Top Key West On the Water - page 3

Key West Historic Seaport Food & Walking Tour

(657)

Free Cancellation
3 hours

from $93

Take advantage of Key West’s paradisiacal scenery, and get up close and personal with its coral reefs and aquatic attractions, on this multi-stop snorkeling trip. Pick between daytime and sunset tour times (available seasonally), and hop aboard a speedy catamaran. Then, following professional instruction on board, grab your gear and snorkel around two different reef locations where you can see marine life before relaxing with beer and wine.

Key West Double-Dip Snorkel Tour-Two Stops, Twice the Fun!

4.6

(185)

Free Cancellation
3 hours

from $80

4.8

(126)

Key West Kayak Rental

Free Cancellation
2 hours

from $40

This isn’t a packed tourist boat — it’s a true small-group adventure with a maximum of 6 guests. You’re not watching dolphins from far away; you’re close enough to feel that electric moment when they swim right next to the boat. Our captains know the dolphin pods by territory and behavior, so you spend more time with them and less time searching. After the dolphin encounter, we take you to hand-picked spots that big boats can’t access: clear, shallow water, quiet backcountry reefs, and hidden sandbars. Beginners feel safe, families feel relaxed, and experienced snorkelers get genuinely good underwater visibility. Personalized, unhurried, and run by a local crew that actually cares — that’s what sets this trip apart.

Dolphin Watching and Snorkeling Key West

5.0

(25)

Free Cancellation
3 hours 30 minutes

from $135

3.9

(587)

Key West Glass-Bottom Boat Tour with Sunset Option

Free Cancellation
1 hour 45 minutes to 2 hours

from $70

4.7

(547)

Key West Reef Snorkel & Sail Adventure

Free Cancellation
3 hours

from $79

Not only is Key West a playground paradise for adults, it is for dolphins, too. See how many of these playful creatures you can spot on this small-group sailing tour. You’ll board Our SQUID, we designed and built SQUID from scratch to ensure our guests, and the animals, have the best wildlife experience possible. This catamaran will take you and a crew trained by biologists into the waters around Key West. After watching dolphins swim, you’ll jump into the water and snorkel around the coral reefs to view other marine life.

Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

(529)

Free Cancellation
4 hours

from $143

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

4.4

(376)

Free Cancellation
3 hours

from $60

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.

Schooner Appledore Day Sail with Full Bar in Key West

(111)

Free Cancellation
2 hours

from $49

Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set out on a half-day adventure aboard our luxurious Manitou Cruise—a spacious, smooth-riding tri-toon with a deluxe swim deck, perfect for soaking up the Key West sun in comfort and style. Guided by one of our licensed, experienced captains, your private charter explores the untouched beauty of Key West’s backcountry—customized to your pace and preferences. Cruise to local sandbars, glide through scenic mangroves, or venture farther to spots like Mud Key, Snipes Point, and the Dolphin Playground, where wild dolphins often play in their natural habitat. Swim, snorkel, relax on remote beaches, or simply enjoy the ride with a drink in hand—it’s your trip, your way. Perfect for families, couples, or small groups seeking a flexible and private escape into the real Key West.

Key West Boat Experience — Swim, Sip & Soak Up the Sun!

4.4

(9)

Free Cancellation
4 hours

from $600

Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure

Likely to Sell Out

4.8

(166)

Free Cancellation
2 hours

from $81

Explore the serene mangrove waterways of Geiger Key on this guided eco-tour. Perfect for all ages and levels of experience. Choose between a single kayak, double kayak, or stand-up paddleboard as you glide through the lush scenery. Your knowledgeable guide will point out the hidden gems of this unique Florida Keys ecosystem, ensuring a memorable and educational experience. With safety gear, paddle instruction, bottled water, and dry bags provided, all you need to bring is your sense of adventure. Enjoy complimentary shuttle pick-up from Key West and immerse yourself in nature for two hours of tranquility.

Guided Mangrove Eco Tours Kayak or Paddleboard Adventure

(14)

Free Cancellation
2 hours

from $75

4.6

(649)

Ultimate Sea Doo Jet Ski Tour of Key West-Additional Rider Free!

Free Cancellation
1 hour 30 minutes

from $150

While most boat tours travel on small private vessels or luxury yachts, this sunset cruise takes travelers around Key West on Jolly II Rover, the only square-rigged, topsail schooner in the area. Board your ship at the historic Seaport at the corner of Elizabeth and Greene streets and sail out to see some of Key West’s best sights, including the Man O War Harbor, Christmas Tree Island, Fort Taylor, and others.

Sunset Sail Cruise in Key West

(275)

Free Cancellation
2 hours

from $95

Step onto our one-of-a-kind catamaran for an all-you-can-eat seafood boil and premium open bar! This trip promises a perfect blend of adventure, relaxation and excitement. Our catamaran is designed for comfort with speacious decks, plenty of seating and shaded areas. Ideal for lounging and enjoying the scenic views of Key West's iconic turquiose waters. Snorkel at two of Key West's prime snorkeling locations, such as Sand Key or another nearby location known for its vibrant coral and diverse marine life. Premium snorkel gear is provided and experienced guides are available for instructions perfect for all levels of experience. After snorkeling, lounge on deck and enjoy a classic Low Country boil, a classic Southern dish. Our menu typically includes shrimp, corn on the cob, potatoes, all seasoned with a magic blend of spices, cooked together. Expect a laid-back and enjoyable trip while unwinding with a cocktail served from our premium open bar.

Key West Low Country Seafood Two Stop Snorkel Adventure

4.5

(31)

Free Cancellation
4 hours

from $79

Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

(969)

2 hours

from $109

Going fishing while in Key West is a must, and this deep-sea fishing tour takes you on a comfortable boat for an easy day out. Whether you’re a beginner or an experienced angler, your captain and crew assist with your fishing skills. Fish for reef species like snapper, grouper, and mackerel. A fishing license and all bait are included, and the boat features restrooms, shaded seating, and a small galley with snacks and drinks for your convenience.

Key West 6-Hour Party Boat Fishing Trip – Affordable Reef Fishing

4.4

(329)

Free Cancellation
6 hours

from $89

You’ll see more than swimmers playing in the tropical waves of Key West. Hop on this boat cruise and watch pods of dolphins leap from the waters just off the coast of the Florida Keys. When the boat slows, it’s time to strap on your snorkel equipment and dive down to the reef system. Spot more sea life as you glide across the water back to shore, enjoying your fill of unlimited beer and soft drinks.

Key West: Dolphin Watching cruise & Snorkeling unlimited beer & soda

4.2

(12)

Free Cancellation
3 hours

from $90

Likely to Sell Out

Explore Key West through the eyes of a local on a craft cocktail tour that stops at six off–the–beaten–path establishments for drinks and food tastings, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.

Key West Craft Cocktail Crawl

(563)

Free Cancellation
3 hours

from $94

Likely to Sell Out

4.7

(591)

Key West Champagne Sunset Catamaran Cruise

Free Cancellation
1 hour 30 minutes

from $59

Special Offer

Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks such as Boot Key Harbor, the Atlantic Ocean, and the historic Seven Mile Bridge. Relax on deck and enjoy the changing colors of the sky while sipping a complimentary champagne toast. The catamaran offers plenty of seating, shaded areas, an onboard restroom, and a cooler stocked with ice, water, and soda. This tour provides a laid-back and memorable way to experience the Keys at golden hour—perfect for couples, families, and anyone who wants to unwind on the water.

Island Sunset Cruise 2 Hour Catamaran Tour in Marathon Florida

5.0

(8)

Free Cancellation
2 hours

from

$97

$102

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

Private boat Charter key west, Dolphin tour, Snorkeling & Sandbar

5.0

(24)

Free Cancellation
3 hours 30 minutes

from $792

Key West is the Southernmost Point of the Continental United States and is surrounded by sparkling blue water teeming with fish. Get out on the water and reel in a big catch during this private half-day inshore fishing charter. This customizable trip lets you decide how often you drop a line. Head to multiple fishing holes or kick it on the sandbar while letting the lure and bait do the work.

KeyWest Half-Day Inshore Fishing Private Charter

(66)

Free Cancellation
4 hours

from $750

Key West's Island Adventure Sandbar Tour with Kayaking

4.7

(600)

Free Cancellation
3 hours 30 minutes

from $120

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Top Attractions in Key West

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Attractions

What are people saying about Key West

Key West's Favorite Afternoon Dolphin Sail

Evgenia_N, Mar 2026

Dolphins Drinks & Amazing Cruise

The crew was fun and amazing super friendly The boat was beautiful and the weather was perfect! Drinks were great we saw 6-7 dolphins They are wild so don’t expect them to put on a show. Bring cash to tip because they are worth it! Highly recommended !!

Guided Night Kayak Adventure Tour in Luminous Lagoon

Nakeesha_T, Mar 2026

Johnathan was an...

Johnathan was an excellent guide, laid back and all around just a good vibe. I had so much fun on this tour and would recommend it probably a million times over. I don’t know if that’s just because I got to see a bunch of nurse sharks this tour or just because the whole experience was top notch! Either way, don’t miss out on this!

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

Amy_A, Mar 2026

Highly Recommend Danger Charters!

Overall, the sailing, snorkeling, and kayaking tour was great! Danger Charters and the staff that took care of us were the best part! Mary and Bible were friendly, knowledgeable, and they went above and beyond to make people feel comfortable and welcomed. The unlimited alcohol and included lunch/snacks made our tour even extra special. Although we didn’t see many fish snorkeling, we did see a string ray and it was fun using the pool noodles to snorkel. During kayaking, we learned about the history of the mangroves and got to see lots of birds, as well as a couple sea turtles! On our way back, we were even lucky enough to see a dolphin, which Mary and Bible helped keep an eye out for. I highly recommend using Danger Charters for your Key West tours.

Key West Craft Cocktail Crawl

Kelly_R, Mar 2026

What a blast! We had a...

What a blast! We had a great time with our tour guide, Mike! He was very knowledgeable about our drinks as well as the history of Key West. We were having so much fun with him, we were hoping he’d join our crew on the next stop! The crawl took us into places we wouldn’t have discovered otherwise. The drinks were awesome as was the experience as a whole. I highly recommend!!

Key West Mangrove Kayak Eco Tour

Cathy_D, Mar 2026

Two hour Kayak Tour with Lazy Dog

Our kayak through the mangroves was truly a fun and educational trip. Our guide Ian talked about things we will see along the way and how the groves protect the areas. We saw and held a jelly fish & saw a bunch of nurse sharks. Ian was very pleasant and took his time answering questions. Would highly recommend the Lazy Dog Kayaking two hour tour.

Dry Tortugas National Park Day Trip by Catamaran from Key West

Bryan_P, Sep 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 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

Joshua_D, Aug 2025

Sunset Cruise and Snorkeling Experience

We signed up for the Sunset Cruise and Snorkeling Experience...it was so fun and amazing! The Captain and Crew were so friendly and helpful...we had a blast! There was a lot of marine life activity at our first stop (some of the people seen a sea turtle surface)...the second stop was not as productive, but was still an experience that my family and I will never forget! On the way back in, we had a small pod of dolphins swim next to the boat!

Key West Ultimate Watersports Adventure with Snorkeling Upgrade

Stephanie_A, Aug 2025

Almost perfect day.

We had a fantastic day on this excursion! The activities were amazing, and the staff (with one exception) was friendly, helpful, and made the experience enjoyable for both kids and adults. I originally booked the excursion for our children, but my husband and I ended up having just as much fun. The only less-than-positive interaction was with one of the parasailing crew members, Alex, who came across as a bit rude and sarcastic. I didn’t appreciate that one bit! Everyone else was phenomenal and went above and beyond to make the day great. One thing I wish I had known in advance is that the cost of the excursion does not include photos. Both the parasailing and catamaran crews offer pictures at $40 each, so we spent an additional $80 for photos. On top of that, there are expected tips for both the parasailing and catamaran teams, which added another $120. In total, we spent about $200 beyond the excursion price. Still, it was an unforgettable day filled with fun and adventure — just be prepared for extra costs beyond the base price. Would 100% do it again!

Key West Sailing & Snorkeling: A Reef Adventure

Cindi_S, Jul 2025

A must snorkel trip

Oh my gosh, what a great snorkeling trip we had. The crew was fantastic. Going out on the sailboat was peaceful and low key. We were in no hurry and this was not a cattle boat trip!!! We had our own gear, but their gear was good quality. I would highly recommend it. We would go with these guys again. We are from Oregon and Hunter the “right hand man and does everything guy” was also from there. We had a great chat.