The Best Luxury Yachts, Booze Cruises, Boat Rentals & Fishing Charters in Sarasota
From sleek sailboats to upscale yachts and family-run fishing fleets, these top-rated experiences invite you to see Florida’s Gulf Coast from its most dazzling perspective: the deck.
With sun-soaked days, turquoise waters and a coastal breeze, the Sarasota area is made for life on the water. Whether you’re looking to sip champagne aboard a private yacht, join a laid-back booze cruise with friends or cast a line on a deep-sea fishing adventure, Sarasota offers an array of boating charters and local tours to fit every kind of traveler.
Luxury Yachts
Glide across Sarasota Bay’s glimmering blue waters aboard a luxurious private yacht. Whether you’re celebrating a special occasion or soaking up the sunset with friends, Sarasota-area yacht rentals offer personalized service, spacious decks and unforgettable views.

Photo courtesy of Sail Venice
Sail Venice
Departing from Crow’s Nest Marina at Venice Inlet, Sail Venice offers relaxing two-hour sailing adventures along Florida’s Gulf Coast. Choose from daytime or sunset cruises aboard a comfortable sailing yacht for up to six guests. Enjoy dolphin sightings, sea breezes and stunning coastal views on this laid-back voyage that perfectly captures the charm and tranquility of Venice.
Marina Jack II Cruises
A Sarasota institution, the Marina Jack II yacht offers a variety of cruises right from Bayfront Park's Marina Jack restaurant—including their popular Sunset Dinner Cruise. Indulge in a white-tablecloth meal paired with your drink of choice as you glide along the scenic waterfront and under the iconic John Ringling Bridge.
With breathtaking views of the city skyline, this luxury cruise is a feast for the senses while champagne flows and new friends are met along the ride.
Kokomo Charters
Set sail in comfort with Kokomo Charters, a family-owned company offering luxury private cruises through Sarasota Bay and around the nearby islands. Kokomo’s sleek powerboats are ideal for dolphin watching, sandbar lounging, or sunset toasts on the water. Each charter includes a friendly crew, complimentary refreshments and plush amenities—creating a relaxed, island-inspired escape for couples, families or friends seeking the perfect day on the Gulf.

Key Sailing
For an authentic Sarasota sailing experience, choose Key Sailing, led by husband-and-wife team Captain Tim and First Mate Jan. Their award-winning private charters invite guests to learn the ropes, take the helm or simply unwind as the breeze fills the sails. Known for warm hospitality and personal touches, Key Sailing offers an intimate, scenic escape across Sarasota Bay.
Kathleen D Sailing Catamarans
Sail away aboard the Kathleen D, a spacious sailing catamaran offering daily cruises and private charters from downtown Sarasota. Glide through Sarasota Bay or out into the Gulf, where dolphins often play in the boat’s wake and tangerine sunsets deepen the sky. With a knowledgeable crew and years of experience, Kathleen D Sailing Catamarans offers a peaceful and memorable way to explore the region’s coastal beauty.
Booze Cruises
One of the best ways to unwind on vacation is grabbing a drink with friends and family. Sure, you could go to the bar for a frozen daiquiri or tote some beers to the beach, but have you considered a cruise while you booze? We have several ways to hit the water while you toast to a good time.

Photo courtesy of LeBarge Tropical Cruises
LeBarge Tropical Cruises
For a true tropical experience, LeBarge Tropical Cruises blends relaxation and revelry on its narrated sightseeing cruises, sharing the history and culture that built Sarasota. Float along the peaceful waters of Sarasota Bay while enjoying refreshing and tropical drinks from the onboard bar on the top deck of the boat.
This vessel is easily recognized in the marina of Bayfront Park for its artificial palm trees lined along the top and an iconic mermaid statue. Themed cruises and live entertainment make for a lively and enjoyable voyage at sunset hour, which embarks from downtown's Bayfront Park daily.
Cruisin' Tikis Sarasota
There's no better way to end a day in paradise than by watching the sun dip below the horizon aboard a floating tiki bar. Aboard Cruisin' Tikis, sip on handcrafted cocktails, local beers or your favorite wine as the sky paints a mesmerizing palette of colors. With friendly staff, fun music and a relaxed ambiance, this cruise guarantees a good time.
Tours range from 90 minutes to three hours, motoring through destinations like Sarasota Bay and the Intracoastal Waterway. Excursions accommodate up to 6 people (10 years old and over) and are customizable based on availability.
Fishing Charters
Fishing the Gulf offers a respite from life's frenetic pace. Explore remarkable guide operators, each offering a chance to enjoy the expansive waters of Sarasota County. Navigate the intricate Intracoastal Waterway, meander along the scenic bayfront and reel in that trophy fish you've been dreaming about.
Flying Fish Fleet
Cast off with Flying Fish Fleet, Sarasota’s premier name in sportfishing for more than 60 years. Operating out of Marina Jack, this trusted fleet offers a variety of deep-sea and nearshore fishing trips, ranging from half-day party-boat excursions to private charters with experienced captains. All equipment is provided, and passengers can relax on board while reeling in grouper, snapper and other favorites.
CB’s Saltwater Outfitters
Located near the South Siesta Key Bridge is CB's Saltwater Outfitters—the largest bait-and-tackle shop on the water. A one-stop shop for all your boating needs, CB’s offers a wide range of rentals, from fishing boats to pontoons and kayaks. They also provide fishing gear, bait, sun protection, apparel, snorkel and dive gear, safety equipment and more. With a knowledgeable and friendly staff, CB's is an excellent choice for those new to boating or those looking for a hassle-free experience.
Boat Rentals
Looking to explore Sarasota’s stunning waterways on your own terms? These local rental companies offer an effortless way to get on the water—rent by the half-day, day, week or month!

Suntex Boat Rental at Marina Jack
Located right in the heart of downtown Sarasota, find Marina Jack, whose fleet, operated by Suntex, includes double-decker pontoon boats with slides, center consoles and deck boats. Rent for two, four or eight hours, and enjoy Bluetooth stereo, a cooler and shade from Bimini tops. Fish, swim or sunbathe, or stop by favorite waterfront restaurants.
Cannons Marina
Out on Longboat Key, Cannons Marina lets you choose from a fleet of center-consoles, deck boats, pontoons and runabouts for cruising, fishing or sandbar-hopping. The marina is perfectly positioned for adventures to Jewfish Key, Beer Can Island and the Gulf's most clear swimming spots. Friendly, experienced staff will help plan your route, find hidden gems and pack your day with dolphin sightings, island lunches or sunset sails.
Freedom Boat Club
Founded in Sarasota, Freedom Boat Club is the world's largest members-only boat club with hundreds of locations across the U.S. In Sarasota County alone, you can find seven different clubhouses to launch from. Freedom takes care of all the maintenance, cleaning, repair, insurance and storage. You just show up and go!
The Coastal Concierge
Let The Coastal Concierge craft your perfect getaway with seamless service and curated coastal experiences. This luxury lifestyle and vacation concierge specializes in arranging private yacht charters, fishing excursions, private chefs, transportation and other bespoke adventures. Whether you’re celebrating a milestone while in the Sarasota area or simply savoring a day on the water, their team handles every detail so you can relax.
Boating Safety in Florida
To operate a motorized watercraft of 10 horsepower or more in Florida, state law requires anyone born on or after January 1, 1988, to successfully complete an approved boating safety course. Passing this course will grant you a Boating Safety Education Identification Card (also referred to as a Lifetime Boating License) issued by the Florida Fish and Wildlife Conservation Commission (FWC).