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

Should you visit Pensacola or Woodstock?

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 Pensacola and Woodstock can help you decide which place is right for you.

Where Should I go: Pensacola or Woodstock?

Pensacola

With sands as white as sugar grain and a sky devoid of grey clouds and innumerable downpours, Pensacola is known by many as the "Western Gate to the Sunshine State." Located in northern Florida, Pensacola is a waterfront city known for its pristine beaches and rich Floridian history. As one of the earliest European settlements in the U.S., Pensacola is riddled with museums and landmarks that commemorate the state's history, making the city quite appetizing for history buffs and students alike. However, if you are simply looking to get the most out of the all-around good weather of Florida, Pensacola's protected beaches complemented with high-class restaurants and stores make this a vacation capital for many.

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 Bicycle Tours in United States of America, Tours for Outdoor and Nature Lovers in United States of America, The Best Coach Bus Tours in United States of America, and The Best Adventure Tours to United States of America.


Which place is cheaper, Woodstock or Pensacola?

These are the overall average travel costs for the two destinations. These travel costs come from the actual spending of real travelers.

  • Pensacola Prices
    USA Prices
    Woodstock Prices
    USA Prices
  • Average Daily Cost Per person, per day
    Pensacola $234
    Woodstock $178

The average daily cost (per person) in Pensacola is $234, while the average daily cost in Woodstock is $178. 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 Pensacola and Woodstock in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Pensacola $115
    Woodstock $81
  • Accommodation Typical double-occupancy room
    Pensacola $230
    Woodstock $162
Compare Hotels in Pensacola and Woodstock

Looking for a hotel in Pensacola or Woodstock? 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 Pensacola


Hotels in Woodstock


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: Pensacola Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Pensacola $64
    Woodstock $60
Typical Local Transportation Prices in Pensacola

Below are a few samples from actual travelers for transportation costs in Pensacola:


  • Boca Grande Causeway Toll
    $5.00

Is it cheaper to fly into Pensacola or Woodstock?

Prices for flights to both Woodstock and Pensacola 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
    Pensacola $84
    Woodstock $59
Typical Food Prices in Pensacola

Some typical examples of dining costs in Pensacola are as follows:


  • Two Ice Creams
    $6.00

Food Tours and Cooking Classes in Pensacola

Also, here are some specific examples of food and dining related activities in Pensacola.

  • Palafox Palete Food Tour: $50
  • Seville Haunted Luncheon or Dinner and Ghost Tour: $50

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Pensacola $13
    Woodstock $35
Typical Entertainment Prices in Pensacola

Some typical examples of activities, tours, and entrance ticket prices in Pensacola are as follows:


  • Bike Rental
    $16

Tours and Activities in Pensacola

Some specific costs of activities, tours, and entrance tickets for Pensacola are as follows:

  • Pensacola's Famous Ghosts Smartphone Guided App Walking Tour: $7.75
  • Scavenger Hunt Adventure in Pensacola by Wacky Walks: $10
  • The Great Pensacola Birthday Party Tour & Scavenger Hunt: $20
  • Scavenger Hunt Adventure in Pensacola by Zombie Scavengers: $20
  • Pensacola Beach Splash and Dash Tour & Scavenger Hunt: $20
  • Pensacola Ghost Tours: Perdition, Pirates, & Purgatory: $24
  • Spooky Stories Walking Ghost Tour: $25
  • Pensacola Walking Cemetery Tour: $25
  • Penscola Most Haunted: Ghost Tour and Scavenger Hunt: $30
  • Pensacola Haunted Walking Tour with Ghost Equipment: $30
  • Pensacola Amazing Race Tour & Scavenger Hunt: $30
  • Pensacola Back to the Future Tour & Scavenger Hunt: $30

Alcohol
  • Alcohol Drinks for one day
    Pensacola $44
    Woodstock $22

Sample the Local Flavors in Pensacola

Also in Pensacola, these are the prices for nightlife and alcohol related activities from various tour providers:

  • Walking Ghost Tour Pub Crawl - Boos with Booze : $20
  • Walking Pub Tour : $21
  • Party Bike Pub Crawl of Downtown Pensacola : $45


When we compare the travel costs of actual travelers between Pensacola and Woodstock, we can see that Pensacola 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 Pensacola would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Pensacola 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 Pensacola Expensive? and Is Woodstock Expensive?.


Which is Bigger, Pensacola or Woodstock?

Pensacola has a larger population, and is about 30 times larger than the population of Woodstock. When comparing the sizes of Pensacola 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 Pensacola 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 Pensacola or Woodstock in the Summer?

Both Woodstock and Pensacola are popular destinations to visit in the summer with plenty of activities. Most visitors come to Pensacola for the beaches, the hiking, and the family-friendly experiences during these months.

In July, Pensacola is generally a little warmer than Woodstock. Daily temperatures in Pensacola average around 82°F (28°C), and Woodstock fluctuates around 74°F (24°C).

It's quite rainy in Pensacola. In July, Pensacola usually receives more rain than Woodstock. Pensacola gets 7.4 inches (189 mm) of rain, while Woodstock receives 3.4 inches (87 mm) of rain each month for the summer.


  • Summer Average Temperatures July
    Pensacola 82°F (28°C) 
    Woodstock 74°F (24°C)

Should I visit Pensacola or Woodstock in the Autumn?

Both Woodstock and Pensacola during the autumn are popular places to visit. The autumn months attract visitors to Pensacola because of the hiking trails and the shopping scene.

Pensacola is much warmer than Woodstock in the autumn. The daily temperature in Pensacola averages around 69°F (21°C) in October, and Woodstock fluctuates around 53°F (12°C).

It rains a lot this time of the year in Pensacola. Pensacola usually gets more rain in October than Woodstock. Pensacola gets 4.2 inches (107 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 Pensacola.


  • Autumn Average Temperatures October
    Pensacola 69°F (21°C) 
    Woodstock 53°F (12°C)

Should I visit Pensacola or Woodstock in the Winter?

The winter attracts plenty of travelers to both Pensacola and Woodstock. The museums, the shopping scene, and the cuisine are the main draw to Pensacola this time of year.

Be prepared for some very cold days in Woodstock. In the winter, Pensacola is much warmer than Woodstock. Typically, the winter temperatures in Pensacola in January average around 51°F (10°C), and Woodstock averages at about 25°F (-4°C).

Pensacola gets a good bit of rain this time of year. In January, Pensacola usually receives more rain than Woodstock. Pensacola gets 4.6 inches (117 mm) of rain, while Woodstock receives 3.3 inches (83 mm) of rain each month for the winter.


  • Winter Average Temperatures January
    Pensacola 51°F (10°C) 
    Woodstock 25°F (-4°C)

Should I visit Pensacola or Woodstock in the Spring?

The spring brings many poeple to Pensacola as well as Woodstock. Many travelers come to Pensacola for the beaches.

In April, Pensacola is generally much warmer than Woodstock. Daily temperatures in Pensacola average around 67°F (20°C), and Woodstock fluctuates around 49°F (10°C).

Pensacola usually gets less rain in April than Woodstock. Pensacola gets 3.4 inches (87 mm) of rain, while Woodstock receives 3.7 inches (95 mm) of rain this time of the year. Also, June to November in Pensacola is the hurricane season.


  • Spring Average Temperatures April
    Pensacola 67°F (20°C) 
    Woodstock 49°F (10°C)

Typical Weather for Woodstock and Pensacola

Pensacola Woodstock
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 51°F (10°C) 4.6 inches (117 mm) 25°F (-4°C) 3.3 inches (83 mm)
Feb 54°F (12°C) 5.4 inches (137 mm) 28°F (-2°C) 3.2 inches (81 mm)
Mar 60°F (16°C) 5.6 inches (143 mm) 38°F (3°C) 3.8 inches (97 mm)
Apr 67°F (20°C) 3.4 inches (87 mm) 49°F (10°C) 3.7 inches (95 mm)
May 74°F (24°C) 4.2 inches (107 mm) 60°F (16°C) 3.5 inches (89 mm)
Jun 80°F (27°C) 6.4 inches (163 mm) 69°F (21°C) 3.5 inches (90 mm)
Jul 82°F (28°C) 7.4 inches (189 mm) 74°F (24°C) 3.4 inches (87 mm)
Aug 82°F (28°C) 7.4 inches (188 mm) 72°F (22°C) 3.9 inches (100 mm)
Sep 78°F (26°C) 5.3 inches (135 mm) 64°F (18°C) 3.5 inches (90 mm)
Oct 69°F (21°C) 4.2 inches (107 mm) 53°F (12°C) 3 inches (77 mm)
Nov 61°F (16°C) 3.5 inches (90 mm) 43°F (6°C) 4.3 inches (110 mm)
Dec 54°F (12°C) 4.3 inches (109 mm) 30°F (-1°C) 4.1 inches (103 mm)