Top Florida Cruises & Sailing

Step aboard a fun sightseeing cruise in Miami, showcasing beautiful views of Biscayne Bay and the homes of the rich and famous. Enjoy panoramic views of Miami's skyline, the vibrant Port of Miami, secluded Fisher Island, and the sun-kissed shores of Miami Beach, all with bilingual commentary. Witness the opulence of Miami Beach mansions and create lasting memories. Check-in at the Bayride Ticket Kiosk behind Victoria's Secret at Bayside Marketplace.

Explore one of Florida's most picturesque harbors on this Tampa history cruise that transports travelers back in time across stunning blue waters. See the real-life pirate ship known as Gabriella up close and take in views of million-dollar homes, popular museums, and the famous 'Plant Hotel' as you listen to expert commentary about the city's rich past.

Spice up any Florida vacation with a cruise on the Gulf of Mexico. Beginning in St. Petersburg, enjoy a beautiful sunset (depending upon the time of year) and listen to live music on board the elegant 'StarLite Sapphire' yacht. Choose from the open-air observation deck or the climate-controlled cabin inside. Either way, the view is spectacular. Then dance the night away or take a romantic stroll along the deck.

Cruise to Shell Island and search for wild dolphins on a catamaran sailing trip from Panama City Beach. The catamaran’s broad, stable deck makes it a comfortable alternative to smaller boats prone to rocking in the waves, and since it’s stocked with paddle boards, snorkeling gear, and a waterslide, it’s the perfect base for playing in the clear water off Shell Island.

Climb aboard a schooner for an afternoon of sailing in Clearwater Beach with this tour. Enjoy sea breezes and admire views you wouldn't get if you stayed on shore during this scenic cruise. Keep an eye out for wildlife like dolphins and manatees during the sail. Guests are permitted to bring alcoholic beverages on board the schooner.

Cruise out on the Gulf of Mexico and watch the sun dip below the horizon on this cruise from Clearwater. Sail along the Intercoastal Waterway, keeping an eye out for bottlenose dolphins and listening to commentary about your surroundings. Just as the sun is setting, guests 21 and older enjoy a champagne toast before sailing back to the dock.

Soak up sunset views from the water's edge, and admire a perspective many visitors miss, on this Key West sailing tour. Sample up to eight different wines and/or five different beers as you sail, and indulge in a selection of gourmet hors d'oeuvres to accompany them. As you go, learn more from your crew, and enjoy a festive and celebratory way to toast to your trip.

Watch as day turns into night off the coast of Florida on this sunset cruise from Clearwater. Enjoy the scenery and peaceful calm of a late-afternoon cruise on board a vessel with plenty of space to stretch out and soak up the breathtaking view. Watch a beautiful Florida sunset as the sun glows and gently settles into the Gulf of Mexico. Toast the new evening with a glass of Champagne.

Discover the crystal blue Miami waters with a captain’s help on your own private 12-person boat. Choose from various tour durations, and even a sunset option, and relax on the deck or soak up the sunshine on a floating mat. Take in views over the Miami skyline, Bayside Marketplace, the Port of Miami, and more, while your crew does the navigating for you.

Simplify your arrival to Port Canaveral with a private transfer to Orlando Airport. After your cruise, meet a private driver at Port Canaveral and receive assistance with luggage. Skip the hassle of shared shuttles or taxi lines and travel in the comfort of an air-conditioned vehicle to Orlando Airport. Get dropped off at the airport on time.

Avoid crowded bars and opt for a more fun way to listen to great music and enjoy your favorite drinks—a cruise that passes through downtown Fort Lauderdale, Port Everglades, and Las Olas Boulevard. No need to worry about expensive bar tabs—you can bring your own drinks and use the cooler boxes on the boat. The afternoon tours stop at the legendary sandbar in front of Millionaire's-mile for a swim, while the evening cruises through downtown and explores the yachts and mansions.

Set sail on this beautifully appointed Catamaran, "Cool Beans", and start making lasting memories! Cool Beans Cruises is the perfect way to see SW Florida, By Water! Choose from a 2.5 hr. Day-Sail or a 2 hr. Champagne Sunset Cruise. With quick access to the Gulf of Mexico, you will experience true sailing with limited motoring. A stop for a swim to a secluded pristine beach for shelling can be part of the Day Sail Only(weather permitting). Keep your cameras ready to capture a photo of the local wildlife to see along the way! Cool Beans Catamaran will accommodate up to 20 passengers. PRICE INCLUDES SODA, WATER, BEER, & WHITE WINE . A CHAMPAGNE TOAST AT SUNSET IS INCLUDED FOR THE SUNSET CRUISE. Please note that parties of 7 or more, an 18% gratuity is added to our base price and is due and payable to the Captain. Also available is our 25 Ft .Pontoon, Lil' Beans! Perfect for up close eco/nature /shelling and island hopping. Book a Private tour for a group for up to 6 guests

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico offers a great opportunity to relax and leave your worries behind. Listen to tropical music as you enjoy a complimentary beverage on board Panama City Beach’s best sunset cruise! At our on board bar we have snacks and a full liquor bar for additional beverages available for purchase. Enjoy a variety of cocktails, including our signature Privateer Punch! Please note our bar accepts debit/credit card transactions only. Our Sunset Sails offer you an opportunity to see some of our area's greatest sights while enjoying the breezes of the water. Be on a sharp lookout for dolphins as these majestic creatures seem to be more active in the later afternoons.

Harken back to yesteryear on a fun Fort Lauderdale sightseeing cruise aboard the Carrie B paddlewheeler. Sail past yachts, mansions, and cruise ships along the New River, Intracoastal Waterway, and Port Everglades. Spend time on the open sun deck, sit outside under a canopy, or in air-conditioned comfort on the main deck. The captain narrates the tour and a full-service bar and light snacks are available to purchase.

Take time out from the daily grind and enjoy wine, beer, prosecco, and frozen cocktails on this two hour cruise along Miami’s coastline. Relax as the sun sets over Miami and then enjoy Miami’s spectacular nighttime skyline light up before you. You get 2 hours of relaxing music, unlimited drinks, and beautiful sights to unwind and de-stress with your family or friends. Seats are limited so make sure to book early. Please note this is not a party cruise, it is a way to relax after a hard week and enjoy the beautiful sights with an eclectic mix of music.

See St. Augustine from a new perspective with this leisurely sunset cruise. Climb aboard a boat for a scenic cruise including views of Castillo de San Marcos National Monument, the Bridge of Lions, and the St. Augustine Lighthouse. Sip beer or wine from the on-board bar with the Osprey, 21 and older option, or select the Island Breeze option for a family-friendly experience.

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico offers a great opportunity to relax and leave your worries behind. Listen to tropical music as you enjoy a complementary glass of wine, Sangria, cold beer or non-alcoholic beverage on board Panama City Beach’s best sunset cruise! At our on board bar we have snacks and a full liquor bar for additional beverages available for purchase. Enjoy a variety of cocktails, including our signature Footloose Punch! Please note our bar accepts debit/credit card transactions only. Our Sunset Sails offer you an opportunity to see some of our area's greatest sights while enjoying the breezes of the water. Be on a sharp lookout for dolphins as these majestic creatures seem to be more active in the later afternoons.

Discover 28 miles (45 kms) of the Floridian coast on a 1.5-hour Jet Ski tour. With several daily tours, you can easily find a time that fits with your schedule. The tour is priced per Jet Ski, so you can ride tandem with a friend at no additional cost. Your guide is on hand at all times to lead the way on your aquatic adventure.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, numbers are restricted to 24 so you have a spot at the rail when it’s time to capture photos of the setting sun.

Take a relaxed sunset cruise launching from St. Pete Beach and view a different side of the city on this shared small group boat ride. Although it’s shared, the passenger count is kept low to create a semi-intimate experience as you cruise through residential canals to view local mansions. As you pass by Tierra Verde, you might see dolphins swimming near your boat. Bottled water is provided, as well as blankets in the cooler months.

Perfect for those who want to squeeze a lot of sightseeing into a limited amount of time. A fully narrated 90-minute cruise along the New River through Fort Lauderdale will let you soak up such sights as the lavish homes and mega yachts along Millionaire's Row.

Experience a famous Florida Keys sunset from a boat with this private tour. Bring up to six people for a private cruise into Key Largo Bay. Keep an eye out for local wildlife including dolphins, manatees, and birds during the tour. Slow down and watch the sunset from a fresh perspective during this cruise.

Discover the sights and marine life of Naples on a sightseeing cruise. You have the opportunity to see birds, dolphins, and, season permitting, manatees. The cruise also takes you past the area’s top mansions, Keewaydin Island, and more. Relax and learn about local history, wildlife, and celebrity real estate during on board commentary. It’s the perfect time to take unobstructed photographs of the city and its natural surroundings.