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

Should you visit San Juan or Portland?

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

Should I visit San Juan or Portland? 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: San Juan or Portland?

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.

Portland

Referred to as "The City of Roses", Portland is the largest city in Oregon. It sits on the banks of the Columbia River and offers breathtaking views of Mount Hood when the weather allows. Portland is famous for its alternative vibe, live music scene, and popular microbreweries. It's also a mecca for environmentally conscious urban planning. The downtown area is quite compact and walkable. While the city itself may be smaller than you expect, it is still the largest metropolitan area between San Francisco and Seattle.

For some great organized tour ideas, see The Best Family-Friendly Tours to United States of America, and The Best Wildlife Tours to United States of America.


Which place is cheaper, Portland or San Juan?

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 San Juan is $218, while the average daily cost in Portland is $211. 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 San Juan and Portland in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    San Juan $124
    Portland $97
  • Accommodation Typical double-occupancy room
    San Juan $248
    Portland $194
Compare Hotels in San Juan and Portland

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


Hotels in Portland


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: San Juan Hotel Prices and Portland Hotel Prices.

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

Hired Cars and Shuttles in San Juan

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

  • Transfer in Puerto Rico with Minivan from Airport: $280
  • Transfer from San Juan to Ponce or Ponce to San Juan: $125
  • Transfer SJU Airport to Ponce and Juana Diaz. Hotels and Airbnb Vice Versa 1 Way: $260
  • Transfer SJU Airport to Dorado. Hotels and Airbnb. Vice Versa One Way Trip.: $140
  • Single ATV Adventure: Private Hacienda Experience with Transfer: $195
  • San Juan hotels to San Juan PR Cruise Port - Departure Transfer: $30
  • San Juan Puerto Rico Private Transfers: $105
  • San Juan Puerto Rico Cruise Port to San Juan hotels - RoundTrip Private Transfer: $119
  • San Juan Port to San Juan Airport (SJU) - Departure Private Transfer: $60
  • San Juan Luxury Private Round-Trip Transfer: SJU Airport - Cruise Pier - Hotel : $80
  • SJU Airport Private Transfer to Dorado: $115
  • Roundtrip-Transfer in Puerto Rico: From Airports, Hotels, Cruises: $71

Hired Cars and Shuttles in Portland

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

  • Private Transfer from Portland Airport (PDX) to Astoria Port: $226
  • Private Transfer from Astoria Cruise Port to Portland city hotels: $226
  • Private Transfer from Portland City Hotels to Astoria Cruise Port: $226
  • Portland Airport (PDX) to Portland downtown - Round-Trip Private Transfer: $91
  • Portland Airport (PDX) to Beaverton hotel - Round-Trip Private Transfer: $91
  • Portland Airport (PDX) to Tigard hotel or address - Round-Trip Private Transfer: $91
  • Portland Airport (PDX) to Lake Oswego - Round-Trip Private Transfer: $91
  • Portland Airport (PDX) to Beaverton hotel or address - Arrival Private Transfer: $46
  • Beaverton hotel to Portland Airport (PDX) - Departure Private Transfer: $46
  • Portland Airport (PDX) to Tigard hotel or address - Arrival Private Transfer: $46
  • Tigard hotel or address to Portland Airport (PDX) - Departure Private Transfer: $46
  • Portland Airport (PDX) to Lake Oswego - Arrival Private Transfer: $46

Is it cheaper to fly into San Juan or Portland?

Prices for flights to both Portland and San Juan 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
    San Juan $62
    Portland $74

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:

  • Old San Juan Food Tour with 7 Tastings of Authentic Local Flavors: $139
  • Private San Juan Cooking Class with a Local Expert: $146
  • Authentic Flavors of San Juan Food Tour: $165
  • FlyDining: 4 Courses Dinner with City Lights & Ocean Breeze: $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

Typical Food Prices in Portland

For Portland, here are some examples of average food and meal prices for travelers:


  • Afternoon Drinks (for 2)
    $9.50

Food Tours and Cooking Classes in Portland

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

  • Walking Food Tour – Warm Donuts & History: $57
  • Walking Pizza Tour: $75
  • Pasta Making Cooking Class at a Local Brewery: $75
  • Westside Food Tour Like a Local: $90
  • Downtown Food Tour of 6 Local Favorites Dishes: $100
  • Portland Downtown Food Tour: 6 Tastings of Local & Global Flavors: $109
  • Alphabet District Food Tour: $119
  • 2.5-hour Dinner Cruise on Willamette River: $127
  • Willamette River 2.5-hour Dinner Cruise: $127
  • All-Inclusive Downtown Portland Food Tour: $128

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    San Juan $49
    Portland $25
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
  • Rum Craft Cocktail Tour in San Juan: $65
  • "Yo Soy de PfknR" Bad Bunny Party Bus Experience: $145
  • 1 Hour Historical UTV Tour in San Juan: $200
  • 1-Hour Freestyle Jet Ski Adventure in the Bay: $150
  • 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
  • ATV Double Rider Adventure Near San Juan - Hacienda Campo Rico: $221
  • ATV Single Rider Adventure Near San Juan - Hacienda Campo Rico: $149
  • Bio Bay Night Kayak Tour with Transport from San Juan: $115
  • Bioluminescent Bay Chiliboats Waterbike Tour in La Parguera: $79

Tours and Activities in Portland

For Portland, here are a few prices for actual activities, tours, and tickets provided by various companies:

  • 2-hour Brunch Cruise on Willamette River: $104
  • 2-hour Lunch Cruise on Willamette River: $87
  • 7 Wonders of the Gorge 3.5-hour Jetboat Cruise: $90
  • 90 Minute Sailing Tour of Portland: $99
  • A Guided Walking Tour of Vibrant Downtown Portland: $44
  • Afternoon Half-Day Multnomah Falls and Columbia River Gorge Waterfalls Tour from Portland: $85
  • Astoria Full Day Private Tour : $169
  • Best of Private Walking Tour with a Local: $107
  • Capture your Oregon Adventures in a Magical Place: $189
  • Coffee Roasters of Portland Eastside Walking Tour : $55
  • Coffee, Donuts & Chocolate Tour : $69
  • Columbia Gorge Waterfalls and Mt. Hood Tour - Full Day: $129

Alcohol
  • Alcohol Drinks for one day
    San Juan $12
    Portland $17

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
  • Puerto Rico's First and Only Craft Beer Brewery Tour! : $99

Sample the Local Flavors in Portland

Some specific costs for nightlife related activities in Portland:

  • Power Through Portland Bar Crawl: $12
  • Private or Shared Party Bike Pub Crawl: $25
  • Ghosts Boos and Booze Haunted Pub Crawl: $30
  • Oregon Priority Wine Tasting Pass: $40
  • Haunted Underground Shanghai Tunnel Tour with Brewery Tastings: $48
  • Guided Bike Tour with Brewery Visits: $65
  • Fun Pasta Making Class at a Local Brewery in Portland: $75
  • Fun Sushi Making Class at a Local Brewery in Portland: $75
  • Sushi Making Class at a Local Brewery: $75
  • Portland, Maine: Old Port Brewery & Pub Walking Tour: $99
  • Portland, Maine: Local Brewery & Spirits Bus Tour: $99
  • Urban Wine Tasting Tour: $139


When comparing the travel costs between San Juan and Portland, we can see that San Juan 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 San Juan is in Caribbean Islands and Portland is in North America, 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 San Juan Expensive? and Is Portland Expensive?.


Which is Bigger, San Juan or Portland?

Portland has a larger population, and is about 29% larger than the population of San Juan. When comparing the sizes of San Juan and Portland, 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 San Juan or Portland?

Portland 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 San Juan or Portland in the Summer?

The summer attracts plenty of travelers to both San Juan and Portland. Warm weather and sunshine bring visitors to San Juan year-round. Also, most visitors come to Portland for the hiking, the small town charm, the music scene, and the family-friendly experiences during these months.

San Juan is a little warmer than Portland in the summer. The daily temperature in San Juan averages around 28°C (83°F) in July, and Portland fluctuates around 68°F (20°C).

People are often attracted to the plentiful sunshine in Portland this time of the year. In San Juan, it's very sunny this time of the year. San Juan usually receives less sunshine than Portland during summer. San Juan gets 287 hours of sunny skies, while Portland receives 338 hours of full sun in the summer.

In July, San Juan usually receives more rain than Portland. San Juan gets 95 mm (3.7 in) of rain, while Portland receives 0.7 inches (18 mm) of rain each month for the summer.


  • Summer Average Temperatures July
    San Juan 28°C (83°F) 
    Portland 68°F (20°C)

Should I visit San Juan or Portland in the Autumn?

The autumn brings many poeple to San Juan as well as Portland. San Juan attracts visitors year-round for its warm weather and sunny climate. Also, the autumn months attract visitors to Portland because of the hiking trails, the shopping scene, the music scene, the small town atmosphere, and the natural beauty of the area.

In the autumn, San Juan is much warmer than Portland. Typically, the autumn temperatures in San Juan in October average around 28°C (82°F), and Portland averages at about 55°F (13°C).

People are often attracted to the plentiful sunshine in San Juan this time of the year. In the autumn, San Juan often gets more sunshine than Portland. San Juan gets 235 hours of sunny skies this time of year, while Portland receives 155 hours of full sun.

San Juan receives a lot of rain in the autumn. San Juan usually gets more rain in October than Portland. San Juan gets 135 mm (5.3 in) of rain, while Portland receives 2.6 inches (67 mm) of rain this time of the year.


  • Autumn Average Temperatures October
    San Juan 28°C (82°F) 
    Portland 55°F (13°C)

Should I visit San Juan or Portland in the Winter?

Both Portland and San Juan are popular destinations to visit in the winter with plenty of activities. The warm climate attracts visitors to San Juan throughout the year. Also, the museums, the shopping scene, and the cuisine are the main draw to Portland this time of year.

It's quite cold in Portland in the winter. In January, San Juan is generally much warmer than Portland. Daily temperatures in San Juan average around 25°C (77°F), and Portland fluctuates around 40°F (4°C).

The sun comes out a lot this time of the year in San Juan. San Juan usually receives more sunshine than Portland during winter. San Juan gets 240 hours of sunny skies, while Portland receives 86 hours of full sun in the winter.

It rains a lot this time of the year in Portland. In January, San Juan usually receives less rain than Portland. San Juan gets 58 mm (2.3 in) of rain, while Portland receives 5.2 inches (132 mm) of rain each month for the winter.


  • Winter Average Temperatures January
    San Juan 25°C (77°F) 
    Portland 40°F (4°C)

Should I visit San Juan or Portland in the Spring?

Both Portland and San Juan during the spring are popular places to visit. Plenty of visitors come to San Juan because of the warm climate and sunshine that lasts throughout the year. Furthermore, many travelers come to Portland for the small town charm and the natural beauty.

San Juan is much warmer than Portland in the spring. The daily temperature in San Juan averages around 26°C (79°F) in April, and Portland fluctuates around 51°F (11°C).

In Portland, it's very sunny this time of the year. It's quite sunny in San Juan. In the spring, San Juan often gets more sunshine than Portland. San Juan gets 272 hours of sunny skies this time of year, while Portland receives 231 hours of full sun.

San Juan usually gets more rain in April than Portland. San Juan gets 69 mm (2.7 in) of rain, while Portland receives 2.4 inches (61 mm) of rain this time of the year.


  • Spring Average Temperatures April
    San Juan 26°C (79°F) 
    Portland 51°F (11°C)

Typical Weather for Portland and San Juan

San Juan Portland
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 25°C (77°F) 58 mm (2.3 in) 40°F (4°C) 5.2 inches (132 mm)
Feb 25°C (77°F) 41 mm (1.6 in) 44°F (7°C) 3.9 inches (98 mm)
Mar 26°C (78°F) 45 mm (1.8 in) 47°F (9°C) 3.6 inches (92 mm)
Apr 26°C (79°F) 69 mm (2.7 in) 51°F (11°C) 2.4 inches (61 mm)
May 27°C (81°F) 120 mm (4.7 in) 57°F (14°C) 2 inches (51 mm)
Jun 28°C (82°F) 82 mm (3.2 in) 64°F (18°C) 1.5 inches (39 mm)
Jul 28°C (83°F) 95 mm (3.7 in) 68°F (20°C) 0.7 inches (18 mm)
Aug 28°C (83°F) 130 mm (5.1 in) 69°F (20°C) 1 inches (25 mm)
Sep 28°C (83°F) 130 mm (5.1 in) 63°F (17°C) 1.7 inches (44 mm)
Oct 28°C (82°F) 135 mm (5.3 in) 55°F (13°C) 2.6 inches (67 mm)
Nov 27°C (80°F) 132 mm (5.2 in) 46°F (8°C) 5.4 inches (136 mm)
Dec 26°C (78°F) 92 mm (3.6 in) 40°F (5°C) 6.1 inches (156 mm)