A Travel Price Comparison for United States of America Winston-Salem vs. Portland, Maine for Food, Nightlife, Families, and Couples

Should you visit Winston-Salem or Portland, Maine?

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

Should I visit Winston-Salem or Portland, Maine? 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.

Winston-Salem

Winston-Salem is a friendly, under-rated, and welcoming city. Other popular activities here include shopping, museums, and nightlife. See Winston-Salem travel costs.

Portland, Maine

Portland, Maine is a laid-back, scenic, and picturesque coastal town. With stunning beauty, Portland, Maine attracts visitors from all around. Other popular activities here include beaches, hiking, and shopping. See Portland, Maine travel costs.

Winston-Salem and Portland, Maine: Pros and Cons

Pros
  • Popular museums and historical sights
  • Active nightlife
  • Scenic old town
  • Family-friendly
  • Good for students
Things to Consider
  • Less popular with couples
Pros
  • Active nightlife
  • Popular beach
  • Good for hiking
  • Popular at Christmas
  • Known for its beauty
  • Family-friendly
  • Good for couples and romance
  • Impressive beauty


Is there more to do in Winston-Salem or Portland, Maine?

Visitors will generally find more to do in Portland, Maine than Winston-Salem. While Winston-Salem is larger than Portland, Maine, Portland, Maine has more sights, attractions, and activities for tourists. Portland, Maine is very popular for its beaches, hiking, and impressive beauty, while Winston-Salem attracts visitors for its museums and attractions and historical sights. Portland, Maine is more touristy than Winston-Salem and is known for its seafood restaurants, scenic lighthouse, and coastal walks. It is also well known for The Portland Head Light. Winston-Salem is famous for it's southern character and quaint college campuses.

How is Winston-Salem different from Portland, Maine?

Which is Better for a Holiday?

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

Are the Museums and Historical Sights Better in Winston-Salem or Portland, Maine?

Winston-Salem
Portland, Maine

Winston-Salem is a popular place for its museums and landmarks. However, Portland, Maine does not have museums and landmarks.

If you're looking for an educational opportunity, there are a decent number of museums and historical sights around Winston-Salem. Old Salem has a nice concentration of museums and gardens. Outside of the old town you'll find several art museums like the Museum of Early Southern Decorative Arts and the Reynolda House Museum of American Art.

Portland, Maine does not have museums and landmarks.


Is the Food Better in Winston-Salem or Portland, Maine? Which Destination has the Best Restaurants?

Winston-Salem
Portland, Maine

There are opportunities to sample the local cuisine at nice restaurants in both Winston-Salem and Portland, Maine.

There are many up and coming restaurants in the Winston-Salem area. North Carolina barbecue is popular around town. The city is also the birthplace of Krispy Kreme donuts and during the holiday season you should sample the local Moravian Cookies.

There are plenty of up and coming restaurants around Portland, Maine. The town has grown into a foodie destination that takes advantage of its waterfront setting. Many restaurants make use of the fresh seafood with lobster rolls and oysters on the half shell being popular. You'll also find a lot of dishes that use haddock and whole lobsters.

Is Winston-Salem or Portland, Maine Better for Nightlife?

Winston-Salem
Portland, Maine

Evening events are nice in both Winston-Salem and Portland, Maine.

There's a variety of activities in the evening in Winston-Salem. Local breweries are popping up around town. You'll also find active nightlife venues near the colleges and universities.

With a handful of venues, visitors can find a fairly lively vibe in Portland, Maine. The city has many microbreweries, wine bars, taverns, and pubs. You'll find many places concentrated in the Old Port, which has a charming and fun atmosphere.

Is Winston-Salem or Portland, Maine Better for Beaches?

Winston-Salem
Portland, Maine

Portland, Maine is notable for the beach. However, Winston-Salem is not a beach destination.

Portland, Maine is considered a top beach destination. It has many sandy and calm beaches. The water may be too cold to swim, but the beaches are perfect for flying a kite or hanging out with family.

Winston-Salem is not a beach destination.


Is Winston-Salem or Portland, Maine Better for its Old Town?

Winston-Salem
Portland, Maine

Winston-Salem is a popular place for its historic old town charm. However, Portland, Maine does not have a historic old town.

Winston-Salem offers a nice historic old town area. Nearby Old Salem is filled with historic museums, gardens, and restaurants. A ticket is required for most of the venues, but the atmosphere and architecture are charming.

Portland, Maine does not have a historic old town.

Is Winston-Salem or Portland, Maine Better for Hiking?

Winston-Salem
Portland, Maine

Portland, Maine is a popular place for the nearby hiking options. However, Winston-Salem is not a hiking destination.

Portland, Maine is a good destination for hiking. In addition to bike trails, there are several good hikes in the area.

Winston-Salem is not a hiking destination.

Is the Shopping Better in Winston-Salem or Portland, Maine?

Winston-Salem
Portland, Maine

Both Winston-Salem and Portland, Maine are nice shopping destinations.

Many visitors go to Winston-Salem to go shopping. You'll find a mix of larger shopping malls, retail outlets, and shopping centers around town.

Plenty of visitors enjoy shopping while in Portland, Maine. The town has many nice local boutiques to explore. Head downtown for the best local venues and the most interesting shopping opportunities.


Is Winston-Salem or Portland, Maine More Beautiful?

Winston-Salem
Portland, Maine

Portland, Maine is notable for its scenery and beauty. However, Winston-Salem is not a destination known for its beauty.

With stunning beauty, Portland, Maine attracts visitors from all around. Set against the water's edge, the town offers many beautiful scenes and picturesque settings.

Winston-Salem is not a destination known for its beauty.

Is Winston-Salem or Portland, Maine Better for Families?

Winston-Salem
Portland, Maine

Kids will enjoy a visit to either Winston-Salem or Portland, Maine.

Winston-Salem is a family-friendly place to visit. There are interactive museums like the Kaleideum science museums. There are also outdoor parks and playgrounds, kid-friendly restaurants, and a children's theater.

Portland, Maine is a family-friendly city. It is a charming town with a number of kid-friendly museums, walks, and waterfront activities. You can visit the Portland Observatory, Bug Light Park, or grab ice cream in the Old Port. There are also children's museums such as the Children's Museum & Theatre of Maine.

Is Winston-Salem or Portland, Maine Better for Couples?

Winston-Salem
Portland, Maine

Portland, Maine is a popular place for couples. However, Winston-Salem is a mediocre city for romance.

Portland, Maine is a good coastal town for couples to visit. Couples will enjoy the beautiful waterfront setting, the fine dining restaurants, and everything that the city has to offer. Head to the Old Port for romantic restaurants and a great atmosphere or catch a show at Portland Stage.

Winston-Salem is not the best destination for a couple to visit. There are restaurants and movie theaters that make for a nice date night. There are also parks and walks that will get you outdoors.


Is Winston-Salem or Portland, Maine Better for Students?

Winston-Salem
Portland, Maine

Winston-Salem is a popular place for students. However, Portland, Maine is not popular with students.

Winston-Salem is popular with students. Wake Forest University as well as colleges such as Salem College give parts of the city a collegiate vibe.

Portland, Maine is not popular with students.

Is Winston-Salem or Portland, Maine Better for Public Transit? Which Is Easier to Get Around Without a Car?

Winston-Salem
Portland, Maine

Winston-Salem is a city with a few options for its public transit. However, Portland, Maine is not particularly known for times when you don't have a car.

Public transit is generally limited in Winston-Salem. There are bus routes, but they are limited in their frequency and convenience, making a car essential for most visitors.

Public transit is quite limited in Portland, Maine. There is a very basic bus system but you really must have a car to explore the city.

Is Winston-Salem or Portland, Maine a more walkable city?

Winston-Salem
Portland, Maine

Winston-Salem and Portland, Maine both are reasonable when exploring on foot.

Winston-Salem is generally not very walkable. The downtown area is the most pedestrian-friendly part of town, but most of the city requires a car.

Portland, Maine is generally not a very walkable city. Downtown is very walkable but if you want to travel to other areas you'll need a car.


For even more information, also check out Is Winston-Salem Worth Visiting? and Is Portland, Maine Worth Visiting?.

Should I spend more time in Portland, Maine or Winston-Salem?

How long in Winston-Salem or Portland, Maine?

Visitors can find plenty of fun things to do in both Winston-Salem and Portland, Maine. With generally more activities and things to do, visitors tend to spend more time in Portland, Maine than in Winston-Salem. Usually, 1-2 days is a good amount of time for Winston-Salem, and 2-3 days is enough time in Portland, Maine.

Couples should spend more time in Portland, Maine than Winston-Salem. You'll find plenty of romantic sights and fun activities in Portland, Maine that are perfect for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Portland, Maine than Winston-Salem 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, Maine.


  • How many days in Winston-Salem or Portland, Maine? Ideal Length of Stay
    Winston-Salem 1-2 
    Portland, Maine 2-3

One day in Winston-Salem or Portland, Maine?

The welcoming destination of Winston-Salem offers nightlife and food. Take your pick from the many activities offered here. One day is usually enough time to experience most activities.

Many travelers enjoy the shopping and nightlife when visiting the picturesque destination of Portland, Maine. You'll find plenty of activities on the beach. Your budget might influence how long you stay. Since there is so much to do in the area, one day is probably not enough for all of it.

A weekend in Winston-Salem or Portland, Maine?

The city of Winston-Salem offers food and shopping. A weekend here is typical. The entire region has so many activities, and you'll want time to do everything. A weekend is often enough time to do most activities.

It's hard to know how much time to spend in Portland, Maine. Most people come for the beaches. It has many unique tourist attractions and fascinating things to do. For many, it makes a great getaway for a weekend. A weekend is usually enough time to experience most activities.

Five days in Winston-Salem or Portland, Maine?

Winston-Salem is a great place to explore. This city offers something for everyone. Most people find that five days is more than enough time to see everything.

Travelers enjoy the food and shopping when visiting the seaside destination of Portland, Maine. Many visitors spend time at the beach while visiting the area. This coastal town offers a variety of activities to choose from. 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.


A week in Winston-Salem or Portland, Maine?

Many people enjoy the museums and nightlife when visiting Winston-Salem. The length of your trip often depends on your style of travel. One week is plenty of time to see everything, even with extra days to spare.

You'll find shopping and nightlife around the beautiful coastal town of Portland, Maine. People usually spend lots of time at the beach. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. The length of your ideal trip is an individual decision.


For some great organized tour ideas, see The Best Train & Rail Tours in United States of America, The Best Sightseeing Tours in United States of America, The Best Cruise Tours and Packages in United States of America, and The Best Cultural Tours in United States of America.


Which place is cheaper, Portland, Maine or Winston-Salem?

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

  • Winston-Salem Prices
    USA Prices
    Portland, Maine Prices
    USA Prices
  • Average Daily Cost Per person, per day
    Winston-Salem $181
    Portland, Maine $227

The average daily cost (per person) in Winston-Salem is $181, while the average daily cost in Portland, Maine is $227. 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 Winston-Salem and Portland, Maine in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Winston-Salem $91
    Portland, Maine $115
  • Accommodation Typical double-occupancy room
    Winston-Salem $182
    Portland, Maine $230
Compare Hotels in Winston-Salem and Portland, Maine

Looking for a hotel in Winston-Salem or Portland, Maine? 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 Winston-Salem


Hotels in Portland, Maine


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: Winston-Salem Hotel Prices and Portland, Maine Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Winston-Salem $23
    Portland, Maine $34

Hired Cars and Shuttles in Portland, Maine

Some specific examples of transportation prices in Portland, Maine:

  • Private Transfer from Portland city to Portland Cruise Port: $75
  • Private Transfer from Portland Cruise Port to Portland city: $75
  • Private Transfer from Portland Port to Portland Jetport (PWM): $136

Is it cheaper to fly into Winston-Salem or Portland, Maine?

Prices for flights to both Portland, Maine and Winston-Salem 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
    Winston-Salem $73
    Portland, Maine $84

Typical Food Prices in Portland, Maine

Below are a few samples from actual travelers for food and meal costs in Portland, Maine:


  • Breakfast for 2
    $17
  • Dinner for 2
    $30

Food Tours and Cooking Classes in Portland, Maine

Also, here are some specific examples of food and dining related activities in Portland, Maine.

  • Portland: Walking Food Tour – Warm Donuts & History: $57

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Winston-Salem $20
    Portland, Maine $39

Tours and Activities in Winston-Salem

Some specific costs of activities, tours, and entrance tickets for Winston-Salem are as follows:

  • Old Salem's Ghost Self Guided Outside Walking Tour: $7.75
  • Winston-Salem Historic Guided Walking Tour: $19
  • Winston-Salem True Crime Tour: $19
  • Winston Salem African American History Tour: $19
  • Carolina History & Haunts Winston-Salem Historical Ghost Tour: $26

Tours and Activities in Portland, Maine

Here are a few actual costs in Portland, Maine for available activities, ticket prices, and tours:

  • Audio Guided Walking Tour from Old Port of Portland, Maine: $7.75
  • Historical Walking Tour of Portland’s Old Port District: $7.99
  • Scavenger Hunt Adventure in Portland by Crazy Dash: $10
  • Portland Maine Self-Guided Walking Audio Tour: $12
  • Ultimate Portland Self-Guided Driving GPS Audio Tour: $15
  • Portland Maine Self-Guided Driving & Walking Audio Tour Bundle: $20
  • 2-Hour Portland Old Port Ghost Walking Tour: $29
  • Port City Lights Cruise: $39
  • Portland: Sightseeing Cruise to Portland Head Light: $41
  • Vintage Fire Truck Sightseeing Tour of Portland Maine: $42
  • Tour in Vintage Fire Engine: $43
  • Portland: Land and Sea Tour Duck Tour with a Guide: $47

Alcohol
  • Alcohol Drinks for one day
    Winston-Salem $24
    Portland, Maine $24

Sample the Local Flavors in Portland, Maine

Here are a few nightlife and alcohol tours and activities from local tour providers in Portland, Maine:

  • Portland Old Port Wine Tasting Walking Tour: $99
  • Local Brewery & Spirits Bus Tour: $99
  • Old Port Brewery & Pub Walking Tour: $99


When we compare the travel costs of actual travelers between Winston-Salem and Portland, Maine, we can see that Portland, Maine is more expensive. And not only is Winston-Salem much less expensive, but it is actually a significantly cheaper destination. So, traveling to Winston-Salem would let you spend less money overall. Or, you could decide to spend more money in Winston-Salem 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 Portland, Maine would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Portland, Maine than you might in Winston-Salem.

If you're trying to decide if either of these two destinations are within your price range, also see Is Winston-Salem Expensive? and Is Portland, Maine Expensive?.


Which is Bigger, Winston-Salem or Portland, Maine?

Winston-Salem has a larger population, and is about 3 times larger than the population of Portland, Maine. When comparing the sizes of Winston-Salem and Portland, Maine, 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 Winston-Salem or Portland, Maine?

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Winston-Salem or Portland, Maine in the Summer?

The summer attracts plenty of travelers to both Winston-Salem and Portland, Maine. The summer months attract visitors to Winston-Salem because of the family-friendly experiences. Furthermore, the beaches, the hiking, and the family-friendly experiences are the main draw to Portland, Maine this time of year.

Winston-Salem is a little warmer than Portland, Maine in the summer. The daily temperature in Winston-Salem averages around 81°F (27°C) in July, and Portland, Maine fluctuates around 69°F (20°C).

People are often attracted to the plentiful sunshine in Portland, Maine this time of the year. In Winston-Salem, it's very sunny this time of the year. Winston-Salem usually receives around the same amount of sunshine as Portland, Maine during summer. Winston-Salem gets 273 hours of sunny skies, while Portland, Maine receives 282 hours of full sun in the summer.

Winston-Salem gets a good bit of rain this time of year. In July, Winston-Salem usually receives more rain than Portland, Maine. Winston-Salem gets 4.4 inches (112 mm) of rain, while Portland, Maine receives 2.6 inches (66 mm) of rain each month for the summer.


  • Summer Average Temperatures July
    Winston-Salem 81°F (27°C) 
    Portland, Maine 69°F (20°C)

Should I visit Winston-Salem or Portland, Maine in the Autumn?

The autumn brings many poeple to Winston-Salem as well as Portland, Maine. The shopping scene are the main draw to Winston-Salem this time of year. Additionally, many travelers come to Portland, Maine for the hiking trails, the shopping scene, and the natural beauty of the area.

In the autumn, Winston-Salem is much warmer than Portland, Maine. Typically, the autumn temperatures in Winston-Salem in October average around 62°F (17°C), and Portland, Maine averages at about 49°F (9°C).

People are often attracted to the plentiful sunshine in Winston-Salem this time of the year. In the autumn, Winston-Salem often gets more sunshine than Portland, Maine. Winston-Salem gets 212 hours of sunny skies this time of year, while Portland, Maine receives 196 hours of full sun.

Winston-Salem usually gets less rain in October than Portland, Maine. Winston-Salem gets 3 inches (75 mm) of rain, while Portland, Maine receives 3.3 inches (84 mm) of rain this time of the year.


  • Autumn Average Temperatures October
    Winston-Salem 62°F (17°C) 
    Portland, Maine 49°F (9°C)

Should I visit Winston-Salem or Portland, Maine in the Winter?

Both Portland, Maine and Winston-Salem are popular destinations to visit in the winter with plenty of activities. Many travelers come to Winston-Salem for the museums, the shopping scene, and the cuisine. Also, many visitors come to Portland, Maine in the winter for the Christmas ambience, the shopping scene, and the cuisine.

Portland, Maine can get quite cold in the winter. Be prepared for some very cold days in Winston-Salem. In January, Winston-Salem is generally much warmer than Portland, Maine. Daily temperatures in Winston-Salem average around 40°F (4°C), and Portland, Maine fluctuates around 21°F (-6°C).

Winston-Salem usually receives around the same amount of sunshine as Portland, Maine during winter. Winston-Salem gets 169 hours of sunny skies, while Portland, Maine receives 163 hours of full sun in the winter.

In January, Winston-Salem usually receives around the same amount of rain as Portland, Maine. Winston-Salem gets 3.2 inches (82 mm) of rain, while Portland, Maine receives 3.4 inches (86 mm) of rain each month for the winter.


  • Winter Average Temperatures January
    Winston-Salem 40°F (4°C) 
    Portland, Maine 21°F (-6°C)

Should I visit Winston-Salem or Portland, Maine in the Spring?

Both Portland, Maine and Winston-Salem during the spring are popular places to visit. Also, most visitors come to Portland, Maine for the beaches and the natural beauty during these months.

Winston-Salem is much warmer than Portland, Maine in the spring. The daily temperature in Winston-Salem averages around 61°F (16°C) in April, and Portland, Maine fluctuates around 43°F (6°C).

In Portland, Maine, it's very sunny this time of the year. It's quite sunny in Winston-Salem. In the spring, Winston-Salem often gets more sunshine than Portland, Maine. Winston-Salem gets 248 hours of sunny skies this time of year, while Portland, Maine receives 212 hours of full sun.

Winston-Salem usually gets around the same amount of rain in April as Portland, Maine. Winston-Salem gets 3.1 inches (80 mm) of rain, while Portland, Maine receives 3.3 inches (85 mm) of rain this time of the year.


  • Spring Average Temperatures April
    Winston-Salem 61°F (16°C) 
    Portland, Maine 43°F (6°C)

Typical Weather for Portland, Maine and Winston-Salem

Winston-Salem Portland, Maine
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 40°F (4°C) 3.2 inches (82 mm) 21°F (-6°C) 3.4 inches (86 mm)
Feb 43°F (6°C) 3.4 inches (86 mm) 24°F (-5°C) 3.5 inches (89 mm)
Mar 52°F (11°C) 3.7 inches (94 mm) 33°F (1°C) 3.6 inches (91 mm)
Apr 61°F (16°C) 3.1 inches (80 mm) 43°F (6°C) 3.3 inches (85 mm)
May 69°F (21°C) 3 inches (77 mm) 53°F (12°C) 3.3 inches (85 mm)
Jun 77°F (25°C) 3.9 inches (99 mm) 63°F (17°C) 3.1 inches (79 mm)
Jul 81°F (27°C) 4.4 inches (112 mm) 69°F (20°C) 2.6 inches (66 mm)
Aug 80°F (26°C) 4.3 inches (109 mm) 67°F (20°C) 2.6 inches (66 mm)
Sep 73°F (23°C) 3.5 inches (90 mm) 59°F (15°C) 3.1 inches (78 mm)
Oct 62°F (17°C) 3 inches (75 mm) 49°F (9°C) 3.3 inches (84 mm)
Nov 53°F (12°C) 2.6 inches (67 mm) 39°F (4°C) 4.8 inches (123 mm)
Dec 44°F (7°C) 3.1 inches (80 mm) 27°F (-3°C) 4.1 inches (103 mm)