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Florida Vacation Packages for Families, Couples, Scouts and Youth Groups for a Florida Keys Sailing Vacation 

Florida Vacation Packages begin here,

At Sail The Keys we offer Florida Keys vacation package deals

Sail The Keys is the provider for overnight and multi-day Florida Keys sailing charters. Our Sailing Vessels are the safest and most modern vessels in the area. Our excursions offer guests the experience sailing, snorkeling, and wildlife viewing throughout the Key Largo and Key West waters.

Looking for a quick getaway for your Florida Keys Vacation Package?

Need a day to kick back and relax? Join us at Sail The Keys on our 3 Hour Sailing and Snorkeling Charter.These half day excursions are perfect for anyone looking spend a time  visiting the best snorkeling and wildlife viewing spots in the Florida Keys

Highlights of our 3 hour sailing and snorkeling charter can include weather permitting:

  • Snorkeling at Hens & Chicken reef, just south of Islamorada.
  • Lunch and wildlife sightseeing at Cheeka Rocks.
  • More snorkeling at Alligator reef, named after the anti-pirate schooner which struck the reef and was destroyed in 1822.
  • If weather is not great or seas are too rough we can go snorkel bayside, excellent for beginner snorkelers.

All of our crew boasts years of sailing experience in these waters. We take pride in knowing the best snorkeling spots the Keys have to offer, so come let us show you!

Keys Sunset Sail-Give yourself the opportunity to experience one of the most beautiful sunsets in the world during our Sunset Sail. A sunset experience with Sail The Keys is always unique. Climb aboard for an intimate evening of sailing.

Highlights of our 2½ hour sunset sail include:

Firing  a real cannon for your own Keys Sunset Salute! 

  • Witnessing a Florida Keys sunset in full.
  • Crackers and cheese, fruits provided right on the boat.
  • Champagne toast under the beautiful skies of a Florida sunset.

If you are New to sailing? Not much time? Our Islamorada Insight Tour is the perfect way to survey the beautiful Islamorada wildlife and explore the most spectacular reefs in Florida. This overnight guided excursion is perfect for anyone looking for the best snorkel and wildlife viewing spots on the Florida Keys.

For the Ultimate Florida Vacation package choose our  Cruise The Keys sailing excursion, departing from Key Largo- arriving at Key West. This 6 day Cruise The Keys sail combines the best sailingsnorkeling, and sightseeing that the Florida Keys has to offer. Let us show you why a "Cruise the Keys" Charter with Sail The Keys is an experience of a lifetime. 

We have over a dozen years experience as a  provider of choice for the Boy Scouts of America Florida Sea Base with their National High Adventure programs.

We offer custom Florida Vacation Packages for your trip to make it memorable.

With so many years of experience, and a passion for the area, Sail The Keys can provide an unforgettable experience for any group up to 6 per vessel, if your group is larger we can still accommodate you by chartering more than one vessel- we can sail close together and raft up (tie up side by side) at mealtimes and at snorkel sites. Call us for more information on this.  When you book a charter with Sail The Keys you are booking the entire vessel with an experienced crew.

For info on what to look for when you charter a vessel check out...