Sample 5-Day Florida Itineraries

Cruise the Gulf Coast on this perfect 5-day charter starting at Vinoy Marina and exploring stops like Gulfport, Treasure Island, John’s Pass and Shell Key.

Day 1: Head to Gulfport (13 nm, just over 2 hours)

  • Arrive at the Vinoy Marina for your 9 am briefing from our Base Manager.
  • Head south to Tierra Verde where you will find a beautiful little Caribbean chain of islands with crystal blue waters.
  • Have lunch at the Island Bar and Grille, a lovely beach bar and the perfect place for your first vacation cocktail! (they have their own dock.. almost too convenient to pass up!)
    Home (
  • Spend the afternoon exploring the sandbars and swimming to your hearts content.
  • Climb back aboard your yacht and head for Gulfport Marina, your home for the night. They offer moorings and slips but be sure and call ahead to reserve: Marina | City of Gulfport ( 727.893.1071.
  • Follow the sound of live music to any number of bars and restaurants that line the waterfront street.
  • Pia’s Trattoria is one of the most impressive Italian restaurants in St. Pete and is walking distance: Home Page (

Day 2: Head to Treasure Island (5 nm, just under 1 hour)

  • Explore the little town of Gulfport!
  • Checkout the Gulfport Brewery and make sure to stop in to the renowned O’Maddy’s Bar and Grille for lunch! Caddy’s is also another fantastic option. O’Maddy’s – Home (
  • If you are feeling sporty, hop into a game of beach volleyball right across from the strip of waterfront restaurants.
  • Climb aboard your vessel and head north to Treasure Island. There you can stay overnight at The Club at Treasure Island, be sure to call ahead and be mindful that they are closed Mondays & Tuesdays Marina – The Club at Treasure Island (
  • Explore this popular tourist town and walk around to find your ideal restaurant or have dinner right in your front yard at the club! 

Day 3: Travel further north to John’s Pass (2 nm, under 30 min)

Day 4: Head to Shell Key (10 nm, about 1 hour)

  • Hope you’re well rested for this big day of sailing and snorkeling!
  • Pack a lunch and head south to Shell Key in hopes of a spectacular underwater show.
  • Dolphins, manatees, and rays are all known to frequent this gorgeous little island.
  • If you are not all-snorkeled-out by this point, continue south and find a nice anchorage on Egmont Key.
  • Continue scowering the sea floor for some aquatic companions before returning to the yacht for a sunset cocktail and a moonlit dinner.
Waypoints Florida Charter Guests Having Fun on Charter

Day 5: Head back up to the Vinoy Marina (15 nm, about 3 hours)

  • Start your day off with a morning swim before heading north back towards the Vinoy Marina.
  • Be sure to factor in time for a final waterfront lunch at Doc Ford’s Rum Bar & Grille right on the pier! St. Pete Pier – Doc Fords Rum Bar & Grille

Return your yacht back to the hands of our staff in the marina and take this opportunity to wander around Beach Drive. Some of my favorite spots are the Dali Museum or Ceviche for tapas! Ceviche | St. Pete