Top Key West Cruises &amp; Sailing

(3,757)

from $79

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

4.5

(377)

from $72

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

4.3

(1,841)

from $93

Sunset Sail in Key West with Beverages Included

1 hour 30 minutesFree Cancellation

Picture yourself aboard our unique tiki boat, the Lazy Lady, cruising through the crystal-clear waters toward a secluded sandbar. The sun is shining bright, and the air is filled with the scent of salt and sunshine. As you approach the sandbar, the boat glides over shallow waters, revealing stretches of soft, white sand inviting you to explore. Once you anchor, the fun begins! You can jump off the boat and wade into the warm, shallow waters, where the gentle waves lap at your feet. The atmosphere is relaxed, with laughter and conversation floating through the air. Some folks might set up beach games, while others enjoy swimming or soaking in the sun. Time seems to slow down as you enjoy this little slice of paradise, surrounded by friends or newfound acquaintances. Whether you’re collecting seashells, taking a dip, or simply lounging in the sun, a sandbar trip on a tiki boat is a perfect blend of relaxation and adventure.

(961)

from $79

Key West Sandbar Safari on One of a Kind Tiki Boat

Key West Sandbar Safari on One of a Kind Tiki Boat

3 hours 30 minutesFree Cancellation

(135)

from $139

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres

Key West's Favorite Afternoon Dolphin Sail

(1,452)

from $135

2 hours 30 minutesFree Cancellation

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.

(201)

from $59

Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West Sunset Sail with Live Music, Drinks and Appetizers

(1,011)

from $80

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

2 hours 30 minutesFree Cancellation

(748)

from $89

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar & Sunset Cruise! This exclusive trip takes you to a beautiful sandbar, where you can lounge on our floating lily pads while our crew turns into your personal bartenders, serving up unlimited draft beer, mimosas, wine, and champagne. For those looking to explore, grab a snorkel and discover the underwater world teeming with tropical fish, stingrays, and other marine life. As the sun starts to set, we’ll cruise through the Florida Marine Sanctuary, giving you a front-row seat to Key West’s famous sunset—keep an eye out for dolphins, sea turtles & more! Savor a taste of Key West at the sandbar! Enjoy Cuban sandwiches, veggie wraps, fresh fruit, cheese & crackers, pita with hummus & more—all paired with unlimited beer, wine, mimosas & champagne. The perfect happy hour on a boat! Whether you’re here to relax, party, or explore, this trip has it all.

Key West's Happy Hour Sandbar & Sunset Cruise - Unlimited Drinks

Key West's Happy Hour Sandbar & Sunset Cruise - Unlimited Drinks

4 hoursFree Cancellation

4.5

(31)

from $150

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Key West, promising an unforgettable experience for all. As you sail further into the sunset, the full open bar comes to life, offering an enticing array of cocktails, wines, and spirits to complement the evening's splendor. Sip on our signature Schooner Bloody Mary or Dark & Stormy as you watch the sky ignite with color. The skilled bartenders are on hand to craft your favorite drinks, ensuring that your glass is never empty as you drink in the sights and sounds of the sea. As the schooner begins its journey back to Key West, you find yourself lost in the timeless rhythm of the sea, grateful for the opportunity to witness the beauty of a Key West sunset from the deck of a historic schooner.

Classic Key West Schooner Sunset Sail with Full Open Bar

Classic Key West Schooner Sunset Sail with Full Open Bar

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

(242)

from $109

2 hours

4.8

(178)

from $65

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

(175)

from $70

Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Skipjack Resort & Marina, this serene cruise includes a complimentary champagne toast and seasonal local seafood appetizers such as fresh Florida stone crab or shrimp (when in season), offering an authentic taste of the region. Our spacious 52’ catamaran provides a smooth, comfortable ride — perfect for couples, families, and small groups seeking relaxation with panoramic ocean views. Enjoy island music, warm breezes, and vibrant sunset colors as the day fades into tropical paradise. Departure times adjust seasonally to align with the actual sunset, ensuring you experience the most spectacular sky colors possible. Your confirmed departure time will be reflected in your booking confirmation.

Florida Keys Sunset Cruise with Champagne Toast and Seafood

Florida Keys Sunset Cruise with Champagne Toast and Seafood

Key West Reef Morning Snorkeling with Breakfast and Mimosas

5.0

(21)

from $85

4.5

(675)

from $50

Get ready for fun in the sun—and leave all the planning to someone else—on this half-day sailing, kayaking, and snorkeling adventure off the coast of Key West. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef teeming with marine life. Snacks, beer, wine, and soft drinks are included.

Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset

Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset

4 hours 30 minutesFree Cancellation

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.

(1,774)

from $125

All-Inclusive Sandbar Safari with Dolphin Playground Encounter

All-Inclusive Sandbar Safari with Dolphin Playground Encounter

5 hoursFree Cancellation

4.8

(578)

from $150

Parasailing in Key West at Smathers Beach

1 hourFree Cancellation

(145)

from $60

Key West Champagne Sunset Catamaran Cruise

1 hour 30 minutesFree Cancellation

(592)

from $59

Discover the enchanting beauty of the Florida Keys with Island Girls Excursions. This adventure combines relaxing sandbar experiences with stunning sunset cruises. Unwind on your spacious 52’ catamaran, complete with complimentary snacks and drinks while soaking up the sun or exploring the crystal-clear waters. Your experienced crew will ensure a smooth sailing experience, showcasing the best spots in the area. Perfect for groups seeking relaxation, celebration, or exploration, this tour promises unforgettable memories in paradise. - Enjoy a leisurely sandbar trip with paddleboarding and floats - Experience breathtaking sunset views while sipping drinks - Spacious and comfortable 52’ catamaran with Wi-Fi - Friendly and knowledgeable crew dedicated to your safety and enjoyment

Sandbar Adventure Cruise in the Florida Keys

Sandbar Adventure Cruise in the Florida Keys

4 hoursFree Cancellation

Get ready to spend a half-day soaking up the sun and enjoying Key West’s diverse ecology during this fun sandbar and mangrove tour. Discover the backcountry waters and secluded sandbars around the busy island, all while sipping on cold drinks. This guided kayak ecotour takes you into the mangrove isles to spot dazzling marine life before heading to a sandy beach to knock back a few alcoholic or nonalcoholic beverages.

(10)

from $102

Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks

Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks

5 hoursFree Cancellation

4.8

(374)

from $150

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 Tiki Bar Boat to Popular Sand Bar with Turquoise Waters

4.4

(381)

from $60

4 hoursFree Cancellation

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vessel for a day of exploration and relaxation. Sailing away from the bustling Key West harbor, feel the gentle breeze on your skin and the warmth of the tropical sun overhead. As the catamaran glides smoothly over the crystal-clear waters, you'll have the opportunity to soak in panoramic views of Key West's picturesque coastline, dotted with palm-fringed beaches and vibrant coral reefs. Keep your eyes peeled for playful dolphins frolicking in the waves or graceful seabirds soaring overhead. After a leisurely sail, stop at a secluded snorkeling spot, where the underwater world awaits exploration. After working up an appetite, indulge in a delicious gourmet breakfast and unlimited mimosas, all while enjoying stunning views and the company of fellow travelers.

(137)

from $565

Per group

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

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

(129)

from $35

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Top Attractions in Key West

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Attractions

What are people saying about Key West

Gabrielle_M, May 2026

The adventure of a life time

Despite unfavorable conditions the captain and crew improvised beautifully. Their stress on hospitality and positive vibes made up for any change in direction. The snorkeling itself was also a great time! We saw 8 large stingrays, cool fish, and got to explore deep open waters for the first time.

Sunset Sail Cruise in Key West

Douglas_G, May 2026

Enjoy the sunset without the rowdiness

Crew members were very engaging. They got younger passengers to participate in the raising of sails and steering the boat. Assisting everyone as needed getting aboard without calling attention to the effort necessary due to passenger’s health or fitness level. Provided water and snacks. Made the entire experience very pleasant. Great trip for a quiet sunset for couples and family without the rowdiness of a booze cruise. No loud music or party atmosphere.

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

James_C, May 2026

Great!

You’re gonna enjoy it! It may be cloudy and you may not get to see the sunset like you’re expecting, but if you’re with good people, you will enjoy and have a great time. Lots of different wines and beverages to enjoy. Several different cheeses to enjoy.

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 Reef Snorkel & Sail Adventure

Graeme_M, Apr 2026

Great experience

This was a wonderful outing and the skipper and assistant were terrific Lots of beautiful fish to see, particularly brilliant blue fish, a few quite large. Perhaps at one time in the past there was coral but not now. We didn’t go sailing. Perhaps this was because the wind was not strong enough, but likely it was because there was not time for it and it is hard to imagine them having time. For that it really needs to be a 4 hour trip. However, in summary it was fantastic and we liked the fact it was more intimate. We just had 9 people aboard, much better than the cattlemarans (as they termed it)

Key West's Favorite Afternoon Dolphin Sail

Gary_G, Apr 2026

The Captain knew exactly...

The Captain knew exactly where to go to see the dolphins. I can’t even guess at how many we saw. The ride was math and the atmosphere was great. Best of all the crew was amazing. Grace was the first mate and bartender. She walked around and spoke with everyone. Simply put - she was amazing!

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

Deirdre_F, Apr 2026

nice Sunset cruise

Nice relaxing activity, saw a few dolphins for about 30 seconds. but still cute. wouldn’t expect much from seeing them. appetizers were very yummy but only a few. staff was great. Finn and Captain Shay were fun and friendly. can go with any age as long as you don’t have to use the bathroom. that looked like an adventure going down the hatch.

Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

Dawn_C, Apr 2026

Amazing evening and memories!

We booked the morning off because we are the type of people that like to wake up and decide what we feel like doing the day of….come early and check in at desk to sign the waiver. There are many restaurants at the marina….we arrived about 2 hrs before and had plenty of time to eat, use restrooms apply our sunscreen and look around the docks at the fish and even saw a manatee hanging out under on our the bigger boats!!! It was a windy day so waters were a bit cloudy and choppy but nobody can control Mother Nature! My daughter and I had an amazing time and were still able to see lots of beautiful fish. The time slotted at each of the 2 coral reefs was just enough for us, as this was our first time snorkeling out in the open water and we were a little nervous to venture too far from the boat. The sunset was breath taking on the boat ride back-I would recommend getting a spot to snuggle up on the top deck for the best view! They stopped the boat as we passed a family of dolphins-it wasn’t a dolphin excursion but they may as well have been paid actors!! The crew was great and very knowledgeable! The one girl also gave us the best easy chill dinner recommendations after we docked. My 15 year old daughter had the best time and was all smiles from ear to ear the rest of the night!! Thank you!!!

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Robin_M, Mar 2026

Great sail

This was a fantastic sail. Staff was great. Capt Janet was great too. Food was nice too. We had ranch and veggies, cheese and crackers, boiled shrimp and a brownie for dessert. The drinks were free flowing also. I would do this again on the next visit. The only problem is finding the ticket booth. We went to three different ones before we found the correct one. It could be market for easier access.

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast

Brisleizy_P, Sep 2025

Best in Key West

We had a great time ! This is our third year coming to KW for Labor Day weekend . We have tried several tours but I have to say this one was my favorite of them all. Breakfast was great and drinks! The boat and the snorkeling equipment are in better conditions than all the other we have done. I will deff be doing this tour going forward ! Grace was very funny and super nice making sure everyone was having a great time. Loved our snorkeling time !