3 Best Sailing Experiences In Clearwater

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Sailing options in Clearwater, Florida range from intimate vessels to larger dinner cruises, each offering distinct bay experiences.

The cozy Schooner Clearwater Afternoon Cruise stands out with its small group setting and reliable dolphin sightings. For music lovers, the Daytime Yacht Music Cruise combines bay views with onboard entertainment. The Evening Yacht Cruise impresses with its combination of city lights, fine dining, and live music.

We especially like the Schooner cruise for its authentic sailing experience and personal atmosphere – you’ll feel like you’re out with friends rather than travelers.

The evening dinner cruise gets our vote for special occasions, serving up quality food with stellar views.

Let’s explore our favorite Clearwater sailing tours in detail.

Key Points

  • The Schooner Clearwater Afternoon Sailing Cruise offers a 5.0-rated, intimate sailing experience with a maximum capacity of 20 travelers.
  • The Clearwater Daytime Yacht Music Cruise provides a lively experience with picturesque bay views and live music entertainment on a larger yacht.
  • The Clearwater Evening Yacht Cruise features a gourmet 3-course meal, live music, and opportunities for dancing while enjoying the Clearwater skyline at night.
  • The Schooner Clearwater Afternoon Sailing Cruise is praised for its knowledgeable and friendly crew, as well as the opportunity to spot dolphins.
  • The Clearwater Daytime Yacht Music Cruise and Clearwater Evening Yacht Cruise are wheelchair and stroller accessible, catering to a wide range of travelers.

Schooner Clearwater- Afternoon Sailing Cruise-Clearwater Beach

Schooner Clearwater- Afternoon Sailing Cruise-Clearwater Beach

The Schooner Clearwater offers an afternoon sailing cruise in Clearwater Beach, Florida. Rated 5.0 based on 199 reviews, the cruise is highly recommended by 98% of travelers.

Providing a true sailing experience, the cruise offers beautiful views, sunset sightings, and the chance to spot dolphins.

The cruise accommodates a maximum of 20 travelers, ensuring a comfortable experience. Passengers meet at the Schooner Clearwater’s ticket booth located at the Clearwater Beach Municipal Marina boat slip #20.

Complimentary chilled sparkling water is provided, and guests 21 and older may bring alcoholic beverages.

While the cruise isn’t wheelchair accessible and not recommended for those with medical conditions, passengers praise the knowledgeable and friendly crew, highlighting the relaxing atmosphere and memorable experiences.

Many reviews emphasize the professionalism of the staff and the stunning scenery. The Schooner Clearwater delivers an enjoyable and smooth sailing outing.

Read our full review: Schooner Clearwater- Afternoon Sailing Cruise-Clearwater Beach Review
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Clearwater Daytime Yacht Music Cruise With Optional Dining

Clearwater Daytime Yacht Music Cruise With Optional Dining

Clearwater Daytime Yacht Music Cruise offers a memorable experience sailing along the picturesque Clearwater Bay.

With a capacity of up to 400 passengers, this lunchtime cruise aboard the StarLite Majesty yacht provides an opportunity to enjoy beautiful coastal scenery and live music. Guests can choose between open-air observation decks or the air-conditioned dining cabin. For an additional fee, they can upgrade to a three-course lunch with a variety of entree options, including seafood, vegetarian, and chicken dishes.

The cruise also includes local taxes, live narration, and live entertainment. Beverages and cocktails can be purchased on board.

The yacht is wheelchair accessible, stroller accessible, and allows service animals. Reviews praise the cruise’s food quality, staff friendliness, and relaxing atmosphere, with suggestions for clearer communication on cruise duration and parking.

The Clearwater Daytime Yacht Music Cruise is an excellent way to enjoy the beautiful surroundings of Clearwater Bay while indulging in live music and dining.

Read our full review: Clearwater Daytime Yacht Music Cruise With Optional Dining Review
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Clearwater Evening Yacht Cruise With Optional Dining

Clearwater Evening Yacht Cruise With Optional Dining

Operated by Starlite Cruises, the evening yacht cruise on Tampa Bay offers an intimate setting for guests to enjoy the picturesque Clearwater skyline at night.

Lasting approximately 3 hours, the cruise aboard the elegant StarLite Majesty yacht features both open-air observation decks and a climate-controlled dining cabin. Travelers can opt for a gourmet 3-course meal, with entree choices like starlight chicken spinaci, vegetarian harvest, and chef’s selection seafood.

Beyond dining, the cruise provides live music entertainment and opportunities to dance or stroll the deck. With a maximum capacity of 260 travelers, the evening cruise is well-suited for couples seeking a romantic date night.

While reviews highlight the enjoyable atmosphere and food, some note issues with air conditioning and service efficiency. Parking is available at the Clearwater Beach Marina, and the experience is wheelchair and stroller accessible.

Read our full review: Clearwater Evening Yacht Cruise With Optional Dining Review
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The Sum Up

Clearwater offers a range of sailing experiences, from afternoon cruises on historic schooners to evening yacht excursions with optional dining. Whether you’re looking for a leisurely daytime sail or a more formal evening outing, the city’s waterfront provides ample opportunities to enjoy the coastal breeze and scenic views. These cruises provide a delightful way to explore Clearwater’s picturesque shores and create lasting memories.