A Travel Price Comparison for United States of America Hilton Head Island vs. Boston for Families, Food, Beaches, and Couples

Should you visit Hilton Head Island or Boston?

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

Which city is more affordable and which is best for your travel style? If you're trying to figure out where to go next, comparing the travel costs between Hilton Head Island and Boston can help you decide which place is right for you.

Hilton Head Island

Hilton Head Island is a family-friendly, relaxing, and peaceful coastal town. It's a gorgeous place to visit. It's also known for food, beaches, and shopping.

Boston

Boston is a proud, loyal, and historic city. As it's a big city, visitors will find plenty to do, too. It offers plenty of beauty for visitors. As this is a very quaint destination, you'll find it has a special atmosphere. It's also popular because of the theater, nightlife, and live music.

Hilton Head Island and Boston: Pros and Cons

Is there more to do in Hilton Head Island or Boston?

Visitors will usually find more to do in Boston than Hilton Head Island, as it offers more sights, attractions, and activities. Boston is better known for its museums, theatre productions, food, nightlife, music, historical sights, christmas markets, big city activities, and quaint atmosphere, while Hilton Head Island is more popular for its resorts and beaches. Hilton Head Island is well known for its long sandy beaches, many golf courses, popular tennis camps, and accessible bike trails. Boston is well known for its enthusiastic sports fans, influential history, beautiful parks, and world-class universities. Also, Boston is famous for The Freedom Trail.

How is Hilton Head Island different from Boston?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Boston and Hilton Head Island. Then, you can decide for yourself which place is better for your next trip.

Are the Museums and Historical Sights Better in Hilton Head Island or Boston?

Boston is terrific for its museums and history. However, Hilton Head Island does not have museums and landmarks.

With plenty of landmarks, attractions, and museums, Boston has many famous sights for visitors. The city itself feels like a living museum. It is famous for Faneuil Hall, the Museum of Fine Arts, the Isabelle Stewart Gardner Museum, the USS Constitution, as well as the many sites along the Freedom Trail. There are also many museums on the campuses of the world renowned universities in the city.

Hilton Head Island does not have museums and landmarks.

Is Hilton Head Island or Boston Better for Theater?

Boston is a very popular place for its shows and theatre. However, Hilton Head Island is not a theatre destination.

Boston has a number of performance venues where you can see a variety of shows. The city has many historic, beautifully restored theaters where you can enjoy a show. Head to the theater district for some of the most famous venues.

Hilton Head Island is not a theatre destination.

Is the Food Better in Hilton Head Island or Boston? Which Destination has the Best Restaurants?

Boston is a very popular place for its restaurants. Also, Hilton Head Island is not quite as popular, but is fairly good for its restaurant scene.

Boston has a number of nationally recognized food spots and restaurants. There are many local dishes that utilize fresh caught seafood and comfort food flavors. The cuisine also takes advantage of the city's Italian and Irish populations. Famous local foods include New England Clam Chowder, lobster rolls, and baked beans. You'll find hearty sandwiches and filling meals that warm your soul.

Hilton Head Island offers number of good local restaurants to choose from. The island has many famous restaurants but reservations during the summer are a must. Restaurants can get very crowded during peak times. For some of the best restaurants head to Shelter Cove or Harbour Town. Popular local dishes include fried seafood and oysters.

Is Hilton Head Island or Boston Better for Nightlife?

Boston is a very popular place for its evening party scene. However, Hilton Head Island is lacking in good options for nightlife.

Boston has a large number of nightlife venues. The city is known for its breweries, craft beer, and vibrant university neighborhoods. It also hosts regular outdoor movies and world class sporting events. The nightlife scene is varied, with some areas catering to the student population and other areas focused on the professional or sport-loving crowds.

Things get quiet in the evenings in Hilton Head Island. There are a few sports bars and comedy clubs, but nightlife isn't really a thing in Hilton Head. This is very much a family destination that shuts down with the sunset.

Is Hilton Head Island or Boston Better for Music?

Boston is very good for its music scene. However, Hilton Head Island is not a live music destination.

Music lovers will find a few good venues in Boston. Popular music venues include Lizard Lounge, Blue Hills Bank Pavilion, and The Middle East.

Hilton Head Island is not a live music destination.

Is Hilton Head Island or Boston Better for Resorts?

Hilton Head Island is notable for its resorts. However, Boston is not a resort destination.

There are plenty of resorts in Hilton Head Island to choose from. Most of the accommodation in the area is in the form of weekly condo rentals, which usually include a pool and outdoor space. Tennis and golf are also popular on the island so many resorts have facilities for each.

Boston is not a resort destination.

Is Hilton Head Island or Boston Better for Beaches?

Hilton Head Island is notable for its beaches. However, Boston is a mediocre city for the beache.

Many people visit Hilton Head Island for it's beautiful beaches. The island has nice beaches that are popular with families. They are great for swimming during the spring, summer, and fall seasons. While some beaches may get a bit crowded during peak holidays, they're usually pretty relaxed and less crowded than many nearby beaches.

You can check out the beach in Boston. There are a few urban beaches in the greater Boston area that you can explore on a nice day.

Is Hilton Head Island or Boston Better for its Old Town?

Boston is terrific for its historic old town charm. However, Hilton Head Island does not have a historic old town.

Boston has a unique history which comes to life in its historic area. Boston is famous for its Freedom Trail, which takes visitors around the city's rich history. The oldest parts of the city are known as Boston Proper and include the neighborhoods of Beacon Hill, Historic Downtown, the North End, and the West End.

Hilton Head Island does not have a historic old town.

Is the Shopping Better in Hilton Head Island or Boston?

Shoppers can find a variety of notable stores in both Hilton Head Island and Boston.

Hilton Head Island has a variety of shopping areas worth visiting. The area has upscale shopping with designer names and local venues. Popular shopping areas include Shelter Cove Town Center and Harbor Town.

Boston is a great destination for shopping. Head to Back Bay for some of the best high end shops. There are luxury brands and boutique venues that sell local art or crafts.

Is Hilton Head Island or Boston Better for Christmas?

Boston is a very popular place for its Christmas holiday experiences. However, Hilton Head Island does not offer Christmas activities.

Since it has plenty to do, Boston is a very popular place to visit during Christmas. Christmas comes to life in the city with its Christmas Trees, holiday shows, and festivals.

Hilton Head Island does not offer Christmas activities.

Is Hilton Head Island or Boston Better for Christmas Markets?

Boston is a very popular place for visiting Christmas markets. However, Hilton Head Island does not offer Christmas markets.

Boston has plenty of Christmas markets during the holiday season. There are a number of European style Christmas markets that pop up during the holiday season around town.

Hilton Head Island does not offer Christmas markets.

Is Hilton Head Island or Boston Better for Families?

You'll find first-rate kid-friendly activities in either Hilton Head Island or Boston.

Hilton Head Island is one of the most popular family destinations. This area is a popular family-friendly beach destination with a number of summer events for the whole family, peaceful beaches, and family-friendly restaurants throughout. Older kids will enjoy cycling around the island's many bike trails or attending a popular tennis camp.

Boston is an amazing family-friendly coastal town to visit. It's filled with history, but there are also many activities for kids who need a break from all of the historical stuff. Popular activities for all ages include the Museum of Science, the New England Aquarium, and exploring the waterfront, gardens, and parks around town.

Is Hilton Head Island or Boston Better for Couples?

Both Hilton Head Island and Boston are notable destinations to visit as a couple.

Hilton Head Island is a good coastal town for couples to visit. While the area is most popular with families, it is a fun place to explore as a couple because of the many high end restaurants and the beautiful setting. Couples can rent bikes to explore or play a friendly game of tennis.

Boston is a nice destination for couples. Couples who enjoy history will enjoy exploring the city. Take a swan boat ride in the Public Garden and wander the unique route along the Freedom Trail. There are also many sporting and entertainment options around town.

Is Hilton Head Island or Boston Better for Backpackers and Budget Travelers?

Boston is very good for backpackers and budget travelers. However, Hilton Head Island is not a backpacker-friendly destination.

Boston is popular with backpackers and budget travelers. Like most larger American cities, the city has a handful of hostels to choose from.

Hilton Head Island is not a backpacker-friendly destination.

Is Hilton Head Island or Boston Better for Students?

Boston is terrific for its student-friendly activities. However, Hilton Head Island is not popular with students.

Students come from all over the world to visit Boston. It is a city of students, with a number of world renowned universities located here including Harvard University, Boston College, and MIT. Many neighborhoods are filled with students and there are many student-centered activities around town including festivals and an active nightlife scene.

Hilton Head Island is not popular with students.

Is Hilton Head Island or Boston Better for Public Transit? Which Is Easier to Get Around Without a Car?

Boston is terrific for times when you don't have a car. However, Hilton Head Island is lacking in good options for its public transit.

The thorough and effecient public transit system of Boston can take you anywhere. There's the T, which is the subway, as well as a trolley, bus, and water transportation system.

Public transit is limited or non-existant in Hilton Head Island. You must have a car to get most places on the island, unless you bike. Rush hour during summer months can have intense traffic.

Is Hilton Head Island or Boston a more walkable city?

Boston is terrific for its ease of walking around. However, Hilton Head Island is lacking in good options for its walkability.

It's very easy to get around on foot in Boston. The many parks and compact neighborhoods are best explored on foot.

Hilton Head Island is generally not very walkable. You really need a car to get around, but for those who are motivated, there is a great network of bike trails. It's mostly used for recreational purposes though.

For even more information, also check out Is Hilton Head Island Worth Visiting? and Is Boston Worth Visiting?.

Should I spend more time in Boston or Hilton Head Island?

How long in Hilton Head Island or Boston?

In either Hilton Head Island or Boston, you'll find plenty of activities to fill your time. Most visitors tend to spend more time in Hilton Head Island than Boston because of the overall number of sights and activities. Usually, 5-7 days is a good amount of time for Hilton Head Island, and 3-5 days is enough time in Boston.

Families should spend more time in Boston than Hilton Head Island. Because of the many family-friendly attractions and fun things to do for kids in Boston, it's a great place to visit with the whole family.

Couples should spend more time in Boston than Hilton Head Island. You'll find plenty of romantic sights and fun activities in Boston that are perfect for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Boston than Hilton Head Island if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Boston.

One day in Hilton Head Island or Boston?

Many travelers enjoy the shopping and food when visiting the destination of Hilton Head Island. It's a great spot for a beach vacation. But since there are so many activities, you'll likely want to spend more than one day exploring.

Boston is a loyal big city where you can fill many days. This city offers something for everyone. Most people visit for the museums. Exploring the old town is a popular activity. But since there are so many activities, you'll likely want to spend more than one day exploring.

A weekend in Hilton Head Island or Boston?

Hilton Head Island is a great place to explore. With so much to do, a weekend is probably not enough time to see everything. Your budget might influence how long you stay.

Boston is a popular place to visit. Boston is a traditional city where you can fill many days. Most people visit for the museums. Make sure you visit the old town while you're here. With so much to do, a weekend is probably not enough time to see everything.

Five days in Hilton Head Island or Boston?

It's hard to know how much time to spend in Hilton Head Island. For many, it makes a great getaway for five days. Most people come for the beaches. With all of its activities, you can easily fill five days here. It has many unique tourist attractions and fascinating things to do.

Boston is a big city destination where you can fill many days. This is a popular place to visit for five days. Most visitors spend time around the old town while in the area. Anyone can find something fun to do here. Most people visit for the museums. Five days is a great amount of time to relax and see the many things that Boston has to offer.

A week in Hilton Head Island or Boston?

Many travelers enjoy the food and shopping when visiting the beautiful destination of Hilton Head Island. This coastal town offers a variety of activities to choose from. Many visitors spend time at the beach while visiting the area. If you have one week, this is a great place to go. This would be the perfect place to spend one week, as it has just the right amount of activities.

Boston is a popular place that is full of things to see and experience. Visiting the old town is also a must. It offers something for everyone. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days.

For some great organized tour ideas, see The Best One-Week (7-Day) Tours from Anchorage, The Best One-Week (7-Day) Tours from Los Angeles, The Best One-Week (7-Day) Tours from New York City, and The Best 2-Week Tours from New York City.

When comparing the travel costs between Hilton Head Island and Boston, we can see that Boston 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. Since both cities are in North America, it's no surprise that their costs are relatively close, as many destinations here have somewhat similar travel prices overall.

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

Which is Bigger, Hilton Head Island or Boston?

Boston has a larger population, and is about 20 times larger than the population of Hilton Head Island. When comparing the sizes of Hilton Head Island and Boston, 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 Hilton Head Island or Boston?

Both places have a temperate climate with four distinct seasons. As both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Hilton Head Island or Boston in the Summer?

The summer brings many poeple to Hilton Head Island as well as Boston. Many visitors come to Hilton Head Island in the summer for the beaches and the family-friendly experiences. Also, most visitors come to Boston for the beaches, the city activities, the music scene, and the family-friendly experiences during these months.

In the summer, Hilton Head Island is a little warmer than Boston. Typically, the summer temperatures in Hilton Head Island in July average around 82°F (28°C), and Boston averages at about 73°F (23°C).

The sun comes out a lot this time of the year in Boston. People are often attracted to the plentiful sunshine in Hilton Head Island this time of the year. In the summer, Hilton Head Island often gets less sunshine than Boston. Hilton Head Island gets 267 hours of sunny skies this time of year, while Boston receives 304 hours of full sun.

Hilton Head Island receives a lot of rain in the summer. Hilton Head Island usually gets more rain in July than Boston. Hilton Head Island gets 7.9 inches (200 mm) of rain, while Boston receives 2.9 inches (74 mm) of rain this time of the year.

Should I visit Hilton Head Island or Boston in the Autumn?

Both Boston and Hilton Head Island are popular destinations to visit in the autumn with plenty of activities. Most visitors come to Hilton Head Island for the shopping scene and the natural beauty of the area during these months. Also, the autumn months attract visitors to Boston because of the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

In October, Hilton Head Island is generally much warmer than Boston. Daily temperatures in Hilton Head Island average around 68°F (20°C), and Boston fluctuates around 54°F (12°C).

The sun comes out a lot this time of the year in Hilton Head Island. Hilton Head Island usually receives more sunshine than Boston during autumn. Hilton Head Island gets 223 hours of sunny skies, while Boston receives 194 hours of full sun in the autumn.

In October, Hilton Head Island usually receives less rain than Boston. Hilton Head Island gets 2.8 inches (71 mm) of rain, while Boston receives 3.3 inches (84 mm) of rain each month for the autumn.

Should I visit Hilton Head Island or Boston in the Winter?

Both Boston and Hilton Head Island during the winter are popular places to visit. The winter months attract visitors to Hilton Head Island because of the shopping scene and the cuisine. Furthermore, the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine are the main draw to Boston this time of year.

It's quite cold in Boston in the winter. Hilton Head Island is much warmer than Boston in the winter. The daily temperature in Hilton Head Island averages around 48°F (9°C) in January, and Boston fluctuates around 29°F (-2°C).

In the winter, Hilton Head Island often gets more sunshine than Boston. Hilton Head Island gets 176 hours of sunny skies this time of year, while Boston receives 153 hours of full sun.

Hilton Head Island usually gets less rain in January than Boston. Hilton Head Island gets 2.9 inches (74 mm) of rain, while Boston receives 3.4 inches (87 mm) of rain this time of the year.

Should I visit Hilton Head Island or Boston in the Spring?

The spring attracts plenty of travelers to both Hilton Head Island and Boston. The beaches and the natural beauty are the main draw to Hilton Head Island this time of year. Furthermore, many travelers come to Boston for the beaches, the activities around the city, and the natural beauty.

In the spring, Hilton Head Island is much warmer than Boston. Typically, the spring temperatures in Hilton Head Island in April average around 67°F (19°C), and Boston averages at about 48°F (9°C).

People are often attracted to the plentiful sunshine in Boston this time of the year. In Hilton Head Island, it's very sunny this time of the year. Hilton Head Island usually receives more sunshine than Boston during spring. Hilton Head Island gets 275 hours of sunny skies, while Boston receives 225 hours of full sun in the spring.

In April, Hilton Head Island usually receives less rain than Boston. Hilton Head Island gets 2.9 inches (74 mm) of rain, while Boston receives 3.5 inches (89 mm) of rain each month for the spring.

Typical Weather for Boston and Hilton Head Island