3 Days in Hilton Head Island, South Carolina

Hilton Head Island is world famous for being home to some of the best golf courses and tennis clubs in the world, in addition to miles of wide, spotless sandy beaches. This coastal resort town is a popular vacation destination year-round due to the mild year-round climate and the presence of many luxury oceanfront resorts. The Island offers no shortage of activities for the sports enthusiast, beach goer, or anyone seeking a laid-back, relaxing vacation destination.

A vacation to the island would not be complete without staying at a fantastic resort. There are many great choices on the island, including the luxurious Omni and Sonesta brands. Both offer convenient access to the beach, beautiful beachside pools, and luxury amenities. Mike surprised me with a wonderful birthday trip to the Omni. We enjoyed the resort amenities as well as the easy access to gorgeous beaches.

Below I have organized a sample itinerary for a 3 day stay. Leisure, entertainment, great dining, and recreation are all part of a fantastic vacation, and thus, I have tried to incorporate a bit of each into the schedule.

Day 1

3:00pm – Check into your luxury 4 star oceanfront resort. The Omni Hilton Head Oceanfront Resort is a gorgeously landscaped tropical oasis; the perfect place for a relaxing weekend getaway. It’s such a beautiful property – I was really impressed with the landscaping, the gorgeous pools, and the many amenities.

In addition to having access to the Palmetto Dunes golf and tennis courts, the resort offers a basketball court, sand volleyball court, bean bags, and a life size chess game. It was really fun to play some of these outdoor games while the weather was a bit cooler.

I really loved the direct access to the beach. Located just steps away is Palmetto Dunes, a wide, sandy, immaculate beach with hard packed sand that is perfect for bike riding, jogging, or taking a leisurely stroll. If you prefer more of a resort setting, you can choose to sunbathe, swim, and relax amongst the resort’s 3 pools. We chose to enjoy a combo of both. Really, there is no point in visiting this gorgeous island without spending some time at the beach. But then again, you also don’t want to miss out on the beautiful resort pools you are paying for.

Outdoor firepits, live dinner music, an onsite restaurant and coffeeshop, and a spa are some of the other amenities you will find. Rooms are large and include private balconies with views of the courtyard or beach. Most of our vacations involve a lot of driving and walking, so having all amenities on site was a really nice change of pace.

5:00pm – I recommend dinner on the patio of HH Prime, conveniently located on the resort property. During the dinner hour, you will be able to enjoy fantastic live music. Plus it’s all lit up and cozy with fireplaces during the cooler fall months. Great food and an accommodating staff that will cater to food allergies make it an ideal choice for all guests.

7:00pm – Enjoy a drink by one of the outdoor fire pits. In addition to a full bar, you also have a handy on-site Starbucks. We enjoyed listening to the live music on a cool fall night while we sipped hot tea.

Day 2

7:00am – Get up early and enjoy a beautiful sunrise on the beach. The views are absolutely spectacular and it would be a shame not to take advantage of the convenient access. A long stroll with a cup of tea or coffee in hand is the perfect way to start a relaxing morning on vacation. This area seriously has the best sunrises. I couldn’t wait to get up early every morning and take in the views. I love that we didn’t have to drive anywhere. Some tourists are lucky enough to see dolphins, but unfortunately we didn’t see any on this visit.

9:00am – Enjoy a 2 hour guided kayak tour from Hilton Head Kayak. This tour company offers scenic narrated tours on the still waters of Broad Creek. Opportunities for wildlife sightings (dolphins and manatee) give you something exciting to look forward to along the way. We saw one manatee before we set off but nothing else on the actual tour. I enjoyed the beautiful views of the marsh. This was my first time kayaking and it was a great experience. A little scary with the choppy water, but fun and a great way to enjoy the scenery. Note: advance reservations are required.

11:00am– Enjoy a light lunch at A Low Country Backyard, a friendly Southern restaurant offering classic southern comfort foods along with modern options. When the weather is mild, the cozy, country style outdoor seating area is perfect for a relaxing lunch. They offer a number of fresh sandwiches, salads, and seafood based entrees. Highlights include a pimento cheese dip served with flatbread, Shrimp and Grits, and Shrimp and Wild Mushroom Cobbler. I enjoyed a fresh salad with beans and avocado.

1:00pm – Head back to the Omni for a little R&R in the hotel’s pools and hot tubs. The hot tub here is so relaxing and I really loved all the palm landscaping. I really felt like I was on vacation and could get away from it all for awhile. If you would rather relax down by the beach, you can rent an umbrella and chairs from the resort. Kayaking is fun, although you still get in a decent workout, so take some time to relax! My upper body was a bit sore after all that paddling. Enjoy some poolside service from the Buoy Bar (you are on vacation!).

6:00pm – Enjoy dinner at Live Oak Restaurant, located inside Sea Pines Resort. Although a bit of a drive from the resort, the views are outstanding, service is excellent, and the food delicious. I enjoyed a delicious Vegan Tasting meal, a delicious 3 course meal which included these amazing quinoa cakes pictured below. Note: reservations are recommended. Update: Live Oak is unfortunately closed. Michael Anthony’s Cucina Italiana is a nice highly regarded Italian restaurant.

8:00pm – Return to the Omni for another relaxing night listening to the wonderful live music. Grab a rocking chair by the fire pit and let all your cares drift away as you enjoy the relaxing Southern setting. My favorite part of this trip was relaxing at night with a tea or hot cocoa by the firepit. As someone who stares at the computer pretty much 24/7 during the week, it was nice to just relax away from all technology.

Day 3

7:00am – The island is famous for their extensive network of bike trails. You can rent a bike from the resort to use on the trails, 5 of which are located directly on the resort. Another option is to take the bike right down to the beach. The hard sand is perfect for riding, plus you can take in the fabulous views along the way! Either setting is equally beautiful.

9:00am – I recommend grabbing a light breakfast at this resort. Palmetto Cafe, a convenient coffee shop and cafe, offers a selection of pastries, breakfast sandwiches, and fresh brewed Starbucks coffee.

11:00am – Take a day trip to Savannah, located only an hour away from Hilton Head. Savannah is a beautiful historic city featuring gorgeous old architecture, fantastic parks, and numerous historic sites. A ride on Old Town Trolley or a guided walking tour (I recommend Noble Jones) will give you a great overview of the city’s most beautiful and historic landmarks. Check out my full Savannah guide for tips on the best attractions, tours, public squares, and local restaurants.

4:00pm – Make the drive back over to Omni.

5:00pm – Treat yourself to a spa treatment at Ocean Tides Spa. Nothing says vacation more than a relaxing spa in a great relaxing atmosphere. My massage was a wonderful treat after a long day of walking around Savannah. Note: reservations required.

7:00pm – Spend the rest of the night enjoying all the wonderful activities at the Omni including: a life size chess game, Bean Bags, sand volleyball, basketball, and the resort hot tub. It was so nice to enjoy a relaxing soak after a full day of walking.

9:00pm – Pack up your luggage so there is no stress in the morning. Get everything ready and you can spend your last few hours enjoying the beach!