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.

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.

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.

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.

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.

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!

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.

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.

We are the only paddling outfitter with kayak access to this spectacular area in the clear waters between Anna Maria Island and Longboat Key, which means no crowds and more exclusive wildlife viewing opportunities! Wildlife-viewing here is outstanding! Our expert naturalist guides set the gold standard for hospitality in our beautiful corner of the world and are always very respectful of any wildlife encountered on the tour. While larger groups can easily be accommodated upon request, we always limit our tours to small groups and we are rewarded with a very relaxed and happy group of paddlers. This excursion is perfect for families, couples, groups, and individuals with any level of paddling experience. First-time paddlers are always welcome. If you are looking for an incredibly relaxed and memorable adventure during your visit to Anna Maria Island and Longboat Key, this is it!

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!

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.

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.

Whether you are a family, group of friends, couples (we have done engagements!) or celebrating a special occasion, we are the best private boat charter on and around Siesta Key! We have been in business 10 years and made incredible memories for the many thousands of guests we have had out. You plan your day! We offer so many fun activities such as snorkeling, paddleboarding, sandbar and beach hopping, fun fishing, sunsets, dolphin and wildlife watching. Another popular option is lunch at one of the excellent waterfront restaurants between the North end of Sarasota Bay all the way down to Venice. We can help you decide the right one for you. There are also many fun tiki bars to hit by boat! Just let us know what sounds good to you and we will help you make it the perfect day! We are here to answer any questions or help you in the planning.

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.

Welcome aboard Giddy Up, a striking Cruisers Yachts GLS 42 designed for stylish coastal cruising and unforgettable evenings on the water. With her sleek profile, expansive open layout, and seamless indoor-outdoor flow, Giddy Up delivers a sunset experience that feels both intimate and energetic. As the sky shifts into warm hues of gold and rose, this modern yacht provides the perfect setting to relax, celebrate, and unwind. Refined. Social. Effortlessly coastal. Your sunset charter offers a refined way to experience Sarasota Bay at its most beautiful. Cruise along the coastline as the light softens, anchor for cocktails and conversation, or enjoy the gentle motion of the water as the skyline illuminates. Perfect for celebrations, romantic evenings, or stylish gatherings with friends, sunset aboard Giddy Up is defined by comfort, atmosphere, and effortless luxury.

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.

Your private boat charter with captain for the day! You'll have the best time experiencing our beautiful waters around Siesta Key and Sarasota. We will help you make it the best day of your vacation, making amazing memories. You will nearly always see dolphins and manatees up close, sometimes getting the dolphins to play and chase the boat! Experience fun sandbars and beach stops for swimming, snorkeling and paddleboarding. Just want to enjoy a cold drink and float in the pristine waters while enjoying your music? That's fine too! Maybe you would like to stop at a fun tiki bar or excellent restaurant on the water for a drink or bite. There are so many fun options for your day. You will leave wishing you had more time and we will hope to see you again!

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.

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!

Welcome aboard Peace, a refined Prestige 630 that embodies European design, modern elegance, and effortless performance. With sleek lines, expansive glass, and beautifully appointed living spaces, this yacht delivers a world-class yachting experience designed for those who appreciate sophistication on the water. Spacious yet intimate, powerful yet graceful, Peace offers the perfect balance of luxury and comfort for full-day coastal cruising, celebratory gatherings, or indulgent escapes along the Gulf Coast. Whether cruising along the shoreline, anchoring in calm turquoise waters, or hosting an elegant gathering, Peace offers an elevated yachting experience defined by style and serenity. Cruise past waterfront estates, explore secluded anchorages, enjoy a leisurely lunch stop at a waterfront destination, or spend the afternoon anchored in tranquil waters. Each charter is shaped by your preferences and the day’s conditions, ensuring a bespoke experience from departure to return.

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.

The Experience Step aboard Superstar, our iconic 112’ Westport, for a full day of true superyacht living. Inspired by the legendary yachts of the Caribbean and delivered on the Gulf Coast, this is an elevated, immersive on-the-water experience from start to finish. Arrive by luxury tender from The Quay, cruise scenic coastal waters, anchor at beautiful swim locations, and transform the stern into a private floating beach club—all while enjoying polished, five-star service. This is not a standard yacht charter. A full day aboard Superstar feels like a floating luxury resort, offering expansive decks, refined service, and experiences typically reserved for much larger superyachts.

The Experience Step aboard Superstar, our iconic 112’ Westport, for a full day of true superyacht living. Inspired by the legendary yachts of the Caribbean and delivered on the Gulf Coast, this is an elevated, immersive on-the-water experience from start to finish. Arrive by luxury tender from The Quay, cruise scenic coastal waters, anchor at beautiful swim locations, and transform the stern into a private floating beach club—all while enjoying polished, five-star service. This is not a standard yacht charter. A full day aboard Superstar feels like a floating luxury resort, offering expansive decks, refined service, and experiences typically reserved for much larger superyachts.