Starting this month (the kick-off festival was May 1st) and running through October, SoWa Open Market (460 Harrison Ave, Boston) will offer “…a shopping experience like no other in Boston,” according to its website. Each Sunday, an ever-changing group of artisans will set up shop in an open-air market setting, hawking their trendy wares to throngs of people descending upon the South End neighborhood. Festival goers can peruse everything from hand-crafted accessories, designer clothing, original artwork, and more.

Despite the apparent contradiction, it’ll pay to be prompt for this haute event. Located at the foot of historic Beacon Hill, the swanky Liberty Hotel (215 Charles Street,
Boston, 617.224.4000) plays host to Fashionably Late Thursdays each week, where leggy, elegant models decked out in designer duds strut their stuff among bourbon-sipping bystanders.

On June 4, Best Buddies will partner with Audi to present the Audi Best Buddies Challenge, a high-end fundraising event with all the gourmet trimmings. Munificent participants have the option of cycling from Boston to scenic Hyannis Port, or running 5K with former Olympic gold medalist Carl Lewis.

It stands to reason that the Hard Rock Café would celebrate a milestone anniversary like…well, like a rock star. Touting itself as “music’s greatest memorabilia collection,” the Hard Rock on Wheels (a big-rig truck outfitted with a high-end collection of priceless rock items) rolled into Boston’s City Hall Plaza on Saturday as part of a cross-country tour to celebrate the restaurant chain’s 40th anniversary.

Designed by famed restaurant architect Peter Bentel, Island Creek Oyster Bar (500 Commonwealth Avenue, Boston, 617-532-5300) draws its interior inspiration from its namesake oyster farm in Duxbury. Ten of thousands of oyster shells fill Gabion cages to create a stunning three-dimensional art project (the wall took eight months to complete), and a dark, oversized photograph of Duxbury Bay (snapped by local photographer Stephen Sheffield) is splashed across the back wall, providing diners with a South Shore-inspired coastal oasis amidst a bustling Boston metropolis.

It’s time to get your bow ties straightened and your Nantucket Reds pressed: from now through Sunday, May 22, the world’s top-tier winemakers and connoisseurs are boarding the ferry to Nantucket to indulge in exquisite cuisine, perfectly-paired wines, and VIP parties at the 15th annual Nantucket Wine Festival. Presented by Nantucket Combined Charities, the haute festival’s headquarters is The White Elephant, a historic waterfront inn recently named Travel and Leisure’s number one resort in Massachusetts for 2011.

Open just in time for the summer season, Local 149 (149 P Street, South Boston, 617-269-0900) takes “eating good in the neighborhood” to a whole other level. (Apologies to Applebee’s, but there’s simply no comparison) Located on the corner of P Street across from the water, this South Boston high-end eatery — specializing in globally-influenced American cuisine — is decked out in vintage chic (from fire extinguisher beer taps to a collection of colorful vintage seltzer bottles against one wall), and its eclectic menu is as enviable as its décor.

Some of life’s best gifts come but once a year. Craft beer enthusiasts rejoice: Jamaica Plains-based brewery Samuel Adams has just unveiled the 2011 batch of its most extreme (and expensive) beer: Samuel Adams Utopias.

You don’t have to sit at home this summer watching Gilligan reruns on Nick at Night, dreaming about sailing the high seas with the wind at your back and Sperry Top Siders on your feet. Departing from the Seaport’s Rowes Wharf, Odyssey Boston Dining Cruises (60 Rowes Wharf, Boston, 1.866.307.2469) offer a three-hour tour of their own around Boston Harbor with fine dining (brunch, lunch, and dinner excursions are available), live entertainment, and not a bumbling, red-shirted first mate in sight.