A Travel Price Comparison for Families, Couples, and Backpackers Islamorada vs. San Juan for Vacations, Tours, and Honeymoons

Should you visit Islamorada or San Juan?

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

If you're trying to decide where to visit between Islamorada or San Juan, 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 San Juan?

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.

San Juan

If you've ever set foot on a Caribbean cruise, you've probably spent a bit of time in San Juan, Puerto Rico. However, maybe you should consider spending more than just a port day in this beautiful and historically rich city.

As the capital and largest city in all of Puerto Rico, San Juan is home to approximately 400,000 people. Established in 1521, it is also the second oldest European-founded settlement in the Americas.

As this city fuses a historic paradise with modern day energy, it has absolutely everything to offer. Intellectual wanderers, beach bums, rainforest adventurers and radical surfers will all find plenty to do in San Juan.

For some great organized tour ideas, see The Best Polar Tours & Cruises in United States of America, and The Best Walking Tours in United States of America.


Which place is cheaper, San Juan or Islamorada?

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

The average daily cost (per person) in Islamorada is $179, while the average daily cost in San Juan is $218. 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 San Juan in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Islamorada $79
    San Juan $124
  • Accommodation Typical double-occupancy room
    Islamorada $158
    San Juan $248
Compare Hotels in Islamorada and San Juan

Looking for a hotel in Islamorada or San Juan? 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 San Juan


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 and San Juan Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Islamorada $28
    San Juan $14

Hired Cars and Shuttles in San Juan

Also for San Juan, here are a few examples of actual transportation services:

  • Double ATV Adventure: Private Hacienda Experience with Transfer: $289
  • Transfer in Puerto Rico with Minivan from Airport: $280
  • Transfer SJU Airport to Ponce and Juana Diaz. Hotels and Airbnb Vice Versa 1 Way: $260
  • Carabali Rain Forest Round Trip Private Taxi Transfer: $200
  • Single ATV Adventure: Private Hacienda Experience with Transfer: $195
  • Private Airport Transfers to Ceiba Ferry Terminal and Airport: $155
  • Transfer SJU Airport to Dorado. Hotels and Airbnb. Vice Versa One Way Trip.: $140
  • Puerto Rico Island Wide Transfer, 16Pax Mercedes Van, Select Zone: $130
  • Transfer from San Juan to Ponce or Ponce to San Juan: $125
  • Puerto Rico Island Wide Private Transfers, 14Pax Lux Sprinter Van: $124
  • San Juan Puerto Rico Cruise Port to San Juan hotels - RoundTrip Private Transfer: $120
  • Arrival Private Transfer SJU Airport to Old San Juan by Sedan: $120

Is it cheaper to fly into Islamorada or San Juan?

Prices for flights to both San Juan 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 $81
    San Juan $62

Food Tours and Cooking Classes in San Juan

For San Juan, here are some samples of tours and activities related to meals and dining experiences:

  • Authentic Flavors of San Juan Food Tour: $165
  • FlyDining: Sunset & City Lights Dinner Over Old San Juan: $165
  • Morning Old San Juan Food Tour: $169
  • Cooking and Connecting with a Local in Puerto Rico: $173
  • Savor the Sunset: Old San Juan Walking Food Tour: $179

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Islamorada $19
    San Juan $49

Tours and Activities in Islamorada

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

  • 1.5 Hour (20 miles) Waverunner Tour. See Mangrove Tunnels, 20 Islands & SandBar: $259
  • 2 Hour Private Eco-Tour: $950
  • From Miami: Key Largo & Islamorada Private Open-Top Bus Tour: $1,515
  • Private Boat Tour with Snorkeling and Sandbar: $950
  • Private Snorkel & Sandbar Adventure: $599

Typical Entertainment Prices in San Juan

For San Juan, here are some examples of average entertainment and activity prices from previous travelers:


  • Horseback Riding Tour
    $40
  • Full Day Snorkeling Trip
    $100
  • 1 Hr Windsurfing Lesson
    $75

Tours and Activities in San Juan

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

  • Culebra Swim with Turtles Adventure and Flamenco Beach by Ferry: $130
  • El Yunque Rainforest Tour Half Day Earlybird/ Small Groups: $85
  • Full-Day Tour: El Yunque, Luquillo Beach, Bio Bay Night Kayaking: $155
  • Puerto Rican Food Experience: $99
  • "Exclusive Tour": VIP Rum Tasting at San Juan Artisan Distillers: $150
  • "Yo Soy de PfknR" Bad Bunny Party Bus Experience: $145
  • 1 Hour Historical UTV Tour in San Juan: $200
  • 2 Tours in 1 Day: Rainforest Waterslides & Beach Tour w/Transport: $60
  • 3 Tours in 1 Day: Old San Juan, Rainforest, Beach with Transport: $75
  • 30-Minute Freestyle Jet Ski Adventure in the Bay: $100
  • ATV Double Rider Adventure Near San Juan - Hacienda Campo Rico: $221
  • ATV Single Rider Adventure Near San Juan - Hacienda Campo Rico: $149

Alcohol
  • Alcohol Drinks for one day
    Islamorada $15
    San Juan $12

Sample the Local Flavors in San Juan

Some specific costs for nightlife related activities in San Juan:

  • Old San Juan Bar Crawl: Experience Local Hotspots: $65
  • The Pinones Pub crawl Bar crawl : $70
  • Local Puerto Rican Rum Distillery Tour - Ron Pepon: $90
  • Puerto Rico's First and Only Craft Beer Brewery Tour! : $99


When we compare the travel costs of actual travelers between Islamorada and San Juan, we can see that San Juan is more expensive. And not only is Islamorada much less expensive, but it is actually a significantly cheaper destination. Since Islamorada is in North America and San Juan is in Caribbean Islands, this is one of the main reasons why the costs are so different, as different regions of the world tend to have overall different travel costs. So, traveling to Islamorada would let you spend less money overall. Or, you could decide to spend more money in Islamorada 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 San Juan would naturally cost you much more money, so you would probably want to keep your budget a little tighter in San Juan than you might in Islamorada.

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


Which is Bigger, Islamorada or San Juan?

San Juan has a larger population, and is about 60 times larger than the population of Islamorada. When comparing the sizes of Islamorada and San Juan, 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 San Juan?

Islamorada has a temperate climate with four distinct seasons, but San Juan experiences a warm climate with fairly sunny weather most of the year.

Should I visit Islamorada or San Juan in the Summer?

Both San Juan and Islamorada are popular destinations to visit in the summer with plenty of activities. Many visitors come to Islamorada in the summer for the beaches, snorkeling, and the family-friendly experiences. Plenty of visitors come to San Juan because of the warm climate and sunshine that lasts throughout the year.

Islamorada is around the same temperature as San Juan in the summer. The daily temperature in Islamorada averages around 84°F (29°C) in July, and San Juan fluctuates around 28°C (83°F).

It's quite sunny in San Juan. The sun comes out a lot this time of the year in Islamorada. Islamorada usually receives more sunshine than San Juan during summer. Islamorada gets 328 hours of sunny skies, while San Juan receives 287 hours of full sun in the summer.

In July, Islamorada usually receives less rain than San Juan. Islamorada gets 3.3 inches (83 mm) of rain, while San Juan receives 95 mm (3.7 in) of rain each month for the summer.


  • Summer Average Temperatures July
    Islamorada 84°F (29°C) 
    San Juan 28°C (83°F)

Should I visit Islamorada or San Juan in the Autumn?

Both San Juan and Islamorada during the autumn are popular places to visit. Most visitors come to Islamorada for the shopping scene and the natural beauty of the area during these months. Warm weather and sunshine bring visitors to San Juan year-round.

In the autumn, Islamorada is around the same temperature as San Juan. Typically, the autumn temperatures in Islamorada in October average around 80°F (27°C), and San Juan averages at about 28°C (82°F).

In San Juan, it's very sunny this time of the year. It's quite sunny in Islamorada. In the autumn, Islamorada often gets more sunshine than San Juan. Islamorada gets 258 hours of sunny skies this time of year, while San Juan receives 235 hours of full sun.

San Juan gets a good bit of rain this time of year. It rains a lot this time of the year in Islamorada. Islamorada usually gets around the same amount of rain in October as San Juan. Islamorada gets 5.1 inches (129 mm) of rain, while San Juan receives 135 mm (5.3 in) of rain this time of the year. Also, the hurricane season in Islamorada is June to November.


  • Autumn Average Temperatures October
    Islamorada 80°F (27°C) 
    San Juan 28°C (82°F)

Should I visit Islamorada or San Juan in the Winter?

The winter attracts plenty of travelers to both Islamorada and San Juan. The winter months attract visitors to Islamorada because of the museums, the shopping scene, and the cuisine. San Juan attracts visitors year-round for its warm weather and sunny climate.

In January, Islamorada is generally cooler than San Juan. Daily temperatures in Islamorada average around 70°F (21°C), and San Juan fluctuates around 25°C (77°F).

People are often attracted to the plentiful sunshine in San Juan this time of the year. In Islamorada, it's very sunny this time of the year. Islamorada usually receives around the same amount of sunshine as San Juan during winter. Islamorada gets 252 hours of sunny skies, while San Juan receives 240 hours of full sun in the winter.

In January, Islamorada usually receives less rain than San Juan. Islamorada gets 1.7 inches (43 mm) of rain, while San Juan receives 58 mm (2.3 in) of rain each month for the winter.


  • Winter Average Temperatures January
    Islamorada 70°F (21°C) 
    San Juan 25°C (77°F)

Should I visit Islamorada or San Juan in the Spring?

The spring brings many poeple to Islamorada as well as San Juan. The beaches and the natural beauty are the main draw to Islamorada this time of year. The warm climate attracts visitors to San Juan throughout the year.

Islamorada is around the same temperature as San Juan in the spring. The daily temperature in Islamorada averages around 77°F (25°C) in April, and San Juan fluctuates around 26°C (79°F).

The sun comes out a lot this time of the year in San Juan. People are often attracted to the plentiful sunshine in Islamorada this time of the year. In the spring, Islamorada often gets more sunshine than San Juan. Islamorada gets 326 hours of sunny skies this time of year, while San Juan receives 272 hours of full sun.

Islamorada usually gets less rain in April than San Juan. Islamorada gets 0.8 inches (21 mm) of rain, while San Juan receives 69 mm (2.7 in) of rain this time of the year. Keep in mind that June to November is the hurricane season in Islamorada.


  • Spring Average Temperatures April
    Islamorada 77°F (25°C) 
    San Juan 26°C (79°F)

Typical Weather for San Juan and Islamorada

Islamorada San Juan
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 70°F (21°C) 1.7 inches (43 mm) 25°C (77°F) 58 mm (2.3 in)
Feb 71°F (21°C) 1.4 inches (36 mm) 25°C (77°F) 41 mm (1.6 in)
Mar 74°F (23°C) 1.7 inches (42 mm) 26°C (78°F) 45 mm (1.8 in)
Apr 77°F (25°C) 0.8 inches (21 mm) 26°C (79°F) 69 mm (2.7 in)
May 81°F (27°C) 2.7 inches (68 mm) 27°C (81°F) 120 mm (4.7 in)
Jun 83°F (28°C) 4.5 inches (114 mm) 28°C (82°F) 82 mm (3.2 in)
Jul 84°F (29°C) 3.3 inches (83 mm) 28°C (83°F) 95 mm (3.7 in)
Aug 84°F (29°C) 3.9 inches (98 mm) 28°C (83°F) 130 mm (5.1 in)
Sep 83°F (29°C) 5.7 inches (144 mm) 28°C (83°F) 130 mm (5.1 in)
Oct 80°F (27°C) 5.1 inches (129 mm) 28°C (82°F) 135 mm (5.3 in)
Nov 76°F (24°C) 2 inches (50 mm) 27°C (80°F) 132 mm (5.2 in)
Dec 72°F (22°C) 1.4 inches (35 mm) 26°C (78°F) 92 mm (3.6 in)