Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then Colonel George Patton "When the war is over and if I return, Bea and I will sail around the world!" Step foot on the gorgeous teak... More

Let's go Sailing!  Experience Miami's Biscayne Bay aboard one of Destino Charters Beneteau stylish vessels in the company of experienced, but mostly fun, well traveled, passionate captains. A Private Sailing tour aboard Destino ... More

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More

Price Includes up to 25 Pax Ask for add Pax, MAX capacity 34 Pax Discover the magic of the ocean in Miami! with Dolphin Water Sport. Our +850 reviews on Google with a 4.9 score guarantee our quality. Immerse yourself in a unique... More

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More

Enjoy a beautiful Key West sunset while sailing on our 42' Sailing Catamaran. It has over 1000 feet of deck space. We will make sure that you will enjoy this catamaran sailing in Florida. Our crew are biologists or trained by one!... More

Set sail aboard Hawkeye, a brand-new 47-foot luxury sailboat made locally by Island Packet Yachts. Cruise along Downtown St. Petersburg’s scenic waterfront and watch the city glisten in the setting sun. This is a luxury, two-ho... More

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 ... More

Set sail aboard Hawkeye, a brand-new 47-foot luxury sailboat made locally by Island Packet Yachts. Cruise along Downtown St. Petersburg’s scenic waterfront and watch the city glisten in the setting sun. This is a luxury, two-hou... More

Enjoy the day on the water with friends and family with Dolphin Water Sport. Our +650 reviews on Google with a score of 4.9 guarantee our quality. Come aboard our Boat and Yacht to enjoy an incredible Boat Trip in Miami. We'll cr... More

Cowfish offers a smooth and comfortable ride, versatility, and ample space for 6 or fewer in a small package. Whether you want to lounge on the sandbar, snorkel at your own pace, or enjoy dolphin watching, Cowfish provides a great... More

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for t... 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! You'll sail around Shell Island into the Gulf of Mexico, while you enjoy dol... More

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 ... More

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.... More

There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stiletto Catamaran. Harnessing the power of the wind as we sail along these beautiful waters is magical. You might even get to experie... More

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. E... More

TripAdvisor SPECIAL MONDAY ONLY Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple daily sails that include a quarter day and sunset sa... 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

Experience a magical sunset in with Cocoa Beach Catamaran Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the bea... More