St Petersburg, Florida, isn’t just about art galleries and beaches—it’s also a fantastic place to get out on the water. Thanks to its calm bays, scenic coastlines, and lively harbor, this city offers a variety of sailing experiences that cater to different interests and budgets. We’re particularly fond of the Suncoast Sunset Sailing because of its intimate, romantic vibe, and the Day Sailing Experience for those who want a more laid-back adventure without the crowds. Whether you’re celebrating a special occasion or just want to enjoy the open water, St Petersburg has something to offer every sailor.
What makes sailing here especially appealing is the diversity of options—ranging from affordable sunset cruises to luxury yacht charters. You can enjoy an evening watching the sunset over Treasure Island, dance the night away on Tampa Bay, or spend a relaxing day exploring Boca Ciega Bay. The waters are often calm, making it easy for beginners, and the scenery is striking whether you’re looking for wildlife, city views, or shoreline mansions.
1. Suncoast Sailing’s Sunset Sailing Experience
At number 1 on our list, the Suncoast Sailing’s Sunset Sailing Experience combines affordability with a truly romantic setting. For just $64.99 per person, you spend about 2.5 hours aboard a classic schooner called Suncoast Horizon, sailing off Treasure Island. What sets this cruise apart is its late-afternoon timing—setting sail about an hour before sunset when the sky turns a perfect shade of orange, casting a glow over the water.
The boat is equipped for comfort—blankets are provided in case the evening gets chilly, and there’s a cooler with ice if you want to bring your own drinks. The crew, led by Captain Ritchie, is praised for their friendly, laid-back attitude, making it easy to relax and soak in the scenery. The reviews highlight how the crew is both informative and fun, and many mention how cozy blankets and the starry sky add to the experience. It’s a great choice for couples seeking a romantic, low-key evening that doesn’t break the bank.
Bottom Line: This cruise offers a relaxed, romantic experience that’s perfect for a sunset date or a quiet evening with friends. It’s highly rated and offers good value for the money.
2. Evening Yacht Cruise with Optional Dining in St. Petersburg
Number 2 on our list is an elegant evening yacht cruise aboard the StarLite Sapphire. Priced at $32.06 per person, this cruise lasts about 2.5 hours and provides a different vibe—more sophisticated, with live music and a chance to dance or simply enjoy the breathtaking Gulf views.
Guests can choose between the open-air observation deck or a climate-controlled cabin, making it suitable for all weather conditions. You’ll cruise past beautiful sunset vistas depending on the time of year, and there’s an option to purchase dinner onboard. Drinks are also available for purchase at the bar, adding to the relaxed, party-like atmosphere. Many reviews highlight the friendly staff, good service, and the overall calming ambiance.
This cruise is particularly appealing if you want an entertaining evening with the option to dine—a fine way to elevate a typical sunset cruise into a night of music and gentle dancing. It’s best suited for those who want a lively, social atmosphere.
Bottom Line: An upscale, music-filled cruise with optional dining, ideal for couples or groups wanting a bit more sophistication and entertainment.
3. Suncoast Sailing’s Day Sailing Experience
The Day Sailing Experience offers a more active side of sailing—perfect for those who want to see the coast without the crowds. For $59.99, you get about 2.5 hours aboard a schooner, sailing either in the Gulf of Mexico or Boca Ciega Bay, depending on weather conditions. Unlike the sunset cruise, this one allows you to enjoy the daytime scenery, with plenty of opportunities for wildlife viewing.
You’ll have access to soda and bottled water during the trip, and a cooler is provided for your own drinks. The crew is known for their friendly, fun attitude and their commitment to safety and comfort. Several reviewers mention how relaxing and enjoyable the trip is, with highlights like cruising past John’s Pass under the drawbridge—a real treat for boat lovers.
This experience is ideal for families or anyone wanting a short, laid-back day on the water with beautiful coastal views. It’s a great way to experience local water without the time or expense of a private charter.
Bottom Line: A relaxed day cruise suited for families or first-time sailors looking for good scenery and friendly guides without a hefty price tag.
4. Yacht Charter Madeira Beach and Tampa Bay
Number 4 is the Yacht Charter Madeira Beach and Tampa Bay—a more luxury experience. For approximately $1,700 per group (up to 18 people), you’ll hop aboard the WildSide, an 18-passenger catamaran, for a 4-hour sunset cruise. This is the only experience on the list that feels like a private yacht charter, complete with narration from the captain and an intimate atmosphere.
Guests can bring their own drinks, with a cooler and ice provided, and enjoy cruising past lush coastal homes and scenic landmarks. The boat features a modern, comfortable layout with a dining table, wet bar, sun pads, and a full bathroom, making it perfect for celebrating a special occasion or just indulging in a luxurious day on the water. The reviews emphasize the exceptional value—many loved the personalized vibe and the opportunity to relax in style.
This tour is best suited for those seeking a private, upscale experience or celebrating a special event. It’s less about sightseeing and more about enjoying a personalized, high-end outing.
Bottom Line: An excellent choice for groups wanting privacy and luxury, ideal for special celebrations or a romantic getaway.
5. Daytime Yacht Sightseeing Cruise with Optional Dining
Number 5 offers a more educational approach, blending sightseeing with relaxation. For about $26.70, you’ll cruise along Tampa Bay for around 2 hours on the StarLite Sapphire yacht, with options to upgrade to a lunch. The cruise includes commentary from the captain about the local area, passing sights like Pass-a-Grille Beach and Dolphin sightings.
Guests can choose between outdoor deck space or an air-conditioned interior, which is perfect for those who want comfort during the trip. The reviews praise the friendly crew, the good value, and the peaceful atmosphere. Many mention how relaxing and scenic the ride is, with some noting the surprisingly good food available for purchase.
This cruise is an excellent option for those who want a short, scenic tour with a bit of education. It’s suitable for families or solo travelers who want to enjoy Tampa Bay’s beauty at a relaxed pace.
Bottom Line: A well-rounded, affordable sightseeing cruise, especially good if you want a quiet, informative experience with optional lunch.
6. Daytime Yacht Dance Cruise with Optional Dining
Number 6 is a lively dance cruise on Tampa Bay. For $32.06, you get about 2.5 hours of non-stop music, dancing, and scenic views aboard the StarLite Sapphire. Whether you’re a dance pro or just want to sway to the beat, this cruise features live music and a fun, energetic atmosphere.
Guests can choose between the outdoor deck or the climate-controlled interior, with a captain providing engaging commentary. Many reviews mention how much fun they had, often highlighting the good music and friendly atmosphere. It’s perfect for those who want to combine sightseeing with a bit of active fun.
This cruise is best suited for energetic travelers or groups celebrating birthdays or special occasions. It’s a lively alternative to the more tranquil cruises.
Bottom Line: A spirited, music-filled cruise for those who want to dance and enjoy Tampa Bay’s scenery simultaneously.
7. Yacht Party Cruise in St. Petersburg to Shell Key
Finally, the Yacht Party Cruise to Shell Key offers a different flavor—an private party atmosphere on a modern power cruiser. Up to six people can rent this boat for around $765 for about 4 hours, making it ideal for small groups celebrating special moments.
The boat features a Bluetooth sound system, a wet bar, sun pads, and a full kitchen and bathroom. The itinerary includes a visit to Shell Key Preserve, a large undeveloped barrier island with native wildlife and pristine shells. The reviews are limited but emphasize the boat’s luxury features and the opportunity to explore unspoiled Florida nature away from the crowds.
This option suits those who want a fully customizable, private experience, whether for a birthday, anniversary, or just a day of unwinding with friends.
Bottom Line: Perfect for private groups seeking luxury, privacy, and a scenic, wildlife-rich destination.
$765.00 per group (up to 6)
How to Choose Your Perfect Sailing Experience
Choosing the right sailing trip depends on your budget, interests, and the kind of experience you seek. If you’re after a romantic sunset, the Suncoast Sunset Sailing is a top pick. For a more lively night with music and dancing, consider the Daytime Yacht Dance Cruise. Want a luxury private yacht? The Madeira Beach yacht charter offers a high-end, personalized day on the water.
Budget-conscious travelers will appreciate the affordable sunset or sightseeing cruises, while those celebrating a special occasion may prefer a private, upscale charter. It’s best to book early, especially during peak seasons, to secure your preferred date and boat.
St Petersburg’s waters are a treasure trove of memorable sailing adventures, whether you’re seeking romance, fun, or tranquility. For a quiet sunset with your loved one, try the Suncoast Sunset Sailing. If you want to dance under the stars, the Yacht Dance Cruise will deliver. For those who want luxury and privacy, the Madeira Beach Yacht Charter offers a top-tier experience. Whichever you choose, making an early reservation guarantees you’ll enjoy this vibrant coastal city from its best vantage point—on the water.