A Travel Price Comparison for United States of America Key West vs. Portland for Nightlife, Families, Couples, and Backpackers

Should you visit Key West or Portland?

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

Should I visit Key West 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.

Key West

Key West is a bustling, active, and lively town. This is a charming small with plenty of activities, too. This is also a very beautiful destination which attracts plenty of visitors. Because of its quaint atmosphere, it draws plenty of visitors, too. Other reasons to visit include food, scuba diving and snorkeling, and beaches.

Portland

Portland is a laid-back, progressive, and quirky city. It's a very nice small town not to be missed. It's a beautiful place to visit, too. And you can't forget about the nightlife, live music, and hiking.

Key West and Portland: Pros and Cons

Is there more to do in Key West or Portland?

Travelers will usually find more to do in Key West. Although Key West and Portland are popular destinations, Key West has more sights and attractions for tourists. Key West is very popular for its food, nightlife, resorts, scuba diving & snorkeling, beaches, historical sights, impressive beauty, and quaint atmosphere, while Portland attracts visitors for its museums, music, hiking, and shopping. Key West is more touristy than Portland and is popular for its festive nightlife, quirky town center, colorful personality, adrenaline-filled watersports, stunning beaches, turquoise water, and location at the southernmost point of the continental U.S. It is also well known for Duval Street. Portland is famous for its independent and vintage shops, thriving art scene, lush parks and gardens, progressive and quirky personality, and easy access to amazing natural beauty.

How is Key West different from Portland?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Portland and Key West. Then, you can decide for yourself which place is better for your next trip.

Are the Museums and Historical Sights Better in Key West or Portland?

Portland is a moderate city for its sights and museums. However, Key West does not have museums and landmarks.

Portland offers a handful of options for museums and historical sights. Visitors usually come for the city's outdoor recreation and eclectic personality more than the landmarks and museums. There are a few places to visit on a rainy day though including Pittock Mansion, the Portland Art Museum, and the Oregon Museum of Science and Industry.

Key West does not have museums and landmarks.

Is the Food Better in Key West or Portland? Which Destination has the Best Restaurants?

Key West is a town with good options for its restaurants. However, Portland is lacking in good options for its restaurant scene.

There are plenty of up and coming restaurants around Key West. Head to town for local restaurants with quirky atmospheres. There are many local dishes to sample, be the town is most known for its stone crabs, conch fritters, and Mahi Mahi sandwiches. You'll also find cold drinks and waterfront dining areas.

You'll find the standard options when it comes to food in Portland. The town is more famous for it's craft beer than it's food, but there are still a number of local restaurants that offer unique Oregon dishes. You'll find no shortage of vegetarian and vegan options on most menus. There is also a big farm-to-table scene with many farmers markets around town as well.

Is Key West or Portland Better for Nightlife?

Key West is a very popular place for nightlife. Also, Portland is not quite as popular, but is fairly good for nightlife and partying.

Key West has a large number of nightlife venues. This area has some of the most lively nightlife in the Florida Keys. There are quirky bars and fun hangouts where you can spend the evening. The party starts at Mallory Square around sunset and many bars stay open well into the early hours. You can also enjoy sunset cruises or pass your time at one of the many tiki bars.

Portland has an active nightlife scene for those who seek it out. Famously, this town's nightlife is all about the craft beer and local breweries. Make sure you check out Bailey's Taproom, The Big Legrowlski, and The Commons Brewery.

Is Key West or Portland Better for Music?

Portland is a popular place for its live music scene. However, Key West is not a live music destination.

The music scene in Portland is active and vibrant. The town has a thriving live music and international folk dancing scene.

Key West is not a live music destination.

Is Key West or Portland Better for Resorts?

Key West is a very popular place for its luxury resorts. However, Portland is not a resort destination.

In Key West, you'll find some of the region's top resorts. There are a number of high end resorts around the island, many with recognizable names such as the Hyatt and Hilton. Prices can be high, but these resorts often come with reliable luxury.

Portland is not a resort destination.

Is Key West or Portland Better for Scuba Diving and Snorkeling?

Key West is a town with good options for the nearby scuba diving and snorkeling. However, Portland is not a scuba or snorkeling destination.

It's fun to get in the water and check out the local marine life in Key West. There are a number of dive shops and snorkeling excursions that leave from Key West. Like many tourist areas these days, the coral shows its damage from the crowds, but you'll likely see some barracuda or a Grouper.

Portland is not a scuba or snorkeling destination.

Is Key West or Portland Better for Beaches?

Key West is a very popular place for its beaches. However, Portland is not a beach destination.

The beaches at Key West attract visitors from all over. One of the best beaches in the area is Fort Zachary Taylor Historic State Park. The beach has soft sand and stunning turquoise water. As is typical in the Keys, the water stays shallow for great distances.

Portland is not a beach destination.

Is Key West or Portland Better for its Old Town?

Key West is a very popular place for its historic old town. However, Portland does not have a historic old town.

Key West is an extremely popular place to visit the historic old town area. The town has the most charming Old Town areas in the Florida Keys. Head to Mallory Square for the sunset street performers and explore the historic streets around Duval Street.

Portland does not have a historic old town.

Is Key West or Portland Better for Hiking?

Portland is notable for the nearby hiking options. However, Key West is not a hiking destination.

Portland is a popular spot for hiking. Just outside of town you'll find amazing hikes and stunning natural beauty. In town there are many urban hikes through parks and gardens, but in just a short drive you also have access to Mount Hood and many of the region's most beautiful hikes around the Columbia River Gorge.

Key West is not a hiking destination.

Is the Shopping Better in Key West or Portland?

Portland is a popular place for its shopping opportunities. However, Key West is a mediocre town for its shopping areas.

Portland offers some nice shopping areas. To fully experience shopping in town, head to the local vendors and thrift shops. There are many vintage clothing shops, book stores, and independent sellers around town. The city is also full of farmers markets. For some of the most interesting shopping, check out the Pearl District, Pioneer Place, Union Way, and Downtown neighborhoods.

Key West has some good spots for those that want to go shopping. While it definitely has its share of gimmicky souvenir shops and t-shirt stores, there are still a number of art galleries and local shops around Key West where you can enjoy shopping.

Is Key West or Portland Better for Families?

Key West is a very popular place for its kid-friendly activities. Also, Portland is not quite as popular, but is fairly good for its family-friendly activities.

Key West is a very family-friendly destination. Families that enjoy snorkeling, aquariums, water sports, and exploring new places will enjoy visiting this part of the Florida Keys. There are many ways to get out on the water from kayaking and snorkeling to glass bottom boat tours and sunset cruises. There are also many kid-friendly beaches in the area. The town can have a party atmosphere, but it's not hard to find a more family-friendly area where everyone can have fun.

You'll find plenty of kid-friendly things to do in Portland. This is an outdoor city by nature, so families will appreciate the many parks and outdoor recreational activities around town. It's easy to fill a couple of days exploring and having fun with the kids. Kid-friendly activities include the zoo, the aerial tram, and several great museums.

Is Key West or Portland Better for Couples?

Key West is a very popular place for romance. Also, Portland is not quite as popular, but is fairly good for its romantic activities.

Key West makes for a fun place to visit for a couple. From Mallory Square to the beautiful nearby parks, Key West makes a wonderful, romantic destination. Whether it's your honeymoon, an anniversary, or simply a couples' retreat, Key West is a great option. You can sip wine on a sunset cruise or dine at one of the many character-filled restaurants in town. If you are looking for a party, it's not hard to find, but if you want a more laid back holiday, that's also possible.

Portland makes for a fun place to visit for a couple. The laid-back, alternative vibe is fun to explore as a couple. There are independent bookstores, nice parks, and plenty of outdoor activities to choose from. Couples who enjoy an eclectic city, breweries, and nature, will find a lot to do in town.

Is Key West or Portland Better for Backpackers and Budget Travelers?

Portland is notable for backpackers. However, Key West is a mediocre town for backpackers and budget travelers.

Portland is a great city to visit for backpackers. The town has drawn young explorers for years, and backpackers who like to step away from the mainstream will feel right at home here.

Key West is a challenging destination for budget travelers and backpackers due to the higher prices. Key West is a pretty expensive destination, but there are Airbnbs and even a hostel or two that cater to budget backpackers.

Is Key West or Portland Better for Students?

Key West is a very popular place for its student-friendly activities. Also, Portland is not quite as popular, but is fairly good for students.

Students come from all over to stay in Key West. It's a great spring break destination with a quirky personality and many great activities.

Portland is popular with students. It's a young and relaxed city that attracts independent thinkers. There are many bookstores and breweries around town. The cost of living can be a bit high though.

Is Key West or Portland Better for Public Transit? Which Is Easier to Get Around Without a Car?

Portland is a popular place for its public transit. However, Key West is a mediocre town for times when you don't have a car.

Portland has a few public transit options. The town has a bus and light rail system as well the Aerial tram.

Public transit is quite limited in Key West. Public transportation in Key West is limited to a few buses.

Is Key West or Portland a more walkable city?

Portland is notable for its high level of walkability. Also, Key West is not as famous, but is still a good town to visit for its ease of walking around.

Portland is a very walkable city. It is quite walkable, particularly in the tourist areas such as Downtown, Pearl, and Old Town Chinatown.

Key West is a somewhat walkable town. The town is the most walkable part of the Florida Keys. The area around Mallory Square and Duval Street is the most pedestrian friendly.

For even more information, also check out Is Key West Worth Visiting? and Is Portland Worth Visiting?.

Should I spend more time in Portland or Key West?

How long in Key West or Portland?

Visitors can find plenty of fun things to do in both Key West and Portland. With generally more activities and things to do, visitors tend to spend more time in Key West than in Portland. Usually, 5-7 days is a good amount of time for Key West, and 2-3 days is enough time in Portland.

Families should spend more time in Key West than Portland. Because of the many family-friendly attractions and fun things to do for kids in Key West, it's a great place to visit with the whole family.

Couples should spend more time in Key West than Portland. You'll find plenty of romantic sights and fun activities in Key West that are great for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Portland than Key West if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Portland.

One day in Key West or Portland?

The beautiful town of Key West offers nightlife and food. Exploring the old town is a popular activity. With so much to do, one day is probably not enough time to see everything. It will give you the chance to have new experiences.

The city of Portland offers nightlife and live music. Many visitors also spend a good bit of time hiking. With so much to do, one day is probably not enough time to see everything. It will give you the chance to have new experiences.

A weekend in Key West or Portland?

Key West is a popular place that is full of things to see and experience. People enjoy relaxing at one of the resorts. But since there are so many activities, you'll likely want to spend more than a weekend exploring. Take your pick from the many activities offered here.

Portland is a popular place that is full of things to see and experience. If you have a weekend, this city makes for a great vacation. Make sure you spend some time hiking while you're in the area. While some people choose to spend more or less time in Portland, a weekend is sufficent for most. Take your pick from the many activities offered here.

Five days in Key West or Portland?

Key West is a popular choice for travelers. Five days here is typical. While some people choose to spend more or less time in Key West, five days is sufficent for most. The entire region has so many activities, and you'll want time to do everything.

Portland is a popular choice for travelers. Five days is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips. The entire region has so many activities, and you'll want time to do everything.

A week in Key West or Portland?

Key West is a great place to explore. It is common to spend one week here. Visiting the old town is also a must. One week is a great amount of time to relax and see the many things that Key West has to offer. This town offers something for everyone.

Portland is a great place to explore. Hiking can easily take up a good amount of your time here, too. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. This city offers something for everyone.

For some great organized tour ideas, see The Best One-Week (7-Day) Tours from Los Angeles, The Best One-Week (7-Day) Tours from New York City, The Best 2-Week Tours from New York City, and The Best 2-Week Tours from Anchorage.

When we compare the travel costs of actual travelers between Key West and Portland, we can see that Key West is more expensive. And not only is Portland much less expensive, but it is actually a significantly cheaper destination. So, traveling to Portland would let you spend less money overall. Or, you could decide to spend more money in Portland 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 Portland.

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 Portland Expensive?.

Which is Bigger, Key West or Portland?

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

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 Key West or Portland in the Summer?

Both Portland and Key West during the summer are popular places to visit. Many visitors come to Key West in the summer for the beaches, snorkeling, the small town charm, and the family-friendly experiences. Furthermore, most visitors come to Portland for the hiking, the small town charm, the music scene, and the family-friendly experiences during these months.

In July, Key West is generally a little warmer than Portland. Daily temperatures in Key West average around 84°F (29°C), and Portland fluctuates around 68°F (20°C).

In Portland, it's very sunny this time of the year. It's quite sunny in Key West. In the summer, Key West often gets around the same amount of sunshine as Portland. Key West gets 328 hours of sunny skies this time of year, while Portland receives 338 hours of full sun.

Key West usually gets more rain in July than Portland. Key West gets 3.3 inches (83 mm) of rain, while Portland receives 0.7 inches (18 mm) of rain this time of the year.

Should I visit Key West or Portland in the Autumn?

The autumn attracts plenty of travelers to both Key West and Portland. Most visitors come to Key West for the shopping scene, the small town atmosphere, and the natural beauty of the area during these months. Furthermore, 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.

Key West is much warmer than Portland in the autumn. The daily temperature in Key West averages around 80°F (27°C) in October, and Portland fluctuates around 55°F (13°C).

In Key West, it's very sunny this time of the year. Key West usually receives more sunshine than Portland during autumn. Key West gets 258 hours of sunny skies, while Portland receives 155 hours of full sun in the autumn.

Key West gets a good bit of rain this time of year. In October, Key West usually receives more rain than Portland. Key West gets 5.1 inches (129 mm) of rain, while Portland receives 2.6 inches (67 mm) of rain each month for the autumn. The hurricane season in Key West is June to November.

Should I visit Key West or Portland in the Winter?

The winter brings many poeple to Key West as well as Portland. The winter months attract visitors to Key West because of the shopping scene and the cuisine. Additionally, 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 the winter, Key West is much warmer than Portland. Typically, the winter temperatures in Key West in January average around 70°F (21°C), and Portland averages at about 40°F (4°C).

People are often attracted to the plentiful sunshine in Key West this time of the year. In the winter, Key West often gets more sunshine than Portland. Key West gets 252 hours of sunny skies this time of year, while Portland receives 86 hours of full sun.

It's quite rainy in Portland. Key West usually gets less rain in January than Portland. Key West gets 1.7 inches (43 mm) of rain, while Portland receives 5.2 inches (132 mm) of rain this time of the year.

Should I visit Key West or Portland in the Spring?

Both Portland and Key West are popular destinations to visit in the spring with plenty of activities. The beaches, the small town charm, and the natural beauty are the main draw to Key West this time of year. Also, many travelers come to Portland for the small town charm and the natural beauty.

In April, Key West is generally much warmer than Portland. Daily temperatures in Key West average around 77°F (25°C), and Portland fluctuates around 51°F (11°C).

It's quite sunny in Portland. The sun comes out a lot this time of the year in Key West. Key West usually receives more sunshine than Portland during spring. Key West gets 326 hours of sunny skies, while Portland receives 231 hours of full sun in the spring.

In April, Key West usually receives less rain than Portland. Key West gets 0.8 inches (21 mm) of rain, while Portland receives 2.4 inches (61 mm) of rain each month for the spring. June to November is the hurricane season in Key West.

Typical Weather for Portland and Key West