Maximizing Weekend Getaways For Fun While Minimizing Cost

weekend-getawayWeekends! The joy of anyone living in the workaday world. We’ve got to make the most of them because sometimes it’s the only thing to work for. Although I can’t really complain about the ~5 weeks I’ve had off this year, this basically means doing my best to make the weekends a blast. And I sure do a good job of that. I’m rarely at my apartment in New Haven on weekends. In fact, I’ve been gone the last four weekends, and I barely spent a weekend at home the past summer, too.

But it’s not about shelling out a ton of money on flights, hotels, and restaurants for these short getaways. It’s really about leveraging the connections that you have to make the most of what’s close by. Some of my recent trips have been to Vermont, Boston, Rhode Island, and Chicago. Here’s how I manage to do it all.

Travel with friends

This was the best part about our recent trip to Vermont. We rented an awesome house that went for about $500 per night! But we split the cost 11 ways, so it ended up only costing $90 each for the weekend. We enjoyed the 8-person hot tub, pool table, fireplace, large kitchen and more for a budget price. Plus, it was a lot of fun to just hang out with friends.

Cheaper accommodations

I’m always up for camping, and it’s always a deal compared to just about any other way to stay. We camped during my trip in August, and most campgrounds are only $10-$20 per night. Of course, staying for free with people you know can’t really be beat, either.

Stretch the weekend

When I’m heading out of town for  the weekend, I want to make it’s worth my while if I’m going to travel for 2+ hours. Lately, I’ve been leaving work as early as possible on Friday (around 4pm) and traveling back Monday morning. It’s a little tiring to head straight from the bus to work on, but it’s totally worth it to have a great weekend. Plus, I can always rest up during the workweek, which is usually less exciting than the weekend anyway.

Find deals

More and more deal sites, like Groupon, are coming out with travel options now. I took advantage of a Groupon deal last year to get a night at a nice little B&B in Western Massachusetts for only $80, including breakfast for two. I’m also loving Travel Zoo these days. They send out a “Top 20” email every week that outlines some of the best deals they have to offer. I’ve seen several deals for cheap tickets to Broadway shows, and I think I’ll take them up on that very soon.

Go off-season

This is nothing new, but it’s a great way to save. We went to Cancun in August and the place was deserted! I can understand that people don’t want to travel to warm locations when it’s summer and it’s already warm where they live, but it was great to take advantage of the cheap food and drinks without having to fight crowds.

Travel to nearby friends and family

I take advantage of this all the time when I visit my cousins in Boston and my parents on the water in Rhode Island. My cousins have an apartment in a prime location located right in downtown Boston. There’s no shortage of things to do around there, so it’s always a great time. My parents are near Newport, which is a popular location in the summer.  It’s great to have my family so close!

Use cheaper transport

I’ve been living it up on the MegaBus lately and loving it! (Donna at GRS loves Megabus, too) I can’t stop talking about their $1.00 tickets, and I often just buy a bunch if I have any plans to go to Boston. Occasionally I’ll take Amtrak when it’s worth it, especially when I can use rewards for free or cheap Amtrak tickets. Carpooling works great, too, for the group trips.

Cook meals and carry food

While I don’t mind eating out when it’s worth it, I hate buying food simply because I’m traveling and I’m hungry. Prime example: I can’t stand eating at Subway. Their vegetarian option is essentially a lettuce sandwich, which isn’t appealing whether you’re a meat eater or not. I try to hold off on this stuff as much as possible and carry trail mix or cereal bars instead.

For meals, I enjoy mixing it up between eating out and cooking wherever I am. In Vermont again, we cooked two fantastic dinners that I don’t think could’ve been matched by any restaurant around. Eating out is great when it’s something unique and special, but I never underestimate how good a home-cooked meal can be, too.

Stay in

Even though we were in Vermont with lots of stuff around, I mostly enjoyed hanging out by the fire, enjoying some beers, and playing some pool. Sitting by the pool in Cancun under the umbrella with a drink in hand was awesome, too. I even like playing games or just chatting with whoever I’m with. Going out just to go out gets old quickly to me, and I usually don’t do it unless I’m really feeling like exploring somewhere new.

Those are my secrets to mastering weekend travel without overspending. The only downside: I haven’t exactly mastered my working time on the weekend, but that’s next on my list to figure out.

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photo by: Margo!


  1. I love traveling off season.  It’s a great way to do fun things on the cheap, plus you get to avoid the crowds which just annoy me anyways.

    We also try to stay at places where we can prepare our own food.  Such a money saver. 

  2. We often stay with friend and family. The key is to stay no longer than 4 days…family is like fish, after 4 days they stink.

  3. We have been camping a lot during the last few summers. One of the advantages to living in CA, there is always a park within driving distance to stay for a weekend.  We don’t have family near by, otherwise I would go there (if it were my sister or my parents) every weekend 🙂

  4. The title of your post made me think of the deal emails I get each week.  I think living social and groupon both have sections for get aways.  I have seen some for $100 and less so it really leaves me little excuse to enjoy a night away.

    Really great advice here, thanks.


  5. Thanks for sharing such amazing tips. I am planning a weekend trip but I have no idea how to lower down the cost of getaway and stretch the trip to few more days…….

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