Top St Petersburg Holidays

Get out on the water with the whole family on the Royal Conquest Pirate Ship. Cruise out from Madeira Beach for a family-friendly sightseeing and adventure pirate adventure cruise. Onboard, children can enjoy face painting, costumes, water fights, and other activities and entertainment, while adults can enjoy the open bar.

Part-bar, part-boat, all-around fun: this unique boat cruise takes you on a floating tiki bar around the St. Pete Pier. Hop aboard and let a Coast Guard licensed captain sail you through the water while you sip on alcoholic and nonalcoholic beverages. Bring your own food, drinks, and up to five others for a few hours of fun. You can also use the boat’s Bluetooth speaker to play your own music.

Bar hopping and bar crawls can leave your feet exhausted from all the walking. Choose this St. Petersburg Trolley Pub Mixer Tour instead and still get a light workout while you visit four popular bars and breweries without hitting the pavement. Explore the city and grab drinks (own expense) with a guide who keeps you on track and safe.

Get out on the water and look for dolphins and other wildlife with this nature boat cruise. Make your way to Madeira Beach to board “The Big Blue Boat,” the largest and most stable dolphin watching boat in the Tampa Bay area, then cruise out in search of dolphins, manatees, sea birds, and more, with full narration along the way.

If you’re looking for a Florida adventure on the water, but don’t want to have to plan out a daring activity yourself, leave it up to this Madeira Beach Parasail Flight. You’ll go out on the water aboard a boat with a group, and then take to the skies on a parasail. Plus, GoPro and photo packages are available (for an additional cost).

Grab your friends and hop on the premiere sandbar party boat cruise by St. Pete Coastal Cruises. A destination previously only known to local boaters is now accessible to travelers and partiers of all ages! Stormed by hundreds of boats every weekend, the shallow waters of Eleanor Island in John’s Pass are truly a day drinkers paradise! Experience the local weekend hangout in luxury on board St. Pete Coastal Cruises’ fully crewed 50’ power Catamaran! Enjoy our luxury boat amenities like our bar, satellite TV, restroom on board and even some fun floating toys! Pack your sunscreen and a sandwich and come enjoy the day the local’s way at the John’s Pass Sandbar Party!

Spend a fabulous 90 minutes on the water (longer times available) with our professional guide. We often see manatees during the summer months (not guaranteed) and dolphins. We will start our tour from Maximo Park Boat Ramp and visit the Sunshine Skyway Bridge and then onto Ft. Desoto or Shell Key for a walk on the beautiful wide sandy beach or a wade in the beautiful Gulf. There is so much marine life to see and the waters often reach 90 degrees in the summer months. Ft. Desoto sand bar has beautiful white sandy beaches to walk and enjoy. We can also customize lunch on the beach for you or visit other attractions or upgrade time to see other keys and sand bars in the area. There is so much to do and the guided tour allows you to see much more than renting a ski on your own! No limits to the fun you can have!

Elevate your group outing in St. Pete with your own private Trolley Pub. Step onto the Trolley Pub with your crew and embark on a 2-hour journey that combines the thrill of a moving party with the fun of exploring 3 different bar stops. Whether you're celebrating a bachelorette, birthday, team-building, or just looking to bar hop in a unique way, this tour ensures a festive atmosphere. Let your driver know if you want to stop at the Instagramable murals we see along the route for a photoshoot. Customize your route, create your own playlist, and enjoy this parade on wheels as you pedal through Downtown St. Pete. Groups are welcome to bring any food and drinks on board, please no glass. Able to fit groups up to 15 or 30 (minimum 6), this private experience offers a personalized and lively adventure through the city's streets.

The Nauti 'N' Free is a 36 ft. 2016 twin-engine Power Cruiser with state-of-the-art electronics and navigation, plenty of comfortable seating, a dining table, a wet bar, and a sun pad on the bow for lounging or enjoying the views. An air-conditioned cabin, a kitchen, two refrigerators, a grill, and a full bathroom are available for your convenience. Play your favorite music with the Nauti 'N' Free's Bluetooth quality sound system that will make you want to get up and dance or just sit back and relax. We'd love to welcome you aboard to party on our yacht as we cruise on over to Shell Key Preserve. The cruise takes us about 25 minutes to get there depending on how fast you and your crew want to get there. Once there, you can continue the party on the yacht, swim, play on the floating splash pad, paddle around on the stand-up paddle board, and/or explore the island for shells and wildlife. We will remain at Shell Key for approximately 3 hours before returning back to the marina.