Wanderlust is defined as a “strong desire to travel”, but in Virginia, we call it WanderLOVE, and if you’ve ever come across a picture of an awe-inspiring landscape in the Commonwealth, from the breathtaking Blue Ridge Mountains to the wild Eastern Shore of Virginia, you know what it’s all about. Take the next step and satisfy your WanderLOVE using our detailed itineraries to some of Virginia’s most epic outdoor destinations.


kayak james river richmond The historic James River runs through Virginia’s capital city, leading to its nickname as the “River City”. Richmond is one of the only cities in the United States with Class III and IV rapids in an urban setting, and this distinct feature draws adventure-seekers from all over to experience adrenaline-filled experiences both on and off the river. In addition to waterfront adventure, the city has miles of mountain biking and hiking trails within the city and in neighboring parks like Pocahontas State Park, where outdoor enthusiasts can explore the 60+ miles of trails that range from easy to expert. Trip Highlights:
  • Kayaking trip down the James River with Riverside Outfitters
  • Test your mountain biking skills at Pocahontas State Park, then kayak, canoe, paddleboard or fish on beautiful Swift Creek Lake
  • Climbing lesson with Triangle Rock Club
  • Bike to Upper Shirley Vineyards and back on the Virginia Capital Trail
Outfitters and Guides: See the Full Richmond Itineraries, Part 1 & Part 2


Plan a three-day getaway to Virginia’s magnificent Shenandoah Valley for horseback riding, kayaking, and hiking in the foothills of Shenandoah National Park and George Washington and Jefferson National Forest. Trip Highlights:
  • Horseback riding to Edith Gap for views overlooking the Shenandoah River with Fort Valley Ranch
  • Kayaking down the scenic Shenandoah River
  • Hiking at Big Schloss
  • Test your fearlessness with Skydive Shenandoah
  • Mountain bike through challenging terrain at Bryce Bike Park or Massanutten Mountain Bike Park
  • Set out on a rock climbing adventure with Ridge Climbing & Rappelling Excursion
  • Try the new sport of FlingGolf
  • Traverse, climb, and soar through the trees on a Guided Canopy Tour
Outfitters and Guides: See the Full Shenandoah Valley Itineraries, Part 1 & Part 2         


Prince William Forest Northern Virginia’s Prince William County has an abundance of regional, state, and national parks and forests where outdoor enthusiasts can hike, bike, or paddle. From the banks of the Potomac River to the foothills of Bull Run Mountain, you’ll find tons of opportunities to reconnect with nature just 30 miles from Washington, D.C. Trip Highlights Outfitters and Guides See the Full Prince William County Itinerary


With destinations like the Blue Ridge ParkwaySkyline Drive, and the Appalachian Trail, Virginia’s Blue Ridge Mountains abound with both natural beauty and outdoor opportunities. The charming communities within the Blue Ridge Mountains are becoming well-known for these outdoor draws, especially for challenging hiking trails, river sports like kayaking and fishing, and, most importantly, mountain biking. The region was recently recognized as the first and only Silver-Level Ride Center designation on the East Coast by the International Mountain Bicycling Association, quickly earning the title of “America’s East Coast Mountain Biking Capital”. Trip Highlights:
  • Scale rock outcroppings along the Blue Ridge Parkway
  • Cast your line in one of the state’s only urban trout fisheries
  • Try caving on the Adventure Tour at Grand Caverns
  • Paddle the four-mile stretch of the South River that winds through downtown Waynesboro
  • Tackle rugged mountain-bike paths in George Washington and Jefferson National Forests
  • Mountain biking the trails at Carvins Cove with Roanoke Mountain Adventures
  • Paddle the Upper James River with Twin River Outfitters
  • Hike the Peaks of Otter trails
Outfitters and Guides: See the Full Virginia’s Blue Ridge Itineraries, Part 1 & Part 2


Lake Gaston Birding Southern Virginia has miles of rural lands to explore, from the foothills of the Blue Ridge Mountains in Martinsville & Henry County to the shores of Lake Gaston and Philpott Lake. Try your hand at paddling, fishing, hiking, camping, and many other activities that are sure to delight the entire family when you visit Southern Virginia! Trip Highlights
  • Camping, swimming, fishing and more at Philpott Lake
  • Smith River paddling and/or fishing excursions
  • Hiking the Richard P. Gravely, Jr. Nature Preserve
  • Walking, biking, running the Dick & Willie Passage Rail Trail
  • Hunting fairy stones, swimming, horseback riding and more at Fairy Stone State Park
Outfitters and Guides See the Full Southern Virginia Itinerary


Virginia’s Eastern Shore is a coastal outdoor paradise containing over 78,000 acres of parks, refuges, and one of only ten U.S. National Seashores. The peninsula hugs the Atlantic and Chesapeake Bay coastlines and offers five walkable waterfront towns with shops, galleries, museums, and restaurants. Trip Highlights:
  • Kayak out to Holly Bluff, a private, off-the-grid Atlantic island with Burnham Guides. Paddle through a delicate wildlife refuge teeming with wildlife, tour a 1930's hunting lodge and play on the private beach, Relax and picnic on a veranda overlooking the water.
  • Boat out to Virginia's wild barrier islands, the longest stretch of undeveloped outer banks remaining on America's East Coast. Captain Meriwether Payne, of Seaside Ecotours, whose family has deep roots in the area, has extensive knowledge of marine life, shore birds and the history of these mystical islands.
  • Kayak to a winery with SouthEast Expedition’s “Paddle Your Glass Off” Tour
  • Get a bird's eye view of the stunning Eastern Shore peninsula surrounded by water on three sides. You'll be miles above the earth, gliding like a bird in flight, with Virginia Hang Gliding.
  • Hike and paddle Kiptopeke State Park, a beachfront preserve, where you can kayak out to the concrete WWII "ghost ships" and hike miles of maritime forest with stunning views out over the Chesapeake Bay.
  • Experience the wild barrier islands, Chesapeake Bay, and Chincoteague ponies and lighthouse by kayak, while staying in an historic lodging in the 1680 Colonial port of Onancock.
  • Take a sunset boat cruise out of Cape Charles as the sun sets over the vast Chesapeake Bay horizon. You'll meet up with the Cape Charles Boat Tour Company at the town harbor, just a few steps from the town's bustling center.
  • Learn to sail with Onancock Sailing Adventures
Outfitters and Guides: See the Full Eastern Shore Itineraries, Part 1 & Part 2


Great Dismal Swamp Virginia’s coastline is packed with watersports, nature preserves, and scenic waterfront parks. Head to Chesapeake Waterways, a coastal section containing over 22 miles of some of the best kayaking spots in the country. For hiking, stunning trails await at Northwest River Park, which has 763 acres of breathtaking landscapes. Trip Highlights Outfitters and Guides See the Full Chesapeake Itinerary


fredericksburg sup Fredericksburg’s outdoor scene welcomes all experience levels and ages. The city sits on the fall line of the longest free-flowing river in Eastern America, the Rappahannock River, and the banks of this river provide opportunities for paddling, rock climbing, fly fishing, and more. Trip Highlights
  • Stand-Up Paddle Boarding lesson on the tidal section of the Rappahannock River
  • Boards, Boats and Brews Friday Night Paddle
  • Rock Climbing along the banks of the Rappahannock River
  • Fly Fishing the warm waters of the Rappahannock River
Outfitters and Guides See the Full Fredericksburg Itinerary

—ORANGE—Pickers Paradise at The Market at Grelen

Orange and the surrounding region has some of the most jaw-dropping scenery in Central Virginia. Head to The Market at Grelen, where you can take in the scenery by horseback, kayak and even from the sky with their Outdoor Adventure itineraries. An idyllic garden retreat, the Market at Grelen provides the perfect balance of self-paced adventure with the very best of what the area has to offer. Trip Highlights
  • Kayak the Rapidan River with Rapidan River Kayak Co.
  • Riverside picnic lunch provided by The Market at Grelen’s Casual Cafe
  • Tandem skydiving at Skydive Orange
  • Hiking on Grelen’s five-mile trail system
  • Picnic lunch and private sparkling Virginia wine flight at the top of the Overlook Trail
  • Virginia beer flight tasting on The Market at Grelen’s stone terrace
Outfitters and Guides  See the Full Orange Itinerary


New Point Comfort Lighthouse The Middle Peninsula region of Virginia’s shoreline contains the counties of Gloucester and Mathews, both with several kayaking, stand-up paddle board, and charter fishing tours along the Chesapeake Bay. Plan an outdoor expedition on the Bay and don’t miss out on tasting the best of the peninsula’s seafood between your waterway tours. Trip Highlights
  • Take a guided kayak trip and learn about the history of the indigenous peoples of Tidewater before colonists settled.
  • Reel in a fresh catch on a Chesapeake Bay fishing charter. Get down to your roots and pick some fresh blue crabs at happy hour off of Tabbs Creek
  • Take a Deadrise Boat Charter around the East River at sunset where you’ll shuck and eat a fresh raw oyster
  • Kayak around the third oldest lighthouse on the Chesapeake Bay and enjoy the beach
Outfitters and Guides See the Full Middle Peninsula Chesapeake Bay Itinerary

—SOUTHWEST VIRGINIA—Virginia Creeper Trail

The southwest corner of Virginia has become an outdoor adventure mecca. Located in the Blue Ridge Mountains, the town of Abingdon is one of the most popular outdoor spots, and also offers historic charm and a thriving art community. You’ll find world class hiking, biking, fishing, and bouldering all within an hour’s drive of this small Southwest town, and thanks to Abingdon’s numerous guides and shuttle services, you can easily enjoy the Great Outdoors and return to Abingdon in plenty of time to enjoy the innovative restaurant scene and relaxed nightlife. Trip Highlights Outfitters and Guides See the Full Southwest Virginia Itinerary