St. Petersburg, Florida, isn’t just about stunning beaches and vibrant arts scenes — it’s also a fantastic place to enjoy sailing and boating adventures. With its calm Gulf waters and scenic coastal views, this city offers a variety of sailing experiences that cater to different tastes. Whether you’re seeking a romantic sunset, a lively dance cruise, or an educational sightseeing trip, St. Petersburg delivers. Many tours feature live music, dolphin sightings, and informative commentary, making each trip more than just a boat ride. For those looking to add a touch of luxury or excitement to their trip, options range from intimate yacht charters to group dinner cruises. Planning ahead and choosing the right experience can turn an ordinary day into a memorable adventure.
Here, we’ll explore the best sailing experiences in St. Petersburg. From elegant evening yacht cruises to small-group private charters, this list highlights the options that stand out for their atmosphere, value, and unique features. Whether you want to dance, relax, or learn about Tampa Bay’s coastal sights, there’s an experience tailored for you.
1. Evening Yacht Cruise with Optional Dining in St. Petersburg
At number one, the Evening Yacht Cruise with Optional Dining stands out for its balance of elegance and flexibility. Starting in St. Petersburg, this 2.5-hour cruise aboard the StarLite Sapphire offers a perfect way to unwind after a day of sightseeing. The yacht’s open-air observation deck and climate-controlled cabin mean you can enjoy the Gulf’s spectacular sunset views whatever the weather. During the cruise, you can listen to live music, dance to your favorite tunes, or simply take a romantic stroll along the deck.
What makes this tour especially appealing is the option to purchase dinner onboard, along with drinks from the bar. Many travelers appreciate the relaxed atmosphere, as reflected in reviews that mention the beautiful scenery, friendly staff, and excellent ambiance. It’s a solid choice for couples seeking romance, or for anyone wanting to experience Tampa Bay in style without breaking the bank. The $32.06 per person price offers good value for the relaxed, scenic experience.
Bottom Line: This cruise offers a nice balance of scenic beauty, entertainment, and optional dining, making it ideal for a relaxed evening out or a romantic date.
2. Yacht Charter Madeira Beach and Tampa Bay
For those who prefer a more personalized adventure, the Yacht Charter Madeira Beach and Tampa Bay offers a small-group, private experience. Priced at $1,700 per group, this cruise aboard the WildSide, an 18-passenger catamaran, is about 4 hours of cruising along Tampa Bay. It’s perfect for celebrating a special occasion or for travelers who value intimacy and flexibility.
What sets this tour apart is the cap at 18 passengers, creating a more exclusive environment. The captain provides narration about the sights, and you’re welcome to bring your own alcoholic beverages, with a cooler and ice provided. Guests frequently mention the dolphins, coastal homes, and friendly crew. The tour’s tailored nature makes it excellent for families, couples, or small groups who want to customize their experience.
Bottom Line: If you’re after a private, relaxed cruise with personalized touches and dolphin sightings, this charter is hard to beat. The price reflects its exclusivity, making it best for those seeking a special, intimate outing.
3. Daytime Yacht Sightseeing Cruise with Optional Dining
The Daytime Yacht Sightseeing Cruise offers a relaxed, educational tour of Tampa Bay, perfect for families, first-timers, or anyone interested in local sights. Starting from St. Petersburg, this 2-hour cruise on the StarLite Sapphire takes you past significant harbor sites and dolphin sightings. The open-air decks and indoor lounge give options depending on your preference for sun or shade.
A key feature is the live commentary from the captain, providing insights into the area’s history and ecology. For an additional cost, you can upgrade the experience with a delicious lunch, one of six options, making it a great way to combine sightseeing with a meal. Reviews highlight the relaxing atmosphere, friendly crew, and surprise dolphin sightings.
This cruise offers excellent value at $26.70 per person, especially for those wanting a laid-back, educational experience. It’s perfect for travelers who want to learn about Tampa Bay while enjoying the scenery.
Bottom Line: This tour combines sightseeing, wildlife viewing, and a chance to relax, making it suitable for families and curious travelers alike.
4. Daytime Yacht Dance Cruise with Optional Dining
Finally, the Daytime Yacht Dance Cruise offers a lively, fun way to enjoy Tampa Bay. This 2.5-hour cruise, also on the StarLite Sapphire, features live music and a dance party atmosphere. You can dance on the open-air deck or relax in the climate-controlled dining cabin, all while soaking in the views of the coast and passing ships.
What makes this tour stand out is the focus on entertainment—live music, dancing, and engaging commentary from the captain about local points of interest. Many reviewers mention the good music and the friendly, upbeat vibe. The cruise also offers an optional dining service, allowing you to enjoy light bites or drinks as you party.
At $32.06 per person, this experience is great for travelers wanting an active, social day on the water. It’s ideal for groups, couples, or anyone looking to combine sightseeing with a lively atmosphere.
Bottom Line: If you’re looking for a fun, energetic way to experience Tampa Bay and don’t mind a bit of dancing, this cruise is an excellent choice.
How to Choose the Right Sailing Experience
When deciding between these options, consider your priorities: Are you after a relaxed evening with dinner? The evening yacht cruise might suit you best. Want a private, customizable outing? The yacht charter fits the bill. If you’re interested in sightseeing and wildlife, the daytime sightseeing cruise offers both education and scenic views. For a lively, party-like atmosphere, the daytime dance cruise provides music and dancing on the Gulf.
Consider your budget, the type of experience you desire, and who you’re traveling with. For instance, couples seeking romance might prefer the sunset cruise, while small groups celebrating a special occasion might opt for the private yacht. Booking early is wise, especially during peak season, to secure your preferred date and time.
In summary, St. Petersburg offers a range of sailing experiences that fit different styles and budgets. Whether you want a romantic evening, a private adventure, or a lively party on the water, these tours deliver memorable moments on Tampa Bay. For most travelers, the evening yacht cruise provides a beautiful, relaxing introduction to the area’s waterways, but the private yacht charter or lively dance cruise can elevate your trip depending on your interests. Be sure to book early, and enjoy your time on the water in this beautiful Gulf Coast city.