Virginia’s Best Guided Paddling and Biking Adventures

by Johnny Molloy | Posted: Jun 7, 2017 | Updated: Jun 3, 2019

Comments: 1 Comment

When it comes to outdoor recreation, Virginia is hard to beat. Whether it is paddling coastal waterways and mountain rivers or bicycling along Atlantic seashores amid wild woods, Virginia is rich with outdoor activities and venues to exercise your passion for the outdoors.

However, sometimes we don’t know exactly where to go, or we want to leave trip planning and preparation to others. That way we can focus on having a good time rather than concerning ourselves with navigation and logistics. That is where guided paddling and bicycling tours come in. These tours literally steer us in the right direction to the right places at the right time, to maximize our outdoor adventure without worry. Most guided adventures take you to specific places, while others are themed, such as a paddling tour to a winery or bicycling to taste tempting eateries. Still other guided tours combine food, wine and history all rolled into one adventure.

Learn about the following guided paddling and biking adventures then book your trip. Leave your cares behind and let Virginia’s natural beauty shine.




Guide: SouthEast Expeditions

Nearest Town: Exmore

The Paddling Tour: This guided paddle takes you through wildlife-rich tidal creeks of the Eastern Shore to Chatham Vineyards. Debark, view the grounds, then take a tour of the winery. Relax with a glass of wine. Make the return paddle with a glow on your face and a gleam in your eye.

chatham vineyards

Nearby Attractions:

  • The Great Machipongo Clam Shack
  • Barrier Islands Center
  • Shooting Point Oyster Company
  • Exmore Diner


Guide: SouthEast Expeditions

Nearest Town: Cape Charles

The Paddling Tour: This paddling adventure unites nature and the Eastern Shore’s clamming history in one fell swoop. Here, you head out from Cherrystone Point then ply Cherrystone Creek, looking for wildlife – especially birds. Make your way to a clamming bed then do a little in-the-water clamming yourself. Hunt for the tasty morsels with your feet and keep what you find! Paddle back to Cherrystone Point with your tasty treasure.

South East Expeditions Tour

Nearby Attractions:

  • Kelly’s Gingernut Pub
  • Savage Neck Dunes State Natural Area Preserve
  • Hotel Cape Charles
  • Cape Charles Historic District


Guide: Assateague Explorer

Nearest Town: Chincoteague

The Paddling Tour: This tour takes you on a classic, must do Eastern Shore experience. Paddle from Chincoteague, passing the Assateague Lighthouse rising from the shore. Make your way to Assateague Island National Seashore to see the sights, such as the famed wild ponies, shorebirds and the beaches of the Atlantic Ocean. Maybe even see a dolphin or eagle on your return paddle.

Assateague Island Pony Watching from the Assateague Channel

Nearby Attractions:

  • Goddard Space Flight Center
  • Captain Timothy Hill House
  • Chincoteague Nature Tours
  • Chincoteague Natural History Association Wildlife Tours


Guide: Rudee Inlet Stand Up Paddle

Nearest Town: Virginia Beach

The Paddling Tour: Ever wanted to learn how to operate a stand up paddleboard? Ever wanted to see the wildlife and nature of coastal Virginia? Combine your two desires into one guided adventure. Leave Rudee Inlet and your guide will take to the latest wildlife hotspots while helping you become a better stand up paddle boarder or “SUPper” as they say.

Stand up Paddleboarding

Nearby Attractions:


Guide: Rudee Inlet Stand Up Paddle

Nearest Town: Virginia Beach

The Paddling Tour: Bored with your exercise routine? We have the answer for you on this tour. How about mixing stand up paddle boarding with yoga and training while you are atop the SUP? Aw, come on you can do it! The guides here help you not only operate the SUP but also balance yourself with yoga moves while on the water. Fun!

Nearby Attractions:

  • Big Sams Inlet Café & Raw Bar
  • Adventure Parasail
  • Motor World Go Cart Racing Track
  • Captain Jacks Pirate Ship Adventures


Guide: Chesapean Outdoors

Nearest Town: Virginia Beach

The Paddling Tour: Head into the waters off Virginia Beach to see the sun set and spot dolphins frolicking nearby in the reflecting water. A great way to relax on the water while overlooking the lighthouses of Cape Henry and the famed Chesapeake Bay Bridge. This trip is good for a hot day when the evening temperatures will have cooled down.

Cape Charles Sunset

Nearby Attractions:


Guide: Adventure Kayak Tours

Nearest Town: Sandbridge

The Paddling Tour: Paddle through transitioning ecosystems on this tour of upper Back Bay National Wildlife Refuge. Start out in freshwater Ashville Bridge Creek before paddling into cypress-lined Muddy Creek. Look for wildlife along the shores and in the water.

Nearby Attractions:

  • Sandbridge Island Restaurant
  • Back Bay Trams
  • Margie & Ray’s Crabhouse
  • North Bay Shore Family Campground


Guide: Bay Country Kayaking

Nearest Town: Mathews

The Paddling Tour: Mathews County is a paddling paradise and is where the guided tour takes place. Experience multiple oceanic environments — tidal salt marsh, maritime forest, and sandy beach. Leave Mobjack Bay and paddle into Chesapeake Bay to visit New Point Comfort Lighthouse. This historic beacon stands proud in the water. Hit the shore for some beachcombing before returning to the launch site.

New Point Comfort Lighthouse

Nearby Attractions:

  • Mathews Maritime Museum
  • Bethel Beach Natural Area Preserve
  • The Inn at Tabbs Creek
  • Richardson Café


Guide: Rivanna River Company

Nearest Town: Charlottesville

The Paddling Tour: A good introductory guided trip for learning how to guide a canoe or kayak (your choice) through moving water, with light shoals and rapids. Start your adventure on the South Fork Rivanna River then meet the North Fork Rivanna River. The 6-mile trip takes you through numerous Class I rapids as well as three Class II rapids.

Nearby Attractions:


Guide: Riverside Outfitters

Nearest Town: Richmond

The Paddling Tour: Take a whitewater rafting trip into the falls of the James River, the 7-mile stretch of whitewater coursing through downtown Richmond – the only Class II-IV whitewater flowing through the heart of a big city. Includes a scenic lunch stop. Enjoy views of wildlife on the river in the near and towering skyscrapers in the distance.

Riverside Outfitters Rafting Trip

Nearby Attractions:

  • Edgar Allen Poe Museum
  • Belle Isle
  • Agecroft Hall
  • Riverwalk



Guide: Chesapean Outdoors

Nearest Town: Virginia Beach

The Bicycling Tour: Experience riding a fat tire bike on this guided tour that explores several destinations on one ride. Head out on Virginia Beach’s famed oceanfront Boardwalk then enter the North End ultimately to enter and explore First Landing State Park. Enjoy some forested biking and a chance to view wildlife. You’ll leave the park and loop back to the trail’s beginning, soaking in more Virginia Beach vibes. If you’d rather standard mountain bikes are available as opposed to the fat tire bike.

First Landing State Park. Photo:

Nearby Attractions:


Guide: Ocean Rentals

Nearest Town: Sandbridge

The Bicycling Tour: Leave Little Island Park in Sandbridge, then bicycle south, pedaling through Back Bay National Wildlife Refuge. This tour has two options, depending on your preference. The Interior Tour takes you on hardened road through the landward part of the refuge, amid woods and marshes where wildlife can be spotted. The Beach Tour uses fat-tire bikes to pedal along the shore, flanked by picturesque dunes on side and the water on the other.

Sunrise at Sandbridge Beach

Nearby Attractions:

  • Sandbridge Beach
  • Outdoor Resorts RV Resort
  • Sandbridge Island Restaurant
  • Lago Mar Pizza


Guide: Bike and Roll

Nearest Town: Arlington

The Bicycling Tour: Want to see the monument of our nation’s capital in a whole new light – or dark? Leave near sunset and pedal through the National Mall and Potomac Tidal Basin. Along the way, you will see Washington’s most notable monuments and memorials – Jefferson, Lincoln, Martin Luther King, plus the sobering war memorials – World War II and Vietnam, all light up in glory and splendor.

Nearby Attractions:


Guide: Bike and Roll

Nearest Town: Alexandria

The Bicycling Tour: Want to go on a bike tour but you have a slight lazy streak in you? Then this is the perfect tour. Start in Alexandria and take the paved Mount Vernon Trail 9 miles to Washington’s estate Mount Vernon. Tour our founding father’s home and grounds then take a bus back to your starting point. This way you got exercise with a 9-mile pedal but don’t have to make the return trip. Optional tour returns by boat to Alexandria.

Mount Vernon Bike Trail

Nearby Attractions:

  • Potomac Heritage Trail
  • Lee-Fendall House
  • African American Heritage Memorial Park
  • Old Town Alexandria


Guide: Richmond Rides

Nearest Town: Richmond

The Bicycling Tour: This three-hour tour treads along the banks of the James River in Richmond, where much of Virginia’s history has been made. Check out the rapids on the James River, the canals that once brought boats up and down the rapids as well as the downtown sights and scenes that define Virginia’ s capital city.

Nearby Attractions:

  • Virginia State Capitol
  •  The American Civil War Museum- White House and Museum of the Confederacy
  • 7 Hills Brewing Company
  • The Tobacco Company Restaurant


Guide: Richmond Rides

Nearest Town: Richmond

The Bicycling Tour: This guided tour explores Richmond’s most historic neighborhood, explaining Richmond’s rich history. Speaking of rich, the tour also stops by a couple of food destinations. Richmond Rides dubs this their signature tour. You not only learn about places but the people who figured prominently in this storied Virginia town.

Nearby Attractions:


Guide: Basket and Bike

Nearest Town: Charles City

The Bicycling Tour: This 4-5 hour guided bike excursion encompasses a lot into one adventure. Start at a vineyard on the shores of the James River, while your guide weaves the history of this parcel of the rural James River Valley between Richmond and Hopewell into the places you’ll see. Pedal on the Virginia Capital Trail past plantation homes and agricultural lands as well as natural sights en route to a church erected in 1613. Wine tasting included with locally grown lunch optional.

Virginia Capital Trail

Nearby Attractions:

  • Culs Courthouse Grill
  • Weston Plantation
  • City Point Park
  • Beacon Theatre


Guide: Shenandoah Rides and Rentals

Nearest Town: Lexington

The Bicycling Tour: Looking for a multi-day road bicycling tour of the Shenandoah Valley? All roads are paved and two lane. Furthermore, the tagalong van will tote your bike up hills if need be. This 5-day guided tour starts in historic Lexington. Pedal over to Staunton, crossing the Leaving the Potomac River valley for the James River Valley. Make a big loop deep in the Shenandoah Valley, then cap it off with dinner and a play put on by the American Shakespeare Company. Enjoy a parcel of the Blue Ridge Parkway, or lowlands, then enjoy a dinner and concert at the Lime Kiln Theater.

Luray shenandoah valley

Nearby Attractions:


Leave a Reply

Your email address will not be published. Required fields are marked *

One Comment

Avatar Ozzie Weyne says:

First Landing State Park Tour and False Cape Tour sounds amazing. I am saving money to buy a fat bike and the main reason is to be able to bike on the beach. First Landing State Park Tour seems perfect for that.