8 days in St. Augustine & Winchester Itinerary

8 days in St. Augustine & Winchester Itinerary

Created using Inspirock United States visit planner

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Make it your trip
Drive
1
St. Augustine
— 3 nights
Fly
2
Winchester
— 4 nights
Fly

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St. Augustine

— 3 nights
St. Go for a jaunt from St. Augustine to Orlando to see Universal Orlando Resort about 2 hours away. And it doesn't end there: brush up on your knowledge of spirits at St. Augustine Distillery, enjoy the sand and surf at St. Augustine Beach, steep yourself in history at Pena-Peck House and Woman's Exchange of St Augustine, and identify plant and animal life at Wildlife Areas.

To find maps, reviews, and tourist information, go to the St. Augustine sightseeing site.

Charleston to St. Augustine is an approximately 5-hour car ride. You can also fly; or take a bus. Traveling from Charleston in October, expect a bit warmer with lows of 67°F in St. Augustine. Finish up your sightseeing early on the 4th (Mon) so you can catch the flight to Winchester.

Things to do in St. Augustine

Historic Sites · Theme Parks · Outdoors · Tours

Side Trip

Find places to stay Oct 1 — 4:

Winchester

— 4 nights
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Explore the numerous day-trip ideas around Winchester: Great Allegheny Passage (in Cumberland), Gettysburg (Gettysburg National Military Park & Gettysburg National Military Park Museum & Visitor Center) and Charlottesville (Mulberry Row & Monticello). There's still lots to do: explore the stunning scenery at Luray Caverns, wander the wide-open spaces of Rocking S Ranch, and look for gifts at Marker-Miller Orchards.

For photos, ratings, traveler tips, and more tourist information, you can read our Winchester tour itinerary planning app.

Traveling by flight from St. Augustine to Winchester takes 3.5 hours. Alternatively, you can do a combination of bus, taxi, and flight; or drive. Expect a bit cooler weather when traveling from St. Augustine in October: highs in Winchester hover around 67°F, while lows dip to 46°F. Finish up your sightseeing early on the 8th (Fri) so you can catch the flight back home.

Things to do in Winchester

Historic Sites · Parks · Outdoors · Shopping

Side Trips

Find places to stay Oct 4 — 8: