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, l... More

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. WINDSWEPT is metic... More

Come experience the tranquility of gliding through the water under sail on the Black Pearl while appreciating our beautiful Lake Erie sunsets. See Cedar Point Amusement Park from the water, sail past the Marblehead Lighthouse, and... More

Book early, as these tend to sellout! you are free to move about the ship, while the music plays, everywhere.... More

Enjoy an intimate sunset sailing experience aboard a cozy vessel with only six guests. Glide through the picturesque waters of Port Royal Sound as the sun dips below the horizon, painting the sky with brilliant colors. Keep an eye... More

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! Your 90 minute Dolphin Sightseeing Sail on our Daydreams sailboat will inclu... More

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 moo... More

Set sail on North America's largest day sailing Catamaran, The Caribbean Spirit, and Miami's premier sailing and swimming activity. We include water, soda and peanuts and pretzels to snack on while onboard, Our guests are welcome ... More

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine creatures that call the Hawaiian islands home.... More

Your 90 minute Dolphin Sightseeing Sail on our Daydreams sailboat 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... More

Explore the picturesque Intracoastal Waterway and relax with adventure. Experience breathtaking coastal scenery or unwind while spotting local wildlife during serene nature sails. Perfect for couples, families, or anyone looking t... More

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze, some Hawaiian sunshine, and even a splash or two! Experience the south ... More

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback Whale watching at no additional cost. Dolphins, Sea turtle... More

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback Whale watching at no... More

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... More

Relax, take in the views, and discover why Lake Union, in the very heart of Seattle, is one of the city's most fascinating—and beautiful—places to explore. Your captain, Grant, born and raised in the great Northwest, has bee... More

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. U... More

Sail aboard the Palmetto Breeze for a serene and scenic Afternoon Sail through Charleston’s historic harbor. This 55-foot catamaran offers the perfect vantage point to experience the city’s charm from the water, away from the ... More

Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience. This 3-hour Miami booze cruise offers a unique nightclub atmosphere on the water, complete with a FREE open bar serving unlimited... More

On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is th... More