15 days in Shenandoah Valley Itinerary

15 days in Shenandoah Valley Itinerary

Created using Inspirock Shenandoah Valley travel planner

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Make it your trip
Fly
1
Luray
— 3 nights
Drive
2
Shenandoah National Park
— 3 nights
Drive
3
Staunton
— 4 nights
Drive
4
Winchester
— 4 nights
Fly

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Luray

— 3 nights

Cabin Capital of Virginia

Nestled in the heart of the valley formed by the Shenandoah River, Luray draws visitors with a vast underground cavern system adorned with stalactites, stalagmites, and mirrored pools.
Luray is known for nature, museums, and trails. Your trip includes some of its best attractions: explore the stunning scenery at Luray Caverns, whizz through the canopy at some of the top local zipline courses and adventure parks, Head underground at Shenandoah Caverns, and brush up on your knowledge of spirits at River Hill Wine & Spirits.

For ratings, traveler tips, photos, and other tourist information, you can read our Luray trip itinerary site.

Boston to Luray is an approximately 3.5-hour flight. You can also drive; or do a combination of train, bus, and taxi. Expect a bit warmer weather when traveling from Boston in May: highs in Luray hover around 75°F, while lows dip to 52°F. Finish your sightseeing early on the 4th (Tue) so you can drive to Shenandoah National Park.

Things to do in Luray

Parks · Nature · Outdoors · Trails

Side Trips

Find places to stay May 1 — 4:

Shenandoah National Park

— 3 nights
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Shenandoah National Park is known for nature, trails, and nightlife. Your trip includes some of its best attractions: hike along Old Rag Mountain Hike, take in the awesome beauty at Hawksbill Mountain, explore and take pictures at Skyline Drive, and stroll the grounds of Dean Cemetery.

To see photos, ratings, more things to do, and tourist information, refer to the Shenandoah National Park trip planner.

Getting from Luray to Shenandoah National Park by car takes about 1.5 hours. Expect a daytime high around 76°F in May, and nighttime lows around 55°F. Cap off your sightseeing on the 7th (Fri) early enough to go by car to Staunton.

Things to do in Shenandoah National Park

Parks · Nature · Outdoors · Trails
Find places to stay May 4 — 7:

Staunton

— 4 nights
Staunton is an independent city in the U.S. Commonwealth of Virginia. Explore Staunton's surroundings by going to Lexington (University Chapel & Galleries, Virginia Military Institute, &more), Natural Bridge (Caverns At Natural Bridge, Natural Bridge State Park, &more) and Harrisonburg (Edith J. Carrier Arboretum, White Oak Lavender Farm & The Purple WOLF Vineyard, &more). Next up on the itinerary: contemplate the long history of Frontier Culture Museum, examine the collection at Camera Heritage Museum, browse the exhibits of Woodrow Wilson Presidential Library and Museum, and Head underground at Grand Caverns.

For reviews, photos, more things to do, and more tourist information, go to the Staunton trip maker app.

You can drive from Shenandoah National Park to Staunton in 1.5 hours. In May, plan for daily highs up to 74°F, and evening lows to 51°F. Finish your sightseeing early on the 11th (Tue) so you can drive to Winchester.

Things to do in Staunton

Historic Sites · Parks · Museums · Nature

Side Trips

Find places to stay May 7 — 11:

Winchester

— 4 nights
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Winchester is known for museums, historic sites, and nightlife. Your trip includes some of its best attractions: wander the wide-open spaces of Rocking S Ranch, examine the collection at Shenandoah Valley Civil War Museum, contemplate the long history of Patsy Cline Historic House, and take an in-depth tour of Stonewall Jackson's Headquarters.

To find more things to do, where to stay, traveler tips, and other tourist information, use the Winchester sightseeing planning app.

You can drive from Staunton to Winchester in 2 hours. Another option is to do a combination of bus and taxi. Expect a daytime high around 73°F in May, and nighttime lows around 52°F. Finish your sightseeing early on the 15th (Sat) to allow enough time to fly back home.

Things to do in Winchester

Historic Sites · Museums · Shopping · Wineries

Side Trips

Find places to stay May 11 — 15: