How to Book a Charter with Sailing Florida Charters & Sailing School

So, you want to charter a boat and sail off into the sunset, but you aren’t sure where to start. Chartering a yacht is an experience you will never forget. Sailing Florida Charters has over 35 yachts available for charter including sailing, power, and fishing yachts. A new bay every day, waking up in a new anchorage, dolphins swimming off the bow, and breathtaking views from the cockpit, each day more memorable than the last. The freedom of chartering a power or sailboat is almost unrivaled as a leisure activity - a chartered yacht enables you to travel where you want, when you want, and to choose your distance away from the hustle & bustle of land.

Merely 20 minutes from Tampa International Airport or St. Pete Clearwater International Airport. Our charter base is located atThe Legendary Renaissance Vinoy Resort. As a charter guest, you can access all of the resort's amenities for a minimum resort fee. The amenities include wifi, heated swimming pools, hot tubs, state-of-the-art fitness center with a steam room, sauna, and indoor whirlpools. There is also a full-service day spa and salon, and room service can be delivered directly to your boat. With the resort fee, you will also receive a 10% discount at all resort restaurants.

You will depart from beautiful and vibrant downtown St Petersburg and head along the Florida coast from bay to bay, port to port. Think… Clearwater, Sanibel, Captiva, Cayo Costa and Marco Island, or cruise the open waters to the Dry Tortugas National Park and the Florida Keys.

Participation in a regatta, a team-building event or a rally is also very popular for those looking to push their own personal boundaries and/or bring their corporate group together for a new and exciting bonding event. Rooms for out of town guests can be booked through The Renaissance Vinoy Resort. We have conducted Team Building events for groups as large as 165 participants.

Sailing Florida Charters also offers Romantic Getaways, with Ultimate Lap of Luxury package for two, half-day cruises aboard sailing, power, or fishing yachts, and sunset cruises for 12 guests. Please follow link for more information.

To start, there are the 4 questions you should ask yourself:

Who are you taking with you?

What type of boat are you looking for? Power or sail? Monohull or catamaran?

What size vessel do you need to accommodate your group?

What is your budget?

Choose your vessel.

A bareboat charter is where you take possession of the boat and sail it yourself, similar to renting a car. You must be an experienced sailor and generally must have a sailing certificate for this type of charter - you plot your course, raise the sails, deal with the vagaries of weather, drop anchor, and moor. It's exciting and exhilarating but comes with much responsibility.

If you like the idea of a private charter, but would like help with the sailing, you can hire one of our captains who will sail the boat and provide valuable information about the area. Just look for the vessel you desire and request a captain and we'll arrange one for you. This can provide the perfect balance of independence and freedom, while allowing you to relax and worry less. This is a popular and easy arrangement as Sailing Florida has over 30 licensed US Coast Guard captains on the roster. When booking a captained charter, you should also budget 18%-20% of the charter cost for gratuity.

There are two main types of sailing vessels, Monohull (one hull) and Catamaran (two hulls). Both are popular for many reasons and the choice of the "right one " depends on your needs and goals for the charter. Monohulls give you the full feeling of classic sailing, leaning (heeling) with the wind and cutting through the water, where catamarans tend to offer more comfort and privacy, as they have a large salon and more livable area within the two hulls. Sailing Florida Charters has over 35 vessels to choose from and each one has a link with information and pricing. Pick your boat based on the number of people in your group, experience level, and budget. (If taking a captained charter, be mindful that the captain will need a cabin as well.)

Power Yachts -

Sailing Yachts:

If you would like to bareboat, (without a captain) we will need your skipper’s resume. We do not necessarily require any formal training or certification but look at your experience.

Make a reservation.

You pay a 25% deposit with the booking and the balance is due upon arrival for your charter. If you have to reschedule for any reason, you have one year from the date of the original charter to rebook without penalty. If you choose to cancel, the fee is equal to 20% of the total charter amount.

What’s included in my charter?

All of the boats have color chart plotters and laminated charts for our cruising area. We provide linens, towels, blankets, pillows, and galley ware, as well as cleaning supplies with a starter kit of paper towels and toilet paper. All safety equipment, including life vests (for people 30lbs and up) are provided. A BBQ grill with propane tanks is located on the stern rail of each boat.

Plan your itinerary and activities.

The West Coast of Florida has several beautiful destinations to visit. You can check them out on our destinations link. Upon arrival for your charter, you will have a briefing, and the briefing captain will go thru all the systems on the vessel, the charts, your float plan, and you will complete the necessary paperwork.


Downtown St Petersburg has a variety of grocery & liquor stores, wine shops, specialty boutiques, etc. to pick up everything you may need or desire for the adventure that awaits you.

If you still have questions, they should be answered in our FAQ section; if not, you can always call 727.894.7245 or email us at

Now, what are you waiting for? There’s never been a better time to get out on the water!