Top Sarasota Cruises & Sailing - page 2

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!

Welcome aboard Andiamo, a stunning 2026 Absolute Navetta 58 that blends modern Italian design with expansive volume and refined coastal performance. With sweeping glass lines, elevated deck spaces, and beautifully balanced proportions, this yacht offers an exceptional setting for an unforgettable evening on the water. Elegant yet inviting, Andiamo provides generous indoor and outdoor living areas that flow seamlessly together — creating a private, polished atmosphere ideal for golden hour cruising. Your sunset charter offers a refined and unhurried way to experience Sarasota Bay at its most beautiful. Cruise past waterfront estates as the light softens, anchor in calm waters for cocktails and conversation, or remain underway as the horizon glows in brilliant color. Whether celebrating a special occasion or simply enjoying a relaxed evening with friends and family, sunset aboard Andiamo is defined by elegance, serenity, and unforgettable views.

Experience an exclusive private dolphin and wildlife tour through the pristine waters of Bradenton Beach and Anna Maria Island! Exploring the waters of Bradenton Beach and Anna Maria Island with a USCG-licensed captain. On this tour, your group will have the entire boat to yourselves as you cruise the stunning Gulf of Mexico coastline and back bays, searching for dolphins, manatees (seasonal), and coastal wildlife in their natural habitat. Your local captain will navigate the grass flats and intracoastal waterways, where dolphins frequently play and feed. During low tide, watch wading birds like herons, egrets, and pelicans on the exposed flats. In season, you may spot manatees grazing in the shallow waters. This personalized eco-tour offers incredible photo opportunities and an intimate connection with Florida's diverse marine life. Book your private adventure today for an unforgettable Anna Maria Island experience!

Sarasota has a history unlike most cities—one that’s embedded with tales of the circus and its special performers. Avoid guidebooks and book this Sarasota Circus Secrets History Tour led by a circus historian. Hear stories and commentary about the city’s performing past and its quirky art and culture scene, including tales of showmen and performers of the circus.

Welcome aboard Exit Strategy, a bold and unmistakable Pardo 54 — where Italian style meets Sarasota Bay. With sleek European lines, an aggressive profile, and an expansive open deck designed for entertaining, this yacht was built to turn heads. As the sun begins to set and the water reflects shades of gold and crimson, Exit Strategy becomes even more striking. This is not just sunset cruising — it is making an entrance. Your sunset charter offers a refined yet energetic way to experience Sarasota Bay at its most beautiful. Cruise past waterfront estates as the light softens, anchor in calm waters for cocktails, or remain underway as the skyline begins to glow. Perfect for celebrations, romantic evenings, or stylish gatherings with friends, sunset aboard Exit Strategy is defined by presence, atmosphere, and unforgettable views.

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.

Welcome aboard Exit Strategy, a bold and unmistakable Pardo 54 — where Italian style meets Sarasota Bay. With sleek European lines, an aggressive profile, and an expansive open deck designed for entertaining, this yacht was built to turn heads. As the sun begins to set and the water reflects shades of gold and crimson, Exit Strategy becomes even more striking. This is not just sunset cruising — it is making an entrance. Your sunset charter offers a refined yet energetic way to experience Sarasota Bay at its most beautiful. Cruise past waterfront estates as the light softens, anchor in calm waters for cocktails, or remain underway as the skyline begins to glow. Perfect for celebrations, romantic evenings, or stylish gatherings with friends, sunset aboard Exit Strategy is defined by presence, atmosphere, and unforgettable views.

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.

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.

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.

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.

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.

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.

Sarasota has a coveted spot on Florida’s Gulf Coast, offering dazzling sunsets and hours of warm weather. Take a break from the renowned beaches and hop aboard a private charter boat for more fun in the sun. This private charter allows you to pick the activities for your excursion. Ride to beaches and sandbars. Bring drinks to create your own booze cruise. Swim and snorkel or simply see the sunset from the water.

Florida’s Gulf Coast is an angler’s paradise with this private fishing charter in Sarasota, offering a chance to cast a line just off the John Ringling Causeway. Arrive early when the fish start biting or fish during an evening sunset. The captain customizes your tour to target specific fish, and a small sightseeing tour can be arranged if you want a break from fishing.

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.

The fully private 4-hour sandbar boat party is the absolute best way to enjoy a day in Sarasota!! Once you've boarded the boat with your food, drinks and supplies, we'll cruise along the beautiful waters of Sarasota Bay headed to the sandbar. Along the way, be sure to be on the lookout for any of the hundreds of dolphins that call the bay their home. Once at the sandbar you'll be able to hop off the boat and play or lounge in the shallow clear waters. The entire charter is 4 hours long, but depending on which sandbar we go to, you'll have about 3-3.5 hours to enjoy the actual sandbar! Nothing beats a day out on the bay, especially when you're playing at the sandbar!

Welcome aboard "Kai Fin" our exceptional Yellowfin center console. This luxurious vessel is designed for the ultimate entertainment and comfort on the water. Kai Fin is our head-turning Yellowfin designed purely for fun on the water—think effortless sandbar days, smooth sightseeing, dolphin watching, and golden-hour sunset cruises. With a sleek custom wrap and a soft, dry ride, Kai Fin gets you there fast—and in serious style. What a day aboard feels like Glide to clear shallows, step off easily for a swim, lounge up front with friends, then chase a fiery sunset soundtrack on a killer stereo. Your captain handles the plan, the docking, and the details—so you just relax. Whether you’re cruising the coastline or relaxing at anchor, "Kai Fin" offers unparalleled luxury and comfort. Enjoy your time aboard this remarkable yacht!

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.

Welcome aboard Andiamo, a stunning 2026 Absolute Navetta 58 that blends modern Italian design with expansive volume and refined coastal performance. With sweeping glass lines, elevated deck spaces, and beautifully balanced proportions, this yacht offers an exceptional setting for an unforgettable evening on the water. Elegant yet inviting, Andiamo provides generous indoor and outdoor living areas that flow seamlessly together — creating a private, polished atmosphere ideal for golden hour cruising. Your sunset charter offers a refined and unhurried way to experience Sarasota Bay at its most beautiful. Cruise past waterfront estates as the light softens, anchor in calm waters for cocktails and conversation, or remain underway as the horizon glows in brilliant color. Whether celebrating a special occasion or simply enjoying a relaxed evening with friends and family, sunset aboard Andiamo is defined by elegance, serenity, and unforgettable views.

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.

Welcome aboard Memory Maker, our spacious Aquila 44 power catamaran — a 50’ power cat experience designed for comfort, stability, and unforgettable evenings on the water. With four distinct entertaining spaces — flybridge, bow lounge, aft cockpit, and climate-controlled salon — Memory Maker offers multiple vantage points to enjoy golden hour across Sarasota Bay. Her wide beam and twin-hull design provide exceptional stability, making sunset cruising smooth and relaxed from start to finish. This is sunset, elevated. Your sunset charter offers a refined and unhurried way to experience Sarasota Bay at its most beautiful. Cruise past waterfront estates as the light softens, anchor in calm waters for cocktails and conversation, or remain underway as city lights begin to glow. With four separate gathering areas, guests can spread out or come together — creating an atmosphere that feels both intimate and expansive.

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.

Welcome aboard "Kai Fin" our exceptional Yellowfin center console. This luxurious vessel is designed for the ultimate entertainment and comfort on the water. Kai Fin is our head-turning Yellowfin designed purely for fun on the water—think effortless sandbar days, smooth sightseeing, dolphin watching, and golden-hour sunset cruises. With a sleek custom wrap and a soft, dry ride, Kai Fin gets you there fast—and in serious style. What a day aboard feels like Glide to clear shallows, step off easily for a swim, lounge up front with friends, then chase a fiery sunset soundtrack on a killer stereo. Your captain handles the plan, the docking, and the details—so you just relax. Whether you’re cruising the coastline or relaxing at anchor, "Kai Fin" offers unparalleled luxury and comfort. Enjoy your time aboard this remarkable yacht!