Discover All St. Pete & Tampa Bay Have to Offer on a Waypoints-led Flotilla 

Saturday, March 11 – Wednesday, March 15, 2023

Waypoints Florida Logo

Explore the cruising capital of the Gulf Coast with Waypoints Florida on an exciting flotilla with other sailing enthusiasts from March 11 to March 15, 2023. Guided by a Captain and Hostess on board the lead boat, the group of chartered boats will follow an exciting itinerary full of stunning sights and events each day. There is something for everyone on this trip! Book the boat of your choice for the flotilla, head down to St. Petersburg, Florida on March 10 to sleep aboard your boat the night before the trip begins, and get ready for an experience unlike any other. 

Waypoints Florida Charter Guests Enjoying Tampa Bay

Let Waypoints be your guide. In addition to walking you through the booking process, we can assist you with hiring a licensed captain if you are doing a bareboat charter. The lead flotilla boat will guide all charter guests’ boats through several days of activities and entertaining events. From sightseeing to delicious dinners at local restaurants to a beach party, there will be something for everyone to enjoy.

Check Out Our Amazing Itinerary for this Fun-Filled Flotilla!

Day 0 (Friday): 

Arrive at the Vinoy Renaissance Marina by 3:00 pm for a sleep-aboard on your charter boat!  We will have our team do your checkout briefing and chart briefing. While the Captain and First Mate attend the briefing, have the rest of your crew provision your boat and unpack.  Enjoy dinner in downtown St Petersburg. Our base is just a short walk away from the new Pier and Beach Drive.

Finn's Restaurant Near St. Petersburg, Florida

Day 1 (Saturday):

Sail from the Vinoy to Beer Can Island for a few hours of beach time.  Then head over to Apollo to anchor, and dinghy over to Finn’s restaurant for a welcome dinner and drinks.

Day 2 (Sunday):

Head out after a nice breakfast at anchor, then make your way over to Magnussen by 4:30 pm for an evening of fun and a raft-up.

Waypoints Florida Guest on Dingy
Waypoints Florida Charter Guests Having Fun on Charter
Seafood Shack Near St. Petersburg FL

Day 3 (Monday): 

We are off to Longboat Pass (Anna Maria Island)! We will make our way to the Seafood Shack by 4:30 pm to pre-arranged docks for a delectable dinner. (Fill water and pump out facilities will be available).

Day 4 (Tuesday):

Pick up anchor in the morning to make your way over to the Shore Longboat Key Restaurant ( West of Jewfish Key), stop for lunch, and then dinghy over to the sandbar for our beach party!

Friends Drinking Cocktails at Beach Party
Friends Dancing at Beach Party

 Around 3:00 pm, we will head over to the Bradenton Beach Pier and anchor for the evening. Dinghy ashore to explore the beauty of Anna Maria Island. There are lots of activities to do and sights to see including the historic pier.

Brandenton Beach Pier in Florida

Day 5 (Wednesday):

We will make our way back to the Vinoy Renaissance Marina. On the way, we will stop over Egmont Key for the official farewell beach party!  We will need to leave by 1:00 pm to make it back to the Vinoy by 5:00 pm.

Book Your Boat Today and Join Us for Our Flotilla!

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