8 days in Hilton Head, St. Augustine & Miami Itinerary

A Hilton Head vacation may be heaven for a golfer, but the area also offers all kinds of other options for sports fans.

Kick off your visit on the 25th (Fri): take an unforgettable tour with Hilton Head Heli Tours, indulge in some personalized pampering at some of the best spas, then stroll through Hilton Head Island Bike Trails, and finally take in the waterfront activity at Shelter Cove Harbour & Marina. On the next day, look for gifts at Chocolates by the Sea, then race across the water with a speed boat tour, then tour the pleasant surroundings at Coligny Beach, and finally savor the flavors at Carolina Tasting Room.

To see traveler tips, where to stay, reviews, and more tourist information, go to the Hilton Head trip itinerary planner.

Orlando to Hilton Head is an approximately 5.5-hour car ride. You can also fly; or do a combination of train and taxi. Traveling from Orlando in September, expect nights in Hilton Head to be about the same, around 25°C, while days are slightly colder, around 34°C. Finish your sightseeing early on the 27th (Sun) so you can drive to St. Augustine.

St. On the 27th (Sun), gain insight at Flagler College, then make a trip to St. George Street, then enjoy the sea views from St. Augustine Lighthouse & Maritime Museum, Inc., and finally tour the pleasant surroundings at St. Augustine Beach. Get ready for a full day of sightseeing on the next day: sample the fine beverages at St. Augustine Distillery, do a tasting at San Sebastian Winery, then identify plant and animal life at St. Augustine Wild Reserve, and finally go on a hair-raising tour with a ghost and vampire tour.

To see maps, more things to do, traveler tips, and other tourist information, you can read our St. Augustine holiday builder site.

You can drive from Hilton Head to St. Augustine in 4 hours. Other options are to drive; or do a combination of taxi, train, and bus; or fly. In September, daily temperatures in St. Augustine can reach 34°C, while at night they dip to 26°C. Finish up your sightseeing early on the 29th (Tue) so you can go by car to Miami.

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.

Venture out of the city with trips to Island Flow Yoga (in Islamorada) and Scuba & Snorkeling (in Key Largo). There's lots more to do: stroll through South Beach, wander the streets of Art Deco Historic District, admire the striking features of Freedom Tower at Miami Dade College, and explore the world behind art at Wynwood Walls.

For photos, reviews, ratings, and other tourist information, refer to the Miami trip planner.

Traveling by car from St. Augustine to Miami takes 5.5 hours. Alternatively, you can drive; or do a combination of bus and flight; or take a bus. In September in Miami, expect temperatures between 38°C during the day and 29°C at night. Wrap up your sightseeing on the 2nd (Fri) early enough to travel back home.