One of the things I have gotten used to in this new world we live in is the timed tradition of a good road trip. Sometimes it is nice to get away even if it is just for the day, but when I have time, like getting away for a couple of days or the entire week. I mean, we technically are work from anywhere these days, amirite?

Being a New England girl at heart, one of my places to go pre-covid and now is Boston. This city will always have a place in my heart because I went to university there. I call it America’s Paris, since it is a walking city with cobblestone streets in certain parts of the city and definitely possesses some old world charm. Being there reminds me of my European home for the past couple of years. If you are contemplating a road trip this fall, here are the things you should not miss.

Where to Stay

Boston Harbor Hotel & Waterfront shot from Captiva

My favorite neighborhood to stay in is Back Bay. I was lucky enough to stay at an apartment right on Beacon Street for my stay earlier this summer so was steps away from my favorite street in Boston, Newbury Street. The Back Bay area is great if you love the old Boston charm and new England sensibility. I was able to walk and jog along the Charles River in the morning and sometimes after dinner, and it is also the part of Boston where Comm Ave turns into a green tree lined park street that leads you to the Boston Gardens and Boston Common. It’s almost like Park Avenue in NY, but instead of highrises on both sides, you have historic brownstones.

If you are more of a hotel person, I recommend the Eliot Hotel in the Back Bay area. I have not stayed there post covid lockdown, but stayed there regularly when I used to visit for business and pleasure and their service was always top notch and the ambiance was old worldly, which I loved.

For a more modern vibe, I would suggest staying in the new-ish waterfront area. It isn’t really new in the fact that the waterfront area has always existed, but they have truly renovated the area and it is booming with restaurants and new building and shops.

This past trip I stayed at The Boston Harbor Hotel and it was exquisite. The service was above five star and is truly white glove. The rooms were immaculate and clean. My dog came with me on this trip and they had this gorgeous dog bed, plus a lot of treats and boxed water for her—walking in and seeing that in the room, I was truly impressed. The hotel is on the harbor so make sure to book a harbor view room so you can catch the amazing sunrise and see unparalleled views of the moon shining over Boston. I usually sleep with my blinds closed, but this trip I made an exception as the views were truly breathtaking, especially if you wake up at the crack of dawn.

Pro-Tip: Make sure to do your due diligence in researching where you are staying especially in this covid-world. I find the best indicators are looking at the most recent Google Reviews to see how guests felt the properties have been handling service and cleanliness after reopening. What may have been white glove five star before, may not be anymore. Know what you are paying for. I also find it wise to call or email guest relations to see what their processes are and if they are in line with your expectations.

Where to Eat

My favorite area to eat in is the Back Bay and my favorite street to eat on is Newbury Street (shocker). Boston is phase 3a right now, so indoor dining is allowed, but I still prefer eating outdoors and Newbury Street is perfect for that. They already have heatlamps out at some of the restaurants outdoor dining space (told you it was America’s Paris!) so they are fully equipped and ready for any fall visitors. Here are some of my fave places to eat while there.

Sonsie

So this is a true favorite of mine as I’ve been going there since my university days. So glad that it is still around after all of these years. All the food is solid and the drinks are strong and always flowing. Though the crowd is not overflowing in the street like back in the day, Sonsie is still one of my favorite stops for their food and service.

Saltie Girl

One of my new discoveries and very trendy with locals and visitors alike. They are known for their seafood and they do not disappoint. Their assortment and creativity truly won me over—so much so, I visited more than once on my trip there. Definitely get the flatbread and definitely try their tins.

La Voile

My go to French Staple: Confit de Canard

Since I am a sucker for anything French, this became one of my frequently visited places anytime I am in Boston. They have an extensive wine list, which is essential and fare that you would find at a traditional French Brasserie.It’s like I’m back in Paris again!

Select Oyster Bar

If you are craving oysters and fancy lobster rolls, definitely make a trip here during your stay. We tried a variety of dishes, which were all great, but the winner for me was the warm lobster roll. You can get it cold too, but their warm version was a dream I didn’t want to wake up from.

Uni Boston

If you are in the mood for Japanese food with a twist, Uni is great. Located at the Elliott Hotel, they have a prime location where Commonwealth meets Newbury. Love the gastronomical twist on their sushi and if you are a Francophile (or just want to indulge), definitely get the sushi topped with seared foie gras.

Tatte Bakery

If you are looking for a cute brunch spot or just looking to do some takeaway, you MUST go to Tatte Bakery. This Israeli style eatery is something I hope expands to NYC. I have been there a few times this summer and they never disappoint. You can order a true formal brunch and eat at one of the outdoor tables, or just buy some baked goods and coffee. They also have some salads and spreads under their “Tatte at Home” umbrella, so you can enjoy it wherever you are. This trip, I bought out their supply that day so I could enjoy it back in NY.

Dining Out Pro-Tip: Make sure to make a reservation for wherever and whenever you are dining so you are not disappointed. Eating out is the new hot ticket these days, so walk-ins at your spot most likely cannot be accommodated unless you know someone OR speak nicely in French or the native language of the restaurant ;)

Dog-Tip: If you are owner of a pup and take your furry friend everywhere, make sure to call ahead. Apparently some terrible accident happened when someone claimed their dog was a service dog, so some restaurants (based on their own discretion) do not allow dogs to dine with you EVEN if you are seated in their outdoor dining area. Was a real bummer for me, but always found another solution.

What to do

With COVID, activities are pretty limited, but there are still things to do in Boston asides from just taking a self led walking tour or exploring the city.

Drive Out to the Shore

The thing I love about Boston is that you can take many roadtrips to other destinations. My fave places to get away to in New England are Cape Cod, Nantucket and Martha’s Vineyard—they are my usual stomping grounds. This year, I discovered Maine a little. It is a 3 hour drive from Boston, but honestly worth it if you have a few days or more than a few days to venture out.

Shop

I like supporting businesses anytime I am on vacation. For whatever reason, I feel safer shopping in other cities outside of NYC. When I’m back home, I usually order everything online, so vacations are little shopping treats for me. When in Boston, definitely check out the shops on Newbury street—they have a great mix of high end (Chanel, Hermes), boutique (LIT, Soodee, Lipstick) and discount (i.e. Nordstrom Rack and TJ Maxx). I found some of my best finds shopping down the strip this summer. Another great area for shopping is the waterfront area or Faneuil Hall. If you haven’t been to Boston in awhile, definitely recommend visiting the waterfront area as it has a more modern feel. It’s like you are living in two different cities!

Sail Away

Well, no shocker here because I love being on the water, but you can go sailing in Boston, and I’m not talking about one of those touristic duck tours. They do have some sailing tours that give you a tour of Boston Harbor that you can find easily online. Or if you can swing it, I definitely recommend doing a private charter. If you like me, it’s always safety first, so paying the extra premium is worth it for me, especially since sailing should be a relaxing experience. This time I used Classic Sail Boston, but Liberty Fleet also offers private charter options. I chose Classic Sail Boston because I fell in love with their beautiful wooden boat. Captiva is a a 45 foot Classic Chesapeake Skipjack that was built in 2011, crafted to the specifications of the 1890's version. She was custom built generously using mahogany, teak, obeche and other exotic woods. The in person experience was amazing and made the journey more memorable. If I make it back to Boston this fall, will definitely be booking another sail before the season is over.

Sailing Pro-Tip: Do NOT bring a toddler. I repeat, DO NOT BRING A TODDLER.

Overall Pro-Tip: If there is anything you want to do that requires tickets, book those first so you can plot the rest of your trip around it. Other than that, just have fun! Anything too structured is really not relaxing!

Roadtripping in the USA: Boston Calling