A Travel Price Comparison for United States of America Key West vs. Boston for Old Town, Families, Food, and Nightlife

Should you visit Key West or Boston?

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

Should I visit Key West or Boston? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.

Key West

Key West is a lively, quaint, and laid-back town. It's a very nice small town not to be missed. This is also a very beautiful destination which attracts plenty of visitors. This is an attractive and quaint destination worth visiting as well. It's also known for nightlife, food, and scuba diving and snorkeling.

Boston

Boston is a classic, proud, and loyal city. Travelers will also find plenty of sights and attractions here, as it's a big city that attracts lots of visitors. It's a beautiful place to visit, too. This destination also has one of those special and quaint feelings. And you can't forget about the museums, theater, and nightlife.

Key West and Boston: Pros and Cons

Is there more to do in Key West or Boston?

Travelers will usually find more to do in Boston. Although Key West and Boston are popular destinations, Boston has more sights and attractions for tourists. Boston is very popular for its museums & sights, theatre productions, food, music, historical sights, shopping, christmas markets, and big city activities, while Key West attracts visitors for its resorts, scuba diving & snorkeling, beaches, small town charm, impressive beauty, and quaint atmosphere. Key West is more touristy than Boston and is known for its festive nightlife, quirky town center, colorful personality, adrenaline-filled watersports, stunning beaches, turquoise water, and location at the southernmost point of the continental U.S. Boston is famous for its enthusiastic sports fans, influential history, beautiful parks, and world-class universities. It is also well known for The Freedom Trail.

How is Key West different from Boston?

Which is Better for a Holiday?

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

Are the Museums and Historical Sights Better in Key West or Boston?

Boston is renowned for its sights and museums. However, Key West does not have museums and landmarks.

The museums, monuments, and landmarks in Boston are among the most recognizable in the world. 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.

Key West does not have museums and landmarks.

Is Key West or Boston Better for Theater?

Boston is notable for its theatre productions. However, Key West is not a theatre destination.

While in town, many visitors enjoy seeing a show in Boston. 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.

Key West is not a theatre destination.

Is the Food Better in Key West or Boston? Which Destination has the Best Restaurants?

Boston is notable for its local cuisine and restaurants. Also, Key West is not as famous, but is still a good town to visit for its restaurants.

Eating is part of the travel experience when you visit Boston. 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.

Key West is becoming an appealing option for foodies. Head to town for local restaurants with quirky atmospheres. There are many local dishes to sample, be the town is most known for its stone crabs, conch fritters, and Mahi Mahi sandwiches. You'll also find cold drinks and waterfront dining areas.

Is Key West or Boston Better for Nightlife?

Evening events are superb in both Key West and Boston.

Key West has plenty to do after the sun goes down. This area has some of the most lively nightlife in the Florida Keys. There are quirky bars and fun hangouts where you can spend the evening. The party starts at Mallory Square around sunset and many bars stay open well into the early hours. You can also enjoy sunset cruises or pass your time at one of the many tiki bars.

Boston has a lively atmosphere and nightlife is popular here. 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.

Is Key West or Boston Better for Music?

Boston is a popular place for its live music scene. However, Key West is not a live music destination.

The music scene in Boston is active and vibrant. Popular music venues include Lizard Lounge, Blue Hills Bank Pavilion, and The Middle East.

Key West is not a live music destination.

Is Key West or Boston Better for Resorts?

Key West is notable for its resorts. However, Boston is not a resort destination.

There are plenty of resorts in Key West to choose from. There are a number of high end resorts around the island, many with recognizable names such as the Hyatt and Hilton. Prices can be high, but these resorts often come with reliable luxury.

Boston is not a resort destination.

Is Key West or Boston Better for Scuba Diving and Snorkeling?

Key West is a good destination for the nearby scuba diving and snorkeling. However, Boston is not a scuba or snorkeling destination.

Grab a mask and fins and explore the underwater scenery in Key West. There are a number of dive shops and snorkeling excursions that leave from Key West. Like many tourist areas these days, the coral shows its damage from the crowds, but you'll likely see some barracuda or a Grouper.

Boston is not a scuba or snorkeling destination.

Is Key West or Boston Better for Beaches?

Key West is notable for its beaches. However, Boston is a mediocre city for the beache.

Many people visit Key West for it's beautiful beaches. One of the best beaches in the area is Fort Zachary Taylor Historic State Park. The beach has soft sand and stunning turquoise water. As is typical in the Keys, the water stays shallow for great distances.

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 Key West or Boston Better for its Old Town?

Boston is renowned for its old town. Also, Key West is not as famous, but is still a good town to visit for its historic old town charm.

The old town of Boston is one of the most recognized in the world. 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.

There is a nice variety of sights in the old town of Key West. The town has the most charming Old Town areas in the Florida Keys. Head to Mallory Square for the sunset street performers and explore the historic streets around Duval Street.

Is the Shopping Better in Key West or Boston?

Boston is a popular place for its shopping opportunities. However, Key West is a mediocre town for its shopping areas.

Boston offers some nice shopping areas. 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.

Key West has some good spots for those that want to go shopping. While it definitely has its share of gimmicky souvenir shops and t-shirt stores, there are still a number of art galleries and local shops around Key West where you can enjoy shopping.

Is Key West or Boston Better for Christmas?

Boston is notable for its Christmas activities. However, Key West does not offer Christmas activities.

Boston is an extremely popular place to visit during the Christmas season. Christmas comes to life in the city with its Christmas Trees, holiday shows, and festivals.

Key West does not offer Christmas activities.

Is Key West or Boston Better for Christmas Markets?

Boston is notable for its Christmas markets. However, Key West does not offer Christmas markets.

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

Key West does not offer Christmas markets.

Is Key West or Boston Better for Families?

Boston is renowned for its family-friendly activities. Also, Key West is not as famous, but is still a good town to visit for its kid-friendly activities.

As it has a large number of activities for kids, Boston is a very family-friendly destination. 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.

You'll find plenty of family-friendly things to do in Key West. Families that enjoy snorkeling, aquariums, water sports, and exploring new places will enjoy visiting this part of the Florida Keys. There are many ways to get out on the water from kayaking and snorkeling to glass bottom boat tours and sunset cruises. There are also many kid-friendly beaches in the area. The town can have a party atmosphere, but it's not hard to find a more family-friendly area where everyone can have fun.

Is Key West or Boston Better for Couples?

Key West is notable for romance. Also, Boston is not as famous, but is still a good city to visit for its romantic activities.

Key West is a very popular place to visit for couples. From Mallory Square to the beautiful nearby parks, Key West makes a wonderful, romantic destination. Whether it's your honeymoon, an anniversary, or simply a couples' retreat, Key West is a great option. You can sip wine on a sunset cruise or dine at one of the many character-filled restaurants in town. If you are looking for a party, it's not hard to find, but if you want a more laid back holiday, that's also possible.

Boston makes for a fun place to visit for a couple. 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 Key West or Boston Better for Backpackers and Budget Travelers?

Boston is a popular place for backpackers. However, Key West is a mediocre town for backpackers and budget travelers.

Plenty of budget travelers visit Boston. Like most larger American cities, the city has a handful of hostels to choose from.

Key West is a challenging destination for budget travelers and backpackers due to the higher prices. Key West is a pretty expensive destination, but there are Airbnbs and even a hostel or two that cater to budget backpackers.

Is Key West or Boston Better for Students?

Boston is renowned for students. Also, Key West is not as famous, but is still a good town to visit for its student-friendly activities.

Many students frequent 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.

Key West is very popular with students. It's a great spring break destination with a quirky personality and many great activities.

Is Key West or Boston Better for Public Transit? Which Is Easier to Get Around Without a Car?

Boston is renowned for its public transit. However, Key West is a mediocre town for times when you don't have a car.

Boston has a great public transit system. There's the T, which is the subway, as well as a trolley, bus, and water transportation system.

Public transit is quite limited in Key West. Public transportation in Key West is limited to a few buses.

Is Key West or Boston a more walkable city?

Boston is renowned for its high level of walkability. Also, Key West is not as famous, but is still a good town to visit for its ease of walking around.

It is easy to get around Boston on foot. The many parks and compact neighborhoods are best explored on foot.

Key West is a somewhat walkable town. The town is the most walkable part of the Florida Keys. The area around Mallory Square and Duval Street is the most pedestrian friendly.

For even more information, also check out Is Key West Worth Visiting? and Is Boston Worth Visiting?.

Should I spend more time in Boston or Key West?

How long in Key West or Boston?

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

Families should spend more time in Boston than Key West. 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 Key West. 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 Key West 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 Key West or Boston?

Many travelers enjoy the food and scuba diving and snorkeling when visiting the quaint destination of Key West. The old town is one of the main draws for visitors. But since there are so many activities, you'll likely want to spend more than one day exploring.

Boston is a big city with plenty to do. Exploring the old town is a popular activity. With so much to do, one day is probably not enough time to see everything. It will give you the chance to have new experiences.

A weekend in Key West or Boston?

Key West 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 that is full of things to see and experience. Make sure you visit the old town while you're here. But since there are so many activities, you'll likely want to spend more than a weekend exploring. Take your pick from the many activities offered here.

Five days in Key West or Boston?

It's hard to know how much time to spend in Key West. For many, it makes a great getaway for five days. Make sure you visit the old town while you're here. 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 popular choice for travelers. Five days here is typical. It's no surprise that museums is why people visit. While some people choose to spend more or less time in Boston, five days is sufficent for most. The entire region has so many activities, and you'll want time to do everything.

A week in Key West or Boston?

Many travelers enjoy the food and scuba diving and snorkeling when visiting the lively destination of Key West. This town offers a variety of activities to choose from. Most visitors spend time around the old town while in 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 great place to explore. It's no surprise that museums is why people visit. Visiting the old town is also a must. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. This city offers something for everyone.

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

When we compare the travel costs of actual travelers between Key West and Boston, we can see that Key West is more expensive. And not only is Boston much less expensive, but it is actually a significantly cheaper destination. So, traveling to Boston would let you spend less money overall. Or, you could decide to spend more money in Boston and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Key West would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Key West than you might in Boston.

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

Which is Bigger, Key West or Boston?

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

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Key West or Boston in the Summer?

Both Boston and Key West are popular destinations to visit in the summer with plenty of activities. Most visitors come to Key West for the beaches, snorkeling, the small town charm, and the family-friendly experiences during these months. Also, the summer months attract visitors to Boston because of the beaches, the city activities, the music scene, and the family-friendly experiences.

In July, Key West is generally a little warmer than Boston. Daily temperatures in Key West average around 84°F (29°C), and Boston fluctuates around 73°F (23°C).

It's quite sunny in Boston. The sun comes out a lot this time of the year in Key West. Key West usually receives more sunshine than Boston during summer. Key West gets 328 hours of sunny skies, while Boston receives 304 hours of full sun in the summer.

In July, Key West usually receives more rain than Boston. Key West gets 3.3 inches (83 mm) of rain, while Boston receives 2.9 inches (74 mm) of rain each month for the summer.

Should I visit Key West or Boston in the Autumn?

Both Boston and Key West during the autumn are popular places to visit. The autumn months attract visitors to Key West because of the shopping scene, the small town atmosphere, and the natural beauty of the area. Also, the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area are the main draw to Boston this time of year.

Key West is much warmer than Boston in the autumn. The daily temperature in Key West averages around 80°F (27°C) in October, and Boston fluctuates around 54°F (12°C).

It's quite sunny in Key West. In the autumn, Key West often gets more sunshine than Boston. Key West gets 258 hours of sunny skies this time of year, while Boston receives 194 hours of full sun.

It rains a lot this time of the year in Key West. Key West usually gets more rain in October than Boston. Key West gets 5.1 inches (129 mm) of rain, while Boston receives 3.3 inches (84 mm) of rain this time of the year. Keep in mind that June to November is the hurricane season in Key West.

Should I visit Key West or Boston in the Winter?

The winter attracts plenty of travelers to both Key West and Boston. The shopping scene and the cuisine are the main draw to Key West this time of year. Also, many travelers come to Boston for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine.

Be prepared for some very cold days in Boston. In the winter, Key West is much warmer than Boston. Typically, the winter temperatures in Key West in January average around 70°F (21°C), and Boston averages at about 29°F (-2°C).

In Key West, it's very sunny this time of the year. Key West usually receives more sunshine than Boston during winter. Key West gets 252 hours of sunny skies, while Boston receives 153 hours of full sun in the winter.

In January, Key West usually receives less rain than Boston. Key West gets 1.7 inches (43 mm) of rain, while Boston receives 3.4 inches (87 mm) of rain each month for the winter.

Should I visit Key West or Boston in the Spring?

The spring brings many poeple to Key West as well as Boston. Many travelers come to Key West for the beaches, the small town charm, and the natural beauty. Also, many visitors come to Boston in the spring for the beaches, the activities around the city, and the natural beauty.

In April, Key West is generally much warmer than Boston. Daily temperatures in Key West average around 77°F (25°C), and Boston fluctuates around 48°F (9°C).

The sun comes out a lot this time of the year in Boston. People are often attracted to the plentiful sunshine in Key West this time of the year. In the spring, Key West often gets more sunshine than Boston. Key West gets 326 hours of sunny skies this time of year, while Boston receives 225 hours of full sun.

Key West usually gets less rain in April than Boston. Key West gets 0.8 inches (21 mm) of rain, while Boston receives 3.5 inches (89 mm) of rain this time of the year. Also, June to November in Key West is the hurricane season.

Typical Weather for Boston and Key West