Top Key West On the Water

Key West Reef Snorkel – Morning Mimosas or Afternoon Margaritas

Key West Afternoon Reef Snorkeling with Open Bar

4.2

(677)

from $35

(461)

from $60

Sail to a gorgeous snorkeling spot off the coast of Key West to explore a coral reef home to rainbow-colored fish, anemones, eels, and more. On the hour-long sailing trip to the reef, sip included wine, beer, or soft drinks while watching for dolphins and sea turtles. The captain chooses the snorkeling spot according to each day’s conditions, ensuring the best experience for your group.

Key West Sailing & Snorkeling: A Reef Adventure

Key West Sailing & Snorkeling: A Reef Adventure

(234)

from $79

Key West Reef Snorkel & Sail Adventure

(558)

from $79

Key West Half-Day Fishing Charter

5 hoursFree Cancellation

(454)

from $95

Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

6 hours 30 minutesFree Cancellation

4.9

(824)

from $159

Key West: All-Inclusive Watersports Adventure with Lunch & Beer

6 hoursFree Cancellation

4.5

(367)

from $180

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres

(3,777)

from $79

Key West Dolphin and Snorkel Experience

(358)

from $70

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

Guided Night Kayak Adventure Tour in Luminous Lagoon

4.3

(1,862)

from $93

1 hour 30 minutesFree Cancellation

(178)

from $90

Spend a stunning afternoon soaking up the sights of the Gulf of Mexico, chilling out at a sandbar, and watching dolphins at the Florida Marine Sanctuary. With the help of a fun and informative crew, you’ll explore the Floridian sea while your guides tell you all about the area’s history and wildlife. Enjoy lunch as well as unlimited beer, wine, and mimosas on your trip—just remember to drink responsibly.

All-Inclusive Sandbar Safari with Dolphin Playground Encounter

All-Inclusive Sandbar Safari with Dolphin Playground Encounter

5 hoursFree Cancellation

4.8

(600)

from $150

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

Set sail from Key West aboard a spacious catamaran for a morning snorkeling cruise combining relaxation and adventure. Glide across the waters where the Gulf of Mexico meets the Atlantic Ocean before stopping at a secluded snorkeling location. Enjoy a gourmet breakfast and unlimited mimosas on board, offering a convenient way to experience Florida’s coastal scenery before the rest of your day begins.

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

(139)

from $35

The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast to try your luck spotting dolphins, stingrays, turtles, and birds while you learn more about Key West’s waters than you ever would sailing along. Then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat.

Shark and Wildlife Viewing Adventure in Key West

Escape the crowds and discover hidden sandbars on a private eco tour through Key West’s backcountry waters. Swim, snorkel, or simply relax on pristine beaches only accessible by boat, with a flexible itinerary customized just for you. • Watch wild dolphins in their natural habitat • Private eco-friendly tour, just for your group • Cruise Key West’s beautiful backcountry waters • Flexible departure times to fit your schedule • Learn about marine life from a local guide

5.0

(3,300)

from $99

Private Boat Charter Key West, Dolphin Tour, Snorkeling & Sandbar

Private Boat Charter Key West, Dolphin Tour, Snorkeling & Sandbar

Experience the Thrill of Offshore Fishing in Key West Join us for a 4-hour shared deep-sea fishing adventure aboard a top-tier 6-passenger sportfishing boat(max is 6 on a boat)! This trip is perfect for solo anglers or small groups looking to target some of the most exciting offshore species in the waters off Key West. What to Expect Target Species: Depending on the season, you’ll chase Mahi-Mahi, Tuna, Wahoo, Sailfish, Kingfish, and more! Expert Crew: Our experienced captain and mate will guide you every step of the way. Top-Notch Gear: High-quality rods, reels, and tackle are provided! Comfort & Convenience: With a max of 6 guests, you'll have plenty of space to fish and enjoy the experience. Trip Details: Duration: 4 hours Departure: Leaves from Key West Group Size: Max 6 anglers (shared trip) Languages: English Whether you're a seasoned fisherman or a first-timer, this is your chance to experience world-class offshore fishing in Key West! Book your spot now!

5.0

(31)

from $810

Per group

Key West fishing at its finest! A well-earned Mahi for this Army vet

4 Hour Shared Deep Sea Fishing in Key West

4 hoursFree Cancellation

4.1

(27)

from $200

Key West Sunset Sail with Live Music, Drinks and Appetizers

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Dance the evening away or relax on the sundeck or in shaded areas as you sip on a margarita, beer, or other beverages. Unlimited drinks and light appetizers are included so you don’t need to pay extra. A great standalone evening activity or the start of a night out.

Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West's Island Adventure Sandbar Tour with Kayaking

(1,013)

from $73

3 hours 30 minutesFree Cancellation

Key West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters

(613)

from $110

4 hoursFree Cancellation

4.9

(137)

from $565

Per group

Key West Parasailing - Next to Cruise Port with Amazing Views

Go parasailing above the emerald waters of Key West for a thrilling 1-hour tour that provides sweeping views of Florida’s southernmost city and its surroundings. Head out in a 12-passenger state-of-the-art parasailing boat out to the ocean, then your guide secures you into a double or triple-person parasailing device for a ride that gently lifts off and glides above the water, all without getting wet.

Key West Parasailing - Next to Cruise Port with Amazing Views

50 minutesFree Cancellation

4.8

(428)

from $64

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

Snorkel North America’s only living coral reef, then catch an unforgettable Key West sunset, all in one trip. Jump into clear waters with provided gear and spot colorful marine life under the surface. Back on board and after you’re dried off, enjoy rum punch or other beverages on deck as reggae music sets the vibe. A perfect mix of adventure and relaxation, ideal for couples or friends.

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

Key West Mangrove Kayak Eco Tour

(382)

from $57

Key West's Favorite Afternoon Dolphin Sail

4.9

(2,359)

from $80

2 hours 30 minutesFree Cancellation

(203)

from $59

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

2 hours 30 minutesFree Cancellation

Key West's Island Adventure Sandbar Tour with Kayaking

(753)

from $89

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What are people saying about Key West

Amy_G, Jun 2026

Best day ever!

A true Key West Island experience! A must do for any nature and water lover. It was like having a private island all to ourselves. Went kayaking near the mangroves, and went swimming in the warmest most beautiful water. Food, cocktails, and music were an added bonus. Captain Jude and Mate Allie took great care of us. We loved it so much we’re going back tomorrow!

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

Robert_P, Jun 2026

Great and beautiful sunset experience

This was an incredible experience! I would say the trip started with me melting in the hot June sun while walking to the docks. Once there and out to sea, everything changed. The staff were incredible. Old fashioned customer service. Made sure everyone onboard was comfortable, and enjoying the experience. The crew takes care of you. We did see dolphins, and that was excellent. The sunset at the end was stunning. I loved my experience and would highly recommend this.

The Original Key West Island Jet Ski Tour from Barefoot Billy's

Tiffany_B, Jun 2026

Awesome experience.

Very friendly and attentive employees. There was a lot of sargassum that caused issues with the jet skis but the crew fixed this quickly and got us back on our way. The views were great and you got to ride the jet skis for quite a while. Best part, they took pictures and airdropped them to us for free! Highly recommend!

Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

Larry_N, Jun 2026

Excellent Day on the Water

I booked this excursion as a birthday present for my wife. We both had a wonderful time with Captain Anna and crew members Morgan and Carly. They were all very attentive and went above and beyond in making sure all aboard had a fantastic time. After our first stop snorkeling, there was still a little time available before lunch and kayaking that Captain Anna stopped at a nearby sandbar so that we could enjoy being in the water a little longer. It was a very pleasant addition that we were not expecting to the day. Lunch and drinks were then served while we sailed to the next destination for kayaking. The kayaking part of the day through the water and around the mangrove island was very nice and informative as our group leader, Carly, explained to us about the ecosystem there. Both my wife and I had a memorable day on the water with excellent and fun shipmates, captain and crew!!

Key West Half-Day Fishing Charter

Larry_W, Jun 2026

Great time on the Max!

Terrific experience on the Max! First time fishing experience (as I think it was for many who joined - of all ages) but the crew was patient and the instructions were simple. I think everyone caught multiple fish. It was hot hot out but the cabin had a/c which was a nice break. They even stayed out later for us and got to fish in an additional spot. Would highly recommend this trip!

Guided Night Kayak Adventure Tour in Luminous Lagoon

Shareena_M, Jun 2026

Great experience .

Our experience was GREAT! Our tour guide, Gianni, was informative, personable, and made the entire tour enjoyable from start to finish. We booked the 8 PM tour, so there was still a little daylight when we started, but the sun quickly set and the clear-bottom kayaks took the experience to a whole different level. This tour happened during my husband’s and my 20th anniversary trip, and to our surprise, we ended up with a private tour because the other guests didn’t show. It worked out perfectly! We got to see a variety of wildlife, navigate through the mangroves, and really take in the beauty of the area. The mangroves were especially fun to paddle through, and overall it was an amazing experience. My husband and I are experienced kayakers, so we were able to jump right in and get going, but I think beginners would enjoy it as well. KNOW BEFORE YOU GO: * Apply bug spray! It’s the South, and the mosquitoes are definitely out there. * Wear water shoes and clothes you don’t mind getting a little wet. * Bring a waterproof phone case or dry bag. * Our tour guide had a headlamp, but I honestly wish I had brought my own, so if you have one, toss it in your bag. The full 90-minute tour never felt rushed, and we had plenty of time to enjoy the scenery and wildlife. If you’re looking for a unique and memorable experience, I highly recommend.

Key West Sailing & Snorkeling: A Reef Adventure

Robert_S, May 2026

We were the only ones on...

We were the only ones on this trip,which turned out to be an awesome time. When we were informed of this we expected to be told it was canceled. Glad it wasn't, as being the only two on board we were instantaneously treated like VIP's! The snorkeling was the best I've ever done, and I've done dozens of trips all over the Caribbean, and Hawaii. The reef itself was magnificent with rallies, caves, and hiding holes. Saw more fish than any other location. 100's of fish a few juvenile baracudas, and even a small Caribbean reef shark. In summation this trip was well woth the time, and money, the crew 2nd to none!

Key West Signature Sunset Sail with Live Music, Open Bar & Food

ddqualls, May 2026

Amazing sunset!

Great views! Capt Anna and the crew were great! The musician was awesome and played great music. We really enjoyed the tour.The tour was fantastic! We had great views and the captain and crew were incredibly friendly. The musician was also awesome and played some great music. We thoroughly enjoyed the tour.

Key West Afternoon Reef Snorkeling with Open Bar

Starlene_M, Nov 2025

This was a nice, clean...

This was a nice, clean and organized snorkeling trip for our family of four. We on had one stop, but we saw a lot of fish and other sea life. The trip was not very expensive and the bar was free after snorkeling. The drinks were great and not light on the alcohol. The crew was professional and friendly.

Dry Tortugas National Park Day Trip by Catamaran from Key West

Bryan_P, Sept 2025

We had a wonderful time...

We had a wonderful time visiting the Dry Tortugas aboard the Yankee Freedom. The crew of the ship was awesome (special shoutout to Hollywood). They made the trip out to the park easy and comfortable. The Dry Tortugas is one of the most remote and secluded of the National Parks, making our experience there all the more special. Snorkeling through its waters was amazing. It’s a truly beautiful and remarkable place. Bring an extra change of clothes, towels, and plenty of sunblock.

Key West: All-Inclusive Watersports Adventure with Lunch & Beer

Roman_K, Aug 2025

Sunset WaterSports- Lots of Fun!

I’m so glad we booked this 6 hr. day trip. There was something for everyone. We got to jet ski, parasailing, trampoline on the water and other inflatables-kids loved it, banana boat rides, kayaking and snorkeling! Included lunch and drinks! We all had a great day! Crew was fantastic! Would highly recommend this all-in-one day trip with Sunset Water Sports