Now offering e-lessons!

A New & Innovative Approach to Learning to Surf

High 5 Surf offers year-round surf lessons, coaching, guided surf experiences, and gear rentals on Lake Michigan in Milwaukee and Chicago. Our services extend to many cities across the Great Lakes region.

Surfing on Lake Michigan
Surf lesson experience
Winter surfing
Catching waves
Surf coaching

High 5 Surf: Your Surf Experience

We minimize the complexity of learning to surf

Your Surf Journey Starts Online

Before hitting the waves, you'll receive a 2.75-hour e-lesson covering surf safety, winter surf safety, forecasting, etiquette, wetsuit changing hacks, positioning, paddling, pop-ups, stance, shuffling, cross stepping, dismounting, wipeouts, wave selection, board management, wave negotiation/navigation, and more.

Premium Gear & Comfort

On the day of your session, we provide all the equipment — hooded wetsuits, boots, mittens, board, leash, helmet, and life jacket (if you'd like them) — plus individual heated changing tents for comfort.

Independent Surfing with Video Coaching

You'll put your new skills into action independently in the water — no instructor will be in the water with you. Your Surf Guide stays on shore in street clothes, filming your rides, wipeouts, takeoffs, paddle-ins, and wave selection while providing the heated changing tent and equipment.

Personalized Video Coaching

Within 3 days after your session, you'll receive personalized coaching based on your video clips (≈15-30 minutes of recorded analysis), helping you refine your technique. All your surf footage and coaching is yours to keep.

Note: Each session lasts 2 hours, including changing time.

Learn to surf the Great Lakes

Expert coaching, all equipment included, and memories captured on video

2 Hour Sessions
All Equipment
Video Recording
Expert Coaching

To ensure that your surf lesson takes place in the best possible conditions, payment is typically required 3 days in advance. This timing allows us to confirm that the waves will be suitable before finalizing your booking. You’ll receive your e-lesson access the same day you pay

Please feel free to reach out today to start the manual booking process while our online booking system is being finalized. If you prefer, you can also reach out as many days or even weeks in advance, and we’ll assist you with securing your booking.

With High 5 Surf's innovative approach, you get the freedom to surf at your own pace, expert coaching, and unforgettable memories captured on video — all in one unique experience.

* All bookings are non-refundable; however, we're happy to accommodate rescheduling, subject to availability.

1-on-1

$250

Group of 2

$200
per person

Group of 3

$150
per person
Best Value

Group of 4

$125
per person

Enhance Your Surf Session

Customize your lesson with in-water support or expert coaching

In-Water Surf Guide

$100add-on

Want someone in the water with you? Add an In-Water Surf Guide to your session.

  • Help manage your board in the water
  • Give you a push into waves if you want it
  • Basic in-water support (no coaching)

One surf guide per session (solo or group). For groups, the guide divides time among all participants.

Most Popular

Expert Surf Coach in the Water

$200add-on

Get live, in-the-moment guidance with an expert coach in the water throughout your session.

  • Hands-on feedback while you surf
  • Help with positioning, wave choice & technique
  • Board management & push into waves if needed

One coach per session (solo or group).

Important Note About Add-Ons

If you select either in-water add-on (Surf Guide or Expert Coach), the standard video coaching option is not included since our staff will be in the water rather than filming.

If you'd like to keep video coaching + your surf footage, it can be added back for $100 extra.

Pricing with Add-OnsBased on 1-on-1 lesson ($250)

Base + In-Water Surf Guide

No video coaching

$350

Base + Expert Surf Coach

No video coaching

$450

Base + In-Water Surf Guide + Video Coaching

Full package

$450

Base + Expert Surf Coach + Video Coaching

Premium experience

$550

Out-of-Area Lesson Fee

We provide transportation help if wanted or needed! For surf lessons anywhere on the Great Lakes outside of Milwaukee, there's a simple Out-of-Area Lesson Fee.

Ride with us

We'll pick you up in the High 5 Surf Mobile, drive you to the waves and back, and talk Great Lakes surfing along the way.

Meet us at the beach

Drive yourself and meet us at the surf spot — the fee still applies depending on the location.

Fee Details

Milwaukee Area

Meet us at the beach — no trip fee

$100

Chicago Area

Flat $100 fee when you meet us at the beach

Other Great Lakes Locations

85% of IRS mileage rate ($0.67/mi) based on round-trip from Milwaukee

Door-to-Door Service

85% of IRS mileage rate round-trip from Milwaukee — anywhere we go

Premium Cold-Water Surf Gear

Top-quality surf gear built for Lake Michigan, whether you're chasing fall or winter swell or enjoying a mellow summer session.

Available Sizes

  • Hooded wetsuits: Youth through 3XL
  • Boots: Sizes 6–16
  • Mittens: XS to 2XL

Pickup & Delivery

  • Self pickup & return at storage unit: Free
  • Delivery: $20 flat rate (Milwaukee area)
  • Gear pickup from you: $20 flat rate (Milwaukee area)
  • Same-day return by 10PM
Most Popular

Full Surf Setup

Premium soft top surfboards (10' and 8'), 5'11" hard top board, hooded wetsuit (5/4mm or 6/5/4mm), neoprene boots & mittens, leash included

$100per day

Wetsuit Kit Only

Hooded wetsuit, boots & mittens included. No discount for wetsuit-only rentals without boots or mittens

$50per day

Surfboard Only

Multiple soft top boards (10', 8'), 5'11" hard top board available, leash included

$50per day

Check out our merch

High 5 Surf T-Shirt
High 5 Surf Hoodie
High 5 Surf Mug
High 5 Surf Hat
High 5 Surf Bucket Hat
High 5 Surf Tumbler

Book your life-changing
adventure today

We can't wait to see you on the Great Lakes

Contact us