Itineraries: Boston

FRIDAY

Evening:

Get ready to roll out the big bucks if you hope to rest lavishly during your stay in Boston during October. Hotel prices this time of year are outrageous. After much moaning and groaning over not being able to afford the posh Liberty or Fifteen Beacon, we reluctantly handed over our wallet to the Nine Zero, a luxury boutique property conveniently located across the street from the Freedom Trail and one block from posh Beacon Hill. If it hadn’t been double the usual price (thanks Parents’ Weekend and The Head of the Charles Regatta), I would highly recommend it. I just expect ridiculous attention to detail when a room is close to $400/night.

Dinner at South End’s B&G Oyster Company is a must if (like me) you are on a mission to find the best lobster roll in the world. Start with (what else?) a dozen oysters and work your way to the freshest, sweetest Maine Lobster roll I’ve yet to find. Waits can be long, so make a reservation early, when you can enjoy quiet conversation over a meal that makes my mouth water just thinking about it.

SATURDAY

Morning:

Start your day with a casual breakfast at The Paramount in Beacon Hill. Things haven’t changed much since 1937…get ready to wait in line as your food is cooked to order (no sitting until your order is up), but this could be the most satisfying deal in town. And the walk from your hotel isn’t too shabby either. Mansions anyone? Yes please!

Afternoon:

Make your way over to Cambridge for a master lesson in all things prep. We just happened to plan our weekend getaway during the Head of the Charles Regatta, the world’s largest two-day rowing race steeped in tradition. If ever there was a time to pull out those Polos, Rugbys and corduroy blazers, now is the time.

Take a stroll through Harvard Yard and stare hard at anyone wearing a Harvard sweatshirt, wondering if they will be the next Mark Zuckerberg. Try to take a photo next to the famous “Statue of Three Lies,” but become disappointed when all the tourists won’t get out of your way. Instead, make your way to the Harvard Book Store and keep telling yourself that if you would have tried a little harder, you too could have made this your hang out between Microeconomic Theory and Abstract Algebra.

Evening:

Dinner at  Ten Tables in Cambridge, a darling, romantic spot just below ground, where you can cozy up with a great glass of wine and delicious seasonal meal like the Heritage Breed Pork Chop with Red Kuri Spice Puree, Cippolini Onions, Caramelized Brussels Sprouts and Mission Fig Compote.

In need of a nightcap? Taxi over to The Liberty Hotel, and grab a drink while you tour what used to be the Charles Street Jail. The Liberty Bar is lively and sophisticated, located within the 90 foot rotunda. The place to be and be seen, I recommend a reservation unless you mind standing.

SUNDAY

Morning:

A short thirty minute drive and you are in Salem, infamous for the Witch Trials of 1692. Though a strange little place (especially near Halloween), it’s worth a trip. The gorgeous, historic homes are quite the paradox to the cheesy touristy downtown, full of “witches,” wizardry and a wax museum. Make time for The Witch House, former home of Judge Jonathan Corwin, the only standing structure in Salem with direct ties to that time.

Afternoon:

Stop it for a mid-day snack at The Butcher Shop in the South End on your way back into town. Scrumptious Roasted Squash, Antipasto and an extensive wine list are just the pick-me-up you’ll need before heading out on a walking tour of the city. Though a bit pricey, the food and atmosphere are well worth the splurge.

Head out of the Nine Zero and begin the walking tour down the Liberty Trail, a sure way to work up an appetite for dinner. There’s no better history lesson or better way to see Boston than to visit (on foot) such monumental sites as Paul Revere’s house, the Granary Burial Ground and Massachusetts State House.

Evening:

You can’t leave Boston without dining in the North End, home to some of the best Italian food in the country. And you can’t leave the North End without dining at Panza, the best of the best. Offering classic Italian, this was maybe the best Chicken Parmigiana of my life…and the verrrry full glass of Chianti didn’t hurt either! Though I’m sure their desserts are just as fabulous, top of your night (and your weekend) with one perfect cannoli from Mike’s Pastry around the corner. Take it back to the hotel and eat it in bed like I did—maybe the best idea ever.

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