Frequently Asked Questions



Frequently Asked Questions



Frequently Asked Questions

If you have been out with us before, you know that we spend almost all day on the boat teaching wakeboarding and waterskiing; basically just having a great time on the water. This makes it hard for us to find the time to answer the phone when you call. Here are the answers to many of the common questions we get.

If there is a question we haven’t answered here, give us a call. Leave a message. If we don’t answer at first, we promise to call you back by end of day.



No, we do not rent jet skis. Although jet skis are fun to buzz around the lake on, there are laws that prevent operating a jet ski without a proper Personal Watercraft/Safe Boating Certificate. For this reason, we are not able to rent jet skis. Please check local and state laws to confirm where you might be able to rent a jet ski.


HOW MANY People Fit on the Boat?

12 is the maximum number of guests that we can take on any of our boats at one time. This leaves room for the driver and the spotter to operate the boat safely and legally. If you have a group size larger than 12 total, please call us. We are happy to offer creative solutions to make sure everyone in your group can find a way to enjoy the Lake.

What if my party is larger than 12 people?

We understand some of you have big families or more friends than you can count. If you are attempting to have more than 12 people come out during your appointment, please call us to discuss. We can offer some creative solutions.

What is the age limit?

We do not have any age restrictions. We have taught people as young as 4 to waterski and had someone 91 years young waterski behind our boat. People even younger have gone for a tube ride and hung out on the boat.

Lakeside Waterskiing.jpg


We charge a flat rate of $180/hour. Again, this is a flat rate, meaning we charge by the hour. This is NOT a per person charge. If you have a large group, the price per hour remains the same at $180/hour.

This includes the boat time, driver, spotter/instructor, gas, watersports equipment, and safety gear.

We take payment at time of service. You will input your credit card at time of booking but we do not charge this card. Please present payment following your appointment.

should i tip the crew?

The Lakeside staff strives to offer the absolute best time on the water while keeping you safe. It’s customary to offer gratuity, but never required. Gratuity can be added during checkout with a credit card or cash can be handed directly to the crew.



We are incredibly accommodating and are willing to let you and your guests try whatever watersports you would like during your appointment time. Just tell us what activities you’re interested in before we leave the dock, and we will be sure to stock the boat with all the necessary equipment. The cost remains the same per hour regardless of how many activities you try.

What if i Don’t want to go in the water?

We will never force you to go in the water. There is plenty of room on the boat if someone wants to go for a boat ride, stay dry and watch the watersports. We are also happy to offer guided lake tours without any watersports. The cost remains the same per hour for this service.



We leave this decision up to you, but we can help make recommendations. A good rule of thumb for making a booking for a beginner is 20-30 minutes per person per activity. Watersports like wakeboarding and waterskiing are incredibly tiring. 30 minutes per person gives enough time for someone to try without being completely exhausted. It might also leave some extra time for tubing.

Note: We will do our best to manage the time you book and give everyone a chance who wants one. But be advised there are scenarios where too many guests and not enough time booked make that harder to accomplish.

The maximum amount of time i can book online is 4 hours, what if i need more?

First off, you are aggressive and we like it. If you would like more time out on the water during a single appointment, we require that you contact us to discuss this request and make sure we can accommodate this extended booking.



We prefer if you show up 5-10 minutes before your start time. This gives us time to get your waivers filled out, life jackets fitted, and equipment loaded onto the boat for an on-time departure. We book our appointments back-to-back, so there is a possibility that if you show up very early we will not be at the shop and will be out on the water with another group.

If you want to save time on the day of your appointment, each person going on the boat needs to fill out the waiver. If you plan to come back this season, this needs to be filled out once per year per person.

What if there is bad weather DAY OF MY APPOINTMENT?

Reschedule! We recommend booking your appointments early. Waiting until the last minute while watching the weather might mean you get boxed out and run the risk of our schedule booking up completely. If there is a situation where there is bad weather on a day when you have a booked appointment, we are not going to force you to go out on the water. We ask that you stay in communication with us about your plans. If the weather is severe or threatening at the lake, we will reach out to you directly and we will cancel. Since you don’t pay until time of service, you will not be out any money, we just ask that you reschedule to a different time in the summer.


Connecticut: We are located at Pocono Point Marina, 16 Forty Acre Mountain Road, Danbury, CT 06811. Our office is behind the building up both flights of stairs. The front door is the marina, please just walk around back and head up to the sliding door at the top of the building.

New Hampshire: We are located at the Winnipesaukee Pier at Weirs Beach, 263 Lakeside Avenue, Laconia NH 03246. You can check-in for your appointments by walking down the boardwalk to the last shop on the left.


Connecticut: At Pocono Point Marina, there is parking on either side of the street. Wherever you find a parking space that doesn’t block in another car is fair game.

New Hampshire: There is parking all along Lakeside Avenue near the Winnipesaukee Pier. Please find any nearby spot.



Yes! Just as the Lakeside Watersports name suggests, we make lakeside pickups. If you would like to be picked up, you need to specifically tell us that before your appointment. We assume that all appointments will start at our office location unless otherwise instructed. If you want to be picked up, tell us the street address, any helpful landmarks to look for, and what equipment we need to bring.

Connecticut: We can pick you up anywhere on the lake, so long as there is a safe docking location.

New Hampshire: Due to the size of Lake Winnipesaukee, we can only offer lakeside pickup in Gilford, Laconia and Meredith. If you live/are staying outside of these towns, we apologize but you will need to travel to our location at the Winnipesaukee Pier or book more time to compensate for our extended travel time.

Note: Requesting a lakeside pickup has the potential to delay the start time of your appointment by a few minutes while we travel to your location. We will do everything we can to get to your location by the requested start time, but we ask that you be patient based on lake and weather conditions.



You just need to bring your bathing suit and towel. All of the watersports and safety equipment is provided. If you have your own watersports equipment, i.e. wakeboard, wakesurf, etc., feel free to bring that.

Note: We do NOT provide wetsuits. Early season and late season can be chilly, feel free to bring your own wetsuit or drysuit and extra towels.

Can I bring it?


Food 👍

  • It might sound funny, but we ask that you bring “boat friendly” food. What do we mean by that? Things that don’t crumble and can be eaten in one bite. Good examples of this are grapes, fruit snacks, string cheese, etc. Food that we would prefer not be on the boat includes: Potato chips, popcorn, brownies, basically things that are oily or have lots of crumbs.

Camera 👍

  • Capture the moment and relive your time on the water. However, we are not responsible for anything that could happens to the camera while it is on the boat.

No Dice.

Alcoholic Beverages 👎

  • Our insurance provider does not allow for us to allow drinking alcoholic beverages on the boat. We apologize for the inconvenience.

Dogs, Cats and other Pets 👎

  • We love our furry friends, but the vinyl seats on our boats don’t love their claws. We ask that you do not bring your pets with you during your appointment.

Cigarettes, Cigars or other Smoking Devices 👎

  • There is no smoking on or near our boats.


How It Works

How It Works

How It Works

How It Works

Follow these easy steps to enjoying fun on the water this summer:



Lakeside Watersports books by appointment only using our self-service online booking system. This system works on a first-come, first served basis and shows up-to-the-minute availability.

If you are interested in reserving time, please visit our online schedule.

  • Select a length of time you would like to book.

  • Choose from the open dates and times available to accept. Once you have chosen a date and time this slot will be held for 10 minutes.

  • Input your contact information details.

  • Input your payment information. Entering a credit card here simply holds the appointment and protects us in case of a no show. We take payment at time of service, please bring your preferred payment method (cash, check, credit card, gift card) with you to settle up after your appointment.

Cancellation Policy: You are in control and able to cancel or modify your appointment until 24 hours in advance of your start time. After that time, if you need to make changes, you will need to contact us via phone, text or email. If you communicate with us, there will be no charge for appointment modifications. If there is a situation where you have confirmed your appointment and then do not show up, we reserve the right to charge a cancellation fee of up to 50% of the appointment value.

You will receive a confirmation email after booking your appointment. If you didn’t receive an email, this means your booking was incomplete or you may have typed your email address incorrectly. Please reach out to the Lakeside team if you did not receive an email. You will also receive a reminder email 24 hours before your appointment start time. This is one last reminder that you have an appointment booked, we look forward to seeing you one day later!


We book our appointments back-to-back, which leaves a short window of time between groups to get your group fitted for life jackets and the boat stocked with all of the equipment. To save time on appointment day, please fill out the 2019 Liability Waiver before arriving. Every person who will be going out on the boat needs to fill out the waiver regardless of if they will be going in the water. This is a non-negotiable, if you do not have a waiver on file, we cannot let you out on the boat. We only need one waiver filed per person per year. If you filled one out in 2019, you are all set.


A good rule of thumb is to try and arrive 10-15 minutes in advance of your appointment. This will ensure you have time to use the bathroom, get fitted for a life jacket, and choose your equipment. If you show up late, this will likely eat into the time you had booked. We cannot guarantee that we will be able to extend beyond your appointment window and offer the full time if there is another group on the schedule directly following you.

Similarly, if you show up super early, we cannot guarantee that we will be able to take you out right when you arrive. it is likely we will be out with another group and the door could be locked. We have not forgotten about you! We will be back in time for your appointment start time. Please make yourself comfortable while you wait for our crew to return.

Step 4. HAVE FUN

Our job is to offer you a relaxing, fun and safe day on the water. Once we get all of the paperwork out of the way, it is time to kick back relax and enjoy the beautiful backdrop of Candlewood Lake or Lake Winnipesaukee. We are so excited to share these amazing places with you. We will do all of the driving, docking, and equipment handling, plus we will offer as much or as little instruction as you would like.

Step 5. Write a review

For us, reviews make the world go around. Honestly, we pride ourselves on our ability to offer an incredible and seamless watersports experience. It would mean so much to us if you felt inclined to share your experience on any of these major platforms: