How to Plan a Trip to Hilton Head Island, South Carolina

Pick a time. Hilton Head really has wonderful weather almost all year round. During the summer, it gets hot and the beaches are full. The spring and fall are nice seasons, with weather usually hovering in the mid-60's, getting cooler at night. In the winter, it can be as warm as the 60's or so, but often it's colder--say for a light jacket or sweatshirt. Only on rare occasions would you ever really need a heavier jacket in Hilton Head. The island gets busy in March and April and stays that way through September and October. Any time of year is a good time to be in Hilton Head.

Find somewhere to stay. The Island is sectioned off a little differently than other places. A majority of the living options (and many of the dining and entertainment ones as well) are broken off into what they call plantations. The island has about 10 plantations and they all have their own front gate with security guards. You will want to find a house in one of the plantations as these will be nicer areas to live and will have access to a beachfront and golf courses. Sea Pines Plantation is the largest on the island. There are roads, and houses, communities and shopping centers but they are all a part of the same plantation. Some of the nicer ones are Sea Pines, Palmetto Dunes, Port Royal, Shelter Cover and the Hilton Head Plantation (which has a Disney theme and is geared more towards kids). You can just find a hotel in one of the plantations, but many of the houses are available to rent by their owners. It will probably be more expensive than a hotel room, but will be much nicer and have better amenities.

Play some golf. Hilton Head has some great golf courses. The ones on the island are incredibly nice and won't be too far away from wherever you decide to stay. They are more expensive, but much nicer. Some of the best ones are The Ocean and Sea March Courses at Sea Pines, the Golden Bear course and Harbor Town, a course that hosts a PGA tournament each year. This course is pretty expensive and very challenging, but offers some of the island's best views. There are also a number of courses located just off of the island. They are literally just a few minutes from the bridge to the island and these are a lot less expensive without giving up the quality of the course. Some of the better ones are Hilton Head National, Island West and Old South. Generally speaking, the further you get from the middle of the island, the less expensive the golf is.Also, there is a last minute tee time service that can get you great discounts for golf, so look for them in the yellow pages.Many of the plantations in Hilton Head have golf packages, where you can buy multiple rounds at a discounted price. Look for these as they can be great deals.

Bring your family. Hilton Head is an incredibly family-friendly place. There are tons of things to do together. Of course, there is golf, which you can play with the entire family. During the non-busy season, it can be quite affordable for the entire family. There is also Harbor Town, not the golf course, but the area. It's a fantastic place to walk around, shop, eat and just enjoy a wonderful afternoon or evening. During the summers on the weekends, Harbor Town has live entertainment for kids. It's a great show and fun for the whole family. There is plenty of tennis available all around to play with the family too. South Beach is another great place. Located in Sea Pines, It's another area to walk around and relax and go to the famous Salty Dog Cafe, where there's great ice cream.

Eat good food. There are so many good restaurants on the Island, so plan to go to some of the better places when you get there. Jump and Phil's is a good, low-key place and a great place to watch a game. Redfish is an excellent place specializing in seafood and other delicacies. It's really good and they have a very extensive wine selection. The Old Fort Pub is a historic place on the island that has great food. They serve an excellent assortment of fresh seafood in their quaint and funky setting. It's set right on the marsh along the ocean and has beautiful views.