For accommodation, stay at the Harbour Rocks Hotel. This 4-star hotel is in close proximity to other attractions such as the Sydney Opera House, Royal Botanical Gardens, Sydney Aquarium and Darling Harbour. Wotif.com showed rates as low as A$149/night.

Let’s start the day by perusing the stalls at an open air market for art and souvenirs.  The Rocks Market which occupies a closed-off portion of George St from Dawes Point Park down to Hickson Rd. Over 150 stalls can be found under the distinctive yellow sails every Saturday and Sunday from 10am to 5pm.

Next we’ll head to Australia’s oldest Observatory. Built in 1858, Sydney Observatory was essential to ship navigation, meteorology, timekeeping and for studying the southern hemisphere. The Observatory became a museum in 1982. The historic lens telescope in the south dome dates from 1874 and is the oldest regularly used telescope in Australia. In contrast, the mirror telescope in the north dome is fully computer controlled and incorporates the latest technology. The observatory is open daily from 10a to 5p and admission costs A$7.

You may have seen the breathtaking view of the Harbour Bridge from the Observatory. Now let’s head there for a closer inspection. The Harbour Bridge is fondly known as the “Coat Hanger” and is visible from many parts of the Rocks. It is possible to walk over the bridge through a pedestrian walkway. We’ll enter on the western side on Fort St near Observatory Hill. Once on the bridge, let’s climb up the the Bridge Pylon to the Pylon Lookout. For A$9.50 admission fee, the Pylon Lookout offers fantastic views of the city, harbour, and the Opera house.

It’s time to rest our feet and have an oyster & champagne lunch. Let’s head to the Sydney Oyster Cove located on the east side of Circular Quay. This casual spot offers everything from oysters to salmon to lobster. It is also possible to create your own seafood platter for a customized meal. Opt for alfresco dining where you can take in views of both the harbour and the city.

After lunch let’s head to The Sydney Opera House. One of Sydney’s most beautiful and unusual buildings, the Opera House is world famous. It is possible to walk around the building, and some of the foyer areas free of change. For A$35 (or A$29 online), a guided 1-hr tour is available for those interested in seeing the inner workings of the Opera House.

Located a short walk around the water’s edge from the Sydney Opera House, is one of the most breathtakingly beautiful settings you will see anywhere. The Royal Botanics Gardens have more than one million specimens and there is even a hop-on hop-off “train” for speedy access to different parts of the gardens. Entry to the gardens is free and closes at sunset.

Tonight let’s have dinner and enjoy a jazz concert at The Basement Club. Recognized as Australia’s number one jazz venue, The Basement delivers a wide range of styles with bands play almost every night. The dining room offers modern Australian cuisine with a flare of Asian influence. Booking ahead is a must.

The Back Bay neighborhood runs along the Charles River on the opposite side of Cambridge. This trendy neighborhood contains upscale shopping, boutiques, art galleries, and fabulous restaurants. The area is home to Copley Place, Prudential Center and The John Hancock Tower, Trinity Church, and shopping along Newbury Street.

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The home base of the trip is the Charlesmark Hotel a block from Copley Square. This 3-star boutique offers complimentary breakfast and wireless internet starting at $130/night.

Following a continental breakfast at the hotel, head to Prudential Center on Huntington Ave. In front of Shaw’s we’ll board the Duck tour. For $29.95, the World War II amphibious vehicle takes us through Boston landmarks including the State House, Bunker Hill, Fleet Center, The Common, Copley Square, Government Center, Newbury Street, Quincy Market and Prudential Tower. Though the highlight of the 1hr 20min tour is when the Duck splashes into the Charles River for views of Boston and Cambridge.

Returning to the Prudential Center, head north toward Newbury Street for a bit of (window) shopping. Known as the “Rodeo Drive of the East,” Newbury Street serves as Boston’s representative of fashion and style. The street is home to an eclectic mix of independent shops and high-end

For lunch stop in Stephanie’s on Newbury for a bowl of Boston Clam Chowder. The sidewalk cafe offers a nice resting spot for people watching and al fresco dining. Following lunch, continue east on Newbury Street toward the Public Garden.

Shopping isn’t the thing one can do on Newbury Street. There are nearly 40 art galleries for one to wander through. Some notable ones include Vose, International Poster Gallery, Galerie d’Orsay, and Newbury Fine Arts.

Nebury Street end at the Public Garden. Established in 1837 as the first public botanical garden in the United States, the twenty-four acre features a irregularly shaped pond where gardengoers can take leisurely cruise with the foot-pedal-powered Swan Boats for $2.75 during summer months.

Tonight’s dinner destination is Excelsior on Boylston Street. Its epic selection of international wine varietals are strikingly housed in a climate-controlled, three-story glass tower. Dine in the lounge and try the restaurant’s signature lobster pizza. The pizza is a favorite of Sox slugger Manny Ramirez, who eats frequently at Excelsior with his wife, Juliana.

End the evening at the Oak Bar at the Fairmont Copley Hotel. Boston Magazine has named the Oak Bar ‘Best Hotel Bar’. Offering one of Boston’s largest martini menus, the Oak Bar is just the right place for that night cap to end the day.