Top Sarasota Seasonal & Special Occasions

Sunsets in Sarasota are even more spectacular when viewed from the water. Join the Sharkey’s sunset and illuminated night tour to discover Sarasota’s waterways in a new light. You’ll slide into a glass bottom kayak that’s outfitted with LED lights. Paddle into the mangroves and grass flats, viewing marine life beneath you and astounding plant life around you. Use your lights to spot crabs, stingrays, shrimp and more.

This lesson provides everything beginners need to go parasailing above Bradenton Beach and Anna Maria Island: all parasailing equipment, safety instructions, and a motorboat with an experienced crew. Meet at the Bradenton Beach Marina, get harnessed up, and parasail in groups of two or three on approximately 10-minute sessions.

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

Discover Sarasota's thriving nightlife scene—and enjoy cocktails, wine, and more—on this small-group, evening walking tour. Meet your guide in the city center, and head to your first stop: an award-winning cocktail bar. After your first drink, continue to five or six other venues, where you can enjoy nibbles, cocktails, wine, and craft beer; can mingle with locals and hear Sarasota history; and can even catch the sunset.

If you are looking for premium luxury, comfort, style, roominess and a ride that cuts through the water with ease, look no further because you won’t find it anywhere but here! Our 37’ Sea Ray is massive compared to all the other private charter options available. It’s your day, make it the best! All of our charters are custom! We handle everything from amazing “boating with friends” to bachelorette parties, tiki bar hopping, days at the sandbar, dolphin watching, shelling even memorial services at sea! Based in downtown Sarasota, the possibilities are truly endless!! We can head north and explore all the way to Passage Key and Egmont Key, Anna Maria Island, Longboat Key, City Island and Lido Key. OR we can head south and explore Siesta Key, Casey Key and even Venice. The stops along the way are endless. As a premium provider, provisions can be delivered to the boat in advance of your charter. Advertised pricing is for 6 guests, but we can accommodate up to 13 guests.

The Christmas Carol Trolley: Letters to Santa is a 90-minute fun-filled downtown holiday music and lights tour for the whole family with a Christmas carol sing-along, holiday stories, jokes, and trivia, and a charming tour of Sarasota’s downtown neighborhood lights. Special holiday entertainers jump onboard during the tour to share real Letters to Santa and sing your favorite songs! Kids can enjoy a soft drink, while adults sip wine/beer while browsing through our Trolley Cottage Gift Shop full of fun holiday gifts and other treasures before boarding.

Give into temptation and schedule yourself a pampered day in Sarasota at the Sirius Day Spa. You’ll receive full access to the spa, which includes entrance into the Serenity Lounge that includes a refreshment bar. Your body will thank you for a signature spa service of your choice: either a hair blowout with styling, a Dead Sea mud wrap, a massage, an organic facial, or a mani-pedi.

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.

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!

Hop on board for a fun family Halloween party on wheels during this 45-minute Magical Musical Tour with Miss WitchyPOO and her Magic Pumpkin! Don’t forget to dress up—we give prizes for Best Costume on every BooMobile tour! Includes complimentary soft drinks served on the Trolley Cottage porch before the tour.

Discover the magic of St. Petersburg aboard a luxurious private boat charter, accommodating up to 13 guests. Perfect for a range of activities—snorkeling, exploring local sandbars, island-hopping, or even a special proposal—our boat offers something for everyone. Features: Ample seating for relaxation and socializing Climate-controlled cabin that opens up for fresh air Sunbeds for soaking up rays Dining areas for meals on the water A smooth ride even grandma and grandpa will love A cozy estate room for naps Plenty of shaded spots for comfort Experience the epitome of nautical luxury on your next Key West adventure.

If you are looking for premium luxury, comfort, style, roominess and a ride that cuts through the water with ease, look no further because you won’t find it anywhere but here! Our 37’ Sea Ray is massive compared to all the other private charter options available. It’s your day, make it the best! All of our charters are custom! We handle everything from amazing “boating with friends” to bachelorette parties, tiki bar hopping, days at the sandbar, dolphin watching, shelling even memorial services at sea! Based in downtown Sarasota, the possibilities are truly endless!! We can head north and explore all the way to Passage Key and Egmont Key, Anna Maria Island, Longboat Key, City Island and Lido Key. OR we can head south and explore Siesta Key, Casey Key and even Venice. The stops along the way are endless. As a premium provider, provisions can be delivered to the boat in advance of your charter. Advertised pricing is for 6 guests, but we can accommodate up to 13 guests.

If you are looking for premium luxury, comfort, style, roominess and a ride that cuts through the water with ease, look no further because you won’t find it anywhere but here! Our 37’ Sea Ray is massive compared to all the other private charter options available. It’s your day, make it the best! All of our charters are custom! We handle everything from amazing “boating with friends” to bachelorette parties, tiki bar hopping, days at the sandbar, dolphin watching, shelling even memorial services at sea! Based in downtown Sarasota, the possibilities are truly endless!! We can head north and explore all the way to Passage Key and Egmont Key, Anna Maria Island, Longboat Key, City Island and Lido Key. OR we can head south and explore Siesta Key, Casey Key and even Venice. The stops along the way are endless. As a premium provider, provisions can be delivered to the boat in advance of your charter. Advertised pricing is for 6 guests, but we can accommodate up to 13 guests.

Indulge in the ultimate luxury with our Private Sunset Cruise aboard our 36 foot catamaran. Sail the stunning waters of Sarasota Bay and Big Pass as the sun gracefully sets over the Gulf of Mexico. Revel in the serenity, and keep an eye out for playful dolphins and that ever elusive green flash as the sun disappears over the horizon adding a touch of enchantment to your exclusive nautical experience. Unwind and create lasting memories against the backdrop of a breathtaking sunset on this private voyage.