For those who want to be on your own, we are now offering rentals. What makes rentals even better is that we offer local delivery*. That way, your time off stays as relaxing as possible.

Our rental gear consists of 10-to-11-foot softtop boards from Doyle Stand Up Paddle, along with adjustable Doyle and Boardworks paddles.

Three or More
1 Day Rental
$50 ea.
2 Day Rental
$90 ea.
3 Day Rental
$120 ea.
1 Week Rental
$250 ea.

Includes a board, paddle, and PFD. Note that Chesapeake SUP reserves the right to withhold rental based on assessment of paddling situation and paddler fitness/skill. Paddle at your own risk.

* Additional fees may be incurred if the delivery and pick-up is outside our 20-mile-out-and-back delivery area. Delivery cost is $2 per additional mile. If additional fees are incurred we will notify prior to rental and delivery.

While we may occassionally sell used rental gear, we do not retail new boards and gear. However, that doesn't keep us from knowing about the latest boards and gear - and the reputable local shops that sell it. Ask us! We'll give you an unbiased opinion, and our best recommendations.

Chesapeake SUP offers SUP lessons and tours for a variety of skill levels, ranging from rank beginner to seasoned expert. Our instructors have ocean rescue training and are certified in First Aid and CPR.

Maximum student/guide ratio is 4-to-1, so you can be sure you'll always be under a watchful eye. Here are some of the packages that we offer:

1.5-Hour Lesson/Tour
This lesson introduces you to the world of stand up paddling. Starting with a land lesson, we teach safety, proper stance, paddling technique, and how to paddle in a variety of conditions.

Some of the things students will learn include: safety, trip planning, board management, basic paddle stroke, turning, knee paddling, stance, paddle stroke types, movement on board.

3-Hour Lesson/Tour
This lesson and tour delivers the tools you need to become a proficient stand up paddler. Starting with a land lesson, we teach safety, proper stance, paddling technique, and how to paddle in a variety of conditions. From there, we'll move into an extended tour to dial-in the skills you've learned.

Already Have the Basics Down?
No problem. We'll start where your experience ends. We'll work with you on developing your skills in the direction you want to take them. Waves? No problem. Expedition paddling? No problem. Downwinders? No problem. Advanced skills and tricks? No problem.

Lesson/Tour Location
We're mobile! We'll look at the existing weather conditions on the day of the paddle, then find the best place for you to progress.

Chesapeake SUP is a paddling lesson and rental shop offering the best and most experienced paddling instruction in the region. Originally founded by surfers-paddlers-kiteboarders Macky Hall and Steve Casper, we bring a wealth of experience to make the most out of your paddling event.

We'd love to hear from you. Feel free to call 804.725.4420 or email We'll reply as immediately as possible.