The East End’s Premier Surf Experience, by Jamie O’Brien
Jamie O’Brien Surf Experience brings world-class instruction and a luxury-first approach to surf lessons in Montauk, New York — based at the legendary Montauk Yacht Club on Star Island.
We’re proud to call one of the East End’s most iconic properties home. Spanning 16 waterfront acres on Lake Montauk, the Montauk Yacht Club is the Hamptons’ most celebrated resort — a destination built for guests who expect more. Our surf program matches that standard at every level: expert instruction, premium equipment, and an experience designed around you, not the crowd.
Lessons are offered seasonally, from May through October, with surf held at Napeague Beach — one of the most consistent stretches of shoreline on Long Island’s East End. Complimentary round-trip transportation brings you from the Yacht Club to the break and back, so all you have to do is show up ready to surf.
From the Moment You Arrive, You’ll Enjoy:
- Complimentary round-trip transportation from Montauk Yacht Club to Napeague Beach
- Expert, personalized instruction from certified surf professionals — not a camp, not a crowd
- Premium gear included — surfboard, wetsuit, rash guard, leash, and all necessary safety equipment
- Land-based coaching before you ever hit the water
- A seamless, elevated experience from check-in to your final wave
What to Expect:
All lessons are based out of the Montauk Yacht Club, 32 Star Island Road — a property that has hosted yachts and world travelers for nearly a century. The Club’s private setting on Lake Montauk is your basecamp. From there, complimentary transportation takes you directly to Napeague Beach, at the end of Atlantic Drive, where a wide, sandy shoreline gives our instructors the space to set up in the best area for the day’s conditions.
All equipment is provided — surfboard, wetsuit, rash guard, and leash. Just bring a swimsuit and your sense of adventure.
Please arrive 15 minutes prior to your scheduled lesson time for check-in and equipment fitting.
- Check in at the Jamie O’Brien Surf Experience desk at Montauk Yacht Club
- Meet your instructor and get fitted with all required gear
- Learn the fundamentals on land — paddling technique, safety, and the pop-up
- Head to Napeague Beach and surf with your instructor at this iconic East End break
- Return to the Yacht Club when you’re done
Montauk Yacht Club with Jamie O’Brien Surf Experience
CLick Below To Select Your Activity!
Semi-Private Surf Lessons
A private group lesson built for families and friends who want to share the experience — with no outside participants added to your session.
- 2 Guests : 1 Instructor
- 90 minutes
- A fully private session, start to finish — just your group and your instructor
Group Surf Lessons
A social, high-energy introduction to surfing. Our group lessons are nothing like the big camps the East Coast is known for — small ratios, expert guidance, and real progression in the water.
- 2 Guests : 1 Instructor
- 90 minutes
- A social learning environment while maintaining personalized coaching
Private Surf Lessons
The Montauk experience at its most personal — one surfer, one dedicated instructor, and maximum time in the water.
- 1 Surfer : 1 Instructor
- 90 minutes
- Recommended for first-time surfers, children under 12, non-swimmers, and any guest looking for the most personalized instruction
Every Lesson Includes
No matter which format you choose, every session covers:
- Ocean safety instruction
- Surf fundamentals
- Paddling technique
- Wave selection
- Hands-on, in-water coaching
Frequently Asked Questions
Do I need any experience to book a surf lesson?
None at all. We specialize in first-time surfers and beginners. Every lesson starts with land-based instruction before you enter the water, so you’ll feel prepared and confident from your very first wave.
Do I need to bring a wetsuit?
No — wetsuits are included with your lesson. The Atlantic is cooler than the Pacific, and a wetsuit makes for a much more comfortable session. All equipment is provided; just bring a swimsuit.
When should I arrive?
Please arrive 15 minutes before your scheduled lesson time. This gives us time to check you in at the Jamie O’Brien Surf Experience desk and fit you with all your gear before you head to the beach.
How do I get to Napeague Beach from the Yacht Club?
We handle it. Complimentary round-trip transportation takes you from Montauk Yacht Club to Napeague Beach and back, so you can focus entirely on your session.
Are your instructors certified?
Yes. All JOB Surf Experience instructors are CPR and first aid certified, with extensive in-water teaching experience. Safety is always the foundation of everything we do.
Are lessons available year-round?
Our Montauk program is seasonal, running May through October. Book early — summer weekends at the Yacht Club fill fast.