Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Dewey Beach…
    3. /Water Activities
    4. /Surfing Lessons
    5. /Windsurfing Lesson on Rehoboth Bay
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    Windsurfing Lesson on Rehoboth Bay

    Learn to windsurf on Rehoboth Bay with a 2-hour group lesson

    4.9 stars• 806 reviews

    Duration

    2 hours

    Includes

    Instructor, all gear

    Highlights

    Get on the water with an instructor-led windsurfing lesson using windsurf-able paddle boards. Build skills with provided gear in a 2-hour session at Dewey Beach.

    • Meet at 135 Dagsworthy Street in Dewey Beach
    • Practice windsurf basics on windsurf-able paddle boards
    • Learn with an instructor in a small group format
    • Plan a 2-hour session from start to finish
    • Bring water shoes for foot protection in the bay

    What's Included

    • Instructor
    • All gear

    Things to know

    Offered Memorial Day through Labor Day. Minimum age 8 and minimum weight 100 lbs. June–August group lessons require at least 2 people; gratuity is customary at 15%–20%.

    Cancellation Policy

    Cancel at least 24 hours in advance for a full refund. Get a full refund if the operator cancels due to weather or other unforeseen circumstances, such as group size failing to meet minimum requirements. No-shows are charged full price. No refunds within 24 hours.

    Product ID: H7YW57

    FAQs

    Join if you meet the minimum age of 8 and minimum weight of 100 lbs. You should have good physical fitness and coordination; it is not recommended if you have weak knees, bad backs, or overall weakness.

    Yes. During June, July, and August, group lessons require a minimum of 2 people. If the minimum is not met, the operator may cancel due to group size failing to meet minimum requirements.

    Wear a bathing suit or board shorts and a rash guard. Bring water shoes or water booties (the bay is sandy, but you could cut your foot on something sharp unseen in the water), plus water, sunscreen, a hat, sunglasses straps, and a towel.

    Meeting details

    135 Dagsworthy Street, Dewey Beach, DE

    Experience provided by Delmarva Board Sport Adventures

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Adult

    $185.50

    0

    Teen

    $185.50

    Ages 13-17

    0

    Child

    $185.50

    Ages 8-12

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    806 reviews•Google Maps
    564
    8
    3
    4
    3

    This operation has built a stellar reputation around Rehoboth Bay, and it's easy to see why from the consistent praise. Staff members like Sam, Jeremy, and George get called out repeatedly for their patience, friendliness, and going above and beyond. People mention instructors towing tired kids back, switching equipment recommendations based on wind conditions, and helping guests spot wildlife like horseshoe crabs and eagles. The equipment stays clean and well-maintained, with reviewers noting how the team washes everything between uses. The location launches into calm bay waters that first-timers find manageable, though wind can still make paddling a workout on certain days. The marsh areas offer peaceful exploration with plenty of bird watching and wildlife spotting opportunities. One guest couldn't reschedule due to rough water conditions and hoped for a future credit, but overall flexibility seems strong. The entrance can be tricky to find since it's on the opposite side of the hotel from what GPS suggests, so plan for that. This seems like an excellent choice for families and beginners looking for a relaxed paddling experience with genuinely helpful staff.

    What people are saying

    Review 1 of 4
    5/5

    We had the best time, staff were friendly and helpful. I’m so glad we were able to take our dog as well! Such a fun time!

    Photo of Lauryn M.

    Lauryn M.

    August 31, 2026

    Review 1 of 1
    5/5

    We had the best time, staff were friendly and helpful. I’m so glad we were able to take our dog as well! Such a fun time!

    Photo of Lauryn M.

    Lauryn M.

    August 31, 2026

    Nearby activities

    Paddleboard Lesson & 75-Minute Excursion in Dewey Beach
    Paddleboarding

    Paddleboard Lesson & 75-Minute Excursion in Dewey Beach

    Learn to paddle board on Rehoboth Bay with a certified instructor

    Learn to paddle board on Rehoboth Bay with a certified instructor
    4.9 • 806 reviews
    $69/ person
    Rehoboth Bay Kayak Tour with Certified Guide
    Kayaking Tours

    Rehoboth Bay Kayak Tour with Certified Guide

    Explore wildlife-rich Rehoboth Back Bay on a beginner-friendly 60-minute paddle with an ACA-certified guide.

    Explore wildlife-rich Rehoboth Back Bay on a beginner-friendly 60-minute paddle with an ACA-certified guide.
    4.9 • 806 reviews
    $69/ person
    Rehoboth Bay Windsurfing Paddleboard Rental
    Paddleboarding

    Rehoboth Bay Windsurfing Paddleboard Rental

    Ride a stable windsurfable paddleboard on Rehoboth Bay

    Ride a stable windsurfable paddleboard on Rehoboth Bay
    4.9 • 806 reviews
    $106/ person
    Sunset Guided Kayak Tour on Rehoboth Bay
    Kayaking Tours

    Sunset Guided Kayak Tour on Rehoboth Bay

    Paddle Rehoboth Bay at sunset with a certified instructor

    Paddle Rehoboth Bay at sunset with a certified instructor
    4.9 • 806 reviews
    $69/ kayak
    Paddleboard Rental in Dewey Beach
    Paddleboarding

    Paddleboard Rental in Dewey Beach

    Rent a paddleboard in Dewey Beach with hourly, daily, or weekly options

    Rent a paddleboard in Dewey Beach with hourly, daily, or weekly options
    4.9 • 806 reviews
    $95/ person
    Private Paddleboard Lesson in Dewey Beach
    Stand Up Paddle Boarding

    Private Paddleboard Lesson in Dewey Beach

    Private paddleboard or kayak lesson for your group up to 10

    Private paddleboard or kayak lesson for your group up to 10
    4.9 • 806 reviews
    $85/ person