COVID 19?
At Flip Flops Sailing facial coverings are required while the boat is sitting still at the dock. Passenger counts are set at a maximum of 6 on any of our sailing excursions. And the boat is cleaned and sanitized before and after each sail.
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. A public sail is open for other guests to join your party.
After the private or public option, the different sailing excursions opens up. Egmont Key Adventures, Passage Key Adventures, 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, and Passage Key Adventures 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 to book a sail.
Next you input your name, phone number, and email. 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
941-417-9989
Where is the boat located?
The boat is located at the docks behind the Waterline Resort Hotel and Marina.
The address is 5325 Marina Dr. Holmes Beach, FL
The boat is docked in slip 44 which is behind the main building of the Waterline Resort Hotel. Just follow the sidewalk next to the water and other docks around to the back by the pool. Or you can walk through the lobby to the back.
Where is parking then?
Our Mainsail Marina parking lot is by the Waterline resort. Next to, but not in, the Wells Fargo parking lot. There are signs in front of the spaces and they read Mainsail Marina Parking.
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.
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 adventure sails?
Keep in mind that the Egmont Key Sail and Passage Key Sail are adventures. So you will have to go into the water to reach the shore. There is no dock or pier for public use at either island. We do however try to get the boat as close to the beach as wind, waves, and sea conditions allow.
Is there any swimming off the boat?
Yes and no. The only sails that offer an opportunity to go swimming is the Egmont Key and Passage Key Sail. The other sails do not offer enough time to reach a place to safely anchor the boat and jump in the water. So if you’re looking to get in the water check out the Egmont Key Adventure or Passage Key Adventure sail.
What happens if there are thunderstorms?
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. 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 and either first try to reschedule or if need be cancel/refund the sail.
How many passengers can the boat take out sailing?
The boat has been stability tested for and can hold more than 6 passengers, but due to the Covid 19 pandemic and Coast Guard regulations the maximum number of guests is 6. Which means there is plenty of room for everyone to spread out, relax, and enjoy the sail.
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. 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.
As a previous passenger or even a future passenger on Flip Flops, is there anything I can do to help support Flip Flops Sailing? I know that a lot of small businesses have been impacted by the pandemic and are having a tough time in these uncertain times.
Yes there is. Like a lot of small businesses, Flip Flops Sailing has not been immune to the impact of the pandemic. If you have plans to travel to Anna Maria Island when things get better and get closer to normal, you can purchase a gift certificate now and then use that gift certificate to book a sail when you are here and want to go sailing. They also make for great presents for friends and family. I have also setup a Patreon page for Flip Flops Sailing if you are feeling particularly philanthropic and charitable. Patrons of Flip Flops Sailing also get discounts on sailing excursions. To learn more about this just click on the Jolly Roger(Pirate Flag🏴☠️)in the menu section of this website.
At Flip Flops Sailing facial coverings are required while the boat is sitting still at the dock. Passenger counts are set at a maximum of 6 on any of our sailing excursions. And the boat is cleaned and sanitized before and after each sail.
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. A public sail is open for other guests to join your party.
After the private or public option, the different sailing excursions opens up. Egmont Key Adventures, Passage Key Adventures, 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, and Passage Key Adventures 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 to book a sail.
Next you input your name, phone number, and email. 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
941-417-9989
Where is the boat located?
The boat is located at the docks behind the Waterline Resort Hotel and Marina.
The address is 5325 Marina Dr. Holmes Beach, FL
The boat is docked in slip 44 which is behind the main building of the Waterline Resort Hotel. Just follow the sidewalk next to the water and other docks around to the back by the pool. Or you can walk through the lobby to the back.
Where is parking then?
Our Mainsail Marina parking lot is by the Waterline resort. Next to, but not in, the Wells Fargo parking lot. There are signs in front of the spaces and they read Mainsail Marina Parking.
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.
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 adventure sails?
Keep in mind that the Egmont Key Sail and Passage Key Sail are adventures. So you will have to go into the water to reach the shore. There is no dock or pier for public use at either island. We do however try to get the boat as close to the beach as wind, waves, and sea conditions allow.
Is there any swimming off the boat?
Yes and no. The only sails that offer an opportunity to go swimming is the Egmont Key and Passage Key Sail. The other sails do not offer enough time to reach a place to safely anchor the boat and jump in the water. So if you’re looking to get in the water check out the Egmont Key Adventure or Passage Key Adventure sail.
What happens if there are thunderstorms?
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. 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 and either first try to reschedule or if need be cancel/refund the sail.
How many passengers can the boat take out sailing?
The boat has been stability tested for and can hold more than 6 passengers, but due to the Covid 19 pandemic and Coast Guard regulations the maximum number of guests is 6. Which means there is plenty of room for everyone to spread out, relax, and enjoy the sail.
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. 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.
As a previous passenger or even a future passenger on Flip Flops, is there anything I can do to help support Flip Flops Sailing? I know that a lot of small businesses have been impacted by the pandemic and are having a tough time in these uncertain times.
Yes there is. Like a lot of small businesses, Flip Flops Sailing has not been immune to the impact of the pandemic. If you have plans to travel to Anna Maria Island when things get better and get closer to normal, you can purchase a gift certificate now and then use that gift certificate to book a sail when you are here and want to go sailing. They also make for great presents for friends and family. I have also setup a Patreon page for Flip Flops Sailing if you are feeling particularly philanthropic and charitable. Patrons of Flip Flops Sailing also get discounts on sailing excursions. To learn more about this just click on the Jolly Roger(Pirate Flag🏴☠️)in the menu section of this website.
