A Travel Price Comparison for Families, Couples, and Backpackers Grand Cayman vs. Hilton Head Island for Vacations, Tours, and Honeymoons

Should you visit Grand Cayman or Hilton Head Island?

Which is cheaper to visit? Which is more expensive for vacation?

Which city should you visit? Read on to compare the activities as well as the prices of travel for Grand Cayman and Hilton Head Island. We'll break down costs for accommodation, food, transportation and more to help you learn more about these two destinations. Then, you can figure out if either of these two places are accessible based on your travel budget, schedule, and interests. So, let's dig into it.

Where Should I go: Grand Cayman or Hilton Head Island?

Grand Cayman

When people think of the Cayman Islands, they typically think of offshore bank accounts and sunny, cruise ship ports. Grand Cayman has more to offer travelers than a playground for the wealthy or a short stopover for cruise passengers. This tropical island is the largest of the three Cayman Islands, it is a shopper's heaven, a center for global finance and an ideal vacation spot.

Hilton Head Island

Hilton Head, also called Hilton Head Island, is primarily a resort and beach town off the coast of South Carolina. Located on a barrier island, the place is best known for its beaches and golf courses overlooking the Atlantic Ocean.

For some great organized tour ideas, see The Best One-Week (7-Day) Tours from Anchorage, and The Best One-Week (7-Day) Tours from Los Angeles.


Which place is cheaper, Hilton Head Island or Grand Cayman?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Grand Cayman is $214, while the average daily cost in Hilton Head Island is $243. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Grand Cayman and Hilton Head Island in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Grand Cayman $150
    Hilton Head Island $129
  • Accommodation Typical double-occupancy room
    Grand Cayman $300
    Hilton Head Island $258
Compare Hotels in Grand Cayman and Hilton Head Island

Looking for a hotel in Grand Cayman or Hilton Head Island? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Grand Cayman


Hotels in Hilton Head Island


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Grand Cayman Hotel Prices and Hilton Head Island Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Grand Cayman $31
    Hilton Head Island $34

Hired Cars and Shuttles in Grand Cayman

Also for Grand Cayman, here are a few examples of actual transportation services:

  • Private Transfer from George Town or 7 Mile to George Town Port: $53
  • Private Transfer from George Town Port to Owen Roberts AirportGCM: $53
  • Private Transfer from George Town Port to George Town or 7-Mile: $53
  • Privat Transfer from Owen Roberts Airport GCM to George Town Port: $53
  • George Town Port to Owen Roberts Airport (GCM) - Departure Private Transfer: $53
  • George Town Port to George Town / 7-Mile Beach area -Round-Trip Private Transfer: $107
  • George Town Cruise Port to George Town or 7-Mile Beach -Arrival Private Transfer: $53
  • George Town / 7- Mile Beach area to George Town Port -Departure Private Transfer: $53
  • Airport Transfers to North Side Accommodation (GCM Grand Cayman): $265
  • Airport Transfer - Owen Roberts Intl Airport to GeorgeTown or Seven Mile Beach: $88

Is it cheaper to fly into Grand Cayman or Hilton Head Island?

Prices for flights to both Hilton Head Island and Grand Cayman change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Grand Cayman $39
    Hilton Head Island $60

Food Tours and Cooking Classes in Hilton Head Island

For Hilton Head Island, here are some samples of tours and activities related to meals and dining experiences:

  • Dolphin Watching 3-Course Dinner Cruise: $70
  • Sunset Hibachi Dinner Cruise : $102
  • Hilton Head Sunset Dinner Cruise: $106
  • Sunset Dinner Cruise: $106

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Grand Cayman $41
    Hilton Head Island $23

Tours and Activities in Grand Cayman

For Grand Cayman, here are a few prices for actual activities, tours, and tickets provided by various companies:

  • 2-stop Adventure: Stingray City and snorkeling at Cayman Reefs: $79
  • Acquarius Stingray City and Snorkel Tours: $80
  • Cayman Adventure: Starfish Point, Stingray City and Coral Gardens: $99
  • Cayman Crystal Caves & Pedro St James Castle Tour in Grand Cayman: $179
  • Cayman Crystal Caves Tour in Grand Cayman Island: $126
  • Cayman's Classic Food Tasting & Cultural Experience: $179
  • East End Activities and Tour in Grand Cayman: $158
  • East Island Tour : $298
  • Full Day Private Shore Tour in George Town from George Town Port: $276
  • Full Day Private Shore Tour in George Town from George Town Port: $263
  • Grand Cayman Cruise: Starfish Point, Stingray City, Coral Garden: $80
  • Grand Cayman Reef & Stingray City Snorkeling Adventure: $159

Tours and Activities in Hilton Head Island

For Hilton Head Island, here are a few prices for actual activities, tours, and tickets provided by various companies:

  • #1 Historical Horse Drawn Carriage Tour: $35
  • 1 Hour Private Dolphin Tour Hilton Head Island: $250
  • 2-Hour Hilton Head Guided Kayak Nature Tour: $45
  • 90 Minute Hilton Head Dolphin Tour: $48
  • 90 Minute Hilton Head Dolphin and Nature Cruise: $45
  • 90 minute Hilton Head Sunset Dolphin Cruise: $55
  • Beaufort City Minibus Tour: $35
  • Beaufort Ghost Walking Tours : $22
  • Beaufort Gullah Heritage Tour: $49
  • Beaufort’s #1 Horse & Carriage History Tour: $35
  • Complete History and Movie Walking Tour of Beaufort: $30
  • Daufuskie Island Daily Round Trip Ferry Tickets: $54

Alcohol
  • Alcohol Drinks for one day
    Grand Cayman $13
    Hilton Head Island $26
Typical Alcohol Prices in Grand Cayman

Below are a few samples from actual travelers for alcohol and nightlife costs in Grand Cayman:


  • Beer
    $4.97

Sample the Local Flavors in Grand Cayman

Here are a few nightlife and alcohol tours and activities from local tour providers in Grand Cayman:

  • Cayman Spirits Co. Distillery Tour Pass Ticket Only: $24

Sample the Local Flavors in Hilton Head Island

Here are a few nightlife and alcohol tours and activities from local tour providers in Hilton Head Island:

  • Hilton Head's ONLY Distillery Experience: $55


When comparing the travel costs between Grand Cayman and Hilton Head Island, we can see that Hilton Head Island is more expensive. However, the two cities are actually relatively comparable in price, as the difference is somewhat minimal. Generally, this means that you could travel with generally the same travel style and level of luxury in each place. Even though Grand Cayman is in Caribbean Islands and Hilton Head Island is in North America, both of these destinations have relatively similar prices of travel. Generally, the levels of luxury and expenses are the same for these cities even though they are geographically far apart.

If you're trying to decide if either of these two destinations are within your price range, also see Is Grand Cayman Expensive? and Is Hilton Head Island Expensive?.


Which is Bigger, Grand Cayman or Hilton Head Island?

Hilton Head Island has a larger population, and is about 17% larger than the population of Grand Cayman. When comparing the sizes of Grand Cayman and Hilton Head Island, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.


When is the best time to visit Grand Cayman or Hilton Head Island?

Hilton Head Island has a temperate climate with four distinct seasons, but Grand Cayman experiences a warm climate with fairly sunny weather most of the year.

Should I visit Grand Cayman or Hilton Head Island in the Summer?

Both Hilton Head Island and Grand Cayman are popular destinations to visit in the summer with plenty of activities. The warm climate attracts visitors to Grand Cayman throughout the year. Also, many visitors come to Hilton Head Island in the summer for the beaches and the family-friendly experiences.

Grand Cayman is around the same temperature as Hilton Head Island in the summer. The daily temperature in Grand Cayman averages around 28°C (83°F) in July, and Hilton Head Island fluctuates around 82°F (28°C).

It rains a lot this time of the year in Hilton Head Island. It's quite rainy in Grand Cayman. In July, Grand Cayman usually receives less rain than Hilton Head Island. Grand Cayman gets 179 mm (7 in) of rain, while Hilton Head Island receives 7.9 inches (200 mm) of rain each month for the summer.


  • Summer Average Temperatures July
    Grand Cayman 28°C (83°F) 
    Hilton Head Island 82°F (28°C)

Should I visit Grand Cayman or Hilton Head Island in the Autumn?

Both Hilton Head Island and Grand Cayman during the autumn are popular places to visit. Plenty of visitors come to Grand Cayman because of the warm climate and sunshine that lasts throughout the year. Furthermore, most visitors come to Hilton Head Island for the shopping scene and the natural beauty of the area during these months.

In the autumn, Grand Cayman is a little warmer than Hilton Head Island. Typically, the autumn temperatures in Grand Cayman in October average around 27°C (81°F), and Hilton Head Island averages at about 68°F (20°C).

It rains a lot this time of the year in Grand Cayman. Grand Cayman usually gets more rain in October than Hilton Head Island. Grand Cayman gets 238 mm (9.4 in) of rain, while Hilton Head Island receives 2.8 inches (71 mm) of rain this time of the year.


  • Autumn Average Temperatures October
    Grand Cayman 27°C (81°F) 
    Hilton Head Island 68°F (20°C)

Should I visit Grand Cayman or Hilton Head Island in the Winter?

The winter attracts plenty of travelers to both Grand Cayman and Hilton Head Island. Warm weather and sunshine bring visitors to Grand Cayman year-round. Furthermore, the winter months attract visitors to Hilton Head Island because of the shopping scene and the cuisine.

In January, Grand Cayman is generally much warmer than Hilton Head Island. Daily temperatures in Grand Cayman average around 24°C (76°F), and Hilton Head Island fluctuates around 48°F (9°C).

In January, Grand Cayman usually receives less rain than Hilton Head Island. Grand Cayman gets 58 mm (2.3 in) of rain, while Hilton Head Island receives 2.9 inches (74 mm) of rain each month for the winter.


  • Winter Average Temperatures January
    Grand Cayman 24°C (76°F) 
    Hilton Head Island 48°F (9°C)

Should I visit Grand Cayman or Hilton Head Island in the Spring?

The spring brings many poeple to Grand Cayman as well as Hilton Head Island. Grand Cayman attracts visitors year-round for its warm weather and sunny climate. Additionally, the beaches and the natural beauty are the main draw to Hilton Head Island this time of year.

Grand Cayman is a little warmer than Hilton Head Island in the spring. The daily temperature in Grand Cayman averages around 26°C (79°F) in April, and Hilton Head Island fluctuates around 67°F (19°C).

Grand Cayman usually gets less rain in April than Hilton Head Island. Grand Cayman gets 48 mm (1.9 in) of rain, while Hilton Head Island receives 2.9 inches (74 mm) of rain this time of the year.


  • Spring Average Temperatures April
    Grand Cayman 26°C (79°F) 
    Hilton Head Island 67°F (19°C)

Typical Weather for Hilton Head Island and Grand Cayman

Grand Cayman Hilton Head Island
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 24°C (76°F) 58 mm (2.3 in) 48°F (9°C) 2.9 inches (74 mm)
Feb 24°C (76°F) 51 mm (2 in) 52°F (11°C) 2.9 inches (73 mm)
Mar 25°C (77°F) 31 mm (1.2 in) 58°F (15°C) 4.4 inches (112 mm)
Apr 26°C (79°F) 48 mm (1.9 in) 67°F (19°C) 2.9 inches (74 mm)
May 27°C (81°F) 131 mm (5.1 in) 73°F (23°C) 4.2 inches (107 mm)
Jun 28°C (82°F) 183 mm (7.2 in) 80°F (26°C) 5.9 inches (150 mm)
Jul 28°C (83°F) 179 mm (7 in) 82°F (28°C) 7.9 inches (200 mm)
Aug 28°C (82°F) 172 mm (6.8 in) 81°F (27°C) 6.5 inches (164 mm)
Sep 28°C (82°F) 212 mm (8.3 in) 77°F (25°C) 5.6 inches (141 mm)
Oct 27°C (81°F) 238 mm (9.4 in) 68°F (20°C) 2.8 inches (71 mm)
Nov 26°C (79°F) 141 mm (5.6 in) 59°F (15°C) 1.9 inches (49 mm)
Dec 25°C (78°F) 57 mm (2.3 in) 52°F (11°C) 3.3 inches (83 mm)