lucky penny loves jetsetting solo… but without cute boyfriend, it sometimes gets lonely.

in san francisco, the travelocity roaming gnome quickly became her *new* companion. affectionately nicknamed gnomie, he was at her beck and call… croissants at tartine, tacos at la taqueria and ice cream at bi-rite creamery, she soon realized that she was not so lonely after all.

her photos were much more fun than the typical self-portraits, too. complete strangers started to take notice as gnomie was the best ice-breaker of them all.

perfect for any suitcase, the classic 8-inch figurine is available online at the roaming gnome store.

travel tip: make sure he is all wrapped up, or he could end up with no limbs. #boozybirthdaybootcampfail

***psst… photograph taken by jetset penny’s natalie… in front of the painted ladies, alamo square.

lucky penny can often be found lounging by the thompson hotel rooftop pool, but if she closes her eyes hard enough and clicks her ruby red slippers… cute boyfriend will whisk her away to maui for their anniversary.

for six days, the lovebirds enjoyed paddle board lessons on kihei beach, snorkeling in the reef, massages at the grand wailea, and oceanside dinners of grilled butterfish at humuhumu.

all done in her *new* bikini, a white crochet beauty by trina turk… perfect for highlighting her sun-kissed glow.

now to show off her tan lines back home!

lucky penny loves a good gossip sesh… especially all the dish at the society’s annual smut soirée hosted by lainey gossip. this year came with a twist: best-dressed winner gets a $2,000 shopping spree at the bay. hold. the. phone.

her lovely ela, designer of her eponymous handbag collection, was not only chosen as one of four finalists… but she even won!

the secret was in her accessories: colour block sandals by pierre hardy, and her milck clutch in a heart-stopping rouge. it is sexy enough to be the partner in crime to cute boyfriend, but practical enough to hold money, i.d, lipstick (peach, of course), cell and keys.

a clear winner in her book, even though she may be biased. *wink*

***psst… guest blog post written by the charming and witty, natalie taylor, who will also be penning as jetset penny. welcome to the family, love!

lucky penny is a wee obsessed with madewell… a darling, little boutique in soho (nyc, that is) which pretty much resembles her *dream* closet.

she is smitten with this pullover parka by penfield. massachusetts-based penfield, with an adorable polar bear logo, is known for “its top-notch, weather-resistant outerwear—coveted by fans of heritage-style clothing and outdoor enthusiasts alike—since 1975.”

her *new* olive green windbreaker is lightweight yet warm, has drawstrings at the waist and hem, a hooded peak, and pockets for keys and ipod when she is running a neighbourhood 10k… or moving a couch in the pouring rain.

***psst… they deliver to canada! [insert cheering credit cards everywhere.]

lucky penny has fond memories of backpacking through southeast asia.

her first stop, the gateway where most travellers go, was khao san road in bangkok. it is a mecca of hostels, food and bars. market vendors sell cheap fisherman pants and “same same” t-shirts. after a singha beer and pad thai from a food cart, lucky penny felt right at home.

khao san road, the entertainment district’s new kid on the block, channels the energy and chaos of its namesake. the raw space is noisy and friendly… reminiscent of a time whilst chatting with fellow foreigners at her hostel bar. but the food is above and beyond anything she tasted on the streets of bangkok.

chef nuit regular (a former nurse who moved to canada after meeting her husband on an elephant ride in thailand) creates dishes with all the salty, sweet, spicy and sour hallmarks of thai cooking.

lucky penny and cute boyfriend barely said a word to each other while sharing pad gra prao (spicy beef with basil and a fried egg), squash chips with a tamarind dipping sauce, and street-style pad thai, natch.

***psst… also visit sukhothai, the couple’s first restaurant in cabbagetown. just as yummers!