Virginia’s Best Guided Paddling and Biking Adventures

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. The following guided tours will maximize 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.
 

JUMP TO: Paddling Tours | Bicycle Tours
 

PADDLING TOURS

Paddle Your Glass Off Tour

Guide: SouthEast Expeditions

Nearest Town: Exmore

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.

Nearby Attractions:

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

Kayak Clamming Tour

Guide: SouthEast Expeditions

Nearest Town: Cape Charles

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.

Nearby Attractions:

• Savage Neck Dunes Natural Area Preserve
• Hotel Cape Charles
• Cape Charles Historic District

Assateague Pony Tour

Guide: Assateague Explorer

Nearest Town: Chincoteague

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.

Nearby Attractions:

• Goddard Space Flight Center
• Captain Timothy Hill House
• Chincoteague National Wildlife Refuge

Sunset Dolphin Tour

Guide: Chesapean Outdoors

Nearest Town: Virginia Beach

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.

Nearby Attractions:

• Calypso Bar & Grill
• Atlantic Wildfowl Heritage Museum
• Virginia Legends Walk
• Virginia Beach Fishing Pier

Keep planning with our complete guide to visiting Virginia Beach.

Lake Drummond & Great Dismal Swamp Tour

Guide: Adventure Kayak Tours

Nearest Town: Chesapeake

While Adventure Kayak Tours also offers shorter experiences, we're drawn to this six-hour tour of Lake Drummond via the Great Dismal Swamp Canal. Intermediate paddlers will love experiencing the beauty of the coastal environment and the unique nature of the Great Dismal Swamp. 

Nearby Attractions:

• Cavalier Wildlife Management Area
• Great Bridge Battlefield 
• Chesapeake Arboretum

New Point Comfort Beach & Lighthouse Tour

Guide: Craven Expeditions

Nearest Town: Mathews

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.

Nearby Attractions:

• Mathews Museum
• Bethel Beach Natural Area Preserve
• The Inn at Tabbs Creek 
• Richardson's Cafe 

Falls of the James Rafting Tour

Guide: Riverside Outfitters 

Nearest Town: Richmond

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.

Nearby Attractions:

• The Poe Museum
• James River Park System
• Agecroft Hall & Gardens 
• Maymont

Keep exploring the River City with our guide to visiting Richmond. 
 

Rivanna River Tour

Guide: Rivanna River Company

Nearest Town: Charlottesville

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:

• Monticello 
• Pen Park
• Carter Mountain Orchard 

Plan a Cville getaway with our complete Charlottesville guide. 

BICYCLE TOURS

Mount Vernon Tour

Guide: Unlimited Biking

Nearest Town: Alexandria

This is the perfect tour if you're not convinced about biking. Start in Alexandria and take the paved Mount Vernon Trail 9 miles to George Washington's Mount Vernon. Tour the founding father’s home and grounds then return on the trail. 

Nearby Attractions:

• Potomac Heritage National Scenic Trail
• Lee Fendall House Museum and Garden 
• Alexandria African American Heritage Park
• Old Town Alexandria 

Find more things to do with our complete guide to visiting Alexandria. 
 

Monuments at Night Tour

Guide: Unlimited Biking

Nearest Town: Arlington

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 all light up in glory and splendor.

Nearby Attractions:

• Arlington National Cemetery 
• Theodore Roosevelt Island
• Lady Bird Johnson Park
• Arlington House 

Keep exploring Northern Virginia with our complete guide to visiting Arlington. 
 

A Journey Along the James Tour

Guide: BASKET & BIKE

Nearest Town: Charles City

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 en route to a church erected in 1613. Wine tasting included with locally grown lunch optional.

Nearby Attractions:

• Cul's Courthouse Grille
• Weston Manor
• Old City Point Waterfront Park 
• The Beacon Theatre

Add this tour to your Richmond getaway (more on that here).