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My First Trip to Disney’s Hilton Head Resort – PREP 387

My First Trip to Disney’s Hilton Head Resort – PREP 387

Our team spent some rest and relaxation time at Disney’s Hilton Head Island Resort. Shannon recaps the trip and shares what she enjoyed, what surprised her, and what she will do differently next time she visits.

The Basics

This is an annual trip for the WDW Prep Team. Each year there is one trip without to do lists, take photos, and create content. This trip was to explore the Hilton Head resort and have fun! 

Disney’s Hilton Head Resort is very connected to Disney World and Disney systems including the First Visit button, emails, and the reservation system. 

Shannon booked this trip by renting points because this is a DVC Villas resort. She rented a two bedroom villa in February.

The trip was during a very low crowd time and it was very easy to find availability. Shannon was able to check in online but they still had to stop by the front desk to get their room assignment. 

Arrival (Day 1)

They flew into Savannah Airport and that is about an hour from the resort. They had no issues flying into the airport. They reserved a car via Costco travel for Budget. 

Disney's Hilton Head Resort

Shannon did everything beforehand but still had to wait about an hour to wait for their car. This seemed to be everyone’s experience. Once they got their car, they drove about an hour to their resort. 

Because of the delays, they would miss the campfire at the resort, which was disappointing. This was the only time it was offered during their trip.

Disney's Hilton Head Resort signs

When they checked in they were given a lot of information about the resort and the town. They called a Lyft to go to dinner and get some groceries. After dinner and drinks, they walked to a grocery store and it had just closed. 

They went to the Walgreens right next door and at 10:20 p.m. they exited Walgreens with heavy groceries including bottled water. They went to call a ride share vehicle and there weren’t any vehicles available anywhere.

They weren’t even able to get a taxi until midnight! They were finally able to get a ride and didn’t get back to the resort until midnight. The resort was very similar to Old Key West. Some of the rooms have been renovated but not all of them yet.

Holiday decor

There are water views, but the resort is not on the beach. They had a really great first impression of the resort. 

After getting back to the resort at midnight, they went to bed to rest up for their next day! 

Beach (Day 2)

Today they had booked an excursion on a boat on the water to see the sights and dolphins. They had bottled drinks and baked goods for breakfast on the boat. They were able to see lots of animals and it was a lot of fun.

Hilton Head Boat experience.

When they finished on the boat, they got food at the restaurant right at the dock. It was a delicious meal. 

Hilton Head Beach House

To get to the beach, you need to either drive or take a shuttle. During busy times, it can be difficult to get a parking spot. It is very private and family-friendly. 

Waking to the beach in Hilton Head

After the beach, they went to some shops and a restaurant for dinner. Everything was very upscale and really wonderful.

Savannah (Day 3)

This morning breakfast was at the Quick Service experience at the resort. It had everything you’d expect at a Disney Resort.


After breakfast they drove an hour back to Savannah and arrived around noon. They had tickets for the Savannah trolley. It had 15 stops and you can hop on and hop off. 

Savannah Trolley

The Trolley was a mixed experience and they ended up waiting for a trolley a few times, which was frustrating. 

They went to a Tiki bar for dinner and went on a walking tour. As part of the experience, they got free drinks and could walk around with them. 

Team with the Christmas Tree in Hilton Head

It was a wonderful experience and then went back to the resort. Shannon notes that the driving during the day was fine but at night the visibility was very low and difficult to navigate.

Hilton Head (Day 4)

Savannah Distillery

After a delicious lunch, the group made their way to the Hilton Head Distillery for a few hours. They were able to choose different options including rum and cocktails. 

After the distillery they went back to the hotel to check out the hot tub and swimming pool area. They spent several hours in the hot tub, talking with several other folks enjoying the hot tub.

Hilton Head Hot Tub

Departure (Day 5)

After packing up and having breakfast, they went to Savannah to head back home. 

Overall Review

The whole island is very bike-friendly. Shannon recommends renting a bike if visiting. They loved the food and scenery. It was very beautiful.


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