Boston is a fantastic place for people who like history. I’m just not one of those people.
I’m sure all the historical stuff is riveting, actually. I just didn’t have time to be bothered with that while planning a trip for my 11th anniversary.
I was focused on making our own memories instead of re-visiting someone else’s.
The plans for my weekend getaway to Boston with my lovely wife of 11 years, were simple. I was focused on 3 things…
- Food
- Experiences
- Drinks
These may seem superficial or trivial, but you need to understand what I was really focused on… creating strong emotions. When we look back on our trip, what will help us remember this trip with fondness? Emotions.
Emotions help make a memory last, long after the details fade away. Will my wife and I remember 10 years from now what we ate for dinner at Grotto Restaurant during our visit? Probably not. But I’m certain we’ll remember how it felt to be focused on each other while surrounded by candles & bottles of wine on the wall in our private corner.
So, here’s a timeline of our romantic and adventurous visit to Boston with some commentary along the way…
FRIDAY
2:15 PM – Water Taxi to Boston
Landed at Boston Logan Airport and grabbed the #66 shuttle that takes you over to catch a water taxi. Once on the shuttle, I called 617-227-4320 to tell them I would need a water taxi at the airport headed for Rowe’s Wharf. It was $12 per person plus tip and started the trip with a nice private trip on the water.
3:00 PM – Check-in to Kimpton Nine Zero
We stayed at the Kimpton Nine Zero (90 Tremont St, Boston, MA 02108) right next to Boston Common. It’s a swanky hotel that was recently voted best boutique hotel in Boston by Boston Magazine. The location was centrally located, the staff was great, and they provide free bike rentals (stay tuned). We thoroughly enjoyed our stay.
3:45 PM – Late Lunch at Boston Public Market
The Boston Public Market (100 Hanover St, Boston, MA) was a lot of fun and offered a ton of variety, so we could each get what we wanted. I ordered ramen that was so/so, but Kat ordered a delicious lobster roll. The coffee at George Howell wasn’t great. We also grabbed some beer from Hopster’s Alley to avoid $8 cans of beer from the mini-bar. I’d go back again, partly for the variety, but mostly for the people watching.
5:00 – 7:00 PM – Bike Ride Along the Charles River
This was a highlight of the trip! The Kimpton provides bikes at a first come first serve basis for their customers, but there is a bike rental station 1-2 blocks away that you can rent. We made our way like total tourists through the common and roadways over to the Charles River.
We biked to the Harvard pedestrian bridge and crossed over to Harvard for a little while. I would have loved to explore more there, but I wasn’t sure what to see. We thought the weather may turn to rain as well, so we turned back. It was about a 9-10 mile bike ride, but it was all so flat, it wasn’t challenging.
8:30 PM – Dinner at Grotto Restaurant
We were a little late for our reservation at Grotto Restaurant (37 Bowdoin St, Boston, MA). When we arrived, we were seated at the cutest, most romantic table I’ve ever seen. It was in the corner and had dozens of tea candles lit. There were wine bottles along the wall as well. We did the three-course meal and we were blown away by the quality.
You can see the menu here, but we were blown away by the FONDUTA (Fontina cheese fondue, Beef tenderloin tips, Portobello mushrooms, Aged balsamic, Truffle oil), the GNOCCHI (Short ribs, Mushrooms, Gorgonzola), and the red sauce in the CHICKEN PARMIGIANO (Ziti, Tomatoes, Mozzarella) was out of this world!
10:00 PM – Cocktail at No. 9 Park
After a 4 minute walk from dinner towards our hotel, we stopped by No. 9 Park (9 Park St, Boston, Ma) for a drink. We grabbed a spot at the bar and I told the bartender I wanted a spirit-forward gin drink. I was pleasantly surprised and for my wife, they made a “Last Laugh” cocktail with top-shelf champagne to celebrate our anniversary.
Giving the barkeep free reign can be risky business, but this didn’t disappoint at all. We didn’t have food, but it the food is anywhere close to the quality of the drinks, I’m sure it’s great.
SATURDAY
9:15 AM – Coffee at Ogawa Coffee
As a former barista, I go out of my way to research the best coffee in any city I’m visiting. I found a few places that interested me in the city, but Ogawa Coffee (10 Milk St, Boston, MA) was the most unique and the closest to our hotel. I’m not lying when I say that their signature drink, a cold frothed espresso in a martini glass with a cappuccino sidecar was the best coffee experience I’ve had in my life. There wasn’t an ounce of bitterness in my espresso.
The vibe there was cool as well. It’s a Japanese coffee company, so there decor, brain teaser games, and buddha board added to the experience.
Signature Drink from Ogawa Coffee
10:15 AM – Brunch at Frenchie
Three words… Duck. Confit. Hash.
Seriously, Frenchie (560 Tremont St, Boston, MA) was delicious. The vibe was cool. It was a little slow, but it just made it feel intimate instead of being stacked on top of others.
11:15 AM – Blackbird Donuts
I know you’re thinking “you just ate brunch”. First of all, this is a judgment-free zone. Second of all, we took them back to the room for later. The donuts were good, but the only one that really stood out was their savory “Everything” donut. It was a donut topped with everything bagel toppings and stuffed with cream cheese. It was inspired.
12:30 PM – Ferry to Spectacle Island
We took an uber down to the Boston Harbor Island Ferry information stand (191 W Atlantic Ave, Boston, MA) and they pointed us in the right direction to buy ferry tickets down the wharf. (About a 2-minute walk.) We had great seats on our 25-minute ride to Spectacle Island. The weather was great and the ride was smooth with great views of the city along the way.
We hiked along the outer loop near the water and found some boulders to climb down to the shoreline. There was a lot of random debris on the shore, but it was still a fun little walk. We climbed more boulders back up to the path and then saw a ‘Do Not Climb on Rocks’ sign.
We then hiked up to the top of the southern part of the island and took some photos and enjoyed the beautiful views. On our way back down to the welcome center, we found a pile of kites that were free to fly. So, we had a good time flying kites before stopping at the welcome center to wait before the ferry came back.
I know I said this trip didn’t have any history, but the 5-minute video in the welcome center about how Spectacle Island came to be was pretty cool. We then hopped on the ferry home, which took longer than the ride out to the island.
Panoramic View from Spectacle Island
4:15 PM – Snack / Last Lunch at Gourmet Dumpling House
The food at Gourmet Dumpling House (52 Beach St, Boston, MA) was the most authentic Chinese food I’ve had. As a 6’5″ red-bearded giant, it’s safe to say I stuck out like a sore thumb. The food was good, but if there was a long line, I wouldn’t wait for the food. If I had to do it again, I would’ve found a food vendor on the greenway or walked somewhere close to the wharf.
5:30 PM – Pedicures
We found a spot near Chinatown and the pedicures were okay, but the place was a little dodgy. I wouldn’t recommend. We then went back to the hotel and got ready for the evening.
8:30 PM – Beers at Trillium Garden on the Greenway
The beers at Trillium Garden (Atlantic Avenue &, High St, Boston, MA) were, as expected, delicious. The last call was at 9:30 in case you are headed there later at night. They turned a bunch of people away who were trying to get into the garden after they stopped serving.
Trillium Garden on the Green
10:00 PM – Pizza at Pastoral Fort Point
Our waiter at Pastoral (345 Congress St, Boston, MA) was rude, which wasn’t great. The food was good, but nothing overwhelming. If I had to do it again, I’d find a place on the walk back towards our hotel and avoid the uber rides.
SUNDAY
8:30 AM – Coffee at Clover DTX
I stumbled across Clover (27 School St, Boston, MA + many locations) during my research and thought it was a cool concept. It’s a vegetarian fast-casual joint with a high emphasis on technology. For example, you can see on the menu how long it took for them to make their last sandwich or pour-over coffee. I ordered a couple of pour-overs to take back to the room. They tasted great!
I also ordered some food, which tasted good. The flavor was fine, but I think people like the sustainability mission of the restaurant more than anything else.
11:00 AM – Walk the Boston Garden
We biked through part of Boston Common on Friday but totally missed the fact that a huge chunk was the Boston Public Garden (4 Charles St, Boston, MA). A friend recommended we go there and I’m thrilled that we did! It was peaceful and tranquil with Asian inspired musicians adding to the ambiance.
I would highly recommend this as a stop on your trip if you are looking for something free and romantic.
11:30 AM – Brunch at 75 Chestnut
Our friend picked out a brunch stop for us to meet. The bloody mary bar was fun and the pecan cinnamon rolls that they brought to the table before the food came out were delicious! The atmosphere was nice, but the food wasn’t as good as the food we had at Frenchie 1 day prior.
Bloody Mary from Chestnut 75
1:00 PM – Shopping along Charles Ave.
After brunch, we needed to shop for gifts for our 3 kids and my parents, who graciously watched our children all weekend. There were a lot of great shops along Charles Ave. Some of our favorites were Flat of the Hill, Blackstone’s of Beacon Hill, Black Ink, and Whitney & Winston.
4:00 PM – Flight back to Nashville
We grabbed our bags from the hotel and took an uber to the airport. Getting through security was fast and easy. Maybe 10-15 minutes.
A WEEKEND TO REMEMBER
Overall, we had a great time in Boston. The people were nicer than I expected and the crowds of people were not unbearable. Escaping the humidity of Nashville and the noise of our three kids was sublime. I look forward to visiting Boston again!
