Boston, Massachussetts | 2-Day Itinerary

Written By Kaitlin Starr

TENTATIVE PLAN FOR AN UPCOMING TRIP IN JUNE 2025

*Plans and Images Subject To Change*

 

DAY ONE

Boston Commons and Public Garden

  • Photo Op

  • Location Of The Famous ‘Good Will Hunting’ Bench

  • Perfect Picnic Spot

Charles Street

  • Beacon Hill Books and Cafe

  • Beacon Hill Chocolates

  • Flat Of The Hill

  • Shake The Tree

  • Photo Op | Rouvalis Flowers and Acorn Street

Newbury Street

  • It Is A Mile Long 8-Block Stretch Of Stores and Restaurants

  • Central Perk - A Friends Inspired Coffee Shop

  • Brandy Melville

  • All Your Basic Mall Stores + Designer Stores and Smaller Boutiques and Shops

Quincy Market

  • MASSIVE Food Hall With 50+ Eateries, Vendors, and Kiosks

  • This Will Probably End Up Being Our ‘Lunch’

Polcari’s Coffee

  • A Famous Corner Coffee Shop My Dad Is Making Us See

Dinner | Boston Burger Company

  • Recommended Dinner Spot That Looks Banger

Prudential Tower

  • 360 Observation Deck

  • Recommended For Watching The Sunset

 

*Within The 2 Days We Are Also Doing The Freedom Trail*

 

DAY TWO

Breakfast/Coffee

  • Farmers Horse Coffee

  • Blank Street Coffee

  • Buttermilk and Bourbon

Isabella Stewart Gardner Museum

  • Location Of The Largest Unsolved Art Heist In History

  • About 2 Hours To Complete

Red Sox vs Yankees Baseball Game

Dinner | Union Oyster House

Kaitlin Starr
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