Top Sarasota Private and Luxury

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.

Explore the stunning waters of Sarasota Bay with customized private boat tours, featuring dolphin watching, sunset cruises, and wildlife viewing, all led by expert local captain Bobby Smith. Tailor your experience to fit your preferences, whether you're aiming for a relaxing sunset or an adventurous dolphin tour. Enjoy the comfort of a spacious Tritoon boat designed for leisure, complete with plush seating and panoramic views. This is the perfect outing for couples, families, or friends looking to create unforgettable memories on the water. - Private tours accommodating 1 to 6 guests for a personalized experience - Options for dolphin watching, sunset viewing, and sandbar hopping - BYOB policies for a fun, relaxed atmosphere - Customize your tour duration from 2 to 6 hours

Join Watersports Now for a 2 hour clear kayak guided tour minutes from downtown Sarasota. Explore mangroves, seagrass beds, and potentially spot dolphins, manatees, and seabirds from a crystal-clear kayak that lets you see straight down to the sea life below. What to Expect: Launch from Longboat Key near Sarasota Paddle calm bays, mangrove tunnels, and open water Learn about the local ecosystem Our friendly guides welcome all skill levels. Guests should have a basic level of physical fitness and be comfortable paddling for the duration of the tour. A safety briefing and Coast Guard-approved life jackets are provided, with time for photos along the way. Kayak Info: Our clear tandem (2-seat) kayaks have a 385 lb combined weight limit to ensure proper weight distribution and safety. Solo use is available for guests over the limit or for odd-numbered groups—please contact the supplier after booking. Solo riders must not exceed 325 lb for safety and balance.

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!

For something different than beaches, discover one of Sarasota's most unique communities on an insider’s tour of Pinecraft, an Amish vacation enclave right on the outskirts of town. Led by a guide with personal connections to the local Amish and Mennonite communities, learn about their roots in Florida, traditional customs, and beliefs. You’ll also have the chance to shop for handmade gifts and sample famous pie at an Amish cafe.

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.

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.

Try your luck spotting dolphins in their natural Florida habitat on this group boat tour around Anna Maria Island. And don’t keep your eyes peeled for just dolphins—you’re in with a chance of seeing manatees, eagles, osprey, and more. Whether you’re a Holmes Beach local or you’re just visiting, this is an experience nature-lovers won’t want to miss.

Explore Sarasota’s vibrant shopping scene on this unique boutique tour. Enjoy browsing through four locally-owned boutiques, where you can sip on complimentary bubbles while uncovering the rich history of Burns Court and other landmarks. This engaging 3.5-hour experience includes light bites and insights into the local art and culture, making it a delightful outing for shopping enthusiasts and those seeking a taste of Sarasota’s charm. This journey offers a blend of retail therapy and educational exploration without the pressure to make purchases. This is SO fun with friends-get your woman's club, book club or any social group together and enjoy an afternoon downtown!

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.

Let your local guide, who’s also an actor and songwriter, show you around Sarasota on this cabaret-style tour of the city. Start with free wine or beer in the Trolley Cottage Tiki Bar before setting off in an air-conditioned trolley, with stops at Lido Beach in time for sunset, and Sun King Brewery for some craft beer tasting and a tour.

Splash into an unforgettable adventure where playful dolphins, gentle manatees, and crystal-clear waters await—perfect for first-time snorkelers and nature lovers alike, this private tour is your chance to explore Florida’s marine life up close in a relaxed, shallow-water setting

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 calm waterways around Siesta Key, just outside of Sarasota, on this small-group excursion. Choose a kayak or stand up paddleboard, whichever you are more comfortable with, for your journey. Then, follow your guide through the Jim Neville Marine Preserve observing mangrove islands and local wildlife while you paddle towards a secret beach.

Explore the serene waters of Clam Bayou on our clear kayak tours, perfect for adventurers of all skill levels. Paddle beneath a stunning canopy of mangroves with a knowledgeable guide and enjoy the possibility of spotting manatees, dolphins, and birds such as herons and egrets in their natural habitat. Take in the scenic beauty just minutes from downtown St. Pete while learning about the local ecosystem. All gear is provided, including transparent kayaks, life jackets, and paddles. The calm waters are ideal for both beginners and experienced paddlers, offering a unique opportunity to see marine life through the transparent kayak hull. Kayak Info: Our clear tandem (2-seat) kayaks have a 385 lb combined weight limit to ensure proper weight distribution and safety. Solo use is available for guests over the limit or for odd-numbered groups—please contact the supplier after booking. Solo riders must not exceed 325 lb for safety and balance.

Discover the mangroves of Florida with the help of a guide to take you through the waterways of Robinson Preserve on this group kayaking tour. Learn all about the area from your guide and keep your eyes peeled for a chance to spot native birds, fish, and even manatees while you paddle. Your tour guide will also take you up an observation tower to take photos of the scenery.

Discover the charming allure of St. Armands Circle, once owned by circus magnate John Ringling, on this engaging afternoon tour. Delight in a unique blend of shopping and tasting experiences as you browse stylish boutiques while sampling gourmet tea and olive oil. Enjoy a Mediterranean-inspired sampler plate paired with a glass of bubbles, and explore a luxury art and gift boutique with another glass in hand. Conclude your day with a personal shopping experience or visit the enchanting St. Armands Magical Garden, topped off with a sweet treat to savor the day. - Explore locally-owned shops and boutiques on historic St. Armands Circle - Enjoy a Mediterranean-inspired tasting platter and bubbly - Participate in tea and olive oil sampling for a culinary experience - End with a visit to the St. Armands Magical Garden or personal shopping time

Discover some of the finest examples of Sarasota architecture and design in a comfortable, air-conditioned vehicle on this tour of the city. Hear about styles like Art Deco, Mediterranean Revival, and Mid-Century Modern with the help of your local tour guide. It’s a great experience for locals and tourists alike to learn more about Sarasota.

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.

Join a tarot reader to explore a side of Sarasota most tourists don’t get to see. From a sound bath at the Crocker Memorial Church with a sound healer to shopping at the Pixie Dust Metaphysical Boutique, your guide will take you through the city on a comfortable trolley, giving a mini tarot and spirit gallery readings on the way.

Come experience Anna Maria Islands best year round boat tour with Gulf Islands Adventures! With 7+ years in business you are sure to enjoy 2+ hours on the water with our guided Craigcat boat tour. Drive your on Craigcat while following a guide, feeling like a kid the entire trip!

Spend some time appreciating the artistic side of Sarasota during this public art tour. Did you know that there are more than 60 sculptures, murals, and monuments throughout the city? Hop on a trolley, or in a van for smaller groups, and cruise around to view them. Your group will roll through St. Armands Circle and other areas as your guided art expert tells you the history and tales of Sarasota’s art culture.

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.