I visited Hilton Head Island with my wife, kids (age 4 and 1) and my in-laws’ family (a total of 13 people all together) over Memorial Day Weekend 2019. The weather was a bit warmer than usual that weekend but May is an excellent time to go as the summer season is ramping up and all of the island beaches, activities and restaurants are open and lively. From the east coast, you can fly directly onto Hilton Head Island via United (although the direct flights don’t operate every day). You can alternatively fly to Savannah/Hilton Head airport (SAV) which is pretty easy, convenient and operates regular flights across airlines. The drive is a quick 45 min from SAV to the Island. We rented a car as we planned to drive to most dinners and a few activities away from our hotel – this process was easy and pretty inexpensive.
We stayed at The Westin hotel on the Island which we enjoyed very much. The hotel is right on the beach, is affiliated with a golf course, has a nice pool (with a separate covered pool) and an extensive variety of activities for families. The Westin was renovated several years ago so it is in good shape and with Marriott point redemption options, it is reasonably priced.
- Dining: There were many great, casual, family-friendly dining options on the island. We were primarily a vegetarian group so we tended to stay away from the seafood or steak-heavy places. Our favorites were Holy Tequila! for Mexican, Hickory Tavern and The Smokehouse for a great Sports bar and New York City Pizza for Italian. Next time we will likely give Giuseppi's Pizza & Pasta (Italian) a try given how it is certainly very highly recommended but it is best for smaller groups. Our favorite dessert options – ice cream and gelato - were The Frozen MOO and Kilwins on Shelter Cove
- Activities: We spent a lot of our daytime at the Beach and Pool at the Westin and got in a few rounds of golf at the Barony and Robber’s Row courses at Port Royal Golf. We enjoyed an evening walk at the Shelter Cove Boardwalk and we always enjoy mini-golf so Pirate's Island Adventure Mini-Golf is great. Other activities that were recommended – and possible for a future trip – include Atomic VR Virtual Reality Arcade, The Sandbox, An Interactive Children’s Museum, Dolphin Tours – Nature Cruises and Lawton Stables for Horse/Pony rides.
I would recommend Hilton Head as a destination to visit, especially if you are looking for a relaxing, friendly Island-city to vacation with nice summer weather and cost-effective hotel options. We explored much of the Island (which is pretty easy to do) and enjoyed its laid-back feel and hospitality. For a future trip, we may also consider the newly branded Montage Palmetto Bluff (formerly the Inn at Palmetto Bluff) which is between SAV and The Westin, just off of the Island. Enjoy!