The $20 Challenge: The South End

In “The $20 Challenge,” we face the daunting task of eating three square meals in Boston’s most expensive areas for a mere Jackson. As always, we recommend ordering water and getting your meal to go to avoid the expense of a tip.

The South End, with its combination of gorgeous Victorian brownstones and chic cafes, is one of our favorite Boston neighborhoods. Unfortunately for us, it is also one of Boston’s most expensive areas. On the plus side, this love-hate (or more precisely, love-envy) relationship makes it a great place for our inaugural $20 Challenge feature. The South End can be very expensive, but it doesn’t have to be. Behold, a day in the Tremont Street area for a mere $16.50. How? We’re glad you asked.

Breakfast: Francesca’s is a great place to watch the South End’s many fabulous (and fabulously good-looking) gay men flirt over great coffee. Grab a small Cafe Au Lait ($1.50) and one of their near-perfect apple turnovers ($1.75) and eat them in Peters Park off Waltham Street while coveting the adorable puppies that seem to be de rigeur in the neighborhood.

Lunch: Duck into the adorable and tiny Appleton Bakery Cafe for a sandwich on their fresh-baked bread. Treat yourself to the Rome, a veritable festival of caramelized onions, Portobello mushrooms, and smoked Gouda ($5.50). Bring it to Union Square Park and feel profoundly sad that you will never be able to afford to live there…or at least that’s what we do.

Dinner: You’ve been very responsible all day, so treat yourself to a steal that feels like a splurge. Head over to the tremendously popular Petit Robert Bistro. Indulge in some wonderfully hot and rich Lobster Bisque ($7.75). Feel free to eat it in the approachably elegant dining room, since you have enough left over for a tip. Congratulations!

Francesca’s Espresso Bar [MenuPages]
Appleton Bakery [Official Site]
Petit Robert Bistro [MenuPages]

[Photo: Flickr: bagelradio]

The $20 Challenge: The South End