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

Should you visit Pensacola or San Juan?

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 San Juan can help you decide which place is right for you.

Where Should I go: Pensacola or San Juan?

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.

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 Bicycle Tours in United States of America, and Tours for Outdoor and Nature Lovers in United States of America.


Which place is cheaper, San Juan or Pensacola?

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 Pensacola is $234, 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 Pensacola and San Juan in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Pensacola $115
    San Juan $124
  • Accommodation Typical double-occupancy room
    Pensacola $230
    San Juan $248
Compare Hotels in Pensacola and San Juan

Looking for a hotel in Pensacola 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 Pensacola


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: Pensacola Hotel Prices and San Juan Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Pensacola $64
    San Juan $14
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

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 Pensacola or San Juan?

Prices for flights to both San Juan 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
    San Juan $62
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

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.
    Pensacola $13
    San Juan $49
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:

  • 1hr Segway Tour Downtown : $57
  • 2hr Segway Tour of Downtown : $72
  • 3 Hour Sandbar Adventure on Motorized Floats: $69
  • Bay Cruise: $65
  • Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise: $99
  • Daily Dolphin Cruise + Sightseeing Tour on Pensacola Beach: $35
  • Dolphin & Scenic Bay Sightseeing Cruise Up to 49, Pensacola: $50
  • Frisky Mermaid Fireworks Cruise Up to 49 Pax: $65
  • Frisky Mermaid Public Dolphin + Sightseeing Cruise Up to 49 Pax: $39
  • Ghosts and Graveyard Tour of Pensacola: $40
  • Ghosts of Haunted Trolley Tour: $35
  • Half Day Pontoon Boat Rental – Fun & Relaxing Water Adventure: $299

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
    Pensacola $44
    San Juan $12

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

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 comparing the travel costs between Pensacola and San Juan, we can see that Pensacola 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. Even though Pensacola is in North America and San Juan is in Caribbean Islands, both of these destinations have relatively similar prices of travel. Generally, the levels of luxury and expenses are the same for these cities even though they are geographically far apart.

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


Which is Bigger, Pensacola or San Juan?

San Juan has a larger population, and is about 7 times larger than the population of Pensacola. When comparing the sizes of Pensacola 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 Pensacola or San Juan?

Pensacola 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 Pensacola or San Juan in the Summer?

The summer brings many poeple to Pensacola as well as San Juan. Most visitors come to Pensacola for the beaches, the hiking, and the family-friendly experiences during these months. The warm climate attracts visitors to San Juan throughout the year.

In July, Pensacola is generally around the same temperature as San Juan. Daily temperatures in Pensacola average around 82°F (28°C), and San Juan fluctuates around 28°C (83°F).

Pensacola receives a lot of rain in the summer. Pensacola usually gets more rain in July than San Juan. Pensacola gets 7.4 inches (189 mm) of rain, while San Juan receives 95 mm (3.7 in) of rain this time of the year.


  • Summer Average Temperatures July
    Pensacola 82°F (28°C) 
    San Juan 28°C (83°F)

Should I visit Pensacola or San Juan in the Autumn?

Both San Juan and Pensacola are popular destinations to visit in the autumn with plenty of activities. The autumn months attract visitors to Pensacola because of the hiking trails and the shopping scene. Plenty of visitors come to San Juan because of the warm climate and sunshine that lasts throughout the year.

Pensacola is cooler than San Juan in the autumn. The daily temperature in Pensacola averages around 69°F (21°C) in October, and San Juan fluctuates around 28°C (82°F).

It rains a lot this time of the year in San Juan. It's quite rainy in Pensacola. In October, Pensacola usually receives less rain than San Juan. Pensacola gets 4.2 inches (107 mm) of rain, while San Juan receives 135 mm (5.3 in) of rain each month for the autumn. The hurricane season in Pensacola is June to November.


  • Autumn Average Temperatures October
    Pensacola 69°F (21°C) 
    San Juan 28°C (82°F)

Should I visit Pensacola or San Juan in the Winter?

Both San Juan and Pensacola during the winter are popular places to visit. The museums, the shopping scene, and the cuisine are the main draw to Pensacola this time of year. Warm weather and sunshine bring visitors to San Juan year-round.

In the winter, Pensacola is much colder than San Juan. Typically, the winter temperatures in Pensacola in January average around 51°F (10°C), and San Juan averages at about 25°C (77°F).

It rains a lot this time of the year in Pensacola. Pensacola usually gets more rain in January than San Juan. Pensacola gets 4.6 inches (117 mm) of rain, while San Juan receives 58 mm (2.3 in) of rain this time of the year.


  • Winter Average Temperatures January
    Pensacola 51°F (10°C) 
    San Juan 25°C (77°F)

Should I visit Pensacola or San Juan in the Spring?

The spring attracts plenty of travelers to both Pensacola and San Juan. Many travelers come to Pensacola for the beaches. San Juan attracts visitors year-round for its warm weather and sunny climate.

In April, Pensacola is generally cooler than San Juan. Daily temperatures in Pensacola average around 67°F (20°C), and San Juan fluctuates around 26°C (79°F).

In April, Pensacola usually receives more rain than San Juan. Pensacola gets 3.4 inches (87 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 Pensacola.


  • Spring Average Temperatures April
    Pensacola 67°F (20°C) 
    San Juan 26°C (79°F)

Typical Weather for San Juan and Pensacola

Pensacola San Juan
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 51°F (10°C) 4.6 inches (117 mm) 25°C (77°F) 58 mm (2.3 in)
Feb 54°F (12°C) 5.4 inches (137 mm) 25°C (77°F) 41 mm (1.6 in)
Mar 60°F (16°C) 5.6 inches (143 mm) 26°C (78°F) 45 mm (1.8 in)
Apr 67°F (20°C) 3.4 inches (87 mm) 26°C (79°F) 69 mm (2.7 in)
May 74°F (24°C) 4.2 inches (107 mm) 27°C (81°F) 120 mm (4.7 in)
Jun 80°F (27°C) 6.4 inches (163 mm) 28°C (82°F) 82 mm (3.2 in)
Jul 82°F (28°C) 7.4 inches (189 mm) 28°C (83°F) 95 mm (3.7 in)
Aug 82°F (28°C) 7.4 inches (188 mm) 28°C (83°F) 130 mm (5.1 in)
Sep 78°F (26°C) 5.3 inches (135 mm) 28°C (83°F) 130 mm (5.1 in)
Oct 69°F (21°C) 4.2 inches (107 mm) 28°C (82°F) 135 mm (5.3 in)
Nov 61°F (16°C) 3.5 inches (90 mm) 27°C (80°F) 132 mm (5.2 in)
Dec 54°F (12°C) 4.3 inches (109 mm) 26°C (78°F) 92 mm (3.6 in)