Top Sarasota Cruises & Sailing

Experience a sunset to remember with this kayaking tour alongside local marine wildlife. Paddle next to dolphins and look out for local species of birds nesting on islands as you pass by. Learn all about the behavior and habitat of these animals from your guide as you observe them and soak up the Florida sunset on the water.

Immerse yourself in Sarasota's coastal mangrove forests, look out for dolphins and manatees, and practice kayaking or stand-up paddleboarding skills on this immersive, small-group tour. After departing from the Turtle Beach Boat Launch, paddle out on Sarasota Bay and practice with your equipment. Then, head into the mangrove islands of the Jim Neville Preserve for your best chance to see local marine life including dolphins.

You and your party of up to 6, will experience an unforgettable time on the water, whether you decide on a 2 hour day trip or sunset (sunset times will vary throughout the year), You choose how to make the most of the time. Kick back and relax, enjoying the local sea life up close, many times getting the dolphins to play in our wake. During your charter, you will see gorgeous homes, SeaLife, beautiful scenery and Siesta Keys amazing sunset, if that is the charter you prefer. You will ride in comfort in our 25ft Cobalt deck boat. The boat is equipped with Bluetooth so you can enjoy your own playlist. We will bring the bottled water and light snacks like PB crackers and granola bars... but feel free to bring anything else fun to eat or drink! We depart from Siesta Key, making it convenient for tourists and locals alike! After 10 years in business, we know how to show you the BEST time on the water!

Explore the waterways of Sarasota Bay, Bird Key, and Lido Key on a compact two-seater catamaran. Discover a new side of Florida on these unique little speedboats, soaking up the sun and scenery. Make sure you keep your eyes peeled for dolphins and other marine wildlife as you enjoy the ride.

Happy Paddler is the only kayak outfitter with private launch access to the beautiful waters between Anna Maria Island and Longboat Key, avoiding crowded public boat ramps. This gives you a relaxing start to the adventure and more time to enjoy any wildlife you encounter. Happy Paddler always limits tours to groups of 12 or less, allowing you to enjoy more time to explore and much better opportunities for manatee and dolphin encounters. Larger groups can be accommodated. Our expert naturalist guides will lead you through shallow coastal waters, mangrove shorelines and islands while looking for manatees, dolphins, rays, sea turtles and coastal birds. Wildlife sightings vary, but opportunities are outstanding year-round and our guides know exactly where to look. This excursion is perfect for families, couples, groups, and individuals with any level of paddling experience. For visitors to Anna Maria Island or Longboat Key looking for the best wildlife adventure, this is it!

The open water near Sarasota is home to pods of dolphins and manatees—if you know where to find them and can reach them. With this private boat cruise, head out from the North Siesta Key Bridge to search for wildlife while getting comfortable on board. Stop at a sandbar or beach for swimming, sliding, and paddle boarding, and optionally visit a tiki bar and restaurant before returning to shore.

Ditch the typical Florida boat tour crowds and enjoy a way more personal experience on this private dolphin-spotting experience. Try your luck spotting these beloved aquatic mammals, as well as manatees, with the help of a captain who knows all the best spots on the water—it’s an experience lots of Florida tourists miss out on, but they shouldn’t.

Experience a stunning sunset cruise on the waters of Anna Maria Island and Bradenton Beach. This private 90-minute boat tour accommodates up to 12 guests, making it perfect for families, couples, and special celebrations. Your captain will navigate the intracoastal waterways and Gulf of Mexico to the perfect panoramic sunset spots, showcasing scenic views of Anna Maria Island’s coastline and the iconic Sunshine Skyway Bridge. Keep your eyes peeled for dolphins and other coastal wildlife as you cruise through their natural habitat. Enjoy a route designed to highlight the best of AMI, bring your own beverages and snacks (BYOB), and create unforgettable memories as the sun sets over the water. Perfect for romantic dates, anniversaries, birthdays, family reunions, proposals, or simply unwinding with loved ones as the sun paints the sky in vibrant oranges and pinks. Book your private Bradenton Beach sunset cruise today and experience Florida's most magical hour on the water!

What makes this sunset cruise truly unique is the unparalleled combination of natural beauty and effortless relaxation, offering more than just a view, but an immersive experience. As the sun dips below the horizon, you're not simply watching a sunset; you're enveloped in the tranquil waters of the Gulf and Sarasota Bay, witnessing the dynamic interplay of vibrant colors reflecting off the water against the breathtaking backdrop of the Sarasota skyline and nearby keys. Beyond the stunning visuals, our comfortable boat, with its ample seating, provides a truly laid-back and intimate environment, perfect for unwinding whether you’re seeking a romantic escape or quality time with loved ones. Adding to this special journey is the potential for magical encounters with playful dolphins in their natural habitat, turning a beautiful evening into an unforgettable moment of wonder.

Increase your chances of spotting manatees and dolphins during an eco-friendly kayak tour of the Lido Key in Sarasota. Ideal for lovers of nature and wildlife, this experience lets you escape the crowds on land and is suitable for both beginner and advanced paddlers. Plus, traveling in a non-motorized vessel means you’re less likely to scare away animals.

Enjoy one of Florida's best beaches at sunset on an electric bike tour. With 5-level pedal assist and an on-demand throttle, the electric bike allows you to put in as much or as little effort as you want as you ride along Siesta Key. All experience levels are welcome. Booking in advance ensures you won't miss out on this small-group tour.

Discover the delectable highlights of Sarasota's thriving dining scene on this small-group, evening tasting tour. Meet your guide in central Sarasota, and come with an appetite: you'll visit several local restaurants, and will enjoy enough samples to add up to a meal (alcoholic drinks additional expense). As you go, soak up the convivial atmosphere, and learn more about Sarasota's unique culture and culinary offerings.

With a variety of boat tour options available, visitors can explore the natural beauty of the Gulf, learn about local history, spend the day at a sandbar, witness dolphins and local wildlife, spread loved ones ashes, engagement, wedding, bachelor and bachelorette party. Private charters for a one of a kind personalized experience.

History: As we navigate the serene waters, immerse yourself in the rich history of the Cortez Fishing Village. Breathtaking Views: Witness the spectacular sunset over the Gulf of Mexico, as the sky transitions through a palette of colors, from vibrant oranges to soothing purples, all from the best vantage point—the sea. Unmatched Serenity: Glide along the tranquil waters surrounding Anna Maria Island, where the gentle lapping of the waves and the soft glow of the setting sun create a serene atmosphere. Comfort and Convenience: Standout features of our boat are a spacious bathroom, an optional large bow bimini, to provide protection and relief from the sun's intensity and a dive ladder to safely and comfortably get on and off the boat. Wildlife Encounters: Keep an eye out for the diverse marine life that calls these waters home. From playful dolphins to majestic sea birds, our sunset cruise offers a chance to connect with nature in a profound way.

Explore the stunning waters of the Manatee River, Egmont Key and Passage Key on a private charter designed for up to 4 guests. Experience dolphin, manatee and other marine life sightings, snorkel at the submerged ruins of Egmont Key, search for shells and sand dollars or lounge on pristine sandbars at Passage Key and surrounding areas. Enjoy your time with included snorkel gear, a cooler with ice and bottled water, and the knowledge of a seasoned captain. This customizable tour caters to your interests, whether you prefer snorkeling, swimming, shelling, or wildlife watching. Offering 4-hour tours exploring multiple destinations. Escape the crowded tour boats and join us for a laid-back unforgettable time on the water. - Private charter for up to 4 guests, perfect for families or friends - Snorkeling opportunities at Egmont Key and Passage Key - Includes cooler with ice and bottled water - Convenient pickup options available from local locations

Led by an experienced and friendly captain. Comfort and Convenience: Standout features of our boat are a spacious bathroom, an optional large bow bimini, to provide protection and relief from the sun's intensity and a dive ladder to safely and comfortably get on and off the boat. Family Friendly Adventures: We believe in creating memorable experiences for all ages. Our sandbar and island tours are safe, accessible, and relaxing for everyone.

Welcome aboard Wanderlust, a beautifully appointed Bali 4.2 sailing catamaran offering one of the most refined sunset experiences on Sarasota Bay. With four distinct gathering spaces — flybridge, solid forward lounge, aft cockpit, and panoramic salon — guests enjoy multiple vantage points as the sky shifts from soft blue to brilliant shades of gold and rose. Her wide-beam twin-hull design delivers exceptional stability, making sunset sailing smooth, serene, and unforgettable. This is golden hour under sail. Your sunset charter offers a relaxed and elevated way to experience Sarasota Bay at its most beautiful. Sail past waterfront homes as the light softens, anchor in calm waters for cocktails and conversation, or glide gently under sail as the horizon glows. Perfect for romantic evenings, celebrations, or relaxed gatherings with friends, sunset aboard Wanderlust is defined by comfort, space, and breathtaking views.

Ideal for marine wildlife lovers vacationing in Bradenton and the wider Sarasota area, this private boat tour shows you a whole new side of Florida. The route is planned specifically to make your chances of spotting dolphins as high as possible, and the whole experience is family-friendly. The boat even has a big bow bimini, which gives you and the kids protection from the sun.

Discover the best of Sarasota, Florida as you embark on a sightseeing tour of the city. Climb aboard your air-conditioned vehicle and see several points of interest including the Ringling Museum and College, Selby Library, and the Sarasota Opera House. While you ride, learn about the vibrant history and culture of the city from your guide.

Welcome aboard Rally Point, an elegant Absolute Navetta 52 that blends modern Italian design with expansive volume and refined coastal performance. With panoramic windows, sleek lines, and beautifully appointed living spaces, this yacht provides a sophisticated and inviting setting for an unforgettable evening on the water. As daylight softens and golden hues reflect across Sarasota Bay, Rally Point offers the perfect vantage point from both her elevated flybridge and spacious aft deck. Your sunset charter offers a refined and unhurried way to experience Sarasota Bay at its most beautiful. Cruise along the coastline as the light softens, anchor for cocktails and conversation, or remain underway as city lights begin to glow across the water. Ideal for celebrations, romantic evenings, or relaxed gatherings with friends and family, this experience is defined by elegance, comfort, and breathtaking views.

SkyBlue Transport is a locally owned, licensed and insured operator serving Sarasota, Bradenton, and the surrounding barrier islands. Your professional chauffeur arrives on time in a clean, well-maintained executive SUV and handles your luggage door to door, whether you’re heading to a resort, a wedding, or a dinner reservation. Every ride includes complimentary bottled water, WiFi, flight tracking so we adjust when your schedule does, and direct communication with your driver before pickup. Seating for up to six passengers, with no shared rides and no waiting in line.

Are you relaxing on the white sands of Siesta Key and looking for an exciting beach activity? Look no further! Seabobs offer easy-to-use throttle and speed settings that let you cruise effortlessly above or below the waves. Enjoy the adventure solo or share the fun with friends and family today!

What makes this Sarasota Restaurant/Pub Dock Hop truly unique is its seamless blend of culinary exploration and scenic cruising directly along the intracoastal waterways. Unlike traditional dining experiences, you'll embark on a delectable journey by boat, effortlessly hopping between a diverse array of waterfront restaurants, casual beachside eateries, upscale establishments, and vibrant tiki bars – all accessible directly from the water. The breathtaking cruise itself becomes an integral part of the adventure, offering stunning views of the Sarasota coastline, nearby islands, and the chance to witness a spectacular sunset as you navigate between stops. Adding to its distinctiveness, the tour is entirely customizable, allowing your group to tailor the duration and number of stops to your preferences, ensuring a perfectly paced and personalized libation and culinary exploration.