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

Should you visit Islamorada or Woodstock?

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

If you're trying to decide where to visit between Islamorada or Woodstock, this travel comparison, which includes costs, can help. The overall cost of travel is usually a consideration when deciding where to go next, and the cost comparison down below can help you decide based on the average prices from other travelers along with your own travel budget.

Where Should I go: Islamorada or Woodstock?

Islamorada

From its thriving coral reefs to its miraculous botanical gardens, you will find adventure on both land and sea at Islamorada, Florida. Islamorada, or "Village of Islands," is located in Monroe County and holds a population of no more than 6,119. As Islamorada's village is occupied within a cluster of nearby islands, Islamorada is located on Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key and Plantation Key in the Florida Keys. The village is relatively small, expanding to about 7.2 square miles total. Approximately an hour and a half-drive from Miami and a two hour-drive from Key West, Islamorada works swimmingly for those who seek to acquaint themselves with the tropical pleasures of the Keys.

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 3-Week Tours in United States of America, The Best Bicycle Tours in United States of America, Tours for Outdoor and Nature Lovers in United States of America, and The Best Coach Bus Tours in United States of America.


Which place is cheaper, Woodstock or Islamorada?

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

The average daily cost (per person) in Islamorada is $145, while the average daily cost in Woodstock is $154. 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 Islamorada and Woodstock in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Islamorada $79
    Woodstock $81
  • Accommodation Typical double-occupancy room
    Islamorada $158
    Woodstock $162
Compare Hotels in Islamorada and Woodstock

Looking for a hotel in Islamorada 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 Islamorada


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: Islamorada Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Islamorada $28
    Woodstock $60

Is it cheaper to fly into Islamorada or Woodstock?

Prices for flights to both Woodstock and Islamorada 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
    Islamorada $47
    Woodstock $34

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Islamorada $19
    Woodstock $35

Tours and Activities in Islamorada

Also, here are some specific examples of entertainment, tickets, and activities for Islamorada.

  • Snorkeling Experience : $80
  • 2-Hour Snorkeling Adventure on Pontoon : $80
  • Day Tour Glass Bottom Boat In Islamorada: $80
  • Night Tour Glass Bottom Boat in Islamorada: $80
  • Islamorada Florida Keys Sunset Sightseeing Cruise Music : $86
  • Snorkeling Adventure in Islamorada : $90
  • Snorkeling and Beach Adventure from Cheeca Spa: $90
  • Snorkeling and Beach Adventure: $90
  • Guided Tour with Local Highlights: $95
  • Snorkel Adventure & Sandbar Trip: $130
  • Snorkel Adventure & Sandbar Trip from Cheeca Spa: $140
  • Snorkel adventure & Sandbar Trip : $150

Alcohol
  • Alcohol Drinks for one day
    Islamorada $15
    Woodstock $22


When comparing the travel costs between Islamorada and Woodstock, we can see that Woodstock 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 Islamorada Expensive? and Is Woodstock Expensive?.


Which is Bigger, Islamorada or Woodstock?

Islamorada has a larger population, and is about 3 times larger than the population of Woodstock. When comparing the sizes of Islamorada 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 Islamorada or Woodstock?

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 Islamorada or Woodstock in the Summer?

Both Woodstock and Islamorada during the summer are popular places to visit. Many visitors come to Islamorada in the summer for the beaches, snorkeling, and the family-friendly experiences.

Islamorada is a little warmer than Woodstock in the summer. The daily temperature in Islamorada averages around 84°F (29°C) in July, and Woodstock fluctuates around 74°F (24°C).

In Woodstock, it's very sunny this time of the year. It's quite sunny in Islamorada. In the summer, Islamorada often gets more sunshine than Woodstock. Islamorada gets 328 hours of sunny skies this time of year, while Woodstock receives 293 hours of full sun.

Islamorada usually gets around the same amount of rain in July as Woodstock. Islamorada gets 3.3 inches (83 mm) of rain, while Woodstock receives 3.4 inches (87 mm) of rain this time of the year.


  • Summer Average Temperatures July
    Islamorada 84°F (29°C) 
    Woodstock 74°F (24°C)

Should I visit Islamorada or Woodstock in the Autumn?

The autumn attracts plenty of travelers to both Islamorada and Woodstock. Most visitors come to Islamorada for the shopping scene and the natural beauty of the area during these months.

In the autumn, Islamorada is much warmer than Woodstock. Typically, the autumn temperatures in Islamorada in October average around 80°F (27°C), and Woodstock averages at about 53°F (12°C).

In Islamorada, it's very sunny this time of the year. Islamorada usually receives more sunshine than Woodstock during autumn. Islamorada gets 258 hours of sunny skies, while Woodstock receives 197 hours of full sun in the autumn.

Islamorada gets a good bit of rain this time of year. In October, Islamorada usually receives more rain than Woodstock. Islamorada gets 5.1 inches (129 mm) of rain, while Woodstock receives 3 inches (77 mm) of rain each month for the autumn. June to November in Islamorada is the hurricane season.


  • Autumn Average Temperatures October
    Islamorada 80°F (27°C) 
    Woodstock 53°F (12°C)

Should I visit Islamorada or Woodstock in the Winter?

The winter brings many poeple to Islamorada as well as Woodstock. The winter months attract visitors to Islamorada because of the museums, the shopping scene, and the cuisine.

It's quite cold in Woodstock in the winter. In January, Islamorada is generally much warmer than Woodstock. Daily temperatures in Islamorada average around 70°F (21°C), and Woodstock fluctuates around 25°F (-4°C).

People are often attracted to the plentiful sunshine in Islamorada this time of the year. In the winter, Islamorada often gets more sunshine than Woodstock. Islamorada gets 252 hours of sunny skies this time of year, while Woodstock receives 167 hours of full sun.

Islamorada usually gets less rain in January than Woodstock. Islamorada gets 1.7 inches (43 mm) of rain, while Woodstock receives 3.3 inches (83 mm) of rain this time of the year.


  • Winter Average Temperatures January
    Islamorada 70°F (21°C) 
    Woodstock 25°F (-4°C)

Should I visit Islamorada or Woodstock in the Spring?

Both Woodstock and Islamorada are popular destinations to visit in the spring with plenty of activities. The beaches and the natural beauty are the main draw to Islamorada this time of year.

Islamorada is much warmer than Woodstock in the spring. The daily temperature in Islamorada averages around 77°F (25°C) in April, and Woodstock fluctuates around 49°F (10°C).

It's quite sunny in Woodstock. The sun comes out a lot this time of the year in Islamorada. Islamorada usually receives more sunshine than Woodstock during spring. Islamorada gets 326 hours of sunny skies, while Woodstock receives 227 hours of full sun in the spring.

In April, Islamorada usually receives less rain than Woodstock. Islamorada gets 0.8 inches (21 mm) of rain, while Woodstock receives 3.7 inches (95 mm) of rain each month for the spring. The hurricane season in Islamorada is June to November.


  • Spring Average Temperatures April
    Islamorada 77°F (25°C) 
    Woodstock 49°F (10°C)

Typical Weather for Woodstock and Islamorada

Islamorada Woodstock
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 70°F (21°C) 1.7 inches (43 mm) 25°F (-4°C) 3.3 inches (83 mm)
Feb 71°F (21°C) 1.4 inches (36 mm) 28°F (-2°C) 3.2 inches (81 mm)
Mar 74°F (23°C) 1.7 inches (42 mm) 38°F (3°C) 3.8 inches (97 mm)
Apr 77°F (25°C) 0.8 inches (21 mm) 49°F (10°C) 3.7 inches (95 mm)
May 81°F (27°C) 2.7 inches (68 mm) 60°F (16°C) 3.5 inches (89 mm)
Jun 83°F (28°C) 4.5 inches (114 mm) 69°F (21°C) 3.5 inches (90 mm)
Jul 84°F (29°C) 3.3 inches (83 mm) 74°F (24°C) 3.4 inches (87 mm)
Aug 84°F (29°C) 3.9 inches (98 mm) 72°F (22°C) 3.9 inches (100 mm)
Sep 83°F (29°C) 5.7 inches (144 mm) 64°F (18°C) 3.5 inches (90 mm)
Oct 80°F (27°C) 5.1 inches (129 mm) 53°F (12°C) 3 inches (77 mm)
Nov 76°F (24°C) 2 inches (50 mm) 43°F (6°C) 4.3 inches (110 mm)
Dec 72°F (22°C) 1.4 inches (35 mm) 30°F (-1°C) 4.1 inches (103 mm)