Top Sarasota Holidays

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.

Escape the mainland for half a day, and discover some of coastal Florida's most picture-perfect scenery, on this private, half-day boat charter. Pick between morning and afternoon start times, and make your own way to the dock. You can spot manatee and dolphins in Heron Lagoon and Casey Key, see a historic swing bridge, stop at a tropical beach for shelling, pause at a tiki for drinks and snacks (own expense), and more.

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.

See Florida’s Anna Maria Island from a different perspective as you soar above in a parasail. Join a small group and set sail from the marina for the perfect location to begin your flight. Then, gear up and feel the wind beneath you as you soar high above the water, taking in the panoramic views.

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.

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.

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.

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.