A Private Sunset Cruise — Near Tampa

If you're searching for a sunset cruise near Tampa, you're in the right part of the world — but the best evening on the water isn't where you might expect. Tampa's waterfront is stunning, yet the sunset cruises that actually deliver that postcard view tend to leave from the other side of the bay.

Here's what locals and repeat visitors have figured out: the finest sunset cruise in the Tampa Bay area departs from St. Pete — specifically Gulfport, a quick drive from downtown Tampa. You get the same bay, the same golden light, but with one big difference: you're sailing toward the Gulf of Mexico, so the sun drops over open water instead of behind the skyline. Add a private sailboat for up to six guests (no crowded tour boat), and you've got the kind of evening that feels like a proper escape.

This page is for anyone in or near Tampa who's curious about that option: why St. Pete, how far it really is, and what makes the experience different from a typical Tampa sunset cruise.

Most people searching for a sunset cruise in the Tampa Bay area don't realize that Tampa's waterfront — while beautiful — looks west across the bay toward the Pinellas Peninsula. That means the sun sets behind a landmass, not over open water. From St. Pete's western shore, the view is entirely different. The sun drops toward the Gulf of Mexico, lighting up the sky over Boca Ciega Bay with the kind of colors you see on postcards. And when conditions allow, we sail through the passes to the Gulf side of the barrier islands for a completely unobstructed view of the sun melting into the horizon.

The sailing conditions on this side of the bay are better suited to a relaxing evening, too. Boca Ciega Bay is a protected aquatic preserve — calm, shallow water sheltered by the barrier islands, with steady Gulf breezes that are ideal for an easy sail. There's room to breathe out here. You'll pass mangrove islands, spot dolphins feeding in the seagrass flats, and hear nothing but wind and water. Departing from Tampa is a different experience. Port Tampa Bay is the largest port in the state of Florida, moving over 33 million tons of cargo a year and homeporting multiple cruise lines. That means sharing the waterway with container ships, tankers, and cruise vessels — along with the wakes, engine noise, and channel restrictions that come with a working commercial harbor.

Then there's where your evening begins. Our departure point is Gulfport — a walkable waterfront village that feels more like old Key West than modern Florida. Beach and Shore Boulevards are lined with independent restaurants, art galleries, and locally owned shops. There are no chain stores and no parking meters. On any given evening you might hear live music drifting from a waterfront patio or stumble into a gallery opening. It's the kind of place where your night starts feeling special before you even step on the boat — and where you'll want to grab dinner after you step off.

Most sunset cruises operating out of the Tampa Bay area are large motor vessels — dinner cruise ships, party boats, and sightseeing tours carrying anywhere from 49 to several hundred passengers. You're sharing the deck with strangers, following a fixed route, and listening to a PA system over the hum of diesel engines.

This is the opposite of that.

SV Cay Michele is a 45-foot sailing yacht that carries a maximum of six guests — your group only. There's no engine drone, no crowd, and no script. Once the sails go up, the only sounds are wind, water, and conversation. Your USCG-licensed captain adjusts the route based on wind and conditions, so no two sails are exactly alike. Conditions in the Gulf are typically great, and when they are, you're heading through the passes to the open water side of the barrier islands for an unobstructed sunset. On the rare occasion the Gulf is rough, Boca Ciega Bay is almost always ideal — calm water, steady breeze, and dolphins feeding along the flats.

You set the pace for the evening. Bring your own drinks, arrange catering if you'd like, or just settle in and watch the sky change color. It's the difference between being on a tour and being on your own private sail.

Board SV Cay Michele — a 45-foot sailing yacht — at our Gulfport marina and set sail toward the Gulf as the sky begins to turn. Your USCG-licensed captain handles everything while you settle in with your favorite drinks and snacks (we're BYOB-friendly, or arrange catering in advance).

Choose a 3- or 4-hour charter for up to 6 guests. Departure is timed to the local sunset so you're on the water for golden hour.

See full details, photos, and book your sunset sail.