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Absolute Best Guide to 5 Boston Honeymoon Activities

Are you looking for Boston honeymoon activities? Quirky, safe, picturesque, funny, warm-hearted magical Boston, with so much to do and see for all tastes–how could you pick a better honeymoon destination? It’s our very favorite city! Even those who are not oriented to big-city life fall under the spell of this comfortable and beautiful old city, with its gorgeous parks and spectacular buildings, its varied and colorful food and drink options, and especially its romantic spots where memories are made.

There are so many distinct parts of Boston, each with its own unique character. Follow along for our favorite Boston honeymoon activities!

Faneuil Hall and Quincy Market, part of the Boston Freedom Trail and a great part of your Boston honeymoon activities!

Where to Stay for your Boston Honeymoon Activities?

Why, as close to the center as possible of course!! Our two favorites for two entirely different experiences were Boston Park Plaza in the heart of town and a very charming VRBO in the South End/Back Bay Area.

-Boston Park Plaza

This grand old hotel overlooks the exquisite Boston Public Gardens, which has got to be one of the prettiest parks in the US. It’s tucked right in the heart of Boston. There’s magic and romance here–more on that later! The hotel rooms on the front side, on the higher floors, has beautiful views of the park. If you’re lucky–as we were–you might even see a movie being filmed right on the streets below! The location of the Boston Park Plaza is key–you can get almost anywhere from here very easily. https://www.hilton.com/en/hotels/bossrhh-hilton-boston-park-plaza/hotel-location/

-Boston’s Most Charming Bed & Breakfast-Heart of City (South End Brownstone VRBO)

This classic historic brownstone townhouse is located in the picturesque and upscale South End, very close to Back Bay and Downtown. It’s a very quaint guest suite (no cooking, just sink, dishwasher and microwave) on a quiet residential street. We enjoyed our stay there!

2. How to Get Around in Boston

The “T” or the Boston Metro was our favorite way to get around. Accessible from nearly everywhere, it’s the most budget friendly–and fun!–way to navigate Boston. Inside tip–it’s really safe and people watching is a lot of fun! Get your passes at any of the listed locations: https://www.mbta.com/schedules/subway

Uber is always a great option if you don’t want to worry about timelines for trains (although they come every few minutes), or if you need to go somewhere a little off the beaten path. We used Uber to navigate back and forth to Logan International Airport when coming and going from Boston.

What Sights to See for Your Boston Honeymoon Activities?

There are so many amazing choices that it’s really hard to pick favorites. Some of these may surprise you, but take a chance and make some romantic memories–and of course some GREAT pictures! There’s so many great sights to see here!

1. Boston Public Gardens/Boston Commons

-The Embrace

This somewhat abstract sculpture of Martin Luther King Jr and his wife embracing (think just arms) is a very poignant and extremely romantic place to visit for your Boston honeymoon activities. Located in the Boston Common just short of the North End, you can’t miss it!

-The Swan Boats

It doesn’t get more romantic than a picture with your love in the quaint Swan Boats on the pond in the Boston Public Gardens. This Boston icon is definitely worth a visit on a fine day in spring, summer, or early fall!

-Music on the Bridge

Chinese musicians often play their haunting two-stringed instruments on the bridge or elsewhere in the Boston Public Gardens, so find a nice bench, listen to music, hold hands, and watch people enjoying this gorgeous park.

-The Esplanade

This promenade along the beautiful Charles River is a romantic morning or evening stroll. Watch the sculls practicing on the river and don’t miss the beautiful skyline views!

2. North End

Don’t miss the famous Italian section of Boston, also known as Little Italy. Quirky, colorful, and authentic Italian restaurants and pastry shops abound (cannoli!!). Insider tip: you need to bring cash as most of these places don’t take credit cards!!


Don’t annoy the waiters. Seriously. We found their no-nonsense orders and colorful personalities hilarious and endearing. This is like no other place. Just do EXACTLY what they tell you. And it will be priceless, and you will come back again and again. And their fresh bread, oh my!!! https://www.giacomosboston.com


Instead of waiting in line for the famous Mike’s Pastry, try the tiny Parziale’s. They win. I don’t know what magic cream they put in their slightly odd looking lobster tails, but you won’t regret it. Definitely big enough for two to share. http://www.parzialebakery.com


This wonderful smelling coffee, tea, and spice importer is the epitome of everything we love about the North End. The very lively owner does a great job making everyone happy. I dream about this place after we left, and even ordered tea sent home some months later when feeling especially nostalgic. I know it’s unusual, but don’t miss this stop in your Boston honeymoon activities. https://polcariscoffee.com

3. Freedom Trail

You can’t come to Boston without walking the famous Freedom Trail. It is a trail of red bricks that leads you to all the famous historic sights of Boston. It’s about 2.5 miles and can be done in one or two days, or more if you want to take your time. Our favorite Freedom Trail stops are:

-Faneuil Hall

This meeting hall and marketplace from Revolutionary War days was the scene of many stirring speeches by 18thc patriots like Samuel Adams and James Otis. Today, it’s a bustling indoor market with plenty of great food and Boston memorabilia and souvenirs!

-Paul Revere’s House

Paul Revere and his intrepid second wife Rachel raised a very large family here in this remarkable old house from 1680. Ask the tour guides about Rachel’s role in getting the family to safety after Paul’s famous midnight ride!

-Old North Church

This beautiful and understated church from 1723 is the site of the famous lanterns (“One if by land, Two if by sea) set to warn the American patriots of the British movements on the night of Paul Revere’s famous ride.

4. South End/Back Bay

This wealthy and picturesque area of Boston just off the downtown area is definitely worth a visit–and a great place to stay, with amazing restaurant choices. Spend the day shopping in the quaint brownstone boutiques and then head over to our favorite romantic restaurant:

-Wink and Nod

Blink and you’ll miss it, this tiny underground speakeasy in the South End was our favorite Boston restaurant. Tapas style, everything is exquisite and definitely out of the ordinary. The chefs change every month or so, so you never know what is on the menu, but it doesn’t really matter. This is a don’t-miss place for your Boston honeymoon activities.

The drinks are lovely and varied, and the food will not disappoint. When we were there, the arancini (fried rice ball), smashburger tacos, and fried Korean turkey leg were all perfect, and although all of them sound like odd combinations, everything was incredible, so don’t be afraid to step out of the box when ordering.

Bonus: if you stay in the South End, be sure to try another Boston icon, Flour Bakery.

-Flour Bakery

We arrived in the morning just in time to visit Flour Bakery for delicious brunch. Try the breakfast sandwich which is amazing, but don’t forget to leave room for the epic Sticky Buns. Ridiculous crunchy gooey perfection which is impossible to describe. I fantasized about these afterward, The James Beard-nominated chef who created this miraculous breakfast indulgence deserves an award for these. If you’re feeling brave—they sell their cookbook….

-Boston Public Library

For a very luxe and romantic activity, stop in the glorious Boston Public Library. It is truly epic. Take a selfie in the famous and beautiful Reading Room.

5. Beacon Hill

A wealthy and extremely picturesque neighborhood in Boston, it is one of the most photographed places in the city. Walk up the EXTREMELY steep cobblestone and brick streets, and you can feel your jaw drop at some pretty eye-poppingly spectacular Boston brownstones and other mansions.

Don’t forget to allow for some shopping and treats down on Charles Street, which is the location of most of the quaint shops of Beacon Hill. Some have very small doors leading to intriguing tunnels leading to gorgeous shops—this underground aspect of Charles Street was my favorite part!!

These are only a few of our favorite Boston honeymoon activities, but we hope that you will enjoy them! This is a city we love, and hope to return again and again!

For more New England activities, see this guide to Where to Visit in Vermont in Fall! https://foodieontheroad.com/where-to-visit-in-vermont-in-fall/

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