Clearwater’s waters are one of the best reasons to visit this Gulf Coast town, with miles of soft sandy beaches and calm inland waters perfect for sailing. Whether you’re seeking a relaxing afternoon with dolphins, a romantic sunset cruise, or a lively dance party on the water, Clearwater offers a variety of options. We especially like the Schooner Clearwater sailing cruise for its laid-back vibe and wildlife sightings, and the Clearwater Evening Yacht Cruise for a more upscale, romantic experience with optional gourmet dining. Both tours showcase different facets of Clearwater’s waters and are highly rated for their quality and authenticity. If you’re into daytime sightseeing, the Daytime Yacht Sightseeing Cruise provides a relaxed way to see inland waterways and wildlife, while the Daytime Yacht Music Cruise promises a fun, lively afternoon with live bands and dance.
To help you choose the best experience, here’s a quick overview of each tour—detailed descriptions follow to help you get a clear picture of what each entails.
1. Schooner Clearwater- Sailing Cruise-Clearwater Beach
This charming schooner sailing cruise offers a two-hour escape on the water, perfect for those who want to experience Clearwater’s coastline with minimal fuss. You’ll check in at Clearwater Beach Municipal Marina, 45 minutes before departure, and then set sail from the marina. The crew raises the sails as you motor out of the marina, and once outside Clearwater Pass, the engine shuts down, leaving you to enjoy the full experience of sailing under the wind.
What makes this tour stand out is its focus on wildlife sightings—dolphins and manatees are often spotted in the area, and the scenery is picturesque. The boat is equipped with padded seating and beanbag decks, making it comfortable for families or couples. Guests are allowed to bring their own alcoholic beverages, adding a relaxed, picnic feel to the cruise. The captain and crew are praised for their friendly service, and reviews highlight how educational and relaxing the experience is, perfect for a quick getaway that doesn’t skimp on charm.
This cruise is best suited for travelers who want a casual, scenic ride with wildlife viewing and no food restrictions. It’s an affordable, intimate option that provides a real sailing experience, not just a boat ride.
Bottom Line: An ideal choice for those seeking a relaxing, wildlife-rich sailing experience with a friendly crew and gorgeous views, all at an affordable price.
2. Clearwater Evening Yacht Cruise with Optional Dining
At number 2, the Clearwater Evening Yacht Cruise offers a more elegant, romantic way to enjoy Tampa Bay. On the StarLite Majesty, you’ll experience a 3-hour sunset cruise that’s perfect for couples or anyone celebrating a special occasion. The cruise features live music, a chance to dance or simply relax on the open-air decks, and the option to purchase gourmet dinner onboard. The dinner menu includes 11 entrée choices, with salad, dessert, and coffee included, making it a true dining experience.
What makes this tour different is its combination of luxury, entertainment, and scenery. As you glide past the waterfront, the lights and sunset create an unforgettable backdrop. The boat’s interior is plush, with reserved tables and climate control, while the outdoor decks allow you to soak in the view and the breeze. Many reviews highlight the friendly service and memorable atmosphere, especially during sunset.
This cruise appeals to romantic couples and those looking to elevate their evening with good food and music. It’s a great value considering the dinner is optional but available, and the live entertainment adds a lively, festive touch. Just be aware that food costs are extra, so budget accordingly.
Bottom Line: A refined, romantic experience that combines scenic beauty with the option of gourmet dining and lively music—perfect for special occasions or a memorable night out.
3. Clearwater Daytime Yacht Sightseeing Cruise with Optional Dining
For around $26.70, the Daytime Yacht Sightseeing Cruise provides a relaxed, narrated tour along Tampa Bay’s inland waters. The StarLite Majesty yacht is a comfortable vessel with both open-air and climate-controlled options, making it suitable for all weather conditions. Over approximately 2 hours, the captain points out landmarks and shares interesting facts about Clearwater’s waterways and history.
The main draw of this tour is the possibility of dolphin sightings—many reviews mention spotting playful dolphins during the cruise. The tour’s narration makes it educational and engaging, ideal for families, history buffs, or anyone curious about the local environment. For an extra cost, you can add on lunch, which includes a delicious, made-to-order meal from the onboard chef.
What’s unique here is the perfect balance between sightseeing, wildlife viewing, and light education. It’s a straightforward way to enjoy Clearwater’s calm waters without the fluff, making it excellent for travelers who want a laid-back, informative experience. The price point makes it a good value, especially if you add in the optional lunch.
Bottom Line: An affordable, engaging tour suitable for those wanting to learn about the area and see wildlife, with the flexibility to add a tasty lunch.
4. Clearwater Daytime Yacht Music Cruise with Optional Dining
Last but not least, the Daytime Yacht Music Cruise spices up the typical sightseeing trip with live music and dancing. Over about two and a half hours, you’ll cruise Clearwater Bay on the StarLite Majesty, enjoying beautiful coastal scenery and the lively sounds of a band playing your favorite tunes. You can relax on the open decks or sit inside in air-conditioned comfort, making this a versatile option for different weather conditions.
What makes this experience stand out is the focus on music and dancing. You can upgrade to include a 3-course lunch, with six delicious options, served with salads and desserts. The onboard bars offer a variety of beverages (not included), so you can enjoy a cold drink while moving to the beat. Reviews emphasize the “fabulous staff” and “great atmosphere,” perfect for celebrating birthdays or just having fun on the water. The cruise combines sightseeing, entertainment, and a party vibe, making it suitable for groups or travelers wanting a lively day.
This cruise is best suited for those who want a fun, energetic experience with the chance to dance and socialize, with the option to indulge in a gourmet meal. The added lunch is a good value for those looking for more than just a cruise.
Bottom Line: An exciting, music-filled cruise with the option to enjoy a sit-down meal, ideal for travelers who want to combine sightseeing with a lively party atmosphere.
How to Choose Your Clearwater Sailing Experience
When selecting between these tours, think about your priorities. If you want a relaxing, wildlife-focused cruise, Schooner Clearwater hits the mark. For a romantic evening with gourmet dining and live music, the Clearwater Evening Yacht Cruise is a standout.
Looking for a more budget-friendly, daytime option with a focus on scenery and wildlife? The Daytime Yacht Sightseeing Cruise offers great value, especially if you add lunch. For a lively, dance-party atmosphere, the Daytime Yacht Music Cruise combines fun, music, and optional gourmet food.
Practical considerations include budget, preferred time of day, and whether you want a quiet wildlife cruise or a lively party. Booking early is recommended, especially during peak season, to secure your preferred time and seating.
Final Thoughts
Clearwater’s sailing options are as diverse as its coastline—whether you’re after a peaceful wildlife cruise, a romantic sunset sail, or a party on the water, there’s something for all. For a relaxed, intimate experience, the schooner cruise is hard to beat. If you’re celebrating a special occasion, the elegant yacht evening cruise offers a memorable evening with fine food and music. Those looking for fun and excitement will enjoy the lively daytime music cruise with plenty of opportunities to dance and socialize.
No matter which tour you choose, Clearwater’s waters are waiting to greet you. Be sure to book early—these popular experiences fill fast, especially during the busy months. Pack your sunscreen, bring along a sense of adventure, and get ready to enjoy some of the best sailing in Florida.