Written by: that RedVelvet Life™ (@thatredvelvetlife)
Day 1
9:00am
Step back into time at the 1937 Boston diner, The Paramount on Beacon Hill for breakfast. Savor each bite of the gooey, chewy, yet firm Caramel & Banana French Toast - my personal favorite and the best in the world.
10:00am
Dodge the squirrels through a scenic walk of the Boston Public Garden and Boston Common. Follow the Freedom Trail to the Massachusetts State House, Faneuil Hall, USS Constitution up till the end point, the Bunker Hill Monument.
1:00pm
Make your way to James Hook & Co. by the Boston Harbour and try the iconic Boston Lobster and New England Clam Chowder.
2:30pm
Rent a Hubway bicycle and explore the city. Cycle down the alleys of the Financial District to the Zakim Bridge and back to Seaport District. Stop at the The Envoy Hotel Lookout Rooftop and Bar for a cocktail with a view of the sun setting upon the historical Boston Harbour.
6:00pm
Stroll down the picturesque Newbury Street, the most beautiful and popular street in Boston and shop till you drop! Enjoy a Hazelnut Latte at Thinking Cup, a Red Velvet Cupcake at Georgetown Cupcakes or a Dark Hot Chocolate at L.A. Burdick.
7:30pm
Indulge in the best and oldest Pizza in Boston at Regina Pizzeria or for a fancier Italian dinner head to Trattoria Il Panino. Satisfy your sweet tooth at Modern Pastry and drool over the authentic Boston Cream Pie Cannoli.
9:00pm
Watch a show at the Improv Asylum, a splendid improvisational comedy theatre.
10:00pm
Get carried away at the menu-less date spot Drink for a tailor-made round of booze.
Day 2
9:00am
Spend the morning exploring the Fenway area. Catch a Red Sox baseball game or book a tour of the famous Fenway Park. Grab a bite of the juicy Big Tasty at Tasty Burger.
1:00pm
Cross over to Cambridge for a fusion lunch at Little Donkey, serving Ramen Carbonara, Caviar Sandwich and Duck Nachos.
2:30pm
Absorb the intellectual vibes at Harvard Square and stroke the left toe of the John Harvard statue at Harvard University for good luck.
4:00pm
Make a tough decision between Zinneken's for a Nutella Belgium Liege waffle, Tatte for a Tiramisu cake and latte or Insomnia Cookies for an ice-cream stuffed cookie sandwich.
5:00pm
Catch a glimpse of MIT as you head to the Charles River. Rent a kayak and hold your breath while you admire Boston’s beautiful skyline under the sunset.
8:00pm
Dine at Yvonne's for a fancy dinner date or eat and drink with friends amongst a Peruvian vibe at Ruka in Downtown Crossing.
11:00pm
Dance the night away at the sleek Bijou nightclub.