Ogunquit, Maine and Perkins Cove in a Day

Footbridge Beach is located at the northern end of Ogunquit Beach
Footbridge Beach located at the northern end of Ogunquit Beach.

Ogunquit, Maine is gay. I don’t mean that flippantly or as an insult–Ogunquit has been a well-known LGBT destination for decades. It’s considered to be a milder version of Provincetown minus the sex shops and transvestite street-performers.

And that’s fine with us because Ogunquit literally translates to “beautiful place by the sea” in Abenaki–one of the Algonquian-speaking tribes of the northeast.

This town is top-shelf material. It has all of the benefits of a family-friendly community (it’s clean, sophisticated, and fashionable) without the headache of endless traffic on the Sagamore Bridge or a stupid expensive ferry ride to Martha’s Vineyard or Nantucket.

Unlike Cape Cod, generally speaking, Maine is far less crowded and cheaper by comparison. It maintains all the beauty and amenities of its larger, more popular Massachusetts counterpart without many of the negatives.

There are no college fraternity douchebags vomiting in public parking lots. You can actually find parking unlike the time Laura and I visited Newport, Rhode Island and searched for parking for nearly two hours. There are significantly fewer yuppies in salmon-colored pants. The locals are genuinely friendly. Almost suspiciously so…

Ogunquit Beach is 3.5 miles long, so there is always plenty of privacy if you’re willing to carry your luggage and pee in the ocean throughout the day.

A (Refreshing) Day Trip

One of the keys to having a good time on any vacation, no matter how small, is a getting off to a good start. If you get pissed off at the beginning, you might as well pack it in and sleep under your desk at work. So, leave early. It’s that simple. Beach towns are notorious for being cramped and Ogunquit is no exception–one-way roads, small lots, no street parking, and pedestrians everywhere. Traffic builds quickly and there is little relief.

Roll down the exit ramp from I-95 onto historic Route 1 in Kittery, Maine and cruise by the Kittery Outlets where my parents used to drag my brother and I to buy winter coats in August. Take a minute to admire the countless antique stores, clam shacks, and local souvenir shops as you go through York.

Imagine yourself retiring here: coffee by the ocean every summer morning, afternoon walks in the sun, and seafood dinners with Georgia O’Keeffe’s ghost. In the winter, there would be cozy wood fires, creamy hot chocolate, and extra-thick blankets in the living room.

As one might expect, there are dozens of world class seafood restaurants with the world’s freshest lobster and clam chowder competing for your dollar. But there are also some great Italian joints, new American bistros, bakeries, cafes, and coffee shops. Between the great food, relaxed atmosphere, and stellar beaches, we fell head over heels in love with York County and Ogunquit specifically.

All-day parking lot on Beach St. A 5-minute walk from the beach and cheaper than parking directly at the beachfront. There are parking lots all over Ogunquit at varying prices.
Miles and miles of clean, sandy beaches.

Ogunquit Beach is incredibly flat. At low tide, nearly 100-yards of pure sand extends between the protected dunes and the edge of the water. Plenty of room for rambunctious beach activities without kicking sand on the loungers and tanners that just want to relax in the sun. There is minimal seaweed, virtually no rocks, and decent swells for body surfing.

At high tide, the shore becomes rather narrow in certain areas, but the beach stretches down the horizon for about 3.5 miles into the neighboring town of Wells, so you can always find a place to set up camp.

A typical t-shirt and souvenir shop in downtown Ogunquit.

After you get off the beach, rinse your feet at the foot-washing station and head downtown to grab a snack and do some shopping. There are plenty of cheap boardwalk-style stores to pick up refrigerator magnets, t-shirts, sweatshirts, and hats. There are also classy art galleries, studios, and some interesting craft stores like Spoiled Rotten–one of our favorite home decor & gift stores loaded with tons of cool items, some made locally, most made in the U.S.A.

Meander down Shore Rd. past a few more hotels and restaurants to find the entrance to Marginal Way–a gorgeous 1.25 mile scenic trail along the coast of Ogunquit. The entrance is marked with a sign that is easily missed. Start across the street from the Seacastles Resort. Look for a narrow path that travels between two hotels, past a few tennis courts, and eventually opens up to the ocean.

Dahlias in bloom along the Marginal Way.
Dahlias in bloom along Marginal Way.
The view of Footbridge Beach from Marginal Way at high tide.
View of the Ogunquit River on the left as it joins the Gulf of Maine at high tide.

Marginal Way is neatly paved and well-kept. The fencing appears to be brand new and in good condition. The flowers and plants are in excellent shape and the views are astonishing. You can venture onto the rocks at your own risk.

Plenty of benches along the way to rest and soak in the views.
Plenty of benches along the way to rest and soak in the views.
A couple weds at the famous Beachmere Inn.
A couple weds at the famous Beachmere Inn.

Laura and I saw a couple celebrating their wedding on the lawn of the Beachmere Inn. They took wedding photos on the nearby rocks while waves crashed against the cliffs. Coincidentally, I had mentioned to Laura many months ago the various wedding packages offered by the Beachmere. When we saw the happy couple, Laura almost cried. We hope to get married here someday.

A very rare sight--new construction along Marginal Way. A placard on the wall reads "Dreams Do Come True."
Any new construction along Marginal Way is a rare and expensive undertaking. A wooden plaque on the wall reads “Dreams Do Come True” in red lettering.
Perkins Cove
The Basin at Perkins Cove.

At the end of Marginal Way lies Perkins Cove–an idyllic Maine fishing harbor that shares turf with fashion boutiques, jewelry shops, and some kick-ass seafood shacks. Dine next to the water, explore the quaint village shops, and indulge in homemade candy and ice cream.

Take pictures on the fully functional drawbridge and watch as the operator opens and closes the hinges to let the sailboats into the cove.

The Lobster Shack at Perkins Cove. Stay for a lobster roll with chips and coleslaw. Don't forget the clam chowder.
The Lobster Shack at Perkins Cove. Have a lobster roll with chips and coleslaw. Wash it down with a cold beer or six and don’t forget the clam chowder.


Coffee, tea, and pastry with a view from Breaking New Grounds.

You can book all types of sailing tours and cruises that launch from Perkins Cove–everything from cocktail cruises on sailing yachts to deep sea fishing for haddock and cod with crusty old Robert Shaw types.



The blue-ish boat that looks like a child’s bath toy is actually the Bunny Clark–a deep sea fishing charter boat.
Homemade chocolate and candy from Perkins Cove Candies.
Homemade fudge, candy, and other sweet confections from Perkins Cove Candies.

The peaceful towns York County, Maine will continue to be a source of inspiration and relaxation for years to come. Our next summer day trip will be several miles north of Ogunquit to the presidential town of Kennebunkport, where the Bush family famously established a secluded yet beautiful compound on the rocks in the 1980′s.

Hello, Mr. Boosh!
Hello, Mr. Boosh!

A Day at The Breakers Mansion, Newport, RI

The rear and northern corner of the mansion. Beautiful arches, huge windows, and lush greenery everywhere.
The Breakers mansion in Newport, RI

As we crossed over the Newport Bridge and entered the gorgeous seaside town of Newport, Rhode Island, hundreds of yachts and sailboats greeted us as they slowly drifted across the harbor. Lighthouses, docks, and beautiful beach homes lined almost every inch of coast as far as the eye could see. A wonderfully salty, briny sea breeze floated through the car windows and kept us cool even as the mid-morning sun gently baked our skin through the windshield.

It was an idyllic approach to the coastal New England paradise. Then, we hit traffic. I expected it to be bad on a holiday weekend, but getting through town was a total debacle.

The tremendous influx of cars and pedestrians battling for territory was only exacerbated by the fact that Newport is most certainly an historic New England maritime town. That means lots of small, narrow one-way roads and very few traffic arteries. All of the streets seem to connect with each other in small loops or segments so traffic has nowhere to disperse. Tight quarters also means less room for parking and, in turn, heavily inflated prices for what little parking is available.

But, on the bright side, sluggish traffic through town meant Laura and I got to inspect each storefront and landmark in great detail before moving forward in ten foot increments. Newport is fucking beautiful. I wasn’t surprised to learn that JFK married Jackie Bouvier here. The whole town smells of Kennedys.

Eventually, we passed the harbor & the wharf and made it through the congested downtown areas. If the yachts, high-end boutiques, and International Tennis Hall of Fame weren’t clear enough indicators of a wealthy town, the colossal mansions along Bellevue Avenue should do the trick.

Bellevue Ave starts in the heart of downtown Newport (right at the corner of the famous Hotel Viking) and runs south all the way to the ocean. Along the way, there are dozens of amazing privately owned homes on both sides of the street juxtaposed with publicly-supported mansions open for tours and viewing.

And the grandest and most opulent of all the Newport mansions is called…

The Breakers

The rear of the estate faces the ocean.
A rear view of The Breakers mansion which faces the Atlantic ocean.

The Breakers, named after the crashing sound the waves make as they break against the nearby ocean cliffs, is the 17th largest home in the U.S. and is open daily to the public (for a fee). It was built in the 1890’s by the prominent Vanderbilt family and, from my understanding, the Vanderbilts dedicated all of their free time and money to building gigantic houses to piss off their neighbors.

They built numerous other homes in states from Massachusetts down to Florida, including the largest house ever built in New York City.

A front corner of the mansion and pathways through the gardens.
A front corner of the mansion with pathways through the gardens.

As you step inside the massive wooden front doors, a friendly host scans your ticket and hands you a headset. The tours are self-guided and photography is prohibited inside which explains the lack of interior pictures in this blog post. Sorry! I tried to snap a few photos and was quickly reprimanded by watchful attendants.

You can skip parts of the tour or repeat the audio guide as many times as you’d like. Laura and I spent more time studying the sections of the estate nearest the ocean as they were the most impressive to us.

The view from an incredible open-air living room on the second floor. There is so much detail in every inch of the estate, from the columns to the tiles and the fixtures.
The view from an open-air living room on the second floor accessible from two of the bedrooms.

Every single room of this French-inspired mansion was a display of absolutely ridiculous wealth. Fifty-foot ceilings, marble & abalone columns, gold trim everywhere, platinum-coated walls, thousands of rare stones & gems…

I mean, the first fifteen minutes in the Great Hall were legitimately dizzying–there was so much to process that I actually had a difficult time focusing at first. I had never been in the presence of such wealth and immensity before. The level of detail in every fixture and every inch of space was incredible. You could spend an entire month locked in each room and still miss some intricacies.

The Billiard Room opened up to the lawn revealing a remarkable ocean view. A salty breeze wandered through each enormous bedroom window. The bathrooms even had saltwater pumps for therapeutic spa-like treatments and saltwater baths.

The massive kitchen with a single 21-foot coal-burning cast iron stove and a zinc work table.
The stunning kitchen with a single 21-foot coal-burning cast iron stove and a zinc work table.

My favorite room in any home, the kitchen, was beyond breathtaking at The Breakers. I was able to evade the attendants and hide in a security camera’s blind spot long enough to snap a single photo. Yes, I said security cameras. The Breakers is fully wired for electricity and has been that way since its construction. As you can imagine, electricity was not a cheap option in the 1890’s, but fuck it, they’re Vanderbilts.

There was an enormous cast iron stove which was heated as a single unit with coal fires, and a zinc work table for the chefs (who lived on site along with 40 other staff members). The adjacent room was used as storage for mountains of glasses, dishes, and cutlery–so much that it had to be split up into two floors. Interestingly, the entire kitchen facility was built as a separate section away from the rest of the main house to protect it in case of fire.

Just a portion of the massive backyard which drops into the ocean. Visitors relax in the grass and listen to the sound of waves crashing against the rocky cliffs. The peaceful sound gives the estate its name, "The Breakers."
Just a portion of the enormous backyard which drops directly into the ocean. Visitors relax in the grass and listen to the sound of waves crashing against the rocky cliffs.

At the rear of the mansion sits a huge patio and a staircase descending to the backyard which is almost big enough to be a professional baseball field. The grounds are lined with flowers, exotic trees, and pebbled paths that wrap around both sides of the estate.

As Laura and I relaxed in the shade of a very old oak tree, I entertained the fantasy of growing up a Vanderbilt child–spending summers at The Breakers, chasing dragonflies around the lush grounds, and getting grass stains on my new breeches.

It’s funny how indescribably different the life of a Vanderbilt must have been despite the fact that we all start as innocent, pie-eyed children–nothing more than fleshy sacks of water & bone just trying to have a little fun in the summer sun.

Grande Plans: Big Sur, California and The Pacific Coast Highway

Dreaming of the Pacific... (Photo: Medhat Ibrahim, My Shot)
“California Love.” The Bixby Bridge sits in the distance surrounded by cliffs and ocean waves in Big Sur, California (Photo: Medhat Ibrahim, My Shot)

It’s a bittersweet time for us. A dear friend of ours recently accepted a position at a brewery in northern California and leaves in a few days to explore other side of the country. While it’s an incredibly exciting opportunity for him, it will be sad to see an empty seat in the canoe when our crew ransacks the lake house in New Hampshire this summer.

On the bright side, his relocation opens up an opportunity to visit California for the first time and possibly complete a very high-ranking item on my bucket list: drive up the Pacific Coast Highway from Los Angeles to San Francisco in a rented convertible.

That’s right. This New England boy has always dreamed of a legendary On The Road departure–a quarter-life crisis. Just “go Kerouac on everyone’s ass” and disappear in the middle of the night for San Francisco in search of adventure, intoxicants, and any life experiences that may come. In my head, I glamorize the vagabond beat-poet lifestyle: fending off dirty dealers & booze-addled women, sipping coffee at 24-hour diners, and huffing down Marlboro reds.

However, at this point in my life, I’d gladly settle for a fresh fish taco with jalapeno, avocado, and a killer sauce.

The Bixby Bridge spans across the creek along Route 1 on Pacific Coast Highway in Big Sur, California. (Photo: Douglas Croft)
The Bixby Bridge spans across the creek along Route 1 on Pacific Coast Highway in Big Sur, California. (Photo: Douglas Croft)

Early Stages: Planning the Road Trip

The Pacific Coast Highway runs from California to Oregon and is a truly exhilarating, cliff-hugging experience, so I’m told. Perhaps the most famous section is Big Sur, a sparsely populated coastal area named after the Spanish translation for “Big South.” Ironically, LA is nicknamed “Big Sewer” and is farther south.

There are no specific borders or boundaries, but Big Sur stretches along miles of mountainous coastline, epic cliffs, vast bridges, and winding roads with views that make even native Californians gasp in awe. It’s an all-American road, if such a thing exists, ranking among the nation’s most scenic and must-see drives. National Geographic included the route in their book, Drives of a Lifetime: 500 of the World’s Most Spectacular Trips.

Ready to “go Kerouac” yet?

The Pacific Coast Highway is a gorgeous stretch of road running hundreds of miles along the coast from California to Oregon.
The Pacific Coast Highway is a gorgeous scenic road stretching over 1700 miles along the coast from California to Oregon. (Photo: National Geographic)

The Big Sur scenic route starts somewhere in San Luis Obispo and travels north up the coast to Monterey (I’m assuming that’s Californian-speak for “one small surf town to another small surf town”), but Laura and I plan on starting farther away in LA and ending up slightly north of San Francisco to visit our friend. Avoiding all highways turns a leisurely five-hour drive into more than nine. But, we’ve always dreamed of doing this together. We imagine it would be like that movie Sideways except awesome.

Either way, we need a car.

The first thing to do before renting a car is to check for coupons, deals, and promotions. That’s obvious enough.

Rental cars are significantly cheaper away from the airports, so we plan on site-seeing in Hollywood, dry-humping Tom Cruise’s front gate in Beverly Hills, and getting shot in Compton before picking up a car elsewhere. One-way trips always cost more per day, so only reserve a car for the actual road trip, not the entire vacation. Public transportation in LA and San Francisco are far less horrendous than whatever Boston puts forth, so getting around town is not an issue.

It’s no secret that convertibles will cost more to rent than economy cars (in my recent searches on Avis, Budget, and Enterprise up to 400% more in some cases). So, be prepared to pay a premium or settle for something less extravagant.

Fuel up before leaving civilization. Gas on certain parts of the Pacific Coast Highway is notoriously expensive because, well, it’s so god damn remote. Sparsely populated is not hyperbole. Recent reviews and posts on TripAdvisor report gas as high as $7/gallon. I suppose being so isolated has its perks and its pitfalls, so make sure to gas up before leaving. And it probably wouldn’t hurt to pack a gallon or two of water, some energy bars, and a fire-starting tool… just in case.

Don't die out there, kid. Photo: Les Stroud, Survivorman
Please, don’t die out there, dude. (Photo: Les Stroud, Survivorman)

Our first foray on the west coast is still in the works. More research and planning needs to happen to make sure the good stuff isn’t missed and the bad stuff is avoided.

To me, the anticipation that comes from preparing for a big trip is almost as exciting as the actual trip itself. I love researching different restaurants & attractions and getting to know the lay of the land before ever stepping foot on it. I thoroughly enjoy discovering and sharing local hints & tips that the average tourist overlooks.

I also love it when everything goes to shit and you end up wearing a poncho and eating hot dogs in the rain, laughing, trying not to let too much rainwater fall in your beer.

The Infamous Slum of Old San Juan

They say the body acclimates to warm weather over time. A three-hour flight was not enough for this lifelong New England native to prepare for the wilting heat of Puerto Rico. Laura, on the other hand, was born and raised on the enchanted island. She handled the climate much better with her thinner Caribbean blood.

Beads of sweat rolled off my forehead as we wandered through the historic cobbled streets of Old San Juan. The occasional droplet ran down my back. Heat and humidity have a way of breaking me down ruthlessly– my biggest weakness. I toughed it out. Puerto Rico is hot, but it’s absolutely beautiful as well.

A typical colorful street in Old San Juan, Puerto Rico.
A typical street in Old San Juan lined with colonial buildings and colorful walls.

Old San Juan is the historic section of Puerto Rico’s largest city, San Juan. Fortified by Spain in the 1700’s, the city is loaded with beautiful colonial buildings and historic monuments. Steep cliffs and concrete walls were built along the shore as protection against invading forces. Every calle (“street”) has remnants of history, religion, and Caribbean traditions. Generations of families with deep African and Spanish roots still live here. Churches and cathedrals are everywhere.

There are also plenty of bars, theme restaurants, and souvenir shops on every street catering to tourists and locals alike. You can take a walking tour through a colonial-era military fort, buy a computer, and fill a prescription on the same block. The old seamlessly blends with the new.

Under every blue Spanish cobblestone hides a dirty secret.

On our first night in Old San Juan, we met two of Laura’s cousins at a popular restaurant near the harbor. They lived in the neighboring town of Carolina a few minutes up the main strip. They were polite and looked like any other fellows in their early 20’s–flat-brim baseball caps, matching Jordans, and surgically attached smartphones. We introduced ourselves, ordered a few rounds, and discussed island living over plates of roast pork, fried plantains, and white rice. An idyllic start to our Caribbean getaway.

After dinner, they drove us around San Juan to check out the sights and sounds. We passed a few clubs along the harbor that were stuffed to the gills with middle-aged tourists dancing on the open patios, sipping fruity umbrella drinks, and wearing bright summer linens. Police details were on nearly every corner. Luxury resorts were stacked along the beach in orderly rows like Monopoly pieces. As were more cops.

“Avoid people that look like us,” said one of the cousins.

He was referring to a certain breed of young Puerto Rican males–flashy ones with nice clothes, bright jewelry, and expensive cars. They were most often well-connected drug dealers or gang members looking for trouble. Lots of legitimate money runs through these bright and elegant avenidas, but San Juan has a much darker side–a serious criminal underworld lurking in the shade from the palm trees.

That night was the first time I’d ever heard of La Perla.

It’s a hidden slum within Old San Juan. Legendary among locals, it inspires countless stories and rumors about drugs and murder. It’s location outside the city walls secludes its cogs and inner-workings from the curious gazes of nosy tourists.

A cemetery sits between Castillo de San Cristobal and the monument of El Morro in the distance.
On the left, a car exits through one of three main access points into La Perla slum. To the right, a cemetery sits outside the city’s walls.

These two guys knew all about it. They witnessed the plethora of gang activity, drug trafficking, and violent crimes that permeated the streets of San Juan. Shootings and stabbings were incredibly common. They described which sub-barrios to avoid while site-seeing and stressed the importance of self-awareness in Puerto Rico. They warned us about local gang members and their penchant for violence.

About 80% of crime on Puerto Rico is drug-related. The island’s geographic location and political ties with the U.S. make it a critical jump-off point for drug cartels and smugglers looking to sneak their products into America. Cocaine is still a big seller. In recent years, traffickers from Colombia, Venezuela, and Mexico have started funneling drugs through Puerto Rico and Dominican Republic at much higher rates.

Most of the cocaine is destined for major cities along the eastern U.S. seaboard, like Miami, Atlanta, and New York. The rest of it remains on the island leaving gang members to wage violent wars against their rivals over money, drugs, and control of the local drug trade. The sky-high murder rate in Puerto Rico is a direct result of the major increase in drug traffic.

New-Old San Juan

In the 1950’s and 60’s, Old San Juan was in a state of disrepair. Prostitution & drugs plagued the streets, crime was rampant, and the infrastructure was in really poor shape. It was Detroit with palm trees. Politicians started pushing legislation to revitalize local businesses, clean up the neighborhoods, and turn the city into a Caribbean hotspot for tourists and honeymooners. They modeled the redevelopment of San Juan after the wildly successful Disneyfication of Manhattan (which still continues to this day).

The government created tax incentives to attract businesses and eliminated rent control to drive out poor folks. They started building endless hotels, clubs, and restaurants. The poorer segments of society were pushed away from the community–banished to the outskirts of the city where the cost of living was more affordable. That made plenty of room for hotel magnates and restaurant conglomerates to demolish and rebuild.

Overall, the government’s efforts to rejuvenate San Juan (particularly Old San Juan & the colonial neighborhoods) were successful.

Except for La Perla

The next day, Laura and I toured the fortress of Castillo de San Cristobal. A street vendor persuaded us into trying a Puerto Rican delicacy known as piragua (Spanish for “snow-cone”). How exotic! The pineapple flavored one was the best. We stopped to enjoy our frozen treats on a grassy hill as a group of students gathered nearby to eat their lunches.

Then, Laura pointed it out.

La Perla sits between two historic Spanish forts in Old San Juan, Puerto Rico.
The micro-slum of La Perla sits against the ocean, nestled between two historic forts in Old San Juan, Puerto Rico.

Four hundred feet from snow-cone-eating tourists and students on field trips sat La Perla.

The infamous drug-infested slum was smaller than I’d imagined. It stretched about 600 yards or so along the rocky coastline. It was completely secluded and tucked away between the ocean waves and the old fortress walls that once protected the city from invasions. An ideal location for anyone wishing to partake in illegal activities in private.

And it was certainly the most picturesque slum I’d ever seen.

A basketball court on the outskirts of La Perla. Concerts and gatherings are held here. We could hear chickens squabbling nearby.
A basketball court on the outskirts of La Perla where weekly concerts are held in an effort to change the community’s poor reputation.

La Perla originated in the 19th century as a zoning area for cemeteries, slaughterhouses, and slaves to stay outside the city walls away from the community center. Over time, farmers and the city’s poorer residents established their homes there.

With Old San Juan under the scrutiny of a clean-up effort by local government, the drug dealers and gang members moved to La Perla in droves to lay low and begin new enterprises. The DEA estimates about $20 million worth of drugs are sold within the slum each year. Drug traffickers, arms dealers, and slumlords control the neighborhood with impunity.

Laura’s cousins explained that, for the most part, law enforcement leaves La Perla alone. Aside from an incredibly rare police raid in 2011 spurred by international criticism due to record-breaking murder rates, the cops simply hang back and make sure violence doesn’t spill into areas where tourists frequent.

A self-governing system of illegal activity operates within the slum–a real-life Puerto Rican version of The Wire. With cops looking the other way, the black market can thrive out of plain view which keeps crime off the busy streets and away from tourists. The city maintains a safe, positive image and the criminals continue to rake in big profits. Everyone is happy! Except the residents of La Perla

So, is it safe..?

Generally speaking, outsiders and tourists are not the target of violence in Puerto Rico. It’s a safe place to visit and I recommend it to friends and family.

It’s even safe within the boundaries of La Perla, relatively speaking, of course. Outsiders only enter La Perla for one reason: to buy drugs. Dealers don’t want their customers harmed or scared away–that’s bad for business. So, outsiders are usually allowed to enter and exit unscathed during the day.

However, flashy unsuspecting tourists can easily find trouble. Unless you’re desperately trying to feed a bad dope habit, I’d reconsider venturing into the slum for an adventure.

Tourist maps posted in the city often omit the existence of La Perla’s streets to deter tourists from accidentally wandering into the high crime areas. Even though it sits mere steps from major tourist attractions, there are only three main access points to La Perla. Each one is clearly marked with plenty of graffiti and grime–the international symbol for “this is a bad neighborhood.”

We chose not to breach the inner walls of the slum during our stay and only explored the outskirts during the day. We were not willing to take the risk of ruining our rare opportunity for a romantic Caribbean getaway in the name of spontaneous journalistic adventure.

All of the same “Rules of Street Smarts” in the U.S. (or any other country for that matter) apply in San Juan: Don’t flash your cash, look like you belong, walk with confidence, and know exactly where you shouldn’t be.

Get Mugged: Gourmet Coffee in the Ghetto

A single luxury high-rise stands alone in Worcester, Massachusetts stretching twenty four stories into the sky. You can see it from I-290, the highway running through the middle of the city. It’s one of the definitive buildings in Worcester’s modest skyline: The Skymark Tower. I saw floor plans and video tours of the interior when I was apartment hunting last year–it looks really nice. When President Obama was here last week, he stood just blocks away from it. And I’m sure he could see it from Air Force One as he took off from Worcester Airport.

Don’t be fooled. Directly across the street from the tower’s entrance, a homeless guy is pissing himself and blacking out in front of a liquor store in the warm afternoon sun. Further up the block, a shirtless guy is yelling at himself and massaging his own belly fat like a couch pillow, while a crackhead wearing a suspiciously unseasonable winter coat passes by on a girl’s bicycle.

Welcome to my hometown.

Ironically (and perhaps symbolically for locals), the tower marks the entrance to the self-proclaimed ghetto of Worcester–the southern neighborhoods of Main Street affectionately known as Main South.

This is where dreams go to score dope. Visitors rarely venture into this part of town (shockingly, you don’t see many Yelp reviews in these parts) and self-preserving locals know what streets to avoid. Most of the city’s drugs mingle here. Shootings and stabbings are common. Worcester Police recently installed a gunshot detection system that targets several problem areas in the city, including Main South and Grafton Hill (a rising star on the high-crime watch list).

The city’s movers and shakers have tried to gentrify parts of Main South for a long time, focusing their efforts primarily on the area surrounding the iconic Hanover Theatre. Buying up devalued property, raising rent, and pushing poorer residents to the outskirts of the city and surrounding suburbs–Gentrification 101. The tower is one of the most identifiable symbols of “revitalization” in the city.

Results have been moderate and progress has been slow. Main South is still home to low-level street gangs, prostitution rings, and plenty of drugs, but it also has some awesome ethnic food (naturally), highly-ranked Clark University, and…

Acoustic Java

Empty tables at Acoustic Java on Main Street, Worcester, MA.
You’ll forget all about getting robbed at gunpoint and remember the emergency $20 you crammed in your ass (gotta have street smarts). The coffee is that good.

An oasis. Not the shitty British band. This place is a true oasis from the drug-infested shooting gallery that surrounds it. Ok, that’s overly dramatic. This isn’t Compton. But, Main South is definitely a desert wasteland especially if you grew up around here. Thankfully, Acoustic Java on 932 Main Street is a magical pool of glorious life-nectar (and you don’t even have to leave the heavily-patrolled main artery).

It’s a welcomed respite from the grimy streets. The green storefront blends into the row of adjoining shops but there is a dark sign above one of the doorways. Find it and get inside quick.

Have a seat and enjoy a book with your coffee and snack. The troubles outside will seem like a distant memory.
Have a seat and enjoy a book with your coffee. The rough streets outside will seem like a distant memory.

Stocked bookshelves, loaded dessert cases, gourmet coffee & tea, a clean lunch menu, and a really warm atmosphere–all the makings of a great little coffee shop. The smell of coffee beans will smack you in the face as you walk in. Hard. Beans from all over the world. Brazil, Ethiopia, Kenya, Rwanda, Colombia, Costa Rica, and more. I asked for two pounds of Ethiopian and Sumatran. It sounded like a drug deal and I cackled to Laura in the store. I am 28 years old. Why do you ask?

Coffee, tea, sandwiches, snacks... Are we still in Main South?
Coffee, tea, bistro-style sandwiches, pastries… Are we still in Main South?

I’m hittin’ that Ethiopian shit right now, man. Strong stuff.

This should be the future for small businesses in America. The new generation of business owners are not afraid to take chances in developing neighborhoods with lower rents; neighborhoods previously thought to be fruitless and too dangerous. They rely on good relationships with locals to remain relatively unscathed (aside from recent surges in graffiti & tagging) and quality products & services to succeed.

Or maybe they don’t have a choice?

Credit is hard to come by and most cities have made it clear that “presentable” areas of town are reserved for established business owners and national chains. The cool kids table.

Instead of peppering the edges of the ghetto with parking garages and loft apartments, the city needs to attract more small business owners by offering financial incentives and increasing police reinforcement. Get people to spend money in our city again and feel safe about doing it. Let’s keep things funky and grimy without the threat of getting stabbed.

We don’t need to cover our tattoos with cheap suits from Macy’s to pretend we fit in. Rough edges are more interesting.

Paul Revere Ate Here


World Famous Mike's Pastry in Boston's North End
An accordionist serenades customers waiting in line at the world famous Mike’s Pastry in Boston’s North End.

Boston’s North End has come unstuck in time. I think it was the cheering that did it: hundreds of toasted bar patrons wearing blue Italia jerseys screaming with joy as Italy went up 1-0 against England in the World Cup match. The echoes are still bouncing off the narrow alleys if you listen carefully.

The red-brick tenements that once lined the cobbled streets are now upscale restaurants and condominiums sold off to the highest bidder. The floods of Italian immigrants and their children have moved on; replaced by floods of tourists, young professionals, and business owners. Even my beloved Prince Pasta hasn’t been local since 1987–they’re a lone brick in a massive Spanish-owned food conglomerate based in Madrid. Little Anthony would hardly recognize them.

This isn’t all bad, though.

Those toasted bar patrons I mentioned? 99% of them American-born. Maybe their grandparents or parents came here from Italy, but like me, they’re first or second generation Americans now. Those blue Italia jerseys were purchased with good ol’ American greenbacks.

Ever since I can remember, the North End was packed with restaurants, a few designer shops, and a lot of historic attractions. Stiff competition is good for the consumer–with so many Italian restaurants and cafes vying for your dollar, the quality of your experiences will always be top notch. The Italian food in this neighborhood is world-class. It rivals anything that comes out of New York, Sicily, or the Pope’s house. A lower population (barely 25% of its 44,000 peak during the influx of immigrants in the 1930s) means less community services are required, like schools, which leaves more room for development.

But not enough room for parking. Good luck with that.

"The Original Italian Caffe in the North End of Boston" -- T-Shirt from Caffe Vittoria on Hanover Street
“The Original Italian Caffe in the North End of Boston” — shirt from Caffe Vittoria on Hanover Street

I’m not a foofy coffee type of guy, generally speaking. I like my coffee black, my beer dark, and my steak rare. So, this was my first caffe latte experience, appropriately at Caffe Vittoria on Hanover Street. This is a legendary spot directly next to the equally renowned Mike’s Pastry. The two have conspired for decades trying to turn me into a fat piece of garbage.

Remnants of a cafe latte and a sfogliatella at Caffe Vittoria on Hanover Street in Boston.
Remnants of a cafe latte and a sfogliatella at Caffe Vittoria on Hanover Street in Boston.

Ok. It was fucking glorious. The steamed milk was thick, frothy, and buttery–it added a texture and dimension to coffee that I’d never tasted before. A true complement to the bitterness and acidity of a well-made espresso. The sfogliatella was constructed with two million layers of flaky pastry baked around a rich lemon custard. Are you sick and/or aroused yet? Good.

For a moment, sitting in that coffee shop with Italy vs England in the background, I felt new. I felt slow, too, in a good way. Ironic, given the surge of caffeine pulsing through my veins at that moment, but I was in my happy place. The world was no longer in a hurry. My next sip of nectar was my only concern. I felt connected to the history that soaks these streets. I wanted to climb the statue of Paul Revere (that was the caffeine). It re-awakened that desire most people have to drop everything and move to Europe to become a travel writer and work the vineyards in the summer. Not that I’ve looked into it.

That dreamy, haze-filled moment lasted briefly because Caffe Vittoria is cash only.

So, I wandered down Hanover Street…

…for an ATM of which there were many. Yeah, that whole gentrification and development thing again. That should have made for a quick trip while L finished her coffee at our table. But the ATM across the street was out of order. And the one at the end of the block wasn’t reading my card.

I kept walking. The streets were crowded with tourists and soccer fans heading to dinner and taking in the sights. I heard so many different languages. I love that about Boston and city life in general. I counted Spanish, French, Italian, and German within two blocks. I passed two older Italian men standing on the sidewalk holding a bottle of wine. The shorter man was describing, in his broken English, the differences between cabernet sauvignon and pinot noir, while the bald one politely refused to accept the gift. For another moment, I time traveled.

Finally, I came to the statue of Paul Revere. Families and tourists were posing for photos and reading the placards. The North End is a snapshot of history. There is still an “old world” feel down here despite the intrusion of new world amenities and baggage. It’s a reminder of what existed before and what might exist in the future and how they can peacefully co-exist. When I have children, I’ll take them here. And I’ll be sure to bring cash so I don’t pay a $3.50 fee again. Thanks, Paul.