Sample 8 Day Florida Itineraries

Embark on an 8-day yacht charter from Vinoy Marina to either Anna Maria Island and Anclote Key or to the South Gulf Coast Barrier Islands. Enjoy laid-back vibes and stunning beaches on Anna Maria Island, then explore the untouched beauty of Anclote Key. Alternatively, discover the wonders of Caladesi Island, Honeymoon Island, and Egmont Key. Savor warm Gulf breezes and cultural treasures in Fort Myers and Sanibel Island. This unforgettable journey promises beauty, serenity, and cherished memories.

Vinoy Marina to Anna Maria to Anclote Key

Day 1: From Vinoy Marina to Manatee River  

Start your charter adventure off with your briefing at 9 am with our dock staff at the Vinoy Marina. Navigate 11 NM to Apollo Beach to relax at Finns Dockside Bar and Grille for a delicious lunch while docked at Lands End Marina. Take the rest of the afternoon to sail down to Manatee River to anchor overnight.

Apollo Beach, Florida

Day 2: Explore the Manatee River to Anna Maria Island

While many people are interested in the beautiful waters of the Manatee River, there are some easy, accessible trails along its shores that offer stunning views. The most popular of these is at the DeSoto Memorial. Riverview Pointe Preserve is worth a trip to see the Manatee River from a completely different breathtaking perspective. Break for lunch, then sail to Anna Maria Island to Twin Dolphin Marina for a great dockside dinner and overnight!

Day 3: Navigate Up to Johns Pass in Madeira Beach

Take the morning to navigate up to Johns Pass in Madeira Beach. Grab a cocktail at the “World’s Longest Bar” overlooking the pass. Be sure to wave to the Waypoints boats coming in and out through the bridge! 

Day 4: Visit Dunedin

Sail 4 hours up to Dunedin, a cute fisherman’s town. This town is perfect for walking and biking. Be sure to dock at the Dunedin City Marina and check out the nature preserve at Honeymoon Island.

The City of Dunedin
Dunedin Causeway Honeymoon Island State Park

Day 5: Sail Up to Anclote Key

Sail up to Anclote Key to anchor out overnight and enjoy a picnic dinner on the beach while watching the sunset.

Picnic on the Beach

Day 6-7: Tierra Verde to Vinoy Marina

Begin to navigate back down to the Vinoy Marina, but be sure to stop in Tierra Verde at the Island Bar and Grille, our favorite restaurant in the area, and then sail over to Shell Key for an afternoon swimming off the beaches.

Shell Key, Florida

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.

Sailing South-Gulf Coast Barrier Islands

Day 1: From Vinoy Marina to Longboat Pass  

Leaving Vinoy Marina. St. Petersburg, FL

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

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 the Venice inlet is very simple.

Day 3: Cruise Boca Grande

Get up early to get underway for a cruise 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

Port Boca Grande Lighthouse

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 Port Boca Grande Lighthouse Museum. Only as 8 NM sail from Cayo Costa, 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 5: Explore Captiva-Sanibel Island Area

Captiva Island is known for its white-sand beaches and abundance of seashells with an almost magical feel. Be sure to visit the island’s eclectic restaurants and rent a bike to tour the island.

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.