This past weekend my husband, westie and I spent a weekend in Boston for my birthday. Boston is one of my favorite cities so when I saw my birthday landed on a Saturday, I went to work and started planning a quick weekend getaway.
If you’ve ever planned a trip, no matter how big or small, you know it takes a lot of research and time. We really lucked out with all our choices so today I want to share our itinerary in hopes of helping you plan your next weekend in Boston too.
A Weekend in Boston
Where we stayed, what we did, and where we ate!
I highly recommend staying at the Marlowe Hotel if you’re considering a trip to Boston. We had one of the best experiences ever in terms of hospitality. We chose this hotel because it’s dog-friendly (no extra fees for pets!) and our westie truly had the best time. They greeted him by name and had a bed and bowls ready for him in our room. There were also doggy treats at the front desk which he loved.
The staff was fantastic and ready to help us with any questions we had. The hotel location is right across the Charles River from downtown Boston. My husband ran on the trail by the river every morning and loved it. If you can, get a room facing the river. The windows are grand and it’s a beautiful view.
We found the hotel to be centrally located to all the activities we had planned + the area was quiet and great for walks. The hotel is also right next to a mall in case you want to do some quick shopping or forget anything (it’s literally connected to the same self-parking garage).
Other things to take advantage of during your stay:
Polaroid camera use – just sign out for it at the front desk
Hotel bikes for a ride around town
Shoe shine services
Kayak and paddleboard usage
$10 credit per person for your stay (so make sure to use it for room service or their lobby bar, etc)
Complimentary morning coffee and tea service from 6 a.m to 9 a.m. Monday – Friday and 7 a.m. to 10 a.m. Saturday – Sunday in their lobby living room
Hosted wine reception in the lobby from 5 to 6 p.m.
You can find the rest of their amenities here!
We arrived on Friday, September 21 around 4:30-5 p.m after a half work day. We unpacked and decided to quickly explore the area around our hotel to get our bearings. (You can also take advantage of the complimentary wine in the hotel’s lobby!)
- We walked to Tatte Bakery & Café for some coffee and a quick bite before dinner. The walk was about 15 minutes but we stopped at a dog park so our westie could play a bit.
- Afterward, we headed for the trail along the Charles River and followed it back to our hotel. The weather was perfect but I would recommend a light jacket if you’re visiting early fall.
- Dinner was at Lolita Cocina & Tequila Bar at their Back Bay location. I recommend taking an uber because parking is not the best. You need to show I.D. to get in and the vibe feels like it’s a restaurant inside a club. The music is loud but the atmosphere is fun and definitely a place to go if you love a good time – and tequila! As soon as we sat down they offered complimentary grapefruit-flavored shaved ice with tequila in a bowl overflowing dry ice – so fun! The food was delicious: we ordered the crispy empanadas (only comes with 2) and grilled street corn for appetizers. My husband had the hibachi shrimp (so yummy!!) and chicken habanero tacos. I had the grilled steak tacos. TIP: order extra tortillas with your tacos so you can turn your 2 tacos into 4 😉 For dessert we ordered the churros which were delish! They also brought out complimentary watermelon-flavored cotton candy with pop rocks sprinkled on it! Such a fun touch! TIP: Make reservations. I booked about a week in advance and the earliest dinner time available was 10 p.m. We arrived at 9:30 and they were able to seat us right away but just in case you want an earlier dinner, book in advance.
Day two was my birthday and the day we decided to do most of our exploring. We mostly stayed in the Back Bay and Beacon Hill neighborhoods.
- We had breakfast at The Friendly Toast at their Back Bay location. They don’t take reservations (bummer) so account for about a 30 mins. – 1-hour wait, depending on the time you arrive. They take your number and text you once your table is ready so we just walked around and explored while we waited. I had the huevos rancheros with scrambled eggs (instead of poached) and I finished the entire plate! My husband had the chicken & waffles and really enjoyed the chipotle sweet potatoes. The decor is funky and their menu is huge so you’re bound to find something yummy for all taste buds.
- After breakfast, we walked over to the Boston Public Garden which is less than a 15-minute walk. We strolled around and listened to the music and enjoyed some people watching. It’s a great place to unwind, sit at a bench, and take in the day. The earlier you get there the better because it does get crowded around noon/1. This is where you’ll find the Make Way For Ducklings and George Washington statues.
- I really wanted to check out the ever-so-popular Acorn Street so we made our way to Beacon Hill. I loved this neighboorhood because it’s filled with Victorian brick row houses. I could have stayed there all day! Acorn Street was filled with people taking their Instagrams so if you don’t want any photobombers, go early. But honestly, every inch of this neighborhood is picturesque so just go and enjoy the scenery – and wear comfy shoes!
- Afterward, we made a quick pit stop at the Cheers pub to snap a picture and then walked over to Newbury Street to do some shopping. You can also head over to the Boston Public Library since it’s nearby on Boylston Street. TIP: If you’re feeling fancy you can have afternoon tea at The Courtyard Restaurant in the library.
- After shopping, we decided to go back to our hotel to take Scottie out for a walk and relax a bit. Again we enjoyed the scenic trail along the Charles River before we started getting ready for dinner.
- For my birthday we went more intimate and had reservations at Grotto, a small Italian restaurant in Beacon Hill. It’s a super cozy spot that’s perfect for a romantic dinner. The walls are lined with wine bottles and exposed brick. They offer a nightly prix fixe dinner at $36 or $42 per person for a 3-course meal which I found to be an incredible price. The food was top notch and we enjoyed the service. If you love a rich, chocolate dessert, get the Cioccolato – it’s amazing!
This was our last day in Boston (sad face)!
- Because we were checking out of our hotel we knew we had to find a dog-friendly breakfast spot. We went with Café Luna which turned out to be a great choice! They were so accommodating and the staff was super attentive and kind – they brought out treats and a water bowl for our westie. They don’t take same day reservations for Saturday or Sunday so be ready to wait about 30-45 mins. You can do brunch reservations ahead of time by email only. I had a vanilla latté which was one of the best I’ve ever had and the chilaquiles with chipotle chicken. My husband had the Fresh Berry Stuffed French Toast – we enjoyed every bite! They have a huge breakfast menu so you’re bound to find something you like. I had a hard time making a choice!
- Afterward, we drove to Harvard Square where we spent the rest of the afternoon strolling through the shops and Harvard.
Here are more recommendations we received during our search for things to do and some I came across personally:
A game at Fenway Park (duh!)
Isabella Stewart Gardner Museum
Boston Burger Co.
Alden & Harlow
Boston Museum of Fine Arts
My biggest tips would be to book reservations in advance, wear comfy shoes and uber everywhere. Parking is hard to find and if you decide to park in a garage, it’s going to be pricey.
Let me know below if you have any restaurant recommendations or your favorite things to do in Boston! I would love to hear your thoughts!
Thanks for stopping by! If you found this guide helpful, please pin to Pinterest by hovering over the picture below. Until my next post!