5 days in St. Augustine & Hilton Head Itinerary

5 days in St. Augustine & Hilton Head Itinerary

Created using Inspirock United States travel planner

Make it your trip
Drive
1
St. Augustine
— 1 night
Drive
2
Hilton Head
— 3 nights
Fly

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St. Augustine

— 1 night
St. Start off your visit on the 26th (Wed): gain insight at Flagler College, sample the fine beverages at St. Augustine Distillery, then identify plant and animal life at St. Augustine Alligator Farm Zoological Park, then visit a coastal fixture at St. Augustine Lighthouse & Maritime Museum, Inc., and finally take in the exciting artwork at High Tide Gallery Art & Gifts. Here are some ideas for day two: don't miss a visit to St. George Street and then explore the historical opulence of Castillo de San Marcos National Monument.

Plan a St. Augustine trip in moments using our itinerary builder.

Tampa to St. Augustine is an approximately 3-hour car ride. You can also take a bus; or fly. While traveling from Tampa, expect a bit cooler days and about the same nights in St. Augustine, ranging from highs of 83°F to lows of 67°F. Finish up your sightseeing early on the 27th (Thu) so you can go by car to Hilton Head.

Things to do in St. Augustine

Historic Sites · Parks · Museums · Wildlife

Hilton Head

— 3 nights
A Hilton Head vacation may be heaven for a golfer, but the area also offers all kinds of other options for sports fans.
Start off your visit on the 28th (Fri): relax and rejuvenate at some of the best spas, then hike along Hilton Head Island Bike Trails, then sample the fine beverages at Hilton Head Distillery, and finally race across the water with a speed boat tour. Get ready for a full day of sightseeing on the next day: savor the flavors at Carolina Tasting Room, tour the pleasant surroundings at Coligny Beach, then look for gifts at Hilton Head Oils, and finally look for all kinds of wild species at Sea Pines Forest Preserve.

To find ratings, more things to do, traveler tips, and tourist information, read our Hilton Head road trip planner.

You can drive from St. Augustine to Hilton Head in 4 hours. Other options are to do a combination of bus, train, and taxi; or fly. Expect a daytime high around 80°F in May, and nighttime lows around 66°F. You'll have a few hours on the 30th (Sun) to wrap things up before traveling home.

Things to do in Hilton Head

Parks · Outdoors · Tours · Wildlife