Top Florida Sailing Tours - page 2

Planning a night out in Key West with entertainment can add up quickly. This Key West cruise saves you money by combining an open bar with musical entertainment as you sail the waters keeping an eye out for views of the sunset. Plus, it ends early enough to leave you enough time to bar hop afterward if you’d like.

Set off on a unique pirate-themed boat cruise that travelers of all ages will enjoy. Depart Destin and sail the Emerald Coast while kids and kids at heart enjoy pirate-themed games and entertainment with everything from dancing to sword fighting to a treasure hunt. Adults can join in or relax with alcoholic beverages (to purchase) and enjoy the beautiful scenery.

Kick back and relax on this beautiful 53' sailing catamaran that can accommodate up to 44 passengers. Cruise through the prestigious Port Royal neighborhood in Naples Bay and then set sail into the Gulf of Mexico to watch a breathtaking sunset while sipping your favorite cocktail. Cruises are narrated to point out interesting sights along the way. Dolphin sightings are plentiful and fun for all ages. Pack your favorite drinks and snacks in a cooler, and don't forget to take some pictures! We've been cruising the Naples Waterways since 1991 and are family-owned and operated. Guests are welcome to bring small coolers with their favorite beverages and snacks. Alcohol is permitted. Please note this is not a private boat tour, this is a group tour with others onboard Boarding time is 15 minutes prior to scheduled departure time. Please allow enough time to park and walk down the dock. We leave promptly on time.

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. With only six guests or less, this is truly a VIP experience. If you are looking to unwind before dinner or a night out on the town, enjoy a romantic sunset sail with Paradise Adventures. Sailing along the Gulf of Mexico is a great opportunity to relax and leave your worries behind. Your VIP experience includes a complimentary beverage. Listen to tropical music and enjoy this Panama City Beach sunset cruise! Our sunset sails offer you an opportunity to see some of our area’s greatest sights while enjoying the breezes of the water. RED FLAGS DO NOT AFFECT OUR TOURS. Our tours operate in St. Andrews Bay, where conditions are often much calmer than the Gulf.

Sail to a gorgeous snorkeling spot off the coast of Key West to explore a coral reef home to rainbow-colored fish, anemones, eels, and more. On the hour-long sailing trip to the reef, sip included wine, beer, or soft drinks while watching for dolphins and sea turtles. The captain chooses the snorkeling spot according to each day’s conditions, ensuring the best experience for your group.

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.

Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins as well as views of Key West landmarks like the legendary Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Then, relax on the luxury catamaran to watch the sunset as nibble on tapas such as shrimp cocktail served with wine and champagne.

Explore the only living coral reef in North America on this small-group snorkeling adventure aboard a sailing yacht in Key West. You will receive instruction on how to use the equipment, but it’s recommended that participants be comfortable underwater and have the ability to swim. Common sightings include tropical fish, eels, turtles, dolphins, anemones, and urchins.

Experience the best that Key West has to offer with this combination tour that includes a dolphin watch, snorkeling, and a view of the island’s famous sunset. Spot dolphins in their natural habitat in the Florida Keys National Marine Sanctuary and snorkel in the blue waters surrounding Key West during this family-friendly excursion.

Snorkel North America’s only living coral reef, then catch an unforgettable Key West sunset, all in one trip. Jump into clear waters with provided gear and spot colorful marine life under the surface. Back on board and after you’re dried off, enjoy rum punch or other beverages on deck as reggae music sets the vibe. A perfect mix of adventure and relaxation, ideal for couples or friends.

Hop aboard a catamaran for a sailing excursion in Fort Lauderdale available in English and Spanish. Sit back and relax while you tour the waterways of the city known as the “Venice of America.” Next, head out to the Atlantic Ocean and enjoy the rhythm of calypso music and breaking waves. Sip on an ice cold beverage and take a dip in the water.

Swim among coral and tropical fish in Key West's living reef on this snorkeling excursion. Sit back and relax on a custom-built boat, and sail to the reef where a professional crew is on hand to provide snorkeling instruction and guidance. After your swim, enjoy included beer, soft drinks, and water on the boat for your ride back. All snorkeling equipment is provided.

Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pals on our public activities or having an intimate celebration with your chosen ones on private outings. Fancy a tipple while the waves lap around you? Bring your beverage of choice – just remember, BYOB! Safety and fun go hand-in-hand at Tiki Pub. Every voyage is captained by our experienced crew, ensuring your adventure is smooth sailing from start to finish. Plus, for those looking to have a blast without splashing too much cash, we offer a wallet-friendly option to revel in Fort Myers' captivating waterways.

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.

See the beauty of Biscayne Bay from a whole new perspective with this sailing adventure. Ride along the coastline in an eco-friendly wind-powered sailing boat, and visit sandbars, mangroves, and islets along the way. If you're lucky—you may even spot dolphins or manatees—which are frequently spotted around the bay.

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.

Get front row seats to a stunning Florida Keys sunset, without the hassle of chartering your own vessel, on this catamaran cruise from Key West. Sip on your choice of wine, sparkling, beer, margaritas, or sangria as you watch the sun go down over the water. As you sail, catch glimpses of the island and marvel at the views from the turquoise water.

Party on the Florida waters with your pals during this floating BYOB tiki bar experience off Fort Myers Beach. Whether you’d rather sip and sunbathe or mix and mingle with new friends over party games, there’s plenty to enjoy while you float along on the crystal blue sea. All while your crew is on-hand to make sure everyone is staying safe while you have fun.

Immerse yourself in some of Florida’s loveliest scenery—and enjoy a relaxing excursion out on the water—with this private sailing tour. Meet your guide in the afternoon in Goodland, hop aboard your stiletto catamaran, and set sail. You’ll tour the Ten Thousand Islands region, known for its lush seascapes, mangrove forests, and wealth of wildlife. Your guide will point out landmarks and highlights as you go.

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters of Clearwater Beach. Welcome aboard the ultimate coastal adventure with Fins Up Clearwater! Dive into the crystal-clear waters of Clearwater Beach and let us whisk you away on a journey of discovery and delight. Embark on our exhilarating Sandbar Tours, where you can explore hidden treasures and pristine shores. Glide through the waves on our Dolphin Cruises, witnessing these majestic creatures in their natural habitat. Experience the breathtaking beauty of a Sunset Cruise as the sky paints a masterpiece. Let Fins Up Clearwater be your guide to unforgettable moments and endless wonder along Florida’s stunning coastline.

End the day relaxing on the Atlantic Ocean with this sunset cruise. Hop aboard a comfortable catamaran for this evening excursion and take in views of the mansions on “Millionaires Row” and the Florida coastline. Then, head out to the Atlantic Ocean and catch the sun set, casting fiery hues of orange and red on the water.

Spend some time on the water with this half-day sailing charter in Fort Lauderdale. When out to sea, sit back and relax on the boat or jump in for a swim or to snorkel. The boat is equipped with shaded seating areas, a Bluetooth speaker, a freshwater shower, and snorkeling and other water activity equipment. Plus, the captain can instruct you on how to sail yourself.