Half-Day Four Winns Boat Charter — Clearwater Beach Dolphin & Island Tour
Cruise the Gulf aboard a 27-foot Four Winns for private dolphin watching, island hopping and sandbar swims. This four-hour Clearwater Beach charter combines local route knowledge with stops at Caladesi, Honeymoon Island and Three Rooker.
The Experience
Before You Go
Time your trip for calm seas
Mornings offer the calmest water and the best visibility for snorkeling and wildlife viewing; late afternoons are ideal for light and sunsets.
Bring reef‑safe sunscreen
Protect skin and marine life—spray or lotion labeled ‘reef-safe’ reduces harm to seagrass and coral.
Secure essentials in a dry bag
Keep phones, wallets and spare layers dry; the boat has storage but splash and slides are part of the fun.
Respect shore rules and wildlife
Do not walk on dune vegetation, avoid chasing wildlife, and follow any state park landing regulations at Caladesi and Honeymoon.
Local Knowledge
Hidden Gems
- •Early-morning shelling on the north end of Caladesi, before the ferry arrivals
- •The crescent side of Three Rooker Bar for quiet snorkeling and spotting juvenile fish
Wildlife
- •Bottlenose dolphins
- •West Indian manatees
Conservation Note
Erosion and boat wakes affect these fragile beaches—stick to marked landing areas, avoid trampling dune vegetation, and use reef-safe products to reduce impact.
The barrier islands off Clearwater formed over centuries of shifting sands and currents; Caladesi remains one of the few islands accessible only by water and is preserved as a state park.
Photographer's Notes
- • Bow view when approaching Caladesi for dolphin silhouettes
- • Upper deck of the Four Winns for sweeping Gulf vistas
- • Sandbar low-angle shots for reflections and shallow-water textures
What to Bring
Reef-safe sunscreenEssential
Protects your skin and minimizes damage to sensitive coastal ecosystems.
Polarized sunglasses and hatEssential
Cuts glare for better spotting dolphins and improves visibility for photography.
Dry bag (small)Essential
Keeps phone, keys and spare clothes dry when anchoring or using the boat slide.
Snorkel set or water shoes
Makes wading, shelling and shallow snorkeling more comfortable and safe on shell-strewn sandbars.
Common Questions
How many people can join the private charter?
The boat is designed for small private groups; confirm the operator’s current maximum capacity when you book as limits can vary by vessel and regulation.
Is snorkeling and swimming included?
Yes—stops for swimming, snorkeling and sandbar anchoring are standard; bring your own masks or check if the operator can supply them.
Are food and alcohol allowed on board?
The operator provides bottled water and a cooler; most private charters allow bring-your-own snacks and alcohol—confirm specifics and local rules when you book.
What happens if the weather turns bad?
Tours are cancellable for bad weather; the cancellation policy typically allows a full refund if canceled 24 hours in advance due to weather.
Are there restroom facilities?
Smaller boats may not have a full restroom—ask the operator about onboard facilities and plan accordingly.
Can the trip be customized for special events?
Yes, private charters can often be tailored for celebrations, proposals or sunset cruises—discuss your plan with the captain ahead of time.
Book This Experience
Check AvailabilityDuration
4 hours
Location
Clearwater, Florida
Difficulty
moderate
Fitness Level
Suitable for most fitness levels; basic swimming comfort recommended for those hopping off to snorkel or swim.
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