Experience the Charm of Clearwater’s Coastal Waters on a 2-Hour Sailing Cruise
Imagine slipping away from the busy beaches into the gentle rhythm of the sea. For a laid-back escape with stunning views and a touch of wildlife magic, the Schooner Clearwater sailing cruise offers just that. Based in Clearwater, Florida, this tour costs around $85 per person, lasts approximately 2 hours, and promises a true sailing adventure under the guidance of experienced crew members like Captain Tim and Christian.
What we love most about this experience is how authentic it feels — no crowded party boats here. Instead, you get the delight of sailing on a classic schooner, with the wind in your hair and the sound of the sails flapping overhead. The chance to see dolphins and manatees in their natural habitat makes it a memorable outing, especially for wildlife lovers. Plus, the option to bring your own alcoholic beverages adds a relaxed, personalized touch for those wishing to enjoy a drink while soaking up the scenery.
A possible consideration is the physical requirement — you’ll need to be comfortable navigating a dock and moving around the deck, which can be uneven and involves climbing a few steps. Not suitable if you have mobility issues or are traveling with very young children. This tour suits those who appreciate authentic sailing, relaxed atmospheres, and picturesque coastal vistas.
If you’re visiting Clearwater and looking for a short, memorable escape on the water that’s both affordable and charming, this cruise hits the right notes. It’s especially ideal for couples, small groups, or families with children over age 5 who want a taste of sailing without the crowds or commercialism.
Key Points

- Authentic sailing experience on a classic schooner, not a typical tourist vessel
- Wildlife sightings such as dolphins and manatees enhance the journey
- Relaxing atmosphere with a knowledgeable crew and scenic views
- Bring your own drinks (cans or bottles), making it budget-friendly for casual sippers
- Limited group size (max 20 travelers) for a more intimate experience
- Good for kids over 5, but not recommended for those with mobility issues
A Detailed Look at the Clearwater Schooner Cruise

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Setting the Scene: Where and How
The tour departs from the Clearwater Beach Municipal Marina, a conveniently located spot near public transportation, making it easy to reach. After checking in about 45 minutes before your scheduled departure, you’ll receive your boarding pass. The process is smooth, and the staff, including the captain and crew, are noted for their friendliness and professionalism, which sets a welcoming tone from the start.
Once aboard, the crew conducts a safety briefing, and the real fun begins as they raise the sails and start moving out of the marina. You’ll love how the crew, especially the First Mate, works together to get the sails up, giving you a real hands-on sailing experience — if you’re inclined to participate, or just enjoy the view if you prefer to relax.
The Itinerary: What to Expect
The Departure and Coastal Navigation
As the boat slowly pulls out from the marina, the views of Clearwater Beach and the surrounding coastline open up. You’ll appreciate how the captain skillfully navigates Clearwater Pass, passing between Sand Key and Clearwater Beach. This stretch is especially scenic, with plenty of opportunities to take photographs of the shoreline, the barrier islands, and the expansive Atlantic horizon.
The first part of the journey involves a gentle motor out of the marina, but once outside of the pass, the engine is shut down, and the schooner is powered solely by wind. This is when the magic of genuine sailing begins. The quiet, the slight sway of the boat, and the breeze create a calming environment, perfect for relaxing or chatting with fellow travelers.
Wildlife Watching: Dolphins and Manatees
One of the main highlights — and what the reviews consistently praise — is the chance to spot dolphins and manatees in the wild. Several guests mention how unexpectedly close and playful the dolphins are, often jumping out of the water or swimming alongside the schooner. According to reviews, this is not just a chance occurrence but a common part of the experience, adding an element of wonder to the trip.
Onboard Comfort and Facilities
The schooner itself is a well-maintained vessel with padded seating and deck bags, providing a comfortable environment to sit back and enjoy the sail. Since loose-fitting clothing and flat, soft-soled shoes are recommended, you’ll want to dress casually but comfortably. Bringing barefoot is also fine once you’re on deck.
Guests are allowed to bring their own alcoholic beverages, which can include canned beers or a bottle of wine, provided you’re over 21. Disposable cups and a corkscrew are supplied at check-in, but no coolers are permitted onboard. This policy helps maintain the sailing atmosphere while allowing guests to toast the scenery at their leisure.
The Experience: Authentic, Relaxing, and Personal
The reviews repeatedly highlight the personal attention from the crew, especially the captain. For example, one guest appreciated how Captain Tim remained calm during a close encounter with another boat, emphasizing the crew’s professionalism and focus on safety. Guests also note that the trip is “not crowded,” with a maximum of 20 travelers, which fosters a more intimate and relaxed environment.
The two-hour duration is just right, providing enough time to enjoy the scenery, wildlife, and a sense of sailing without feeling rushed or overstayed. Many reviews mention returning for the experience again, citing the perfect timing and peaceful pace.
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Who Will Love This Tour?
This cruise is ideal for those seeking an authentic sailing experience without the crowds or commercialized vibe of larger tour boats. It’s perfect for families with children over 5, couples looking for a romantic outing, or small groups wanting a private feel. The crew’s knowledge and friendly approach often turn the trip into a mini-educational outing, with some sharing local history or interesting tidbits about the wildlife.
Travelers who appreciate scenic coastlines, wildlife, relaxed atmospheres, and the chance to enjoy a drink in good company will find this cruise very rewarding. However, if you have mobility issues or are uncomfortable on uneven decks or stairs, you might want to consider more accessible options.
Value and Pricing
At $85 per person, this experience offers excellent value. You get a genuine sailing adventure on a well-kept schooner, wildlife sightings, and the flexibility to bring your own drinks. The small group size and attentive crew ensure you’re not just another face in the crowd, which is a rare find on busy tourist routes. The fact that the cruise has consistently high ratings (5.0 based on 213 reviews) speaks volumes about its quality and the satisfaction of past travelers.
Final Thoughts: Why You Should Consider This Cruise
If you’re craving a relaxing, scenic escape on the water near Clearwater Beach, this sailing cruise fits the bill perfectly. It’s a fantastic way to see the coastline from a different perspective while enjoying the company of friendly, knowledgeable crew members. The chance to observe dolphins and manatees adds an extra magical element, especially if you’re a nature enthusiast.
This tour is best suited for those who value authentic sailing experiences, small-group intimacy, and the freedom to bring your own drinks. It’s perfect if you want a peaceful outing that balances gentle adventure with comfort, making it suitable for families, couples, or small groups. Keep in mind the physical requirements, and you’ll be rewarded with a memorable day on the water.
FAQs

Can I bring alcohol on board?
Yes, you can bring a couple of canned beers or a bottle of wine if you’re 21 or older. Disposable cups and a corkscrew are provided, but coolers are not allowed.
How long is the cruise?
The cruise lasts approximately 2 hours, offering a perfect window for relaxation and sightseeing.
What should I wear?
Casual, loose-fitting clothing and flat, soft-soled shoes are best. You may go barefoot onboard. Avoid heels or flip-flops for safety and comfort.
Is this suitable for children?
Children over 5 years old are permitted, but the experience might not be ideal for very young children or those with mobility issues. Passengers need to navigate a dock and move around on uneven decks.
What wildlife might I see?
Many guests report seeing dolphins and manatees during the cruise, often quite close to the boat.
What is the group size?
The maximum number of travelers is 20, ensuring a more personal and relaxed atmosphere.
What if the weather is bad?
The tour is weather-dependent. If canceled due to poor weather, you’ll be offered a different date or a full refund. It’s best to check the weather forecast and dress accordingly.
In essence, the Schooner Clearwater sailing cruise delivers a genuine, enjoyable, and scenic experience that’s hard to beat for its intimacy, wildlife encounters, and authentic sailing charm. Whether you’re celebrating a special occasion or just looking to relax on the water, this tour offers a peaceful slice of Clearwater’s coastline that’s sure to leave you with a smile.
More Sailing Experiences in Clearwater
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- Clearwater Daytime Yacht Music Cruise with Optional Dining
- Clearwater Evening Yacht Cruise with Optional Dining
- Private Party Boat to Island Hop, Dolphin Watch, and Swim
- Private Sunset Cruise and Dolphin Watching in Clearwater
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More Tour Reviews in Clearwater
- Sunset Celebration Cruise on Tropics Boat Tours
- Luxury Kayak Tour To An Island Off Clearwater Beach! – (Tandem)
- Helicopter Tour of Clearwater Beach and Belleair Country Club
- 2 Hour Tandem Kayak Tour (Price for 2 People)
- Private Wakesurf, Wakeboard and Tubing- Clearwater Beach
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More Clearwater experiences we've covered
- Sunset Celebration Cruise on Tropics Boat Tours
- Luxury Kayak Tour To An Island Off Clearwater Beach! – (Tandem)
- Helicopter Tour of Clearwater Beach and Belleair Country Club
- 2 Hour Tandem Kayak Tour (Price for 2 People)
- Private Wakesurf, Wakeboard and Tubing- Clearwater Beach
- Clearwater Beach Crusade Scavenger Hunt
- Clearwater Daytime Yacht Music Cruise with Optional Dining
- Private Transfer from Clearwater Beach to Port Canaveral
- Formula 1 Race Car Simulator Experience
- 2.5 Hour Kayaking with Manatee and History Tour in Tarpon Springs
- Clearwater Evening Yacht Cruise with Optional Dining
- The Tour and Wine Tasting Experience at Aspirations Winery
