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

Should you visit Key West or San Juan?

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

Should I visit Key West or San Juan? 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 San Juan?

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.

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 Train & Rail Tours in United States of America, and The Best Sightseeing Tours in United States of America.


Which place is cheaper, San Juan or Key West?

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 Key West is $832, 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 Key West and San Juan in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Key West $132
    San Juan $124
  • Accommodation Typical double-occupancy room
    Key West $264
    San Juan $248
Compare Hotels in Key West and San Juan

Looking for a hotel in Key West 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 Key West


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: Key West Hotel Prices and San Juan Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Key West $51
    San Juan $14
Typical Local Transportation Prices in Key West

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


  • Rental Car for One Day
    $38

Hired Cars and Shuttles in Key West

Some specific examples of transportation prices in Key West:

  • Key West Int Airport (EYW) to Key West - Arrival Private Transfer: $164
  • Key West to Key West Airport (EYW) - Departure Private Transfer: $164
  • Key West Int Airport EYW to Key West Hotels Arrival Transfer: $156
  • Key West hotels to Key West Int Airport (EYW) Departure Transfer: $156
  • Private Transfer from Key West hotels to Key West Cruise Port: $114
  • Private Transfer from Key West Airport (EYW) to Key West Port: $113
  • One Way Airport Transfer Service: $54

Hired Cars and Shuttles in San Juan

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

  • Private Departure Transfer - Hotel / Accommodation to San Juan Airport: $22
  • Premium Transfer in Airport, Hotel, Airbnb, Cruise: $25
  • San Juan Airport (SJU) to San Juan - Arrival Private Transfer: $28
  • San Juan hotels to San Juan PR Cruise Port - Departure Transfer: $30
  • San Juan One-way Transfer - Cruise, SJU, Hotels, Airbnb: $30
  • Private Transfer Puerto Rico:To or From Airports, Hotels &Cruises: $33
  • Puerto Rico Island Wide Private Transfers, Tesla 3 Luxury Sedan.: $56
  • San Juan Port to San Juan Airport (SJU) - Departure Private Transfer: $60
  • San juan Puerto Rico PrivateTransfers Airport,Hotels,Cruise Ports: $66
  • Roundtrip-Transfer from: SJU Airport,Cruises and Hotels in Puerto Rico LuxurySUV: $70
  • Roundtrip-Transfer in Puerto Rico: From Airports, Hotels, Cruises: $71
  • Airport Transfer to Cruise Ships, Hotels, Airbnb in San Juan: $76

Is it cheaper to fly into Key West or San Juan?

Prices for flights to both San Juan and Key West 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
    Key West $667
    San Juan $62

Food Tours and Cooking Classes in Key West

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

  • Sunset Dinner Cruise with Open Bar & Live Music: $74
  • Exploring and Walking Food Tour of Cayo Hueso: $80
  • Key West Cooking Show Chef Demonstration with Meal: $81
  • Cooking Show Chef Demonstration with Meal: $81
  • Key West Sunset Cruise: Dinner, Live Music & Drinks Included: $84
  • Southernmost Food & Cultural Walking Tour by Key West Food Tours: $90
  • Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music: $100
  • Secret Walking Food Tour: $115
  • Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling: $160

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.
    Key West $33
    San Juan $49

Tours and Activities in Key West

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

  • 2 Hour Key West Mini Catamaran Eco Tour: $285
  • 2-Hour Live Music Guided Tour in Key West: $35
  • Day Sailing Adventure in the Florida Marine Sanctuary: $99
  • Day in Key West - Private SUV Tour From Miami: $1,300
  • Florida Key West Self-Guided Walking Audio Tour: $9.99
  • Florida Keys: Aquarium Encounters Day Tour with Lunch: $182
  • Florida Keys: Dolphin Research Center Day Tour with Lunch: $182
  • Florida Keys: Up The Keys Nature Tour: $128
  • From Dolphin Watching Tour with Lunch & Drinks: $150
  • From Sandbar Cruise with Lunch and Open Bar (18+): $151
  • Guided Mangrove Eco Tours Kayak or Paddleboard Adventure: $75
  • Guided Night Kayak Adventure Tour in Luminous Lagoon: $90

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.

  • Transportation in San Juan, Isla verde, Condado, Hotels, Cruises & Airbnb's SJU: $14
  • San Juan Self-Guided Walking Audio Tour: $17
  • Eco Friendly Farming Tour to Explore Dorado's Most Beautiful Farm: $20
  • Discover Superb Self-Guided Audio Tour: $20
  • Group Transportation in airport, cruise ships, hotels, bnb's in San Juan, PR: $23
  • Old San Juan Walking Tour with a Local Certified Guide: $25
  • San Juan Ghost Tour: Shrieks in the Sugarcane: $32
  • Old San Juan Walking Tour: $39
  • Old San Juan City Walking Tour: $39
  • Historic Old San Juan Sunset Walking Tour: $39
  • Top Rated El Yunque Rainforest & Waterslide – VIP SmallGroup Tour: $45
  • Ron del Barrilito Heritage Skip-the-Line Tour: $46

Alcohol
  • Alcohol Drinks for one day
    Key West $16
    San Juan $12

Sample the Local Flavors in Key West

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

  • Key West Bar Crawl: $15
  • Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt: $32
  • Bone Island Haunted Pub Crawl: $32
  • Key West Haunted Pub Crawl Walking Tour: $35
  • Haunted Pub Crawl Walking Tour: $35
  • 2.5-Hour Duval Street Pub Crawl: $43

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 Key West and San Juan, we can see that Key West is more expensive. And not only is San Juan much less expensive, but it is actually a significantly cheaper destination. Since Key West 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 San Juan would let you spend less money overall. Or, you could decide to spend more money in San Juan 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 San Juan.

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 San Juan Expensive?.


Which is Bigger, Key West or San Juan?

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

Key West 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 Key West or San Juan in the Summer?

The summer brings many poeple to Key West as well as San Juan. The summer months attract visitors to Key West because of the beaches, snorkeling, the small town charm, and the family-friendly experiences. The warm climate attracts visitors to San Juan throughout the year.

In July, Key West is generally around the same temperature as San Juan. Daily temperatures in Key West average around 84°F (29°C), and San Juan fluctuates around 28°C (83°F).

The sun comes out a lot this time of the year in San Juan. People are often attracted to the plentiful sunshine in Key West this time of the year. In the summer, Key West often gets more sunshine than San Juan. Key West gets 328 hours of sunny skies this time of year, while San Juan receives 287 hours of full sun.

Key West usually gets less rain in July than San Juan. Key West gets 3.3 inches (83 mm) of rain, while San Juan receives 95 mm (3.7 in) of rain this time of the year.


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

Should I visit Key West or San Juan in the Autumn?

Both San Juan and Key West are popular destinations to visit in the autumn with plenty of activities. 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. Plenty of visitors come to San Juan because of the warm climate and sunshine that lasts throughout the year.

Key West is around the same temperature as San Juan in the autumn. The daily temperature in Key West averages around 80°F (27°C) in October, and San Juan fluctuates around 28°C (82°F).

It's quite sunny in San Juan. The sun comes out a lot this time of the year in Key West. Key West usually receives more sunshine than San Juan during autumn. Key West gets 258 hours of sunny skies, while San Juan receives 235 hours of full sun in the autumn.

It rains a lot this time of the year in San Juan. It's quite rainy in Key West. In October, Key West usually receives around the same amount of rain as San Juan. Key West gets 5.1 inches (129 mm) of rain, while San Juan receives 135 mm (5.3 in) of rain each month for the autumn. The hurricane season in Key West is June to November.


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

Should I visit Key West or San Juan in the Winter?

Both San Juan and Key West during the winter are popular places to visit. Many travelers come to Key West for the shopping scene and the cuisine. Warm weather and sunshine bring visitors to San Juan year-round.

In the winter, Key West is cooler than San Juan. Typically, the winter temperatures in Key West in January average around 70°F (21°C), and San Juan averages at about 25°C (77°F).

In San Juan, it's very sunny this time of the year. It's quite sunny in Key West. In the winter, Key West often gets around the same amount of sunshine as San Juan. Key West gets 252 hours of sunny skies this time of year, while San Juan receives 240 hours of full sun.

Key West usually gets less rain in January than San Juan. Key West gets 1.7 inches (43 mm) of rain, while San Juan receives 58 mm (2.3 in) of rain this time of the year.


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

Should I visit Key West or San Juan in the Spring?

The spring attracts plenty of travelers to both Key West and San Juan. Many visitors come to Key West in the spring for the beaches, the small town charm, and the natural beauty. San Juan attracts visitors year-round for its warm weather and sunny climate.

In April, Key West is generally around the same temperature as San Juan. Daily temperatures in Key West average around 77°F (25°C), and San Juan fluctuates around 26°C (79°F).

People are often attracted to the plentiful sunshine in San Juan this time of the year. In Key West, it's very sunny this time of the year. Key West usually receives more sunshine than San Juan during spring. Key West gets 326 hours of sunny skies, while San Juan receives 272 hours of full sun in the spring.

In April, Key West usually receives less rain than San Juan. Key West gets 0.8 inches (21 mm) of rain, while San Juan receives 69 mm (2.7 in) of rain each month for the spring. June to November is the hurricane season in Key West.


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

Typical Weather for San Juan and Key West

Key West 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)