A Travel Price Comparison for United States of America Key West vs. Woodstock for Vacations, Tours, and Honeymoons

Should you visit Key West or Woodstock?

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

Should I visit Key West or Woodstock? 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.

Where Should I go: Key West or Woodstock?

Key West

Key West is both a city and an island as well as the southern most Florida Key. It is also the southern most city in the continental United States. The island is only about four miles long and one mile wide. The total land mass covers just 4.2 square miles. The most famous street in town is Duval Street, which runs just 1.1 miles from the Gulf of Mexico to the Atlantic Ocean. There are 14 blocks. The size of the island doubled during the 1950s when many of the salt ponds along the eastern side of the island were filled in.

Woodstock

While this town does lend its name to the 1969 Woodstock Festival, the legendary event was actually held on a dairy farm almost 60 miles away in Bethel, NY. So if you are looking to see the field where it all happened and a museum dedicated to its history, you will need to take a day trip outside of town.

Woodstock, New York, however, does stay true to the spirit of the arts. Since 1903, the place lay home to Byrdcliffe Art Colony, the oldest of its kind in the nation, and even attracted artists of the Hudson River School during the late 1800s. Today, artists from all disciplines-visual, ceramic, music, fiction, nonfiction, screenwriting, playwriting, and poetry-take up residence at the colony and have works displayed in galleries open in the main part of town.

Tinker Street and Mill Hill Road are lined with a mix of restaurants and shops all teeming with the essence of hippie living, arts, and spirituality. From shops selling Woodstock paraphernalia, incense, and Himalayan products, to yoga studios, vegan restaurants, and local art galleries-the town of Woodstock is one dedicated to keeping the spirit of the Woodstock Festival and the arts alive.

For some great organized tour ideas, see The Best Train & Rail Tours in United States of America, The Best Sightseeing Tours in United States of America, The Best Cruise Tours and Packages in United States of America, and The Best Cultural Tours in United States of America.

When we compare the travel costs of actual travelers between Key West and Woodstock, we can see that Key West is more expensive. And not only is Woodstock much less expensive, but it is actually a significantly cheaper destination. So, traveling to Woodstock would let you spend less money overall. Or, you could decide to spend more money in Woodstock 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 Woodstock.

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 Woodstock Expensive?.

Which is Bigger, Key West or Woodstock?

Key West has a larger population, and is about 10 times larger than the population of Woodstock. When comparing the sizes of Key West and Woodstock, 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 Woodstock?

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 Woodstock in the Summer?

Both Woodstock and Key West are popular destinations to visit in the summer with plenty of activities. The summer months attract visitors to Key West because of the beaches, snorkeling, the small town charm, and the family-friendly experiences.

In July, Key West is generally a little warmer than Woodstock. Daily temperatures in Key West average around 84°F (29°C), and Woodstock fluctuates around 74°F (24°C).

It's quite sunny in Woodstock. The sun comes out a lot this time of the year in Key West. Key West usually receives more sunshine than Woodstock during summer. Key West gets 328 hours of sunny skies, while Woodstock receives 293 hours of full sun in the summer.

In July, Key West usually receives around the same amount of rain as Woodstock. Key West gets 3.3 inches (83 mm) of rain, while Woodstock receives 3.4 inches (87 mm) of rain each month for the summer.

Should I visit Key West or Woodstock in the Autumn?

Both Woodstock and Key West during the autumn are popular places to visit. The shopping scene, the small town atmosphere, and the natural beauty of the area are the main draw to Key West this time of year.

Key West is much warmer than Woodstock in the autumn. The daily temperature in Key West averages around 80°F (27°C) in October, and Woodstock fluctuates around 53°F (12°C).

It's quite sunny in Key West. In the autumn, Key West often gets more sunshine than Woodstock. Key West gets 258 hours of sunny skies this time of year, while Woodstock receives 197 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 Woodstock. Key West gets 5.1 inches (129 mm) of rain, while Woodstock receives 3 inches (77 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 Woodstock in the Winter?

The winter attracts plenty of travelers to both Key West and Woodstock. Many travelers come to Key West for the shopping scene and the cuisine.

Woodstock can get quite cold in the winter. In the winter, Key West is much warmer than Woodstock. Typically, the winter temperatures in Key West in January average around 70°F (21°C), and Woodstock averages at about 25°F (-4°C).

In Key West, it's very sunny this time of the year. Key West usually receives more sunshine than Woodstock during winter. Key West gets 252 hours of sunny skies, while Woodstock receives 167 hours of full sun in the winter.

In January, Key West usually receives less rain than Woodstock. Key West gets 1.7 inches (43 mm) of rain, while Woodstock receives 3.3 inches (83 mm) of rain each month for the winter.

Should I visit Key West or Woodstock in the Spring?

The spring brings many poeple to Key West as well as Woodstock. Many visitors come to Key West in the spring for the beaches, the small town charm, and the natural beauty.

In April, Key West is generally much warmer than Woodstock. Daily temperatures in Key West average around 77°F (25°C), and Woodstock fluctuates around 49°F (10°C).

The sun comes out a lot this time of the year in Woodstock. 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 Woodstock. Key West gets 326 hours of sunny skies this time of year, while Woodstock receives 227 hours of full sun.

Key West usually gets less rain in April than Woodstock. Key West gets 0.8 inches (21 mm) of rain, while Woodstock receives 3.7 inches (95 mm) of rain this time of the year. Also, June to November in Key West is the hurricane season.

Typical Weather for Woodstock and Key West