Romantic

Key West

Florida

Featured Romantic 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

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

The Florida Keys are home to North America's only living coral reef, hundreds of Atlantic bottlenose dolphins, and other amazing wildlife. The best way to experience it is by getting out on the water on this Private Charter that is completely customizable to your wants and needs. Choose from snorkeling, fishing, dolphin watching, or chilling at local sandbars. The options are endless while your experienced captain takes you to the best spots in the area. Immerse yourself in Key West's culture, book this experience today!

2 Hour 24' Sailfish Charter

The Florida Keys are home to North America's only living coral reef, hundreds of Atlantic bottlenose dolphins, and other...

Good Times 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

4 Hour 24' Sailfish Charter

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

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 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

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

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

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

Get ready to sail in luxury aboard your own private 44-foot catamaran. Sail to your heart's content in the open ocean in the Gulf of Mexico on your 3 or 6 hour sailing excursion and end the day watching the sunset in all of its striking glory. Catered completely to your preferences, have your day your way. Whether you want to paddleboard, swim, or just cruise around and sightsee, this is a great trip for the whole family to be entertained. Grab a drink and feel the warm breeze in your hair. Book your Key West Private Sunset Sailing Cruise experience today!

Key West Private Sunset Sailing Cruise

Get ready to sail in luxury aboard your own private 44-foot catamaran. Sail to your heart's content in the open ocean in...

Bimini Charters

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.

GREAT TIME!!!

John could not have been a better guide. 10/10. Made this the best snorkeling excursion we’ve ever taken! Next time we visit the keys, we already know who we’re requesting!

Best snorkeling excursion I’ve ever taken!

End your day soaking in the sights and sounds of the emerald waves on this Sunset Sail on the Schooner Jolly II Rover. Witness the beauty of Key West, Florida as you admire the sunset from the decks of a schooner. Watch for Florida wildlife, dolphins, turtles, flying fish, pelicans, and more as you coast through the ocean. Help raise the sails, fire the cannons, and take your turn at the wheel for an authentic sailing experience. Enjoy an exciting sailing experience and take in the amazing views. Book your tickets today!

Key West Sunset Sail on Schooner Jolly II Rover

End your day soaking in the sights and sounds of the emerald waves on this Sunset Sail on the Schooner Jolly II Rover....

Schooner Jolly II Rover

Are you looking for the best kept secret in Key West?! If so, then hop in your own personal, mini speedboat and follow your knowledgeable guide into Key West's backcountry. You'll race through lush mangrove islands and see amazing marine wildlife along the way while boating in Key West's magical tropical waters. Book today and set out on an amazing adventure on the water with this Island Hopper Speedboat Excursion for Two!

Island Hopper Speedboat Excursion for Two

Are you looking for the best kept secret in Key West?! If so, then hop in your own personal, mini speedboat and follow...

Fun afternoon on the water with Michael as a great guide!

Fun trip!

We spent a few days in Key West. By far, this was the most fun thing we did.  Our guide was great.  It was truly the highlight of our trip!

Best thing about Key West!

Super fun & the guides were very cool and really nice. Would recommend.

Cow Key hopper tour

6 Hour 24' Sailfish Charter

Enjoy the ultimate combination of adventure, rest, and relaxation on this Half Day Key West Ultimate Sandbar Adventure with Mangrove Kayak Eco Tour. Cruise out to the Florida Marine Sanctuary for an incredible guided kayak eco tour through the mangrove isles and keep your eyes open wide as you never know which of the over 500 marine species of wildlife you will encounter. Your expert guides will take you to the best spots! After the kayak tour, have lunch on the way to a local secluded sandbar and then when you're all done on the kayak tour, the bar is open!! You will have unlimited access of soft drinks, draft beer, and wine selections. Grab a beverage and explore the secluded sandbar. Each trip will have a master captain and two additional crew members catering to your every need. Leave your stress behind and book this amazing sandbar adventure today!

Half-Day Key West Ultimate Sandbar Adventure with Mangrove Kayak Eco Tour

Enjoy the ultimate combination of adventure, rest, and relaxation on this Half Day Key West Ultimate Sandbar Adventure...

Captain Chuck made the trip better than we could have imagined, and even offered to allow our 4 year old son to sit in the captain chair and drive the boat. The two sweet ladies, I believe Brinn, and Sara are their names, were more than accommodating, ensuring our needs were met at all times. Sara even stooped down to be on the same level as my 4y/o son, then shook his hand, introduced herself to him, and offered him an array of appropriate drink choices. The kindness of the staff was clearly nothing but genuine. Truly the best trip!! We will absolutely do this again!!

Florida eco tour kayaking and sandbar trip

8 Hour 24' Sailfish Charter

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

Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across the water in classic sail boat before jumping in magical blue waters to snorkel and explore the underwater ecosystems off the coast of Key West. Then wrap it all up with a world famous Key West sunset. The perfect way to spend time with friends and family, book your private snorkel and sunset sail today.

Private Snorkel and Sunset Sail Excursion

Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across...

We had a lovely time aboard the High Tide Wednesday afternoon!  The Captain and crew We’re skilled and affable, answering our questions.  We had the boat to ourselves and the 4 other members of our party.  We sailed, then we snorkeled, and then we returned to the dock .  We would definitely do this excursion again,

High Tide

If you are looking for a way to float away the day, then this 2 Hour Sunset Cruise on a Tiki Bar Boat is the right choice for you. Key West is famous for its glorious sunsets and this tiki cruise does not disappoint. This custom 20 foot tiki bar catamaran features a private bathroom, Bluetooth stereo, and flatscreen TV. Toast the sunset with your closest companions and favorite libation while experiencing the gorgeous scenery, cotton candy skies, turquoise water, and pure relaxation on this 2 Hour Sunset Cruise on a Tiki Bar Boat. Book today!

2 Hour Sunset Tiki Boat Cruise

If you are looking for a way to float away the day, then this 2 Hour Sunset Cruise on a Tiki Bar Boat is the right...

Great trip!  Captain Vinny was a hoot!  He made our experience a truly great one!  So, thanks Vinny!  We’ll be back!

Private Tiki Boat Sunset Cruise

Trip was perfect! Captain was very nice and very informative of the area. Highly recommend!

Sunset Cruise

Capt. Morgan did a great job of keeping us entertained

Key West Promotions

Soar above an island paradise on a tropical breeze with a Key West Parasailing Adventure. Enjoy miles of breathtaking scenery and panoramic views as you rise above the clear waters and spot dolphins, tropical fish, and more! Share this grand experience with 1, or even 2, of your favorite people as you experience the breathtaking views and thrilling ocean dips together! Venture out on a Key West Parasailing Adventure today for an extraordinary bird's-eye view of paradise! Book now!

Key West Parasailing Adventure

Soar above an island paradise on a tropical breeze with a Key West Parasailing Adventure. Enjoy miles of breathtaking...

We really enjoyed our parasailing experience! It went so smoothly, the driver and the young lady who prepped the harnesses were absolute pros. Very friendly, funny, engaging. Even though they must do this a thousand times, they made it fun and memorable for us. The line to the parasail is motorized so it pushes you out and pulls you in smoothly and without human effort. All harnesses, clips and life jackets were in excellent condition. Totally recommend!