St. Petersburg, Florida

The Wildlife and Nightlife of Florida’s Gulf Coast

The West Coast of Florida is home to beautiful seaside towns, secluded anchorages and fine marinas, white sandy beaches, sparkling blue waters, gentle winds, dolphins, and an array of wildlife. Bring your camera to capture the unforgettable Skyway Bridge and the multitude of seabirds, including ospreys, herons, egrets, and pelicans.

Enjoy a romantic cruise along the beautiful skyline of Tampa Bay and continue your evening aboard a beautiful yacht for an unforgettable night. Let your Waypoints® charter experience specialist plan a luxurious, relaxing trip along the renowned waters of Florida’s Gulf Coast.

Charter St. Petersburg with Waypoints® to Experience:

  • Daily, Weekend, and Week-Long Charters 
  • Skippered, Bareboat, and ASA Certification Charters
  • New Luxuriously Appointed Sailing and Motor Catamarans and Monohulls
  • Yachts Equipped with Air-Conditioning and Ice Makers* 
  • Provisioning and Personal Concierge Services

Suggested Itineraries

1-Day Itinerary

DaysSuggested ItineraryDistance
Option #1
1The Vinoy Marina to Resort & Club at Little Harbor6NM
1Resort & Club at Little Harbor The Vinoy Marina6NM
Option #2
1The Vinoy Marina to Egmont Key State Park16NM
1Egmont Key State Park to the Vinoy Marina16NM

2-Day Itinerary

DaySuggested ItineraryDistanceDescription
1The Vinoy Marina to Resort & Club at Little Harbor6NMEnjoy a relaxing sail across the bay to this Caribbean-style island resort with patio dining at the beachfront Tiki Bar. The Resort offers deep water access with over 200 wet slips and a 250 foot fishing pier.
2Resort & Club Little Harbor to the Vinoy Marina6NM
1The Vinoy Marina to Egmont Key State Park16NM
Tampa Bay offers some beautiful spots for anchoring and spending the day or night. Experience the ruins of Fort Dade at Egmont Key State Park, which is a 126 acre island at the entrance to the Gulf of Mexico.
2Desoto Point Park to The Vinoy Marina15NMAfter a day at Egmont, sail across the bay to relive the experience of splashing ashore at the monument named after Spaniard Hernando de Soto, at Desoto Point Park from 1539.

3-Day Itinerary

DaySuggested ItineraryDistanceDescription
1The Vinoy Marina to Egmont Key

Egmont Key to Desoto Point
Have your camera ready while sailing under the Sunshine Skyway Bridge, The Travel Channel rated #3 on the “Top 10 Bridges” in the World. This itinerary offers the best of both worlds, a night at anchor in exciting Fort Desoto Point Park and a relaxing stay at the upscale Resort & Club at Little Harbor.
2Desoto Point to Resort & Club at Little Harbor15NMAt Egmont Key, you will have the opportunity to explore Fort Dade and discover their famous lighthouse. Later sail to Desoto Point Park and spend the night at this secluded anchorage spot.
3Resort & Club at Little Harbor to The Vinoy Marina6NMDinghy ashore to travel through their trails, which include interpretive signage and waysides that tell the story of the Spanish De Soto Expedition and the natural history of the area. The next day enjoy a trip to the 350 acre Resort & Club at Little Harbor, with a secluded beach and a bounty of recreational amenities.

4-Day Itinerary

DaysSuggested ItineraryDistanceDescription
1The Vinoy Marina to Gulfport14NMSail into Tampa Bay and anchor in Gulfport, which has a unique and eclectic assortment of merchants and great restaurants. This old-Florida town is very laid-back with a friendly attitude that invites shoppers to browse and enjoy the ambiance.
2Gulfport thru Pass-a-Grill to Clearwater26NMSail up the coast to Clearwater and enjoy the beautiful waters and scenery along the way. Visit the world-renowned sparkling Clearwater Beach, which has the distinct Blue Wave Beach classification.
3Clearwater to Tierra Verde28NMContinue your journey to Tierra Verde and enjoy the new marina’s facilities, which are located by Ft. Desoto Park, named America’s Top Beach for the second consecutive year by TripAdvisor.
4Tierra Verde to The Vinoy Marina6NM

7-Day Itinerary

DaysSuggested ItineraryDistanceDescription
1The Vinoy Marina to Longboat Pass24NMLongboat Pass boasts its brilliant blue and green waters as they pour into the Gulf of Mexico.
2Longboat Pass to Venice Inlet28NMVisit Longboat Key Moorings, a first class marina with excellent facilities. Also on Longboat Key, enjoy the famous Moore’s Stonecrab Restaurant.
3Venice Inlet to Boca Grande35NMThis 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. Here you will have the opportunity to swim with the manatees at the Venice Inlet.
4Visit Cayo Costa

Captiva- Sanibel Island Area
12NMThe 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.
5Boca Grande to Venice Inlet35NMAs you continue to sail through North Captiva, the beautiful white sandy beaches of Cayo Costa dominate the landscape. Stop and take a dip.
6Venice to Sarasota/Longboat via Intercoastal Waterway26NMCabbage 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, only accessible by boat. The restaurant’s interior walls are covered with autographed dollar bills; find an open spot to place your buck.
7Longboat to the Vinoy Marina24NM

10-Day Itinerary

DaysSuggested ItineraryDistanceDescription
1The Vinoy Marina to Longboat Pass24NMThis itinerary is for the experienced sailor with a desire to see the entire West Coast of Florida.
2Longboat Pass to Venice Inlet26NMIt requires prior experience with overnight passages and a capable crew.
3Venice Inlet to Boca Grande26NMThis trip provides time in Key West and the Dry Tortugas. Key West is a very fun place and can be as relaxing, romantic, or wild as you want it to be. That includes by day or night.
4Boca Grande to Marco Island32NMFort Jefferson and the Dry Tortugas should be on everybody’s bucket-list. Visitors can enjoy a variety of remarkable experiences including, camping, snorkeling, bird watching, fishing, or just enjoying a view from the top of the massive Fort Jefferson.
5Marco Island to Key West58NMThe Dry Tortugas are situated on the edge of the main shipping channel between the Gulf of Mexico, the western Caribbean, and the Atlantic Ocean.
6Enjoy Key WestA large military fortress, Fort Jefferson, was constructed in the mid-19th century in an effort for the United States to protect the extremely lucrative shipping channel.
7Key West to the Dry Tortugas68NM
8Enjoy Fort Jefferson & Dry Tortugas14NMThe fort is the largest masonry structure in the Western Hemisphere, and is composed of over 16 million bricks.
9Dry Tortugas to Venice – Requires overnight sail148NM
10Venice Inlet to the Vinoy Marina51NM

Contact a Florida Charter Specialist Today

MM slash DD slash YYYY
MM slash DD slash YYYY
This field is for validation purposes and should be left unchanged.
An aerial view of St. Petersburg, Florida