Top Florida Sailing Tours - page 5

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain Kip takes you to the best spots to view the sunset, and see a dolphin.

This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, Deer Point, Fair Point and Deadman's Island. We may also sail east under the Bob Sikes (Pensacola Beach) Bridge, exploring areas of Quietwater Beach and the Santa Rosa Sound. A small group atmosphere makes this tour so enjoyable. The Jolly Mon can accommodate parties of up to 6 guests maximum. Sailing is a unique experience and fun for all ages. This tour is great for families, couples, adventurers and seekers of relaxation alike! Guests can learn from the Captain about the area wildlife, history, and the art of sailing. Take the helm and learn to sail or just sit back and enjoy the sights and sounds. Once we leave the dock and motor through the channel, we set sail for a tranquil excursion. There is something special about traveling across the water with only the power of the wind. Every tour is different, but always such a fun and easygoing activity, so many lasting memories to be made!

KEY LARGO BOAT CHARTERS offers a VIP private sunset excursion for you and your loved ones. No need to worry about large crowds or waiting in long lines. Personalize the trip to your liking. A private charter makes it more personable and creates lifelong memories. Enjoy the beautiful views of the sunset while enjoying your favorite drinks and cocktails.

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast.

We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will leave you satisfied and content. We will get intimate with Biscayne Bay, our boats are designed to visit every corner of the bay, we can reach shallow waters and get up close to mangroves and the wildlife they sustain and attract !

Nature lovers and eco-adventurers will love this private, low-key tour. Take a pontoon boat to explore mangrove forests, winding waterways, and mangrove-lined tidal creeks. Enjoy kayaking, or stand-up paddleboarding in a diverse marine ecosystem. A cooler is provided so guests can bring snacks and drinks, which can be savored on a deserted sandbar.

Step onto a two-level party boat where Miami’s nightlife meets open-air views of Biscayne Bay—no shoulder-to-shoulder crowds, just space to dance, mingle, and take in the skyline as the DJ keeps the energy up. With an unlimited open bar and snacks, it's a great option for birthdays, bachelorettes, or any night worth celebrating. After docking at Bayside Marketplace, a private party bus transfers keep the momentum going with express entry to one of Miami’s top clubs—Revenge, Exchange, or Taboo—so there’s no stress about what comes next.

A private yacht charter in Miami puts the city's coastline and a full range of water sports within reach of your group—without the scheduling constraints of a shared boat tour. A captain and crew handle the vessel throughout, leaving your group free to choose between snorkeling, paddleboarding, and jet skiing, or simply taking in the views from the deck.

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you to create your own adventure. Connect with Key West's abundant wildlife as you cruise the waters in search of our resident coastal dolphins. From there, we'll head to a secluded sandbar, a pristine shallow-water oasis where you can unwind and enjoy the tranquility. This tour is ideal for those who prefer to relax and socialize. Spend your time floating, swimming, or simply lounging with a cold beverage in hand. While snorkeling is an option, it is not a guided activity on this trip, making it perfect for guests who are more interested in a leisurely day on the water than a structured snorkel excursion. We'll provide a snack of fresh, organic fruit from Date & Thyme, and the trip is BYOB so you can bring your favorite drinks.

This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for fun in the sun on this sailing, dolphin watch, beach hopping and snorkeling adventure. Sail away through historic Grand Lagoon and see dolphins swimming alongside the Daydreams, then jump in for a shallow-water snorkel experience to see different species of marine life. Relax, feel the warm sea breeze and enjoy complimentary beverages on board! Again, this is a fully private charter for up to 12 guests. Price is all inclusive and includes fuel, ice, water, soda, beer, wine and rum punch.

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and best marina in SOUTH BEACH... We've found the boats, brought on the food and drinks, and made sure that everything that a good yacht trip needs is already here. And then your crew is going to help you with the FUN! So just relax and enjoy a Miami Beach bachelorette boat-day out the way it should be...

Cruise the waterways of Fort Myers Beach at night on this small-group tiki boat experience. Enjoy a relaxed BYOB format while a captain handles navigation, so that you can focus on the atmosphere. With limited capacity, the cruise offers a social but uncrowded setting, combining music and scenic views for an upbeat, unique way to experience Fort Myers after dark.

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for fun in the sun on this sailing, dolphin watch, beach hopping and snorkeling adventure. Sail away through historic Grand Lagoon and see dolphins swimming alongside the Daydreams, then jump in for a shallow-water snorkel experience to see different species of marine life. Relax, feel the warm sea breeze and enjoy complimentary beverages on board! Again, this is charter for up to 6 guests. Price is all inclusive and includes fuel, ice, water, soda, beer, wine and sangria. You are also welcomed to bring your own food and drinks on board.

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moon comes up over Key West, enjoy star gazing opportunities and a moonlit sky as the boat glides through the majestic waters at night.

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart of Destin Harbor while you soak in the scenery and the good vibes. On this 3-hour excursion, you’ll enjoy snorkeling the best areas in Destin and enjoy the crystal-clear water and white sand. Be sure to call to choose your Food & Beverage add-ons to keep the party going. We provide a cooler, ice, cups and shot glasses, bottle openers, bottled water, and an electric pump for your floats—everything you need for a laid-back, unforgettable day. Parties 7 or more please call 850-200-0573 for availability.

Your Fun Size custom Tiki Boat is the most fun way to explore the bay. Equipped with a waterslide, bar seating for 6 people, on board sound system with Tiki-Oki, and the friendliest most fun captains around. You'll be sure to have the time of your life.

Meet at Miami Beach on Lincoln Road for a 7am departure and we will take a double decker bus and travel to the most famous Key, Key West. When we arrive at 10:30am you will have time to walk around and enjoy Key West. Make it over to The Key West Beach Water Park In Key West, Florida, Smathers Beach Key West FL 33040 and have the best day in the sun with unlimited use of water activities. Go kayaking, paddle boarding, sailing or just seat in your beach chair and umbrella and enjoy the sun. Make sure to be at the bus no later than 4:30 for your return trip to Miami. On the beach you will be able to upgrade and enjoy a parasail ride.

Unwind at the end of the day on a private sunset sail through the Banana River Lagoon. This private catamaran experience offers a calm, unhurried way to enjoy Florida’s Space Coast as daylight fades. With ample space, shaded seating, and onboard facilities, you can relax in comfort while cruising waters known for frequent dolphin and manatee sightings—an easy, peaceful way to enjoy the evening.

Watch the sunset off the coast of Key West on this private sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail onboard a private sailing vessel with a captain and mate. Stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset. Soft drinks are included. A cooler with ice is available to store any beverages brought on board.

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and your guests! You'll sail around Shell Island into the Gulf of Mexico, while you enjoy dolphin watching throughout your trip. Your charter will end watching the breathtaking sunset over the horizon. Enjoy a flexible itinerary during your private charter. The Daydreams is a 46-foot Beneteau monohull sailboat that offers luxury private charters for up to 12 guests. Sail and enjoy a beautiful evening on the water. Private charters aboard Daydreams include complimentary beer, wine and non-alcoholic beverages. You are also welcome to bring your own food and drinks on board. A 20% Gratuity for the Captain and Crew will be requested at check in.

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life. Take the helm, learn how to raise and trim the sails, or just sit back and relax. Enjoy a private sunset cruise off the coast of Key West See the sites of Key West from the water Snacks and beverages included Fun for an entire group or family Private guides for a more personalized experience. Enjoy a private sunset sail off the coast of Key West and see the sights of Key West. Bring your favorite alcoholic beverages to enjoy while watching the sunset. Knowledgeable Captains to explain the art of sailing.

This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become part of the crew. Our goal is to perform as a unit and get the boat to sail as fast as possible. However, if you are looking for a more laid back experience, the captain is equipped to handle the vessel solo. In addition you will be in the hands of captains that are incredibly excited for the sport of sailing and will infuse the experience with a deep enthusiasm for the beauty and art of sailing ! Last but not least Biscayne Bay is the most stunning back drop to the City of Miami !

There's nothing quite like cruising the calm waters of Fort Myers Beach on your custom Tiki Boat. Your Captain/Entertainer will make sure you have everything you need, and bring the party with custom curated playlists, Tiki-Oki, and party games. We'll stop at a secluded sandbar where you can enjoy the on board water slide, Paddleboard, and Floats. Our return trip keeps the party going.

What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting that allows guests to fully immerse in the beauty of the holiday lights without the crowds or noise of typical boat tours. Our yachts offer a more personalized, relaxed atmosphere with comfortable seating, and the option to book private charters. You’ll also be guided by experienced USCG captains who know the waters and the best vantage points to view the city’s spectacular light display. Whether you’re celebrating a special occasion or seeking a peaceful, romantic evening, our tailored sailing experience ensures you enjoy the Nights of Lights in comfort and style.