It’s like Chicago and New York had a baby and created this perfect child named Boston.
Prior to Nantucket, the husband and I spent a night in Boston. It was my first time visiting and Sean is actually from here. Now that I’ve had a taste, I am not sure what took me so long!
If you are looking for a quick and AMAZING getaway from Chicago, Boston is it folks. NYC, Nashville, Michigan or Wisconsin normal come to mind, but Boston has never occurred to me. I’m sure several of you have been, but if not, here is a travel guide for hitting up this amazing city in one day!
ACCOMODATIONS:
Boston Harbor Hotel
Staying on the water is glooooorious. We reserved a room at the Boston Harbor Hotel and I’m telling you guys…It’s top notch. From the location, to the decor, to the staff. It situates on the harbor and within walking distance to so many must see’s. Including fabulous outside, on the water dining. Which if you know me, is the best part. We walked almost everywhere and they even play outdoor movies in the harbor on a large screen. Heaven!
Travel tip: Yes, you may save money staying on the outskirt of town. But you will quickly makeup the difference in cabs or renting a car. Spending a little more on location (where you can walk) results in savings and conveniency. Which makes for a better experience!
And I know this is bad, but the hotel is next door to Starbucks. Girl’s got to get her cappucino!
EAT/DRINK:
Rowes Wharf Sea Grill (part of Boston Harbor Hotel): I suggest hitting this spot as soon as you arrive (whether you stay at the hotel or not). There’s nothing like al fresco lunch on the water, watching boats come in and out. Packed with locals and guests, it’s clearly a hot spot! Can’t go wrong with oysters and champagne, with a side of fries (piping hot and crispy). Sean got the club sandwich made with heirloom tomatoes and a Sam Adams beer. When in Rome right?
Neptune: A fabulous oyster bar, highly suggested by so many people. One of my Instagram followers mentioned going early, putting your name in and grabbing a drink prior to dinner.
Little Italy: A part of Boston with guaranteed top notch Italian food. Rumor has it you can close your eyes and point and you’ll make out quite well.
La Famiglia Giorgio: My friend (thanks Kristina Lipskis!) specifically loves this Italian joint.
Row 34: A modern restaurant with stunning decor and a lively ambiance. Perfect for cocktails and food. You may remember this recommendation from Portsmouth, it’s sister restaurant.
Cheers: The original bar from the oldie, hit TV show. I never saw an episode, but a silly and fun, touristy thing to do. Just be sure to go to the original in Beacon Hill.
Wink and Nod: A speakeasy with handmade, quality cocktails. Perfect nightcap and you’d never know it was there! I ordered their Tiki libations (only 1 is allowed – oops!) and Sean went with the house Old Fashion. He’s a pro when it comes to OF’s and gave it a thumbs up.
Stephanie’s On Newbury: A recommendation from the beautiful and talented Chicago designer, Christina Karin – who is from Boston! Thanks girl.
Sonsie: Another Christina Karin rec.
DO:
A Harborwalk Stroll: The hotel’s huge, multi-story arch makes quite the impression. Sits right over the wharf’s plaza, which makes for a beautiful walk along the water. You’ll spy beautiful yachts, more waterside restaurants, great people watching and can even buy a boat ride.
Faneuil Hall: Wandering around Faneuil Hall with no agenda was one of my favorite things we did. Cobbled streets, shops, street performers (that are surprisingly very entertaining), restaurants and bars galore.
Walk the Freedom Trail: So much history. A 2.5 mile marked walk that leads you to 16, significant historical sites. (Thank you to @gutesbild101 for the rec!)
Acorn Street: The most photographed street in Boston. Picturesque with beautiful front doors and knockers. (Thank you again Antoinetta!)
Fenway Park: Home to the Boston Redsox – I hear it’s even cozier then Wrigley Field.
We of course could not do all of these. But I received so many recommendations from so many people, I had to include it all. I believe genuine suggestions are better than any travel guide. Our concierge did a wonderful job helping us narrow it down and most importantly, directions!
Have you been to Boston? Any other spots or “to do’s” I should add? I will be going back (I fell in love so hard!) so I need all the tips I can get!
Also a huge thank you to The Boston Harbor Hotel for having us as their guest gratis. Every inch of my review is spoken from the heart and I promise we will be coming back sooner than later!
I love Boston! Though being use to the Chicago Grid System, it is definitely quite an adventure navigating around Boston. There’s so much history and beauty there! Sounds like you had a great time!
Hi Lindsay! Yes, navigating around Boston is unlike other – but I think brings part of the charm 😉 Thanks for stopping by.
Oh my gosh, your photos are beautiful! Now I totally want to go back…I think I’ll have to plan a trip 🙂 xx
Thanks Maya! I seriously cannot believe I never had been to Boston. What was I thinking?!