We went to Hilton Head Island 5 years ago... and keep going back
Ahh our most tried and true, very favorite vacation spot. My husband and I first visited Hilton Head about 5 years ago. At the time, we were dating and I was a full time grad student. We were desperate to get away and enjoy some relaxation time, but we were on a very fixed income and needed to find a way to enjoy our trip and stay on a budget. A few days in to searching for the perfect spot, my husband stumbled on the idea of going to Hilton Head (pretty sure this had something to do with the fact that he's also an avid golfer).
We did some investigating and decided it looked like a dreamy getaway and decided to book it. We reserved a fully stocked AirBnB condo across the street from the beach for what I consider a total steal (it was about $100/night) and loaded up the car. 12 short (okay, they weren't all short) hours later, we arrived to the island and immediately fell in love. And if you've ever been there yourself, seriously, what's not to love about Hilton Head? With affordable lodging and beautifully kept beaches, it allows you to enjoy the island life without breaking the bank or fighting off enormous crowds of people when spreading out your towel on the beach.
One recommendation, book your trip for late spring. We've gone during lots of different times of the year (spring to fall) and our favorite time to go is May. The crowds are pretty much non-existent and the weather is gorgeous. This also gets you a little cheaper lodging rates! (Oh, and if you are arriving on a weekend, you better get to the bridge that leads on to the island early to avoid the traffic.)
One absolute must when staying on the island is renting bikes. Hilton Head has bike paths covering almost every inch of the island and they take you through some beautiful scenery. And if you are up for some serious resistance, take them out on the beach! We use Mike's Bikes every year, and it couldn't be more affordable or a smoother process. We just give them a call the night before we arrive and give them the address of our condo and by the time we arrive, the bikes are parked at the bike racks waiting.
If you are someone who enjoys being active, you'll be able to keep busy on the island. Hilton Head is known for some of the most prestigious golf courses and tennis courts in the world and house famous competitions every year. If you are a golfer with a little cash to drop, you can't beat the famous Harbour Town Golf Links, with holes right on the ocean coast and a beautiful view of the Harbour Town LightHouse. Pro tip: even if you don't golf at the course, stop in to the club house and have a drink on their gorgeous back patio and watch golfers tee off! For tennis courts, most condo complexes and hotels will offer free courts on the presmises, but if you're feeling like you want to experience some of the nicest courts the island has to offer, stop by Palmetto Dunes Tennis Resort. You can reserve a court to play on your own or book private lessons to improve your game!
Once you've enjoyed the beach to your hearts content for a few days, take a break and make the hour drive to Savannah, GA. It's a super easy drive down to the peach state and well worth it, in my opinion. Savannah is home to the beautiful Forsyth Park with it's very iconic fountain and great playgrounds. You can enjoy local musicians performing jazz and get the true southern feel. Take a short walk over to the River Walk and enjoy some seriously good candy stores (and the free prailine samples). Before you leave you HAVE to go to The Olde Pink House and order the blue crab beignets. My husband and I still agree this is the best thing we've ever tasted (we even ordered a second serving after fighting each other for the first!). After you finish your meal, ask the server for a tour of the restaurant. It has a fascinating history and the servers are amazing tour guides!
While the Olde Pink House may always be my favorite southern restaurant, when you get back to the island you've got some pretty delicious options as well. If you are someone who either1.) loves casual outdoor dining or 2.) has young kids that are not about to sit still for a long meal, then you need to check out the Skull Creek Boathouse. It's a super fun, casual restaurant that offers outdoor tables with beautiful views of the water. They host live music and have plenty of playground equipment and yard games to keep you or your kiddos entertained while enjoying drinks or waiting on a table (maybe just don't ask where the restaurant gets it's name).
Another great restaurant we frequent while on the island is Scott's Fish Market. Another restaurant with outdoor seating, but this time it's on the marina side with beautiful views of the boats. Take a walk down the marina and there's lots of kayak and boat rentals as well as fishing and dolphin tours to check out!
I'm convinced that Hilton Head is one of the best domestic vacation destinations for pretty much any age or phase of life. Just don't forget your shades and sunscreen!