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In 1991 Billy and Akaisha Kaderli retired at the age of 38. Now, into their 3rd decade of this financially independent lifestyle, they invite you to take advantage of their wisdom and experience.

Santo Domingo Walking Street

Dominican Republic

Billy and Akaisha Kaderli

Map of Santo Domingo, the Colonial part of the city, and the Ozama River

The history of Santo Domingo goes back to 1496 when the brother of Christopher Columbus, Bartolome, left his ship and claimed this land for Spain. It is the oldest European city in the Americas. Today, it has been declared a World Heritage Site by UNESCO. Known as "Zona Colonial" this area of the city is located on the west bank of the Ozama River which bisects the city.

Paved walking street with stores on both sides

Rather like an open air mall, Santo Domingo's walking street has countless stores lining the walkway.


Santo Domingo is in perpetual summer climate

There are benches to sit down and take a rest after walking and shopping, but because Santo Domingo is in a perpetual summer climate, it is warm! Shaded seats are hard to find.

Paintings of all sizes

Flamboyant and colorful, hand painted canvases of all sizes are for sale up and down the walk way.

Colonial style architecture

Archways, flower boxes and wrought iron make this white colonial style building stand out. The main Plaza, or Parque Colon, is located down the center of the photo. This tree-filled square is where you can meet people of all walks of life, stroll around and relax.

The Spaniards used the settlement of Santo Domingo as the first point from which they conquered other Caribbean islands and much of the American mainland. This city was initially the political and cultural hub of Spanish presence in the New World.

In 2010, Santo Domingo was chosen as the Cultural Capital of the Americas. This prestigious nomination is comparable to being selected to host the World Expo or Olympic Games.

Tiny bar/cafe

There are many bars and cafes to choose from on this walking street. This one is WiFi connected and beckons to have you "pasatiempo" or pass some time here.

Another small, more modern bar

People like to come in out of the heat and grab a beer, maybe check their email and, when playing, watch the soccer games on TV. It's a great place for social interaction and a break from baking in the sun.

Special Menu

Restaurants advertise their specialties of the day. This one has a couple of pasta dishes, a cheeseburger and a selection of chicken entrees including baked chicken.

Sombrero store

It is very Latin to wear a hat and men look dashing, women look glamorous. This sombrero store sells various styles of hats including the Panama hat, made in Ecuador.

Store owner in a Panama hat

Did I say dashing? Panama hats are finely hand woven and then formed on a hot mold. Called Panama hats even though they are made in Ecuador, they have maintained popularity and style for many years.

Cesar, our guide, wearing a short, tight number

Besides being stylish, wearing a hat in this heat is a terrific idea!

Restaurant menu

This menu advertises it's Daily Special - either chicken or meatballs - for 165 Pesos, under $4USD.

They also serve pastas, fish, beef, chicken breast, pastries and more.

Emotional, wild dancing

The Dominican Republic is credited for creating the Merengue dance, which is both passionate and sensual.

This couple looks like they know what they are doing.

Themed restaurant

Waitresses wearing native costume call customers inside for this restaurant's daily special.

Bright, clean, and boasting colorful murals and paintings on the walls.

Cafe in the Museum of Chocolate

The history of chocolate begins in Mesoamerica, a region that stretches from central Mexico through Guatemala, Belize, Honduras and El Salvador. This area of the world is very diverse geographically, biologically and culturally and gave rise to societies such as the Olmec, the Aztecs and the Maya.

Dark chocolate, milk chocolate and white chocolate selections

Dark chocolate contains at least 35% chocolate liquor, plus cocoa butter and sugar. Milk chocolate has at least 10% chocolate liquor, plus cocoa butter, sugar and at least 12% milk. White chocolate is not technically one of the types of chocolate because it does not contain any chocolate liquor. It must have at least 20% cocoa butter, 14% milk plus sugar.



We enjoyed the samples available. They were so yummy!

Chocolate is the fermented, roasted and ground bean of the cacao plant. Chocolate beverages have dated back to 1900 BC. The Aztecs believed the cacao seeds were the gift from the God of Wisdom and the seeds had so much value that they were used as a form of currency.

Lots of variety

Originally only prepared as a drink, not as bars we enjoy today, chocolate was served bitter and frothy, mixed with spices, wine or corn puree. It was believed to have aphrodisiac powers and to give the drinker strength.

Zorro, a Mexican restaurant

There were lots of choices of places to relax and have a bite. Dominican food is a combination of Spanish and African styles and usually served without any hot chili or spice. Mexican food with its moles, chiles and tortillas offers a contrast.

Billy, ever the flirt

Billy made a friend with this reserved but amicable police woman, and of course, had to have his photo take with her.

Tourist train driver

Not to be outdone by Billy, this young man obliged me in having my photo taken with him. Speaking a bit of English, we talked about the favorite past time of the Dominican Republic - baseball! Over 800,000 children play organized baseball in the DR, and people here love the sport. Currently, U.S. professional baseball leagues have more than 100 players on their rosters who originated from this Caribbean Island.

The Tourist Train

This is the train that our friend in the above photo drives throughout the city. It's free, and the train takes you all around town, which in hot weather like it is in Santo Domingo, is a welcomed treat!

Another angle of the walking street

Lots of decorative wrought iron on windows, gates, and balconies give this street its charm. Old fashioned street lights run down the center and benches provide a rest stop from all the shopping.

It's hard to imagine today that this city was destroyed by an earthquake in 1562, was burned down in 1586 by Sir Francis Drake, and that the city has survived pirate attacks and invasions.

For more stories and photos of the Dominican Republic, click here

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About the Authors

Billy and Akaisha Kaderli are recognized retirement experts and internationally published authors on topics of finance, medical tourism and world travel. With the wealth of information they share on their award winning website, they have been helping people achieve their own retirement dreams since 1991. They wrote the popular books, The Adventurer’s Guide to Early Retirement and Your Retirement Dream IS Possible available on their website bookstore or on

Retire Early Lifestyle appeals to a different kind of person – the person who prizes their independence, values their time, and who doesn’t want to mindlessly follow the crowd.

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