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Boston Itinerary - Where to Eat, Visit, What to Do & What to Wear

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A full Boston itinerary - from the best places to visit, eat at, and do to what to bring while traveling and what to wear!
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Planner

The best way to plan out your trip.

 
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The best way to plan your trip is with this printable travel itinerary template! Download and plan every trip with this blank template! :)
Travel Itinerary Template
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K. Willsey profile picture
The best way I like to keep my Airbnb gigs organized is with this printable monthly calendar! It's a blank template so you only have to purchase once and can use it over and over every year! :)
Printable Monthly Calendar
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I love these printable calendars to keep my Airbnb gigs organized! They're so adorable and there are so many different calendars to choose from! It's a one time purchase and can be used year after year because of the blank template! :)
Calendars
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What to Wear

The best outfits to wear in Boston.

 
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I love this set for a casual walk around town.
Crop Top & Pants Set
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I love this set not only because it's comfy but I love the streetwear look it gives and it looks super cute for pictures.
Crop Top & Cargo Pants Set
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This set is perfect for a lounge day or walking around town.
Comfy 3 Piece Set
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I absolutely love this dress. It’s so comfy and you can wear it casually for a walk around town or a night out.
Ribbed Mini Dress
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This is one of my favorite sets I own. It's so comfy and you can wear it casually or to a fancy dinner.
Crop Top & Maxi Skirt Set
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What to Bring While Traveling

The best items to bring while traveling to Boston.

 
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Hands down my all-time favorite blue light glasses.
Blue Light Glasses
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This comes in handy when you’re traveling because it folds so easily and fits right in your bag.
Foldable Laptop Stand
 
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This is hands down the best portable charger I've ever used. You can charge it with a wall outlet but I love it because you can put it in the sun while traveling and charge it that way as well! Highly recommend this product.
Portable Solar Charger
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This bag is nice for when you're on the go while traveling. It not only fits your laptop but also your laptop stand and other things you need to carry.
Laptop Bag
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This comes in handy when you’re on a vacation and are trying to get a selfie of you and another or especially an entire group.
Selfie Stick
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Places to Visit

The best places to visit in Boston.

 
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I absolutely love this old-time feel of the buildings and how many places there are to shop! I definitely recommend going.
Downtown Crossing
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This place is beautiful. I highly recommend going here while in Boston!
Boston Common
 
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I loved the atmosphere of this crystal shop and got a lot of good items!
Bodhi Leaf

Food

The best places to eat in Boston.

 
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The cutest bakery. I got a lemonade and croissant and both were so good! I make it a priority to go to this bakery every time I go to Boston.
Tatte Bakery & Cafe
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This bookstore has a sit-down place to eat inside and outside and serves all sorts of food. The pancakes were delicious and the bookstore had a lot to offer.
Trident Booksellers & Cafe
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They had lactose-free options which I loved and the ice cream was so good. I highly recommend this place while visiting Boston!
Emack & Bolios
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Activities

 
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The best time to go is late Spring and Summer because the flowers and plants are fully bloomed and it's a beautiful place to walk through.
Boston Public Garden
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I loved walking along the pathway. It was so peaceful and there were plenty of park benches to just sit and relax. I definitely recommend going here while visiting Boston!
Charles River Esplanade
 
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This place has so many different vendors on each side and has food vendors in the middle along with places to sit and eat. I highly recommend going here!
Quincy Market
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