staff, small group (with nice people), and lots of luck--great weather and enough wind to sail. We'd do it again in a second.

Unbelievable

We loved the experience. The music was awesome. Drinks were abundant and the hors’ d'oeuvre were delicious.

Wonderful time.

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...

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

We had an absolute blast on our triple experience! We loved every minute of the snorkel we saw many fish and even a sea turtle!! Then when we went to the dolphin playground we saw many dolphins flipping and flopping everywhere! The sunset back to the dock was the best way to end a wonderful time! We would highly recommend to anyone else!

Awesome

Set sail on a journey to the only living coral barrier reef in the continental United States with this Snorkel & Sail Adventure on the Floridays! Spend the first hour sailing on the beautiful Key West water in a 54-foot yacht, feeling the breeze and warmth of the sun on your skin. Once at the reef, have some fun and snorkel the surrounding area. Admire the world under the water as you get the chance to see this coral barrier reef and the marine life that calls this place home! As you travel back to the Florida coast, enjoy complimentary drinks as you reminisce with family and friends about your time at the reef. Don't miss out on this once in a lifetime adventure, book your experience now!

Snorkel & Sail Adventure on the Floridays

Set sail on a journey to the only living coral barrier reef in the continental United States with this Snorkel & Sail...

Island Jane Charters

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

All crewmembers (Logan, Brian and Rose?) were extremely friendly, efficient and helpful.  Wines were very good and hor dourves were tasty.  Cloudless sky led to a fantastic sunset.  Nothing but good vibes.  Highly recommended.

Perfect sunset cruise

Enjoy a sunset cruise on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner Bar Boat and give a cheer for every gorgeous sight. 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 or grab drinks at the beach bar at a discounted rate, this trip is a perfect way to end your day. So, don't miss the boat! Book your Rum Runner Sunset Downtown Tour now!

Rum Runner Sunset Downtown Tour

Enjoy a sunset cruise on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner Bar Boat and...

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

Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating for the whole family. The sights you’ll see along the way include a waterside view of Fort Zachary Taylor, the famed Sand Key Lighthouse, Mallory Square, and Sunset Pier. So sit back and feel the warm breeze dance across your skin as you watch the sights of the beautiful waters around Key West. Book your spot today!

Day Sail Aboard Schooner America 2.0

Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in...

Excellent Captain and Crew.  Superb sailing with good winds and beautiful weather

Sailing

We absolutely loved the boat and crew. It was perfect weather and we got to have a blast when the sails went up. They only thing is be you have to pay for beer and wine. They are NOT complimentary like stated on your Day Sail ticket. They also do not provide snacks as stated as well. This is only for the sunset sails.

Loved our day trip

My husband and I enjoyed the day trip.  It was an hour and a half, which was perfect.  Very calm waters and not a cloud in the sky.  We couldn’t have picked a better day and the captain even let us steer the boat.  We will definitely do this again on our next trip to Key West!

Wonderful Time

Experience snorkeling in the Florida Keys on an adventure like no other. Explore the crystal clear waters on this two-stop double-dip snorkel trip. Travel aboard the fastest catamaran around to explore North America's last coral reef. Dive in and venture out amongst the abundant marine life in 2 different locations with top-of-the-line provided snorkeling gear. Get acquainted with some of the most magical marine creatures as you swim around in their natural habitats during this underwater tour. Enjoy complimentary beer and wine served after. Book your spot now!

Double Dip: 2 Stop Snorkel Adventure

Experience snorkeling in the Florida Keys on an adventure like no other. Explore the crystal clear waters on this...

Well organized and fun trip. The crew was friendly and helpful. Perfect amount of time for the 2 stops.

Great trip

Took my 13 year old grandson on the double dip, we had a great time. Grandson telling everyone it was the most fun he had on vacation! He didnt even want to go (being a teenager and hanging out with grandma), but said it was really "Cool". Would recommend to anyone with teenagers, they will love it.