Planning a Family Trip to Boston

This year, our 18 year wedding anniversary aligns with the kid having a couple days off school, so obviously I had to check to see if there were any cheap plane fares to ANYWHERE fun for a long week. I checked a dozen or so potential destinations before selecting Boston.

Why Boston? Well, it will be the fall so the foliage will most likely be beautiful. The price was right. It’s a pretty darn quick flight, at just 90 minutes each way. By flying in early in the morning and leaving later at night, we get to enjoy three full days and two nights in the city.

I’ve actually visited Boston previously for a work conference but had very limited time to go out and about. However, without even realizing it, on a happy coincidence I booked the exact same hotel that I stayed at previously! Our home base will the be the Boston Marriott Copley Place and we plan to do our exploring on foot or by public transportation instead of renting a car.

Here’s what is on our possible adventure list:

Food tasting tour – as much as I would absolutely love to do a guided food tasting tour with a company, they seem to run about $100 a person… so $300 for our group is just too much for us. We want to eat ALL the foods though, so I think we might do a self-guided food tasting tour. Maybe one day will be pizza and another cannoli? I’m not sure yet and need to do some research.

Some places that people on Threads have suggested we visit: Galleria Umberto, Bova’s Bakery, Monica’s Trattoria, Pagliuca’s, Sail Loft, Formaggio Kitchen (for a picnic to take to a park), dumplings in Chinatown, Faneuil Hall’s Quincy Market, Clear Flour Bakery, Union Square Donuts, Harvest (for burgers), Eastern Edge Food Hall, Bowmarket Somerville. So it looks like I have some googling to do.

Walk Around – Copley Square Farmers’ Market, Boston Public Garden, Newbury Street, Beacon Hill, etc… it will be peak fall foliage time, so all the walking and exploring will be on the plan.

Shopping – There’s lots of fun stores to check out around Copley Square, so we will probably poke our heads into anything that looks interesting. The Boston Open Market sounds cool with over 50 artisan vendors. Last time I was in Boston, I also went to a Goodwill that was ginormous (1010 Harrison Ave), so we will probably stop by there too.

Segway Tour? – I did a Segway tour back in 2017 when I was in San Francisco for a conference and have wanted to do one with Travis and Jack ever since. There are a couple Segway tour options in Boston, but I’m not sure if we will feel too rushed to schedule one on this trip.

So, it’s pretty clear I still have a bunch of research left to do for our October trip. Or, it could just be all lobster rolls and waterfront strolls…

If you have recommendations of places to see, stores to shop, or food to eat, please let me know!

My Style: August 2026

Due to personal life turmoil, this entire summer has flown by in a haze. Suddenly, August has passed, schools are in session, and crisp fall weather is right around the corner.

Thankfully, autumn is my favorite season which also contains my birthday and our wedding anniversary, so I’m looking forward to time marching by a bit. Also, I just booked two vacations which gives me all the dopamine and adventures to look forward to.

Let’s take a look at my August outfits:

Office Style

Very similar looks for the office this month — in fact, I wore the same chambray shirt for both. Which is funny to me, because I have historically HATED button up shirts on me. They typically pull at the bust and/or look quite frumpy on my body shape. I thrifted this magical one and added a couple little invisible snaps between the buttons to keep from any bust pulling.

Both skirts were also thrifted and tailored by me. The white one was a maxi skirt that fit oddly around my waist, so I chopped off the top tier and reattached it to the existing waistband. The floral skirt was a vintage Laura Ashley find that I knew was too small for me. Once again, I chopped top tier off. But for this one, I inserted some new elastic to make a new waistband. Love them both now!

Both looks were topped with a lightweight thrifted cardigan. On the left, I wore secondhand Mary Jane Rothy’s and on the right I wore secondhand Eileen Fisher sandals (both from Poshmark).

Casual Outfits

First up, we have two skirt outfits with the same formula: t-shirt + skirt + cute shoes. It’s my typical summer outfit for leaving the house and how I feel the most “me” going out into the world. I thrifted the skirt on the left and it has this magical way of looking cute with pretty much everything. The skirt on the right was a ‘add one more item for free shipping’ purchase last year and it’s still in rotation.

Last, we have two dresses re-styled because they both have spaghetti straps and I like to wear a real bra. For the outfit on the left, I did the old ‘tie a shirt over it’ trick and mixed things up with little polka dots. For the outfit on the right, I just threw on a t-shirt and knotted it in the front for some shape. Easy peasy and comfy.

New vs Secondhand Tally

This month, I count 8 items that I purchased retail and 11 items I purchased secondhand.

Building a Birthday Earring Stack: Studs, Jackets & an Earcuff

It is officially my birthday month! While it’s not a “BIG” birthday… it is the year before a BIG birthday and I really feel the need for a bit of a treat/self care spectacular.

One of my treat ideas for the month is that I’ve been drooling over some earring stacks lately, so it’s the perfect opportunity to curate one for myself. I have one piercing in my left ear and three piercings in my right ear, so I decided to get a little extra fancy on the right.

Here’s what I’ve decided on:

Ear Cuff

I’ve considered getting an additional piercing in my cartilage, but I honestly don’t have the patience to deal with the healing process at this point. So, I decided to get a sparkly ear cuff to add on to my stack – it has all the gorgeous sparkle and none of the pain!

I love this one made of lab grown white sapphires from Aurate, ordered it and I’m waiting for it to arrive. I think it will be great to pop on when I want to add a little extra sparkle.

Studs

In my main (lower) piercings, I wear a set of tiny diamond studs my dad gave me when I was in college. These are my daily earrings that I typically don’t change unless I’m dressing up to go out into the world. In my two higher right piercings, I found these a couple years ago and I LOVE them:

The Star Push Pin Flat Backed Earrings from Maison Miru are the first earrings I ever purchased with a ‘flat back’ design and I’m never going back! I put these in probably 2 years ago and they are the ‘set it and forget it’ kind of earring. Other than cleaning them when they need it, they just stay in my ears 24/7. They are super comfortable and I love the cute little stars.

Jackets

I’ve been following Liz Fox Roseberry on Instagram for quite some time and I absolutely love her earring jacket designs. They are all handmade and many can be worn in a few different ways – in front of the ear, behind the ear, with or without additional chains. They are also made to mix-and-match with different designs in her collection. Each jacket comes with a pair of surprise studs (not made in house by them), that compliment the look.

I had been planning to order one or two of her Curated Mystery Trio sets, but then narrowed down my absolute favorites to three designs that I would love to mix and match. So, for my birthday I added them to my cart.

Source: LizFoxRoseberry.com

The Coneflower – single
The Sapling – single

The Daisy – set of two

I decided to do singles for The Sapling and The Coneflower because I love how they are similar but different. They can both be worn in front of the ear, behind the ear, alone or paired with their little chains. Since I’ll get a set of studs with The Sapling and a different set of studs with The Coneflower, that will give me additional options for mixing and matching too.

I also decided to order a full set of The Daisy. This design will also mix and match well with both The Sapling and The Coneflower. Or, I can wear the full set together. Once again, the earring jacket can be styled in front of the ear, behind the ear, and with or without the chains. However, the chains on The Daisy pair are different than the chains on The Sapling and The Coneflower… so I can also mix and match those little chains with everything else OR even wear them alone behind the ear with any stud.

I can’t wait until my earring stack orders arrive and I can start playing with all the possibilities!

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