Virginia's Premier Guided Paddling and Biking Adventures
Virginia excels in outdoor recreation, offering paddling on coastal waterways and mountain rivers, plus biking along Atlantic shores amid wild woodlands. The Commonwealth brims with venues to ignite your passion for the outdoors.
Navigating the best spots or managing logistics can be challenging. Guided paddling and biking tours handle the details, guiding you to prime locations at ideal times for worry-free adventures. Tours visit specific sites or feature themes like winery paddles, culinary bike rides, or blends of food, wine, and history.
Explore these expert-led tours and book your trip. Immerse yourself in Virginia's stunning natural beauty.
PADDLING TOURS
PADDLE YOUR GLASS OFF TOUR
Guide: SouthEast Expeditions
Nearest Town: Exmore
The Paddling Tour: Navigate wildlife-rich tidal creeks of the Eastern Shore to Chatham Vineyards. Tour the grounds and winery, then enjoy a glass of wine. Paddle back with a contented glow.
Nearby Attractions:
- The Great Machipongo Clam Shack
- Barrier Islands Center
- Shooting Point Oyster Company
- Exmore Diner
CLAMMING TOUR
Guide: SouthEast Expeditions
Nearest Town: Cape Charles
The Paddling Tour: Combine nature and Eastern Shore clamming history. Launch from Cherrystone Point, explore Cherrystone Creek for birds and wildlife, then clam at a nearby bed using your feet. Keep your harvest and paddle back with your bounty.
Nearby Attractions:
- Kelly’s Gingernut Pub
- Savage Neck Dunes State Natural Area Preserve
- Hotel Cape Charles
- Cape Charles Historic District
ASSATEAGUE PONY TOUR
Guide: Assateague Explorer
Nearest Town: Chincoteague
The Paddling Tour: Embark on an iconic Eastern Shore paddle from Chincoteague, past Assateague Lighthouse to Assateague Island National Seashore. Spot wild ponies, shorebirds, Atlantic beaches, and possibly dolphins or eagles.
Nearby Attractions:
- Goddard Space Flight Center
- Captain Timothy Hill House
- Chincoteague Nature Tours
- Chincoteague Natural History Association Wildlife Tours
STAND UP PADDLEBOARD ECO TOUR
Guide: Rudee Inlet Stand Up Paddle
Nearest Town: Virginia Beach
The Paddling Tour: Master stand-up paddleboarding (SUP) while exploring coastal Virginia's wildlife hotspots. Depart from Rudee Inlet with expert instruction to enhance your skills.
Nearby Attractions:
- Rudee Tours Fishing Charter
- Virginia Aquarium & Marine Science Center
- Beach Quarters Resort Hotel
- Waterman’s Surfside Grill
STAND UP PADDLEBOARD FITNESS TOUR
Guide: Rudee Inlet Stand Up Paddle
Nearest Town: Virginia Beach
The Paddling Tour: Revitalize your workout with SUP yoga and training. Guides assist with balance and water-based exercises for a fun, effective session.
Nearby Attractions:
- Big Sams Inlet Café & Raw Bar
- Adventure Parasail
- Motor World Go Cart Racing Track
- Captain Jacks Pirate Ship Adventures
SUNSET DOLPHIN TOUR
Guide: Chesapean Outdoors
Nearest Town: Virginia Beach
The Paddling Tour: Paddle off Virginia Beach at sunset to watch dolphins amid shimmering waters, with views of Cape Henry Lighthouses and Chesapeake Bay Bridge. Ideal for cooling evenings.
Nearby Attractions:
- Calypso Bar & Grill
- Atlantic Wildfowl Heritage Museum
- Virginia Legends Walk
- Virginia Beach Fishing Pier
BACK BAY REFUGE TOUR
Guide: Adventure Kayak Tours
Nearest Town: Sandbridge
The Paddling Tour: Traverse diverse ecosystems in upper Back Bay National Wildlife Refuge, from freshwater Ashville Bridge Creek to cypress-lined Muddy Creek, spotting shoreline and aquatic wildlife.
Nearby Attractions:
- Sandbridge Island Restaurant
- Back Bay Trams
- Margie & Ray's Crabhouse
- North Bay Shore Family Campground
NEW POINT COMFORT BEACH AND LIGHTHOUSE TOUR
Guide: Bay Country Kayaking
Nearest Town: Mathews
The Paddling Tour: In paddling haven Mathews County, experience tidal salt marshes, maritime forests, and sandy beaches. From Mobjack Bay to Chesapeake Bay's historic New Point Comfort Lighthouse, beachcomb before returning.
Nearby Attractions:
- Mathews Maritime Museum
- Bethel Beach Natural Area Preserve
- The Inn at Tabbs Creek
- Richardson Café
RIVANNA RIVER TOUR
Guide: Rivanna River Company
Nearest Town: Charlottesville
The Paddling Tour: Ideal intro to canoeing or kayaking moving water with light shoals and rapids. Cover 6 miles on South and North Forks of Rivanna River, tackling Class I and three Class II rapids.
Nearby Attractions:
- Thomas Jefferson’s Monticello
- Pen Park
- Tavola Italian Bistro
- South Street Brewery
FALLS OF THE JAMES RAFTING TOUR
Guide: Riverside Outfitters
Nearest Town: Richmond
The Paddling Tour: Raft the urban whitewater of James River falls—a rare Class II-IV stretch through downtown Richmond. Includes scenic lunch, wildlife views, and city skyline sights.
Nearby Attractions:
- Edgar Allan Poe Museum
- Belle Isle
- Agecroft Hall
- Riverwalk
BICYCLE TOURS
FIRST LANDING STATE PARK TOUR
Guide: Chesapean Outdoors
Nearest Town: Virginia Beach
The Bicycling Tour: Ride fat-tire bikes (or standard mountain bikes) along the oceanfront Boardwalk, North End, and into First Landing State Park for forested trails and wildlife viewing. Loop back through Virginia Beach vibes.
Nearby Attractions:
- Jungle Golf
- Virginia Beach & Outer Banks Horseback
- Great Neck Park
- Lynnhaven Dive Center
FALSE CAPE TOUR
Guide: Ocean Rentals
Nearest Town: Sandbridge
The Bicycling Tour: From Little Island Park, bike through Back Bay National Wildlife Refuge. Choose Interior Tour on roads amid woods/marshes or Beach Tour on fat-tire bikes along dunes and shore.
Nearby Attractions:
- Sandbridge Beach
- Outdoor Resorts RV Resort
- Sandbridge Island Restaurant
- Lago Mar Pizza
MONUMENTS AT NIGHT TOUR
Guide: Bike and Roll
Nearest Town: Arlington
The Bicycling Tour: Depart near sunset to bike the National Mall and Potomac Tidal Basin, illuminated monuments including Jefferson, Lincoln, MLK, WWII, and Vietnam memorials.
Nearby Attractions:
- Arlington House
- Lady Bird Johnson Park
- Theodore Roosevelt Island
- Ray’s The Steaks
MOUNT VERNON TOUR
Guide: Bike and Roll
Nearest Town: Alexandria
The Bicycling Tour: Pedal 9 miles on Mount Vernon Trail from Alexandria to George Washington's estate. Tour the home and grounds; return by bus (or optional boat).
Nearby Attractions:
- Potomac Heritage Trail
- Lee-Fendall House
- African American Heritage Memorial Park
- Old Town Alexandria
ALONG THE JAMES RIVER TOUR
Guide: Richmond Rides (ALL TOURS CURRENTLY CANCELLED DUE TO COVID-19)
Nearest Town: Richmond
The Bicycling Tour: Three-hour ride along James River banks, viewing rapids, historic canals, and downtown Richmond landmarks.
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
CHURCH HILL SIGNATURE TOUR
Guide: Richmond Rides (ALL TOURS CURRENTLY CANCELLED DUE TO COVID-19)
Nearest Town: Richmond
The Bicycling Tour: Delve into Richmond's historic Church Hill neighborhood, with history insights, notable figures, and food stops.
Nearby Attractions:
- LuLu’s Eatery
- Segway of Richmond
- Forest Hill Park
- The One Bed and Breakfast
A JOURNEY ALONG THE JAMES TOUR
Guide: Basket and Bike
Nearest Town: Charles City
The Bicycling Tour: 4-5 hour ride starting at a James River vineyard, weaving history through plantations, farms, and a 1613 church on Virginia Capital Trail. Includes wine tasting; lunch optional.
Nearby Attractions:
- Culs Courthouse Grill
- Weston Plantation
- City Point Park
- Beacon Theatre
SOUTHERN SHENANDOAH SITES AND SHOWS TOUR
Guide: Shenandoah Rides and Rentals
Nearest Town: Lexington
The Bicycling Tour: 5-day paved road tour of Shenandoah Valley from Lexington to Staunton and beyond, with tagalong van support. Features Blue Ridge Parkway, dinners, Shakespeare play, and Lime Kiln Theater concert.
Nearby Attractions:
- Robert E. Lee Chapel & Museum
- Canoe/Kayak Maury River
- Blue Ridge Parkway
- George Marshall Museum
