Key West Flotilla | Offshore Sailing School

Mile-Building Sailing Adventure

Sail from St. Petersburg to Key West

Join Offshore Sailing School for a six-day sailing adventure along Florida’s Gulf Coast. Build sailing miles, experience overnight sailing, and enjoy time exploring Key West with fellow sailors.

DatesApr 6 – 11, 2027Tuesday to Sunday
Duration6 DaysIncluding two days in Key West
Single Cabin$4,495
Double Cabin$5,995
The voyage · 1000 × 1200 Overnight sailing aboard a cruising yacht
Overnight
Sailing

The Voyage

Six Days. Open Water. Key West Awaits.

Depart from downtown St. Petersburg and set sail on an approximately 150-mile journey to Key West. Along the way, participate in overnight sailing, learn watch-standing practices, and experience life aboard a cruising yacht.

Once in Key West, enjoy two days to explore the island, relax at the marina, and experience its distinctive coastal atmosphere before sailing back to St. Petersburg.

The Route

DepartSt. PetersburgDowntown, Florida
≈ 150 NMOvernight sailing & watch-standing
ExploreKey WestTwo days on the island
≈ 150 NMThe sail back
ReturnSt. PetersburgDowntown, Florida

Experience Highlights

Build Miles. Explore More.

Build Your Sailing Resume · 800 × 1000 Building sailing miles aboard a cruising yacht
01

Build Your Sailing Resume

Gain valuable sailing miles while participating in onboard activities and watch-standing practices.

Experience Overnight Sailing · 800 × 1000 Sailing after dark on an overnight passage
02

Experience Overnight Sailing

Take part in overnight watches and discover the rhythms of sailing after dark.

Choose Your Vessel · 800 × 1000 Catamaran and monohull sailing yachts
03

Choose Your Vessel

Enjoy the journey aboard a catamaran or monohull.

Explore Key West · 800 × 1000 Exploring Key West
04

Explore Key West

Spend two days enjoying the island, with time to explore local dining, entertainment, and waterfront attractions.

Who Is It For?

An Adventure for Sailors Ready to Explore

Extensive sailing experience is not required. Participants should be willing to follow instructions and take part in onboard activities.

Sailing Enthusiasts

Add valuable miles to your sailing resume.

Aspiring Cruisers

Experience overnight sailing and watch-standing practices.

Adventure Seekers

Discover Key West through a coastal sailing journey.

Boaters Building Experience

Participate in onboard activities and shared crew responsibilities.

Trip Details

Everything You Need to Plan Your Adventure

DatesTuesday, April 6 – Sunday, April 11, 2027
Duration6 days
Departure LocationDowntown St. Petersburg, Florida
DestinationKey West, Florida
JourneyApproximately 150 nautical miles each waySubject to weather and route conditions.
Vessel OptionsCatamaran or monohull

Cabin Pricing

Single Cabin $4,495
Double Cabin $5,995

What’s Included

Included
Boat Fuel Captain Marina fees Provisions

Cooking duties are shared among the crew.

Additional Expenses

Not Included
Captain’s gratuity Onshore food and entertainment

The itinerary is subject to weather conditions, and sailing plans may change.

    Enquire About the Key West Flotilla Course

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    Key West Flotilla (Part 2) | Offshore Sailing School

    Your Key West Sailing Adventure Starts Here

    Build your sailing miles, experience overnight passages, and discover Key West on a six-day journey with Offshore Sailing School.

    Join fellow sailors for an adventure that combines practical experience with time to explore one of Florida’s most distinctive destinations.