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Location: Unknown

Day 1 - 14 Oct 2021

Maryland

Unknown, Maryland

Content: We left straight from work on Thursday even though we got to our hotel super late, it allowed us to have a full day in Boston the next day!

Location: Boston

Day 1 - 14 Oct 2021

Wyndham Boston Beacon Hill

Boston, Wyndham Boston Beacon Hill

Content: Absolutely LOVED the location of this hotel. It was right in Beacon Hill and so we actually walked everywhere!

Location: Boston

Day 2 - 15 Oct 2021

Tatte Bakery & Cafe

Boston, Tatte Bakery & Cafe
Boston, Tatte Bakery & Cafe

Content: This is one of the most popular coffee shops in Boston and now I know why! I ordered the gingerbread bake and and a caramel latte!

Rouvalis Flowers

Boston, Rouvalis Flowers
Boston, Rouvalis Flowers
Boston, Rouvalis Flowers

Content: Okay... is this not the cutest shop you ever did see 🧡🌿 Talk about instagramable places in Boston! Rouvalis Flowers lies on the corner of W. Cedar Street in Beacon Hill. They change out their display for each season so no matter when you visit you will experience a unique and beautiful aesthetic.

Louisburg Square

Boston, Louisburg Square
Boston, Louisburg Square

Content: 27 townhouses line this square and they are the most prestigious addresses in Boston. Visit during fall to see the local decor the residents put up! I can’t wait to come back closer to Christmas for all the wreaths and candles!

Acorn St

Boston, Acorn St
Boston, Acorn St

Content: When strolling Beacon Hill, you won’t be able to miss Acorn Street because of its cobblestone path and red brick buildings. These buildings are still occupied today and I can’t help but walk this street and imagine what it would be like to live here! Being transported back into the 19th Century everytime I look out my window would be an absolute dream.

Boston Common

Boston, Boston Common

Content: Boston Common is a public park which is perfect for picnics, riding bikes, morning walks, and throwing a frisbee.

Earl of Sandwich

Boston, Earl of Sandwich

Content: This sandwich shop is right in Boston Common. This was very convenient for us to grab a bite here and relax in the park after a long morning of walking.

Public Garden

Boston, Public Garden
Boston, Public Garden

Content: This garden is something straight out of a story book and was probably my favorite thing about Boston. It was nice to get away from the hustle and bustle and just by the pond and take everything in. I love strolling city gardens and this garden was so big and picturesque that I could explore it for hours! And don’t forget to check out the “Make Way for Ducklings” statues!

Copley Square

Boston, Copley Square

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Boston Public Library - Central Library

Boston, Boston Public Library - Central Library

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Wyndham Boston Beacon Hill

Boston, Wyndham Boston Beacon Hill

Content: Back to the hotel to freshen up before dinner

The Tip Tap Room

Boston, The Tip Tap Room
Boston, The Tip Tap Room

Content: This restaurant is the new up and coming place in Beacon Hill. I ordered the turkey burger which was toped with a cranberry sauce. We absolutely loved the indoor vibe of this place and would definitely recommend putting this restaurant on your list!

Alibi

Boston, Alibi

Content: Although I didn’t stay at this hotel I was sure to put it on my list for places to see! This Hotel actually used to be a prison which they transformed into a chic, classy, luxury hotel with a lot of character. Inside the hotel is their famous restaurant called the Alibi. It was a little on the pricier side so we decided to just go for drinks. We sat outside and let me tell you, it was a vibe!

Location: Boston

Day 3 - 16 Oct 2021

Blackbird Doughnuts Beacon Hill

Boston, Blackbird Doughnuts Beacon Hill
Boston, Blackbird Doughnuts Beacon Hill
Boston, Blackbird Doughnuts Beacon Hill

Content: If you like donuts this is the place for you! Their specialty donuts are to die for, and they're also super cute! I went during fall so I got pumpkin spiced latte, apple cider, and chocolate cupcake with halloween frosting!

Freedom Trail

Boston, Freedom Trail
Boston, Freedom Trail
Boston, Freedom Trail

Content: If you enjoy the historical side of travel be sure to put The Freedom Trail at the top of your list! The trail is a total of 2.5 miles on way so bring your walking shoes! It starts in Boston Commons so this is where we started. We then followed the path and stopped at The Massachusetts State House, Old City Hall, and the Old Stare House before lunch.

Quincy Market

Boston, Quincy Market
Boston, Quincy Market

Content: This marketplace offers over 100 stores, restaurants, and pubs. It is right on the Freedom Trail so it makes for a perfect lunch stop from your long day of waking. We decided to get lobster rolls from Boston and Maine Fish Company… when you are in New England you have to get seafood right?!

Freedom Trail

Boston, Freedom Trail
Boston, Freedom Trail
Boston, Freedom Trail

Content: We continued on The Freedom Trail and visited Marshall Street, The Paul Revere Statue and Little Italy.

Dolce

Boston, Dolce

Content: We stopped in Little Italy to grab a cool snack and admire the charm 🥰

Freedom Trail

Boston, Freedom Trail
Boston, Freedom Trail
Boston, Freedom Trail

Content: Continued to follow The Freedom trail to see The USS Constitution and Bunker Hill which is where the trail ends.

Figs by Todd English

Boston, Figs by Todd English

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Location: Boston

Day 4 - 17 Oct 2021

Brattle Book Shop

Boston, Brattle Book Shop

Content: This is America’s OLDEST AND LARGEST historical bookshop 📚 Even though I am not much of a reader, there is something about browsing bookshops that is so calming. Unfortunately I visited on a Sunday and it was closed…. So I couldn’t get any pictures of the iconic outdoor section. Even though I missed out on those photos, I was obsessed with the storefront. I mean how cute is that huge pencil?✏️

Ogawa Coffee

Boston, Ogawa Coffee

Content: They always have the cutest lattes during each holiday season. If you are visiting Boston in October ask for either a 🎃or 👻

New England Aquarium

Boston, New England Aquarium

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Pasta Beach Boston

Boston, Pasta Beach Boston

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Boston Tea Party Ships & Museum

Boston, Boston Tea Party Ships & Museum

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Fan Pier Park

Boston, Fan Pier Park

Content: We loved walking around her and doing some shopping!

City Cruises Boston Seaport Blvd

Boston, City Cruises Boston Seaport Blvd

Content: We did a sunset cruise this night! They start boarding the cruise 30 minutes before it leaves and you should get their early to grab a drink and a good spot!

Lookout Rooftop and Bar

Boston, Lookout Rooftop and Bar

Content: Make sure to make reservations early!!!

Location: Boston

Day 5 - 18 Oct 2021

Tatte Bakery & Cafe

Boston, Tatte Bakery & Cafe

Content: Because we loved this cafe we decided to go back but to a different location! I mean just look at that vibe!

Fenway Park

Boston, Fenway Park

Content: We did the one hour guided tour which gave an insiders look of the station!

Public Garden

Boston, Public Garden
Boston, Public Garden

Content: We picked up items to make a sandwich as well as some snacks at a market. The. We took it here to have a picnic in the garden while listening to live music!

Location: Newton

Day 5 - 18 Oct 2021

Blue Bikes

Newton, Blue Bikes

Content: We rented bikes with Blue Bikes which is a public bike-sharing system. To rent one you. Need to download the app and sign up. After signing up renters get the first 45 min of each ride for free. It also offers a 24 hour pass, 30 minute pass, and an annual membership.

Location: Milford

Day 5 - 18 Oct 2021

Charles River Bike Trails

Milford, Charles River Bike Trails

Content: Biking is the perfect way to explore a city and this trail has a 23 mile route from Boston to it’s western suburbs Waltham. It takes an average of 7 hours to bike so we didn’t do the whole thing. This trail also tends to get crowded but we rode in October so it wasn’t too bad!

Location: Boston

Day 5 - 18 Oct 2021

Wyndham Boston Beacon Hill

Boston, Wyndham Boston Beacon Hill

Content: Back to the hotel to rest and freshen up before dinner!

Sons of Boston

Boston, Sons of Boston

Content: If you are following the Freedom Trail make this restaurant one of your stops! It is right before Marshall Street and you won’t want to miss it! We loved the vibe of Marshall Street so we decided to come back and try out a restaurant on our last day exploring and the service was amazing 😊If you do stop here try the buffalo wings and cider beer for a fall vibe!

Location: Boston

Day 6 - 19 Oct 2021

Wyndham Boston Beacon Hill

Boston, Wyndham Boston Beacon Hill

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Location: Unknown

Day 6 - 19 Oct 2021

Maryland

Unknown, Maryland

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