Skip to main content
Adventure Collective Logo
Adventure ExperiencesLocal ExpertsLocationsAbout
Menu

The Adventure Collective

The Adventure Collective Discover, plan, and share your outdoor adventures with our global community of explorers.

Add as a preferred

source on Google

Explore Adventures

  • All Adventures
  • Boat Charters
  • Water Activities
  • Fishing
  • Land Adventures
  • Motorized Land
  • Winter Sports

Explore Adventures

  • Aerial Adventures
  • Wildlife & Nature
  • Camping & Overnight
  • Climbing & Mountaineering

Find Local Experts

  • Browse Local Experts
  • Become a Featured Expert

Company

  • About Us
  • Editorial Policy
  • Advertising
  • Add Your Business
  • Contact Us
  • The Adventure Network

Legal & Privacy

  • Privacy Policy
  • General Terms and Conditions
  • Cookies and Marketing Preferences
  • Legal Notice
  • Information according to the Digital Services Act
  • Do not Sell or Share my Personal Information
  • Sitemap

Adventure Town Guides

View All Adventure Towns

© 2026 The Adventure Collective. All rights reserved.

Editorial Policy
Skip to main content
Adventure Collective Logo
Adventure ExperiencesLocal ExpertsLocationsAbout
Menu

The Adventure Collective

The Adventure Collective Discover, plan, and share your outdoor adventures with our global community of explorers.

Add as a preferred

source on Google

Explore Adventures

  • All Adventures
  • Boat Charters
  • Water Activities
  • Fishing
  • Land Adventures
  • Motorized Land
  • Winter Sports

Explore Adventures

  • Aerial Adventures
  • Wildlife & Nature
  • Camping & Overnight
  • Climbing & Mountaineering

Find Local Experts

  • Browse Local Experts
  • Become a Featured Expert

Company

  • About Us
  • Editorial Policy
  • Advertising
  • Add Your Business
  • Contact Us
  • The Adventure Network

Legal & Privacy

  • Privacy Policy
  • General Terms and Conditions
  • Cookies and Marketing Preferences
  • Legal Notice
  • Information according to the Digital Services Act
  • Do not Sell or Share my Personal Information
  • Sitemap

Adventure Town Guides

View All Adventure Towns

© 2026 The Adventure Collective. All rights reserved.

Editorial Policy
SUP 101 | Self-Guided Tour in Deale | SUP, Water Activities, Boat Rental

SUP 101 | Self-Guided Tour in Deale | SUP, Water Activities, Boat Rental

  1. Home
  2. Local Experts
  3. Chesapeake Paddle Sports
  4. SUP 101 | Self-Guided Tour in Deale | SUP, Water Activities, Boat Rental

Adventure Brief

Discover the joys of paddleboarding with Chesapeake Paddle Sports' SUP 101 class. Perfect for beginners, this experience offers expert instruction and a relaxing paddle on Chesapeake Bay’s calm waters.

1.5–2 hours
easy
From $26.50
Family Friendly

Keep the Adventure Going

More ways to explore the area's outdoor wonders

No Experience Required

Located along the scenic shores of Chesapeake Bay, Chesapeake Paddle Sports offers a prime spot for paddleboarding enthusiasts and newcomers alike. Their SUP 101 class opens the door to the world of stand-up paddleboarding with expert instruction tailored to all skill levels. Set against a backdrop of calm waters and picturesque landscapes, this experience isn’t just a workout — it’s a gateway to coastal exploration and outdoor fun.

The class kicks off with fundamentals: proper paddle strokes, balance control, and safety tips, all delivered by certified coaches dedicated to helping you feel confident on the water. Once trained, participants are encouraged to take advantage of a complimentary 30-minute self-guided paddle, offering a relaxed period to practice new skills or simply enjoy the tranquil bay views. Chesapeake Paddle Sports stands out as a community cornerstone, combining professional instruction with a relaxed, welcoming vibe that appeals to families, tourists, and seasoned paddlers.

This experience is ideal for those looking to learn a new water sport in a safe, supportive setting. The calm bay waters and gentle breezes make it a perfect introduction, whether you’re seeking a fun outdoor activity or a new way to view Chesapeake’s coastal environment. The region’s rich wildlife, from ospreys to blue crabs, can often be spotted from your paddleboard, adding a touch of natural wonder to your adventure.

Chesapeake Paddle Sports’s SUP 101 is a top draw for visitors eager to embrace the area’s outdoor lifestyle. It’s not only a chance to master a skill but also an opportunity to connect with Chesapeake’s vibrant aquatic scene. Their commitment to safety, instruction quality, and environmental sustainability makes this a standout destination for water-based recreation.

Get ready for a splash of fun, scenic views, and newfound confidence on the water with Chesapeake Paddle Sports.

Hang tight — photos are loading

This usually takes just a second.

Trip Details from the Operator

Frequently Asked Questions

No prior experience is necessary — this class is designed for beginners and all skill levels.

Wear comfortable, quick-drying clothing suitable for water activities, and bring sun protection.

Yes, Chesapeake Paddle Sports provides all necessary equipment for the class and self-guided paddle.

Key Highlights

Difficulty

easy

Duration

1.5–2 hours

Fitness Level

All skill levels, including beginners, can comfortably participate; some light physical activity is involved.

Local Insights

Wildlife

  • Ospreys nesting nearby
  • Blue crabs in the shallows

History

Chesapeake Bay has a long history as a vital maritime hub since colonial times, and paddleboarding offers a modern way to connect with its rich heritage.

Conservation

Chesapeake Paddle Sports emphasizes eco-friendly practices, including shoreline cleanup efforts and responsible wildlife viewing to protect the bay's delicate ecosystem.

Related Adventures & Guides

  • See other trips from Chesapeake Paddle Sports
  • Explore more Annapolis adventures
  • Browse more water activities experiences

Operated By

Chesapeake Paddle Sports

Discover the joys of paddleboarding with Chesapeake Paddle Sports' SUP 101 class. Perfect for beginners, this experience offers expert instruction and a relaxing paddle on Chesapeake Bay’s calm waters.

About Chesapeake Paddle Sports

Chesapeake Paddle Sports is a Deale, Maryland outfitter focused on accessible paddling experiences around the Chesapeake Bay and nearby creeks. The operation offers kayak rental, paddle board rental, double kayak rental, pedal boat rental, memberships, guided Sunrise SUP and Full Moon Paddle events, SUP 101 instruction, a Kids Summer SUP Camp, and social outings like SUNday FUNday.

Rentals and programs operate on Rockhold Creek, Tracey’s Creek, and Herring Bay, with programming designed to highlight local wildlife and shoreline history while reinforcing safe on-water skills. SUP 101 is taught by certified coaches and includes a complimentary 30-minute self-guided paddle after the lesson. The Kids SUP Camp runs four days for ages 8–14 and combines paddling skills, games, and Chesapeake Bay exploration.

Age and occupancy guidelines are stated for each offering: kayak and paddle board rentals are available to adventurers aged nine and up, and pedal boats accommodate up to two adults and one child. Special events include a guided Sunrise SUP (RSVP by 6 PM the night before) and a 90-minute Full Moon Paddle. Membership options cover SUP Yoga, fitness classes, and guided tours.

Booking and operations are based in Deale, Maryland, with activities staged on the listed creeks and Herring Bay. Chesapeake Paddle Sports emphasizes family-friendly options, certified instruction, and clearly stated age and occupancy guidelines for renters, campers, and class participants. Advance reservations help secure preferred dates and equipment today.

Chesapeake Paddle Sports fleet
Chesapeake Paddle Sports team

Location

Deale, Maryland

Activities launch from Deale on Herring Bay

Tours Offered

11

Rentals, classes, camps, and guided paddles

Kids Camp Ages

8–14

Four-day summer SUP camp for youth

Pedal Boat

2 adults + 1 child

Family capacity for pedal boat rentals

CTA Section Background Image

Reserve a Paddle Adventure in Deale Today

Book rentals, lessons, camps, or guided paddles on Rockhold Creek and Herring Bay — check age limits and RSVP details to secure a spot.

Adventure Tips

Arrive early

Getting to the class a few minutes early allows you to settle in and get comfortable before instruction begins.

info

Wear sun protection

Bring sunscreen, sunglasses, and a hat to protect yourself during your time on the water.

info

Check wind conditions

Ensure weather conditions are suitable for paddleboarding to have a safe and enjoyable experience.

essential

Bring water and a towel

Stay hydrated and dry off after your paddle to keep comfortable throughout the day.

info

Recommended Gear

Swimsuit or quick-drying athletic wear

Light, comfortable clothing suitable for water activities.

summer

Essential

Sunscreen and water

Protect your skin from UV rays and stay hydrated during your paddle.

summer

Essential

Waterproof bag or dry bag

Keep your personal items dry while on the water.

Sun hat or cap

Additional sun protection for your face and neck.

summer

Deale Things To Do
Deale Water Activities
Deale Boat Rental
  • Read our Annapolis travel guide