My Boston Guide + What I Wore [Autumn]

Boston guide fall outfit roundup lifewithjazz

My Boston guide is finally here!! Thanks for everyone’s patience….it’s been a busy, busy few weeks and these travel guides take quite a bit of time to put together…but I’m so happy to share some of my favorite things I’ve experienced in one of my absolute favorite cities!

Boston had been on my bucket list for quite a while and last year was my first time visiting…and I immediately fell in love! [I love anything European-inspired so it comes at no surprise that the most European-like city in the U.S stole my heart haha :)]. Boston reminds me a bit of Europe [Madrid, Spain in particular if you’ve ever been!] and New York. Boston is rich in history, beautiful architecture, quaint neighborhoods, delicious eateries, and serene parks that are perfect to take a a stroll through or spend a relaxing afternoon reading at.

How I Fly Free

It’s been a while since I’ve shared about the Southwest Companion Pass! I’ve been a pass holder for a few years now and haven’t paid for a flight [for me or my companion!] for years now! How you may ask? Well before you book your trip…be sure to check out my full post HERE to find out what it is and my inside tips on how to earn a pass. *Southwest is currently offering up to 100,000 POINTS limited time bonus for signing-up for one of their credit cards! That not only gets you 100k points, but will almost instantly earn you a pass!

Where to Stay

Westin Copley Place

This was my second year staying at the Westin Copley Place and highly recommend! The Westin has some unbeatable views of the city and I absolutely love the location of being in Copley Square/Bay Back area! You are within walking distance of everything. You are steps away from the Boston Public Library, Newbury street [which is lined with so many great restaurants and shops] and the mall [which also has some great dining options and a rooftop bar!]. You are also less than a mile away from one of my favorite spots, the Boston Common and Public Garden central parks, and walking distance to Beacon Hill and North End. You can easily take a Lyft to these further spots but it’s such a beautiful city that I really encourage you to walk to all these locations. Sometimes you find surprising treasures along the way 🙂

W Boston [Downtown]

w boston beer garden — Outfit Details Linked HERE

For this first half of my trip I stayed at the W Boston located in Downtown and this is another location I also recommend! A few of you asked me which location I preferred, but I think each location has their benefits so it will really depend on what you are looking for [because it’s too hard to choose one!].

There is a LOT of fun stuff going on in Downtown Boston, so if you are looking to be closer to Boston’s nightlife, this is THE place! I wish I had more time to spend in Downtown to check out all the different spots, but we still had the chance to check out the W’s new Beer Garden [which is absolutely beautiful and so good!] and grab drinks at their lounge. The W is also located a couple of blocks away from Chinatown [where there are SO many great restaurants to try — including Dim Sum and Pho to help cure your hangover haha]. And probably my favorite part, you are like a block away from the parks!! You can start your day by grabbing coffee & a bite at Tatte’s on your walk over, and then take a stroll through the park [to help burn off some calories/work up an appetite] before grabbing lunch at one of the amazing restaurants in Downtown.

What To Do

Go for a run [if you’re crazy like me and training for a half-marathon] or talk a stroll/spend an afternoon reading at the Public Garden or Boston Commons park
Take a city walking or history tour [I have not done one of these tours yet but want to do one next time! I love Hop-On-Hop-Off tours!]
Visit Newbury Street for lunch or dinner
Explore Beacon Hill, one of Boston’s most picturesque areas
Catch a game at Fenway Park
Visit the Boston Public Library
Go on a ghost tour [we did one in Savannah and it was so cool!]

Where To Eat

I realize there are SO many amazing places to eat in Boston and this list barely even touches on all the options…but here are the places I tried and recommend!

Barcelona Wine Bar: this was one of favorite restaurants and our first stop on both trips! They have delicious tapas and sangria [and wine of course!].
Figs: They have amazing pasta and the BEST eggplant parmesan I’ve ever had [my BF also said the same thing!]. There is a Figs located right outside the Beacon Hill neighborhood/Chestnut Street
Faneuil Hall Marketplace: This market is filled tons of places to eat! I definitely recommend checking this place out!
Eataly Boston: Located on the second floor of the mall, this place has the most gorgeous ambiance & delicious pasta!
Giacomo’s: Another favorite for Italian food, this place is AMAZING [ok I’m drooling just thinking about it…]
W Beer Garden: this newly opened beer garden is located in the W Boston hotel and perfect to grab drinks & food at
Tatte Bakery & Cafe: Perfect to grab coffee at! Walking around you’ll find many locations scattered around the city

What to Pack/What What I Wore [during Autumn]: