8 Amazing And Romantic Things To Do In Boston For Your Anniversary!
OK, this month marks our 25th wedding anniversary and the pressure was on.
But I planned the perfect Boston weekend that was both amazing and romantic. And if you follow these 8 top tips, you will have a perfect anniversary weekend.
(It actually doesn’t have to be an anniversary. Girls weekend. Mother’s Day. Anything you want. Just get into Boston because it’s simply bursting with beauty these days.)
A little background on us first:
Dave and I met in November of 1994. I was an editorial assistant at the Boston Herald on Harrison Ave. (It’s now a Whole Foods. This is wholly depressing, but I digress.)
He was a grad student studying journalism at Northeastern. I was promoted to Teen Page reporter (yes, this was a thing) and he got my old job as EA.
Which meant I got to train him! (Weird flex, but OK.)
Anyway, we became friends. Well, that’s what I had in mind.
He asked me out after three months.
(Can you believe I turned THIS down? I was a BIG DUMMY.)
I said “You don’t have a car. How are you going to take me out?”
I was stalling.
He got a car.
He asked me out again.
This time I said “I really don’t date guys I work with.”
Meanwhile, I was dating ALL the guys I worked with.
Well, then we really did become friends.
We’d hang out. Go to dinner. I’d steal some of his fries off his cafeteria plate.
Here we are meeting the mayor at some work event. Not a DATE, though.
And he’d ask me out and I’d say no and we danced this dance for a long time.
LIKE TWO YEARS LONG.
Yup. He asked me out for TWO YEARS. Can you even believe it?
After two years, I went on vacation for two weeks. And when I came back, Dave had a new girlfriend.
So I called my friend Stacy, who worked with me at the Herald. I said: “Dave has a girlfriend.”
And she said: “Well, you have turned him down for TWO YEARS. It’s time he moved on.”
I said: “Well, maybe I don’t want him to move on.”
She said: “You know you’ll have to kiss him, right?”
I said: “Maybe that’s not such a bad idea.”
To which she replied:
“HANG UP THIS PHONE RIGHT NOW, CALL HIM AND TELL HIM TO BREAK UP WITH HER AND DATE YOU.”
I did. He broke up with the girl. And I eventually did kiss him.
We were engaged nine months later and married nine months after that.
Now it’s been 25 years!
This is my favorite story. Can you tell?
Now, without further ado:
8 Amazing And Romantic Things To Do In Boston For Your Anniversary!
1. Take The Train
Do not drive. One, it’s expensive. Two, you have to drive into the city, which is really not fun. You will fight. Traffic is back with a vengeance. If you don’t take a car, you are forced to walk, which is good for you, you see more of the city and, most importantly, reminds you of when you were young and in love and liked to walk places together.
Also, it was 12 bucks one way for two of us.
2. Stay At The Newbury Boston
I honestly cannot say enough about this hotel. I’ve stayed at a lot of places over the years, especially in Boston, but The Newbury Boston is the tops. It holds a special place in my heart because we got engaged at the Rooftop at the Ritz, which is now Contessa at The Newbury. More on that later.
Sure, it’s splurge, but this completely renovated hotel is located right at the corner of Newbury and Arlington, and looks over the historic and beautiful Boston Public Garden. Some rooms have wood fireplaces, there’s coffee and baked goods in the library off the lobby and the decor is sumptuous. If you can swing it, spring on a corner suite on a high floor. The view is worth every penny. And the staff? Just delightful. It’s also home to two restaurants – the rooftop beauty Contessa and the Street Bar on the ground floor.
11 Amazing And Romantic Things To Do In Boston For Your Anniversary
3. Eat at Contessa
Back in 1998, Contessa was “The Rooftop at the Ritz” and where we got engaged. I was sad when it closed, but now that I’ve been to Contessa, I WEEP NO MORE. This is truly the most beautiful restaurant in the city. We had dinner there the first night and the service (and DRINKS!) were amazing. We split octopus and ravioli.
BUT, I have a pro tip. People are always scrambling for dinner reservations, but Contessa’s a real star during brunch or lunch. This sun-drenched oasis serves up the most elegant dishes – from the Florentine Benedict with prosciutto, fontina, hollandaise and spinach to Squash Carpaccio with arugula, pumpkin seeds and agrodolce (I looked it up. You should, too.) And the drinks? Why are we not all starting our Sundays with their espresso martinis? I don’t know either.
4. Go to the North End
I don’t know why the mayor’s office refuses to let outdoor seating happen in the North End, but the upside is we got to stroll around our old stomping grounds. Dave and I used to go to L’Osteria, which is still there. We went to the Fisherman’s Feast once summer and I danced with an old Italian man in the middle of the street. (Now I get to dance with MY old Italian man in the middle of any street!)
We visited Ciao Roma, which used to be 5 North Square, where Dave took me once on one of our first REAL dates. There was a special table reserved for couples. I forget the number and the table isn’t there anymore, but the spot is – and that’s enough for us!
5. Hit the South End
We spent a lot of time in the South End because it was right near the Herald, but we discovered some new “old” spots. Dave had never been to Charlie’s Sandwich Shop and we’ve never been to Rutland Square, which is a gem! Also, hit it Petit Robert Bistro. It’s a great little French place on Columbus Ave. Get the Bloody Mary. Or the Corpse Reviver No. 2
6. Shop. But Don't Necessarily Buy!
GOOD LORD, Copley Square Mall is filled with stores that are NOT LIKE MARSHALL’S.
Here’s Dave trying on a $2100 jacket! (We took a picture. It lasts longer.)
And this is Dave looking at a $60,000 diamond necklace at Tiffany’s.
We decided to get an affordable drink instead:
7. Visit Where You Met...Even If It's Gone
This is JJ Foley’s in the South End, where we would cash our Boston Herald paychecks every Thursday night (Jerry cashed them right there are the bar. He must have had tens of thousands of dollars back there). We’d spend a little of the paycheck on beers and talk and talk. And the all the Herald reporters and photographers ended up there eventually and we stayed until the last train. It was bliss.
It’s still pretty blissful.
Jerry is sometimes still tending bar there. But this time, we met his 6th child, a son named Jeremiah, who made us perfect martinis. An upgrade from the Bud we used to drink!
And then we stopped by the old Herald building, which is now a Whole Foods and a bank. Bummer. But life goes on.
OH! And we visited the location of our first movie date. It was an old theater that’s now a Summer Shack, across from the new Four Seasons at Dalton Place. We saw “Sleepers” – a really MESSED up movie for a first date.
8. Visit the Public Garden
You guys, we live here. It is the oldest, and most gorgeous park ever. Enjoy it.
(This is our hotel. So pretty, right? And the LOCATION!)
Doesn’t this tree look like it’s going to talk to you? Imagine all it could tell you!
