Sunset Cruises
Watch the Gulf light up gold. The most relaxing hour and a half of your week — for couples, celebrations, or an evening you'll actually remember.
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Naples & Marco Island · Private Gulf Coast Charters
Southwest Florida Is Better From the Water
Private sunset cruises, Key West day trips, and wildlife tours aboard your own charter — captained by locals who know these waters like their own backyard.
Same-day replies. No deposit to ask about a date.
Family-owned & localLicensed & insuredPADI certified5-star rated
The Difference
Not a tour. Your trip.
Every charter is private and built around you — your group, your pace, your perfect day. No crowded boats, no rigid schedule. Just you, the Gulf, and a captain who knows exactly where the dolphins run and where the sunset hits hardest.
The Experiences
Pick the day you've been picturing.
Day Trips to Key West
Cruise down, dock up, spend the day in one of Florida's most iconic towns. Waterfront dining, blue water, zero highway.
Check availabilityEco Tours & Island Trips
Glide through mangroves and barrier islands with dolphins and manatees along the way. Wild Florida, up close.
Check availabilitySnorkeling Adventures
Clear water, reef life, gear included. Perfect for first-timers and seasoned snorkelers alike.
Check availabilityMeet the Fleet
Step aboard the boats that make the day.
Private, spotless, and built for the Gulf. These are the actual boats you'll charter — no stock photos, no surprises.
Boat 01
Cobia
A spacious, spotless center console built for relaxed Gulf days. Plenty of shade, room to move, and a stable, comfortable ride — ideal for sunset cruises and island hopping.
24 ftUp to 12 guestsSunset & Eco tours
Book this boat
Boat 02
Century
Fast, capable, and set up for longer adventures. Cruise to Key West in comfort or reach the best snorkeling spots quickly — this is the boat for full-day Gulf exploration.
30 ftUp to 12 guestsKey West & Snorkeling
Book this boat
Your private slice of the Gulf Coast.
Why Westwind
Locals who do this right.
Family-owned and Gulf-raised. We run a small operation on purpose, so the day belongs to you and nobody else.
- 01Truly private — your group only, never a shared boat
- 02Local captains who've run these waters for years
- 03Fully licensed, insured, and PADI certified
- 04Flexible trips — tell us your ideal day, we'll build it
How It Works
Three steps to a day on the water.
Pick your experience
Sunset, Key West, eco tour, or snorkeling — or tell us you're not sure yet.
Lock your date
Send us your dates and group size and we'll confirm what's open.
Show up and unwind
Meet your captain at the dock. We handle everything else.
Guests
People don't forget these days.
“Best evening of our whole trip. The captain knew exactly where to be for the sunset and it felt like we had the Gulf to ourselves.”
“We did the Key West run with four of us and it was flawless. Smooth ride down, great recommendations once we docked.”
“Dolphins within ten minutes and manatees on the way back. Our kids still talk about it. Easy to book, zero pressure.”
Placeholder reviews — replace with real guest reviews before launch.
Your day on the Gulf is one message away.
Dates fill fast in season — check availability now.
Book Your CharterFree to ask. No deposit until your date is confirmed.
Check Availability
Tell us your ideal day.
We'll reply with open dates and a plan for your group. Prefer to talk? Call (239) 501-5995.