How to Plan a Cheap Long Weekend to Any US City

This year I was lucky enough to visit three different US cities – Washington, D.C. over Easter weekend, Boston over the Fourth of July, and Seattle over a different weekend in July. Two of these trips (Washington, DC and Seattle) were done very cheaply and the other (Boston) was a bit more of a “treat yo self”, so I can definitely share some ways that you can save money while planning!

I try to do one cheap long weekend to somewhere in the US each year, and you can too with the following tips for how to plan a cheap and event-filled three or four days!


 

Washington Monument and cherry blossoms at the annual Kite Festival

Logistics

To go over holiday weekend or not?

One of the big questions you may have about your trip is when to go. Two of my trips this year were over holidays, and one was not. There are advantages and disadvantages to either.

The main advantage is that you may be able to use work holidays instead of vacation days, which is important to me since I hoard most of my vacation days and take one longer trip each year. You also may be able to do some extra fun things if you go during a holiday. For example, we attended the reading of the Declaration of Independence from the balcony of the Old State House (where it was first announced in 1776) while in Boston, which was one of the highlights of our trip. Easter weekend in DC happened to coincide with the kite festival (a part of the cherry blossom festivities each spring), and it was really cool to walk the National Mall and check out the hundreds (if not thousands) of kites!

Of course, in some places there will definitely be increased crowds if you go over a holiday, or depending on which holiday weekend flights and lodging could be more expensive or weather in that destination may not be ideal. You’ll have to weigh the pros and cons and decide which works best for your trip!

 

Using points or miles

I find these shorter trips are a great chance to use points or miles that I may have forgotten about otherwise, or that may take a long time to accumulate. If you’re a regular traveler you may be saving up your miles for an international flight, but look into other sources of points or discounts. Is there an airline you don’t fly often, but have a few miles saved up? Or a seldom-used travel credit card with points sitting around? How about hotel nights or points? Expedia points, for example, are sort of “extra” points in addition to your frequent flyer miles and travel credit card points, so they take a while to accrue, but you may have enough for $10/night on your hotel during your trip, which isn’t too bad!

I used some Expedia points on my trip to DC, and some of the credit card points from the Boston trip helped pay for about half my flight to Seattle. Some credit cards or employers offer extra discounts at museums, so look into those too before you go.

 

Visit friends or family

Do you have friends or family in the city you’re visiting? You may be able to stay with them to save some money, or at least they can recommend a well-located hotel, a cheap-but-delicious restaurant, or let you in on which museums are open for free one day of the week. Plus it can enrich the trip to meet up with people that you haven’t seen for some time, so be sure to consider this!

 

Plan ahead

Last minute deals are hard to come by, so it’ll help you out quite a bit to plan ahead. The Seattle trip was the most last-minute of the three this year, and by the time we started looking hotels were quite expensive. If you book something early (even something refundable, so you can cancel if a better deal comes along) you won’t run into this. It also gives you plenty of time to research public transportation, restaurants, and cheap or free attractions, as well as to track flight prices so you can swoop in when there’s a good deal.

 

View of Boston from the Salem ferry

Transportation

Consider red eye flights

Consider booking red eye flights (those very early in the morning or late in the day) for several reasons. First, because they are often the cheapest flights. The airports are usually uncrowded at these times, and you can get through security lines very quickly. The most important reason, however, is that three or four days really isn’t too long to spend in a new place, and you can make the most of it by arriving as early as possible in the morning the first day and leaving as late as possible on the last day of your trip. Also for this reason, it may make sense to pay a little extra for a direct flight so that you’re not “wasting” any of your valuable sightseeing time in airports or on planes.

 

Budget airlines

Okay, we all know that budget airlines can kinda suck. They generally have less legroom and fewer entertainment options than well-known brands, sometimes don’t offer snacks or refreshments, and are extremely sneaky with the baggage fees. But if you want your long weekend to be as cheap as possible, you’ve gotta make sacrifices. Occasionally you may be treated a little better on the budget airline if you have a co-branded credit card of theirs. It may eliminate or reduce the baggage fees, provide a discount on those pricey snacks, could allow seat upgrades, and at least lets you earn some extra points or miles for your troubles.

 

Pack light!

There are several reasons why this is important – firstly, because budget airlines have such exorbitant fees, sometimes even for carry-on bags. I flew Spirit Airlines to Seattle and saved almost $80 roundtrip by only bringing a “personal item”-sized backpack. Another reason that this is important is that it opens up more lodging and transportation options to you. Hotels can almost always accommodate you leaving your bags there before check-in time when you arrive and after check-out time the day you leave, but Airbnb’s often cannot. Even then, you have the additional time and transportation cost of getting back to the hotel before leaving for the airport. I generally take a Lyft or taxi when I have a carry-on suitcase with me, depending on how much I trust the public transportation and my ability to easily and quickly find my hotel, but if I only have a backpack, a train or subway will work just fine. And of course, you’re only going to be gone for three or four days – packing light should be easy! 😉

 

Use public transportation and walk as much as you can

Walking is the ideal way to get around when you travel, and depending on the city, might actually work as your main form of transportation. Walking is free and gets you out in the city, seeing things both on and off the beaten path. After walking, public transportation is your best bet. It’s cheap, easy in most cities, and lets you experience the city more like the locals would. In Boston I didn’t use any public transportation (hey, I said it was a “treat yo self” trip!) but I could have saved quite a bit of money doing so; probably $50-80.

When I travel I try to ask myself:

  1. Can I walk to this destination?
  2. Is there cheap public transportation that will get me there fairly quickly?
  3. Is there an interesting mode of travel I could take? (For example, we took a ferry between Boston and Salem and were able to enjoy the cool sea breeze and some extra sightseeing we wouldn’t have had otherwise.)
  4. If the answers to all of the previous questions are “no’s” then I’ll get a Lyft or taxi.

 

Rental cars and discounts

Of course, the previous questions don’t consider rental cars at all. If your chosen city isn’t very walkable, or doesn’t have a great public transportation system, and isn’t a scary place to drive, a rental car may be your cheapest option. Keep in mind parking costs in the city too – if they are high then using Lyft or Uber (with walking and public transportation) might be a cheaper option. And if you don’t use Lyft or Uber often, you should look into coupons or discounts (there are even some credit cards that offer Uber credits to your account each year).

 

Our hotel was quite close to Boston Common and Boston Public Garden

Lodging

Location, location, location

This is probably the most important thing to look at when choosing a hotel. If your hotel is close to the main center of activity and you can walk to the majority of your attractions, you can save a lot of money on transportation costs, so it might justify a higher price. If the ones in the middle of everything are very expensive (which they often are), at least try to get one that is quite close to public transportation. In Washington, DC, our hotel was just a couple of blocks from the Dupont Circle Metro station and it made it so easy to get to everything else. Be sure to look at maps of the city so you can tell if that “good deal” on a hotel in the suburbs might not be so good after all, if you have to spend $20 each way and an hour using transportation to get anywhere you want to go!

 

Think beyond hotels

When it came to Seattle, we were planning too late to get any good hotel rooms and since the trip was on a tight budget I’m not sure we would have been able to afford them anyway. Instead we ended up finding a good deal on an Airbnb. It was in a lovely neighborhood with lots of nice restaurant options, and we were able to use either public transportation or Lyft to get everywhere we needed to go. This saved us about $100/night (a little less with some increased transportation costs), so don’t forget about this option when you travel!

Depending on what time of year, when you go, and how adventurous you are, camping might be a good option too. KOAs are generally cheap and have showers and everything else you would need; renting cabins might eliminate the need to pack a tent when you go.

 

Share rooms with travel companions

In Boston we stayed in a wonderful hotel in a great location, very close to Boston Common. It wasn’t cheap, but we were able to save a little money by the three of us sharing one room. It was a little tight but we didn’t have any issues. If you’re traveling with a significant other you’re probably already planning on this, but consider it if traveling with friends too, especially if there are three or four of you, as the savings can be significant!

 

Factor in the value of hotel breakfast

If a hotel offers a free breakfast or even at least coffee, that can offset costs considerably. Reading hotel reviews and checking out pictures of the breakfast offerings can be really helpful, and depending on what’s offered it might completely make sense to spend an extra $10-20/night for a hotel with a great breakfast spread.

 

Delicious Seattle sushi

Food

Ask locals or hotel staff for restaurant recommendations

When you’re in tourist areas you can pretty much expect to pay tourist prices. But if you can get some insider information you may be able to save extra money on food, or at least be sure that the food will be worth what you’re paying! One of my friends on the Boston trip had been there a few times before, and she recommended a place with giant slices of pizza for only $5, and they were delicious. A co-worker’s son lives in Seattle, so I got a recommendation from him on a great sushi place before we went. This is one area that I often forget to research before a trip, but it can save you money and frustration if you do some leg work beforehand!

 

Consider having lunch as the “big” meal of the day

Most of us are used to having dinner or the evening meal as the biggest meal of the day, but dinner menus at restaurants are often more expensive than lunch ones. Consider having lunch as the “big” meal of the day when traveling, and eat a lighter dinner, either somewhere with cheap food or just have appetizers, etc. If your hotel has a fridge and microwave and isn’t too far from the restaurant you can sometimes bring back leftovers which also saves some money.

 

Search out cheap food and consider picnics

One of the best meals we had in Seattle was dim sum from a little restaurant in the International District where most people were ordering food to go. Prices were about 80 cents per piece so we were able to have a feast for a very low price and then sat in a lovely park to eat it. I’ve also had great success in other places creating a picnic by buying, for example, bread, cheese, and an apple from a nice grocery store or a market and pairing it with local wine. Cheap food like this or picnics can often be some of the best and most memorable meals eaten while traveling.

 

Remember that while you’re here, you’re not eating at home

Food expenses are an easy one to worry about while traveling. Especially if you cook all of your meals at home normally, restaurant prices can be a little scary. But remember that while you’re on your trip, you’re not eating at home. This is one expense that you would have either way, so calculate what you would spend on food for the time you’re gone at home and then add that to whatever you have budgeted for food. It can help!

 

Chihuly Garden and Glass

Attractions

Group attractions that are geographically close together

Visiting attractions that are close together on the same day or afternoon/morning just makes sense. It limits walking and transportation costs and reduces the feeling that you’re going back and forth all over the city all day. Yet many people fail to do this research before they go. Buying or downloading an actual physical map of the city can help too; since Google Maps is focused on navigation, it doesn’t give you a good idea of how close attractions are to each other unless you do a whole bunch of random searches on the distances between the places you want to go. Some cities make it easy too. Nearly all the Smithsonians and many of the memorials are on the National Mall in Washington, DC; Boston connects all its Revolutionary War sites via the easy-to-follow Freedom Trail; and Seattle groups the Space Needle, Chihuly Garden and Glass, and the Museum of Pop Culture together with a few other attractions in its center.

 

Research free attractions

Any city you go to will have free attractions, and a quick Google or Pinterest search might be all you need to find them. Washington, DC is full of them between the many monuments and memorials and Smithsonian museums. Doing advanced research can save quite a bit of money. The Center for Wooden Boats in Seattle offers free Sunday boat rides around Lake Union (the catch is you have to wait in line, hoping to get a spot). We really enjoyed ours, and wouldn’t have known about it without doing prior research, since it’s not really on the normal tourist circuit. Many museums will offer free admission once a month or one evening a week, and if you know those details you can take advantage of them to save quite a bit of money.

 

Groupon it up

Groupon can be an overlooked and surprisingly useful source of attraction discounts. I’ve seen everything from local cooking classes to nighttime ghost tours to whale watching to museum admissions heavily discounted on the site, so if there’s an attraction you’re a little hesitant to spend the money on, or your’e just curious what’s available in the city you’re visiting, be sure to check Groupon or other discount sites for deals!

 

Look into combination offers like CityPass to save money

You’re probably planning to visit multiple attractions in the city you’re visiting, and sometimes you can bundle them together to save money. In Seattle we were able to purchase combination tickets to the Space Needle and Chihuly Garden and Glass, which saved about $10. In Boston I booked a custom Go City card and added all the attractions I knew I would visit, which gave me a 20% discount on all of them and saved me a wait in line at a few places. Know which places you want to visit and search for package or city deals to save you extra money and allow you to skip lines!


How often do you like to visit new cities in your home country? Are there any valuable tips I missed? Please share in the comments below!

 

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