How do I book a sail?
To book a sail you click the book sail button on the home page or on the sail description and price page. This will open a new window with the different sail options we offer.
The first option is whether or not you would like a private sail or a public sail. On a private sail it will be just your party on the boat. Private sails have a minimum requirement of 3, Flip Flops will sail with two passengers though on a private sail you will have to purchase three spots. A public sail will sail with two passengers, but is open for other guests to join your party.
After the private or public option, the different sailing excursions opens up. Egmont Key Sails, Passage Key Sails, Day Sails, True Sails, and Sunset Sails. You click whichever sail you are interested in and a calendar will pop up showing which dates are available or not available. Available dates are green and dates that are not available are grey. Pick the date you want to sail and what time of the sail for that day. Sunset Sails, Egmont Key Sails, and Passage Key Sails only offer one time of day. Day Sails and True Sails offer different time options, Morning or Afternoon. After you choose the date and time, a ticket section will appear. Select how many tickets you need. There is a minimum of 2 for a public sail and a minimum of 3 for a private sail in order to book the sail.
Next you input your name, phone number, and email. A confirmation/receipt email will be sent at conclusion of booking a sail and a reminder email will be sent the day before the date of the sail if booked more than a day in advance. Below this will be where you put in your credit card information to reserve and pay for your sail. You can also call the Flip Flops Sailing phone number to book a sail at
Where is the boat located?
The boat is located at the Waterline Resort Hotel and Mainsail Marina in slip #1, which is along Marina Drive and next to but not a part of Keyes Marina.
The address of the Waterline Hotel and Mainsail Marina is 5325 Marina Dr. Holmes Beach, FL
Where is parking then?
Our marina parking is at 5325 Marina Dr. Holmes Beach - Waterline Resort/Marina
You are welcome to pull into Keyes Marina next to the boat which is in slip #1 to unload coolers, bags, and people and then parking is at the Waterline resort hotel in any spot available whether paved or around back in the gravel lot. If you’re booked for a sunset sail and arrive after 6pm then you can park at Keyes Marina right next to the boat since they will be closed. After parking you can walk the sidewalk/boardwalk on the sea wall which runs along the road to reach the boat from the parking area.
Where do you sail?
Flip Flops sails from Holmes Beach on Anna Maria Island out into the waters of Tampa Bay or simply the bay and on the longer sails out to the Gulf of Mexico.
This comes up from time to time. Is there a restroom onboard the boat?
Yes there is. On a boat it is called the head.
What about gratuity?
Giving the crew of a charter boat a tip for an enjoyable sail is customary and greatly appreciated. Here at Flip Flops Sailing you can tip by either using Venmo or by adding the tip directly to your booking. Of course a cash tip is also accepted.
- Christopher Baxter @FlipFlopsSailing
-Last Four 1755
How long does it take to get to Egmont Key or Passage Key?
It takes approximately an hour or so to sail out to Passage Key and roughly an hour and a half to reach Egmont Key depending on wind, sea conditions, and boat traffic at either of the islands. We try to get in as much sailing as possible, but will motor sail on occasion to make sure we reach the islands in a timely manner for you to enjoy the islands themselves.
How do you get to the beach on the island sails?
Keep in mind that there are no docks for public use at either Egmont Key or Passage Key. You will have to go into the water to reach the shore. We do however try to get the boat as close to the beach as wind, waves, current, and other boats will allow. Most of the time we anchor so that off the ladder is about 3 and a half to 4 feet of water.
Is there any swimming off the boat?
Yes and no. The only sails that offer an opportunity to go swimming are the island excursions out to Egmont Key and Passage Key or the Sand Bar Sail south by Longboat Pass. The 2hr and 3hr sunset sails are sailing only as are the morning and afternoon day sails. So if you’re looking to get in the water check out the Egmont Key Sail or Passage Key Sail.
What happens if there are thunderstorms and what about a refund policy?
In the event of thunderstorms in the area, the captain of the vessel will make a decision as to whether or not to continue
with the sail. This is typically a day of decision. Here on Anna Maria Island storms usually pass through rather quickly so do not fret if you have a sail scheduled a few hours away when a storm passes through. More than likely the storm will be gone by the time you are set to depart the dock. If the captain decides that the weather conditions are not conducive to a safe and enjoyable sail, they will attempt to make contact with you about two hours ahead of departure time. Then we’ll either first try to reschedule or if need be cancel/refund the sail.
What about a cancellation/refund policy?
If a sail is cancelled by Flip Flops Sailing, a full refund will be processed.
If a sail is cancelled by the booking party at least 2 days (48 hours) ahead of scheduled sail, a full refund will be processed.
If a sail is cancelled by the booking party between 2 days (48 hours) and 1 day (24 hours) of the scheduled sail, a partial refund will be processed (50%)
If a sail is cancelled by the booking party within 1 day (24 hours) of a scheduled sail, no refund will be processed.
What is the minimum amount of passengers you need to go sailing?
Flip Flops will sail with a minimum of two passengers though on a private sail you will have to purchase 3 spots.
How many passengers can the boat take out sailing?
Though the boat has been stability tested for and can hold more than 6 passengers, the vessel’s Certificate of Documentation and in accordance with the Federal Code of Regulations the Coast Guard has restricted the maximum number of guests to 6. So please, there is no need to call and ask if I can take more than that number. Even if a portion of that number is small children. This 6 passenger max leaves plenty of room for everyone to spread out, relax, and enjoy the sail. Also if you’re reading this a 6 person public sail is a private sail by default. So it’s sort of a discount on a private 6 passenger sail to book it as a public sail.
Are the prices of the sails the same for adults and kids?
All ticket prices are the same. We don’t feel comfortable charging more for kids. We do however let infants sail for free though they do count towards the 6 passenger limit and we ask that you book your sail as a private sail. Call or e-mail before booking with an infant.
What can I bring on the boat?
You are welcome to bring a cooler with snacks and drinks on any of the sails. Bottled water is available on the boat, but if you’d like something stronger than water you’re welcome to bring it aboard. No Red Wine. If you choose to do one of the island adventures you might want to bring towels and footwear that you won’t mind getting wet. Sunscreen is also a good idea. Just remember sunscreen only please, no tanning lotions or bronzer. These two products tend to leave stains behind. If you plan on going out on a sunset sail in the winter months, keep in mind the temperature drops when the sun goes down. So a light jacket or sweatshirt is advised.
Do you offer Gift Certificates?
Yes, click on book sail button and chose the gift certificate option. After putting in the amount and payment information you’ll receive an email confirmation and receipt along with the option to email the gift certificate directly to the person for whom you are gifting.
The boat is a 1998 Maine Cat 30 sailing catamaran. She is 30 feet long and 18 feet wide. There is a head/bathroom aboard on the starboard/right side facing forward and a galley/kitchen on the port/left side facing forward. There are two nets/trampolines that you can lay out on or sit on out on the bow/front. In the covered cockpit there is seating for four at the booth-table and bench seating along each side of the helm. Here are a few pictures for reference.