Sample 2-Day Florida Itineraries

Embarking on a yacht charter from Vinoy Marina opens the door to a plethora of exciting 2-day itinerary options, promising an unforgettable coastal adventure in Florida. From this charming departure point, yacht enthusiasts can tailor their journey to suit their preferences, exploring the sun-kissed wonders of the Gulf Coast.

South in the Gulf of Mexico

Egmont Key, Sail Under the Skyway Bridge, and Overnight in the Manatee River

Day 1: Egmont Key and Manatee River (15 nm)

15 nm SouthWest, Approximately 3 – 3 1/2 hour sail to Egmont Key, One of Tampa Bay’s most popular destinations. Enjoy the journey under the fabulous Sunshine Skyway Bridge. Anchor and jump in the water or dinghy onto the island. You can enjoy the trails, swimming, fishing wildlife viewing as well as visit the historic lighthouse, wear your water shoes!

Leave Egmont and sail South East into the Manatee River for the night, 9.5 nm approximately 2 ½ – 3 hours. Set anchor on the North shore or get a slip at either Twin Dolphin Marina or Safe Harbour Regatta Pointe Marina.

Day 2: Return to Vinoy Marina (21 nm)

Set sail back to Vinoy Marina, covering around 21 nautical miles. The journey will take approximately 5 hours, depending on weather conditions. Relish the memories of Egmont Key and the Manatee River as you head back to the marina.


Anna Maria Island & Apollo Beach

Day 1: Anna Maria Island (20 nm)

Sail approximately 20 nm, approximately 5 – 5 ½ hours, heading south under the Sunshine Skyway Bridge and into the Intracoastal Waterway (ICW). Follow the ICW to the Cortez Bridge and consider stopping at the beloved Seafood Shack on the east side or anchor in the mooring field and visit the town pier, dotted with charming shops, restaurants, and bars. Unwind on the powdery white beaches of the Gulf of Mexico and marvel at the breathtaking sunset.

Credit: Marty Jean-Louis


Day 2: Apollo Beach (26 nm)

Embark on a 26-nautical mile sail, approximately 5 ½ hours, to Apollo Beach. Enjoy the vibrant atmosphere of Finn’s Dockside Bar & Grill or Circles Waterfront. Explore the Apollo Beach Nature Preserve and take a hike up to the tower for spectacular views.

Cover 10.5 nautical miles, approximately 2 hours, and sail back to Vinoy Marina. Cherish the memories of your Anna Maria Island and Apollo Beach adventure.


Jew Fish Key & Longboat Key (23 nm)

Day 1: Jew Fish Key & Longboat Key (23 nm)

Set sail south in the Gulf of Mexico and reach Jew Fish Key, a fabulous sandbar with crystal clear waters and white sand. Enjoy a picnic or head over to Shore for a delightful dining experience. Alternatively, continue to Longboat Key and reserve a slip at The Longboat Key Club Resort for a relaxing night.

Day 2: Longboat Key Exploration

Spend the day at Longboat Key, relishing the beaches, restaurants, and spa amenities. Consider a trip to St. Armond’s Circle for an enchanting island experience.

Sail back approximately 6 hours to Vinoy Marina, reminiscing about your unforgettable journey.

Please Note: Sarasota is not currently recommended for sailboats due to shifting shoals and narrow channels.

Sarasota – Powerboat Only

Sarasota is not recommended at this time for our sailboats. There has been a great deal of shifting shoals and the channels are extremely narrow and shallow.  If you are in a powerboat 34 nm to the South, you can leisurely cruise through the ICW, or open it up on a fast cruise out in the Gulf and enter through Big Sarasota Pass. Dock at Marina Jacks for lunch and get a slip for the night.


North in the Gulf of Mexico

John’s Pass Village & Boardwalk, Madeira Beach & Egmont Key

Day 1: John’s Pass Village & Boardwalk (27 nm)

Sail 27 nautical miles north-west, approximately 5 ½ hours, and reach John’s Pass Village & Boardwalk. Explore the charming village with a variety of restaurants and bars. For a unique experience, head to John’s Pass Sandbar, a local hotspot with lively gatherings.


Day 2: Egmont Key (12 nm)

Embark on a 12-nautical mile sail, approximately 1 ½ hours, to the popular Egmont Key. Discover the island’s trails, swim in its crystal-clear waters, and visit the historic lighthouse.

Sail 15 nautical miles back to Vinoy Marina, cherishing the memories of John’s Pass and Egmont Key.


Clearwater (38 nm)

Day 1: Clearwater (38 nm)

Embark on a captivating sail from the mouth of Tampa Bay to Clearwater, covering 38 nautical miles. Enter the Intracoastal Waterway at Clearwater Pass and reserve a slip at Clearwater Harbor Marina or Clearwater Yacht Club.

Day 2: Return to Vinoy Marina (7 ½ – 9 hours)

Sail back to Vinoy Marina, relishing the return journey that takes approximately 7 ½ – 9 hours, depending on weather conditions.


Caladesi Island State Park

Day 1: Shell Key (20 nm)

Sail to Shell Key, approximately 20 nautical miles or 4 hours from Vinoy Marina. Enjoy a festive gathering with boating friends on this picturesque sandbar.


Day 2: Caladesi Island State Park (22 nm)

Sail 22 nautical miles from Shell Key, approximately 4 hours, to Caladesi Island State Park. Anchor on the gulf side and explore the pristine, white sandy beaches. Take a hike along nature trails or paddleboard amidst the wildlife-filled waters.


Anclote Key & 3 Rooker Island

Day 1: Shell Key (20 nm)

Sail to Shell Key, Approximately 4 hours from Vinoy, 20nm North West

A favorite weekend and holiday get together sandbar with hundreds of festive boating friends! Boats gather on this powdery white sandbar and enjoy the gorgeous Florida water and sunshine! Then anchor for the night near Islan Del Sol or get a slip at Tierra Verde Marina.


Day 2: Anclote or 3 Rooker Island (27 nm)

Enter through Anclote Pass, anchor and dinghy around the islands to enjoy the wildlife in both the water and land. See dolphins, manatees, and hundreds of species of birds.

Returning to the Vinoy Marina from Anclote & 3 Rooker Island 47 nm from the Vinoy Marina, approximately  9 ½ hours if sailing directly there.

(Monohulls not recommended in the ICW due to the shallow waterways. On approach watch nav carefully and eyes on water for depths and shifting shoals.)

North in Tampa Bay

Downtown Tampa & Beer Can Island

Day 1: Downtown Tampa (18 nm)

From the Vinoy Marina you can sail NorthEast 18 nm to Downtown Tampa. Reserve a slip at the Tampa Convention Center or Marriott Water Street Marina. Sail through Davis Islands and view the homes of many of Tampa’s famous athletes and celebrities. Once docked you can walk the riverwalk with numerous restaurants, bars & museums.

Day 2: Beer Can Island (6 nm)

Sail to Beer Can Island for the day and enjoy this  small island where hundreds of small and large boats anchor up on weekends and holidays. They have food stands, bars, dj entertainment, and a bounce house!

Return to the Vinoy Marina 6 nm SouthWest in Tampa Bay