
I have a friend who makes tons of money but hates her job. She despises her everyday life. Not for me. I chose teaching. And while no one gets into the field of education for the money, my everyday life has been pretty amazing for the past 21 years.
(Obviously, the past year and a half have been drastically different, but I’d like to focus on the positive here.)
Whereas my friend assuages her misery with $400 sunglasses, I actually like waking up in the morning. And if you are fortunate, like me, to work hard teaching and guiding young people, you also understand the glorious perk of having two months of summer, stretched out before you to enjoy every year.
I may not have tons of disposable income, but I have time and I make excellent use of it. Summer is only days away, and whether you are a teacher or financial advisor, you are probably dying to vacation somewhere other than your living room.
There are not many people who take better advantage of days away than me, and I’m here to help you to do the same.
Here are my tips to help you pack and plan
for 1-3 day getaways:
Ways to Save:
If you have the time off, go on a weekday and avoid big holidays.
I love beaches in the off season and hotels on weekdays, or off holiday weekends. It’s less expensive and less crowded. I get the need for a scene when you’re single or with girlfriends, but when Joe and I travel with the kids, or it’s just the two of us, we love the freedom to roam and explore crowd-free. Our Lake George trip was the weekend before Memorial Day and we saved a ton of money.
Ask for the discounts!
Do not take the price that pops up as final and don’t be shy. Most hotels want your business right now. Ask about promotions, Triple A discounts, discounts for essential workers and teachers, or packages that include breakfasts and other perks.
Don’t always try for the best room.
We all want the balcony and the ocean view, but most resorts have rooms with lesser views for much cheaper and they include the same amenities as the luxury suites. The Sagamore at Lake George offers rooms adjacent to the main hotel, with a free shuttle to take you all over the resort.
Groupon is still a thing.
Pre-Covid, I lived for Groupon – to the point my husband would poke fun at me.
(“Spend money to save money.”)
Now that the world is opening up again, they are still offering all kinds of hotel discounts, and they make it easy to click drivable getaways from your location. It’s a great way to discover a new place or revisit a favorite city. I just scored a hotel in Newport, RI and another deal in Saratoga Springs, NY.
Put your browser on Private when searching online.
My attempt to remain incognito may seem excessive, but it works. If they don’t see me, they don’t track me and I find better deals.
Now, I’ll help you pack:
Make your bathing suit a pseudo tank top.
I’ve told you about my favorite from Monday Swim – it not only holds in my boobs, it looks great as a fake tank.
After a day in the sun, pair yours with flowy beach pants, a cute necklace, a floppy hat, and off to happy hour you go.
I paired mine with these Cloth and Stone tie dye pants.
And yes, I’m at the tailor. The pants were way too long for me and I waited to take them. I asked her to take my picture “for work.” Gotta do what you can! Thankfully, she was kind enough to agree.
The picture of me at the top of this post and here
features a less expensive, but equally adorable option from Old Navy.
I’m in love with that yellow bikini top – total coverage and I only paid $20 for it. The black pants are from last season, but these are available now.
Pack a maxi dress or jumpsuit that works from day to dinner.
I scored a tie dye maxi on sale at Anthropologie. It’s no longer available, but you get the idea. And my current favorite from Abercrombie may still be on sale!
If you do a jumpsuit, make sure it’s easy on/off. You do not want to be me and wear yours with the zipper halfway down so you can go to the bathroom! I found this one at Pinklily.com – they have a ton of comfy and cute ones for a decent price. And no zippers.
Do the same with your favorite white button down.
Over the years, I’ve had countless white button down shirts. They are classic and can be simple or sexy. Go simple with your favorite denim shorts and a straw hat. Perfect for daytime window shopping or touring a town
.
For dinner, swap the shorts for jeans, add a bangle, (or a few), and a gold necklace. Dare greatly and unbutton one more button at the top!
Wear shoes with more than one outfit.
Don’t hang up. You can do this. I spent years muttering in exasperation and sneaking shoes in my husband’s suitcase until I learned the beauty of one daytime sneaker, (I’m not working out when I only have one-three days away), one pair of flips, and a heel or sandal that works with the day to night attire.
If it’s a quick beach trip, I just do the flips and one other shoe for dinner.
Before a long drive, map out stops and sights along the way.
If the destination is more than three hours away, I make a “getting there” itinerary. I’ll share a Google Doc with my husband beforehand and plan out sights to see on the way, a restaurant for lunch or dinner, and if need be, a hotel to rest for the night.
I’d rather pay for an inexpensive hotel, grab dinner, get a good night’s sleep, and arrive at the destination fresh in the morning. Driving in the dark makes me anxious. We pit stop at a hotel every summer on the way to The Outer Banks, which is about nine and half hours from our home in CT.
(I can’t wait to share everything about OBX soon)
Using Google Docs lets you organize and keep track of where you’ve been, recommendations for the future, where you will go again, and what you can leave behind the next time.
I also just learned about Google Maps Trip Planner. Going to try it out and report back!
Don’t pack full size beauty products.
I reuse spritz bottles for things like toner, and put cleanser, moisturizer and serum in contact lens cases. Total space savers. (Just use a Sharpie to write C/M or S on top.)
If I’m feeling frisky, I’ll even purchase an all-in-one travel kit. Sephora had a great one I featured a past issue, called Clean Me Up. They don’t currently have that one, but if you search mini skincare, you will find others.
Streamline your makeup too.
You do not need your whole makeup collection, especially if you are on a beach. Taking less leaves room for essential tools like a lash curler, eyebrow filler, and a couple of good makeup brushes.
There are so many multi use products available that work on cheeks and lips, and my favorite FUNdamental can be swept across the eyes and the face – it’s all in one.
Speaking of all in one – have one good wallet just for travel.
There are a ton of inexpensive ones on Amazon that let you keep everything in one place and look cute!
Use a backpack
I’ve had the Lorimer backpack from Madewell for years. It never goes out of style and frees up my arms!
I hope this post has been helpful – I know it was a lot!
I love sharing tips and ways to make life easier. Feel free to tell me yours – I’d love to collaborate and share.


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