Day Cruises in Key West
Top 10 Best Key West Day Cruises
Found 17 Day Cruises activities in Key West. Sort by Popularity.Key West Sunset Cruise with Live Music, Drinks and Appetizers
What makes Fury’s Live Music Sunset Sail unique is the combination of luxury and a vibrant, immersive experience. Guests embark on a spacious 65-foot catamaran, ensuring comfort and plenty of room to enjoy breathtaking views of ... More
Sunset Sail in Key West with Beverages Included
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More
PM Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset
Don't miss one of the top things to do in Key West—a half-day sailing tour where you can explore the waters of the Florida Keys and catch a beautiful sunset! You'll cruise out to a mangrove eco-system to kayak through shallow wa... More
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More
Key West Glass-Bottom Boat Tour with Sunset Option
Step aboard the Pride of Key West, the island’s only Glass Bottom Boat. This family-friendly tour invites you to explore North America’s only living coral reef* from our state-of-the-art 65ft catamaran. Glide over crystal-clea... More
Key West Small-Group Sunset Sail with Wine
Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres. This cruise is great for a romantic evening or just to enjoy time with friends. Please arrive 30 minutes prior to ... More
Key West Day Sail on Schooner America 2.0 with 2 drinks
Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean... More
Half-Day Morning Trip from Key West with Kayaking and Snorkeling
Start your day with the ultimate Sail, Snorkel, and Kayak Excursion, a 4.5-hour journey on our shallow draft schooners! Glide through mangrove-shaded channels on user-friendly kayaks, snorkel in crystal-clear waters, and unwind on... More
Schooner Appledore Day Sail with Full Bar in Key West
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 comf... More
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Key West Sandbar Safari on Tiki Boat
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 approac... More
Schooner Bloody Mary Day Sail with Full Open Bar in Key West
Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in paradise! While enjoying your sail remember there is plenty to see on the water’s surface or circling in the blue sky above you. P... More
Free Cancellation
(Saving 20% )
Snorkel, Sandbar & Dolphin Excursion
Max 6 people. Explore the waters around Key West in the Looking Glass, our 28' glass bottom boat. This versatile boat let's you plan your own adventure. Snorkel the reef, explore an offshore island, look for dolphin and other mari... More
Private Tour
Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY
Experience an Unforgettable Fishing Adventure in Key West! Join us for an exhilarating private deep-sea fishing adventure on the vibrant waters of Key West. Led by a skilled and experienced captain, our charters cater to both sea... More
Private Tour
Private Key West Sunset Sail
2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for t... More
Private Tour
Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling
Key West Water Fun with Snorkeling, Sunset Cruise, Dinner, Live Music and open Bar. Enjoy a bright and early morning snorkel Catamaran cruise departing 9 am for a full morning of Snorkeling fun. Return at 12:00pm and have 4 hours... More
Private Tour
Private Historic Harbor Cruise
Experience the charm of Key West from a unique perspective with our Harbor Cruise. About Set sail from historic seaports and meander through picturesque harbors, where colorful sailboats and historic landmarks line the waterfront... More
Private Tour
Key West Sandbar Charter
Come experience the Crystal clear waters and sandbar island surrounding the Florida Keys. This tour can be completely tailored to whatever you have in mind. From drinking and relaxing on the sandbars to a full eco-tour through t... More
Private Tour