Florida Sample Itinerary

The Gulf Coast of the St. Petersburg/Tampa area has tons of options to explore and creates lifelong memories while cruising on a yacht from Waypoints® Florida. Whether you prefer calm waters, diverse wildlife and the great outdoors, or fine art and rich history of the “Sunshine City”, Waypoints® charters are a great way to see everything that the Gulf Coast has to offer.

Sample Itinerary


Day 1: From Vinoy Marina to Longboat Pass  

Disembark and make your way to Longboat Pass, approximately 24 NM sail. Longboat Pass boasts its brilliant blue and green waters as they pour into the Gulf of Mexico. There is an anchorage located just north of the pass that locals call Mar Vista with two restaurants accessible by dinghy.

Day 2: Going from Longboat Pass to Venice Inlet

After a nice evening in Longboat Pass, make your way to Venice Inlet, approximately 24 NM sail. Visit the Crow’s Nest, a favorite marina with a well-known restaurant and convenient facilities. Transiting Venice inlet is very simple.

Day 3: Cruise Boca Grande

Get up early to get underway for sail to Boca Grande, which is approximately a 45 NM sail. This stretch of Florida’s West Coast is not only beautiful but is one of Florida’s most unique adventures. Travel on the outside in the Gulf of Mexico for a quicker journey or use the ICW for a slower-paced scenic route. 

Day 4: Visit Cayo Costa

Visit Cayo Costa to short 12 NM sail to visit the inlet’s barrier island location, it offers deep water dockage and a secluded anchorage. While entering Boca Grande Pass, you will sail by the famous landmark structure, the 1890 Lighthouse Museum.

Day 5: Explore Captiva-Sanibel Island Area

Cabbage Key is a stop off in civilization, as only islanders envision it – with a casual hamburger and seafood joint that boasts a spectacular view surrounded by an inn comprised of cracker cottages, also only accessible by boat. The restaurant’s interior walls are covered with autographed dollar bills; find an open spot to place your buck.

Day 6: From Boca Grande to Venice Inlet

Head out for another wonderful sail back from Boca Grande to Venice Inlet. As you continue to sail through North Captiva, the beautiful white sandy beaches of Cayo Costa dominate the landscape. Stop and take a dip.

Day 7: Sail the Gulf of Mexico

Sail north on Florida’s beautiful Gulf barrier islands. There are marinas just north of Longboat Pass and several anchorages.

Day 8: Heading Back to St. Pete

Make your way back to the beautiful downtown of St. Petersburg. Make sure to plan enough time to have dinner on Beach Drive.