• Sperry Top-Sider (Man’s Best Friend)

    Style | Prep Essentials  

    To understand the top-sider, the clubby icon of summer shoedom, we need to travel back to a winter’s day in 1935 when a sailor and amateur inventor named Paul Sperry took a walk with his cocker-spaniel, Prince. Correction—it wasn’t so much a walk as it was a run, since Prince quickly took off across the snow-covered ice without any slips or slides. Sperry, intrigued by Prince’s stability, took a closer look at his paws and noticed a subtle texture that gave the pooch his traction. He then returned home and, with a penknife and a sneaker, carved the sole that would become the basis for Sperry Top-Siders: a pattern of way cuts called siping that opens and closes when the foot flexes and that squeezes out water to give grip on the slipperiest of surfaces.

    Paul Sperry charged $4.50 a pair for the first boat shoe, demonstrating an early commitment to quality at a value. Speaking to value, Sperry actually offered a peg leg discount. A man who lost his leg in a war contacted Paul Sperry and told him how he hates buying pairs of shoes only to throw one of them away. Sperry gave him a special deal—selling one shoe at half the price.

    After becoming established as a direct mail business, Sperry Top-Sider began to be distributed by Abercrombie & Fitch, then known as The Greatest Sporting Goods Store in the World.

    In 1939 the U.S. Navy negotiated the right to manufacture Paul Sperry’s shoes for its sailors, leading the Authentic Original to become the official footwear of the U.S. Naval Academy’s casual uniform, which continues to this day. As a result of the Navy contract, Sperry’s business was purchased by the U.S. Rubber Co., which then marketed the shoe across the country.

    Sperry’s popularity as a casual street shoe soared during the 1950s as restrictions on the use of leather and rubber associated with World War II were lifted. Photographs of the Kennedy family vacationing in Hyannis Port triggered an international love affair with classic American style in the 60s—of which Sperry Top-Sider’s iconic boat shoes and sneakers were an integral element.

    The Kennedys at their Hyannis Port home

    The founding of Sail magazine the following decade, the film Jaws, the star power of sailors such as Dennis Conner, high fashion’s obsession with nautical style and the creation of the American Sail Training Association created a maritime frenzy that helped fuel Sperry’s rapid growth.

    With the publication of The Official Preppy Handbook, the tongue-in cheek satire that has gained beloved cult status, the Sperry Top-Sider is immortalized as the official footwear of preppy style. Sperry continues to celebrate their nautical heritage by becoming the official footwear of the U.S. Sailing Association.

    Sperry introduces the Gold Cup collection in 2006, a line of luxurious styles offered at a higher price point and designed to take Sperry from the boat house to the boardroom. With features such as deerskin lining, 18K gold-plated eyelets and high tech memory foam, the collection launched to great acclaim and continues to be a popular part of the men’s collection today. In May 2007, the NPD Group, a market research firm, announced that Sperry’s Authentic Original is the best selling men’s shoe in U.S. department stores.

    In 2007 they became the title sponsor of the National Offshore One-Design (NOOD) Regattas, sailing competitions in which all boats entered are identical. Today, the Sperry Top-Sider NOOD Regattas attract over 30,000 competitors and spectators who come to watch 2,000 boats race.

    One-off collaborations have ranged from quirky fashion upstarts such as Modern Amusement to American icons such as Tommy Hilfiger and J.Crew. Sperry announced a collaboration with Scott Sternberg in the fall of 2007, designer of the acclaimed Band of Outsiders. The collaboration to this day continues to generate new fans around the world.

    In addition to supporting the American sailing community by sponsoring some of the sport’s most accomplished athletes and young rising stars, Sperry has dedicated themselves to preserving the health of the sea by partnering with Oceana, an international non-profit dedicated to protecting and restoring the world’s oceans.

    Sperry is releasing a 75th anniversary collection from the archives that features the original outsole Paul Sperry carved onto his sneaker to mimic nature’s ingenious design of Prince’s paw. To celebrate their 75th anniversary, Unabashedly Prep is teaming up with Sperry to give away a pair of boat shoes to one lucky lady and gentleman. Simply jot down where in the world you’d sail to in your new boat shoes and why. A spirit of adventure and vigor encouraged. Contest ends May 19, 2010.

    May 12, 2010 | Permalink (87) Total Comments

    Monogram Me left a comment on 5/20/2010 at 2:02 AM:

    I’d train for the 2011 America’s Cup in my Sperry’s

    Jennifer McIntyre left a comment on 5/19/2010 at 4:50 PM:

    Exotic places - sure. Around my neighbourhood - yes, of course. But what I’d like is to sail around Edgartown Harbour - - hopefully ferrying my kids and grand kids to exciting, local events. . . ahhh. the Vineyard.

    Jonathon left a comment on 5/19/2010 at 4:07 AM:

    I would sail to Charleston, SC and the Isle of Palms and try to reconnect with my first Internet love whom I met in 7th grade.

    Ashton left a comment on 5/19/2010 at 2:07 AM:

    I would sail into the future, my feet planted firmly on deck, my eyes on the horizon.

    Ahab left a comment on 5/19/2010 at 2:05 AM:

    My next voyage is one of revenge.  I plan to set sail shortly, departing off the coast of New England.  It is in those waters of the Eastern Atlantic where my left leg was stolen from me by a brutal creature of the sea (another reason: I only need one shoe!).  The journey will be dangerous.  It will be frightening.  And it will take a toll, physically and mentally, on my men and I.  However, with courage, my mates and I seek to hunt down that fearless sperm whale which has left be crippled.  And we will kill it.  Mark my words.

    Fair winds, mateys

    Sindhu left a comment on 5/18/2010 at 11:24 PM:

    Sail to? Just sail! Around the world, across the pond, anywhere. It’s not about where you go right?

    Lily left a comment on 5/18/2010 at 9:48 PM:

    I’d sail across the pond to Europe…probably spend awhile in the Mediterranean soaking up the sun, and having a blast!

    Daniel D left a comment on 5/18/2010 at 5:51 PM:

    I’d slip on those Sperry’s and sail where ever the wind takes me - it’s the journey, not the destination, that matters.

    dharmabum left a comment on 5/18/2010 at 4:56 PM:

    I would sail from Wellington, NZ up to Australia and spend time sailing on the Great Barrier Reef to expereince the greatness before it is completely gone.

    GD Singh left a comment on 5/18/2010 at 3:21 PM:

    I would go and set sail to the French Polynesian islands, once there, I would lie down in my boat and let the ocean take me where it wants to go.

    Hannah Bottum left a comment on 5/18/2010 at 9:42 AM:

    Being a native of Chicago, I would take my sparkling new Sperrys and hop a ferry to Michigan. Not the most glamorous adventure, but Lake Michigan is completely underestimated. While it may be true that I became ill four hours after getting off the ferry last time, I still enjoyed every minute of the ride. Lake Michigan all the way!

    zon left a comment on 5/18/2010 at 12:52 AM:

    I’d sail up to the San Juans in Washington.  It is gorgeous up there in the summer time!

    Hunter left a comment on 5/17/2010 at 11:51 PM:

    Born and raised in the South and a recent transplant to the heart of Asia - Beijing. To sail from Savannah through the Canal, up the coast of Baja, across the Pacific, making sure to allot plenty of time for Hawaii, and finally sailing into Qingdoa’s harbor. In another life, the city was a German colony. The city is no stranger to sailing, having played host to the Beijing Olympic Games’ sailing events. To travel via the world’s waterways from one homeland to another would be to live a dream.

    Matthew M. left a comment on 5/17/2010 at 10:52 PM:

    I would have to pick a sailing partner vs. a destination. Growing up with a dad that sailed and has since sold his boat, I wasn’t as intrigued by the beauty of the sport as he was. I remember going on small races with him and wondering when they would be over so I could get more involved in anything but being on that boat. There are few things I regret more now than not enjoying those times more with my father. I have since developed a love for it, and with my dad getting a small Sunfish for Christmas, I look forward only to getting lost in conversation and open water with the man who I admire more and more each day.

    John H left a comment on 5/17/2010 at 10:29 PM:

    I would sail around the Mediterranean for a summer, and really soak in the cultures of that area before going back to university.  Starting at Nice, and then going to Italy and the Grecian islands.  How wonderful that summer would be, and all with a perfect pair of Sperry’s.

    Jesse left a comment on 5/17/2010 at 9:19 PM:

    I’d sail down the west coast.  Start somewhere in Canada and work my way to Mexico.

    aliotsy left a comment on 5/17/2010 at 12:10 PM:

    My ancestors crossed the 4,000 mile expanse of the Indian Ocean in outrigger canoes, navigating by the stars to a new home on the island of Madagascar. Why? I like to think they were driven by adventure and hope—chasing the sunset to find a better life beyond the horizon. I’m descended from a fifteen-hundred-year-old sailing heritage. One day, I would love to follow in my ancestors’ wake.

    Brit left a comment on 5/17/2010 at 11:26 AM:

    “When I forget how talented God is, I look to the sea.”  What is better than the nautical sound of sails catching the wind, and the first splash of saltwater as the voyage begins?  Maybe a child’s laugh after a raging storm?  The soft broken word of thanks, from a mother of all the motherless children, an orphanage in a place that is broken?  Haiti.  My first voyage would be to give back.  Give back the kindness that has been poured over me, the rich hospitably of the south, like a cold glass of sweet tea on a blistering hot summer day. My topsider’s and I would load up water bottles, shoes, tents, and more.  I would slide into a pair of cut of cut off kaki shorts, an oxford tied up, and coastal clouds steer clear, because these sperry’s need a story to rep.

    Paul K left a comment on 5/16/2010 at 11:49 AM:

    I would slip on my Sperry’s before taking my wonderful girlfriend of two and a half years, who is transferring to a new college, and sail wherever in the world she desires with the utmost ardor, before parting in September.

    Jonah left a comment on 5/15/2010 at 4:29 PM:

    If I had it my way, I would sail to and fro every island in the Maldives, where the sunsets and sunrises are the most beautiful in the world. I would admire the awesome sea life all around me and perhaps stop by Sri Lanka. However, I’d definitely take my Sperry’s off when I take a dip into the Indian Ocean and latch onto the fin of a whale shark though!

    Josh P left a comment on 5/15/2010 at 3:06 PM:

    Setting sail across the world from my starting point in Santa Cruz, California, I would travel to the Bequia in Grenadines. Sperry’s deserve a spirit of adventure that a world tour provides, and the stories I have heard of the Moonholes of Bequia speak to this. Cast into the rocks of the Grenadines lie fortresses of forgotten times when the sea held so many more mysteries. This is something that I would want to relive and with what better shoe than the Sperry Top-Sider?!

    Andrea S left a comment on 5/15/2010 at 12:44 PM:

    I grew up sailing and - in college - I even set off on a few high-seas adventures.  The rose-colored plans were typically for exotic shores in the South Pacific, but our actual trips were to old Hemingway haunts in the Bahamas or the Keys.  It sounds terribly romantic to set sail with nothing but nautical charts, a GPS unit, and a few supplies.  Reality never quite lived up to the grand plans, but I know my next trip could make up for the past.

    My topsiders and I would take off on a lovely trip down the East Coast.  I live in New York, but we would head away from the Northeast and make a number of stops along the way.  Highlights along the way would include windsurfing at Cape Hatteras, a leisurely afternoon lounging below the Spanish Moss on Hilton Head, and drinks on Palm Beach.  But, my final destination, would have to be the forbidden shores of Havana, Cuba where I would sip mojitos, relax in the sunshine, and admire the old-world ambiance.

    Patrick McGlynn left a comment on 5/14/2010 at 10:46 AM:

    I would sail on the great loop from minneapolis down the mississippi river to the gulf of mexico around the tip of key west up the eastern seaboard and through the St. Lawrence sea way through the great lakes back to Duluth MN.  I would do this with my Sperry’s and my dog Clark

    Chuck Smith left a comment on 5/14/2010 at 10:38 AM:

    One of my dream sailing trips is to explore the waters of Croatia’s Dalmatian Coast.  My Sperry top-siders would carry me well through this amazing trip from Dubrovnik up to Sibenik.  Cool historic Medieval Cities, inviting people, great food, 100s of Islands to discover with amazing waterfalls, diving, on an on—It has been called the best sailing destination in the world.

    Sydney C left a comment on 5/13/2010 at 11:47 PM:

    I would first sail to Nantucket with friends and have a great time in the preppy town, but then I would grab my parents who have always dreamed of sailing the world, and sail worldwide, namely Croatia, I’ve heard it’s absolutely stunning there.

    Ben N left a comment on 5/13/2010 at 10:45 PM:

    Greece would be where I would want to travel.  It is both familiar but also exotic.  I would sail from Corfu to Crete and make various stops along the major cities, such as Athens and just enjoy the views of the mountains and historic architecture on one side and the crisp, blue water of the Mediterranean Sea on the other.  Plus, I would want to experience first hand the culture and authentic cuisine (which is often revamped and dramatized in entertainment).

    Astrild left a comment on 5/13/2010 at 10:08 PM:

    My beautiful dog Kojka and I would set sail for Iceland, land of volcanoes, skyr and Viking sagas, where she and I would run across glaciers under the midnight sun and explore Reykjavik with our high-traction feet. No doubt the day would end with a scene like the last photo, since my dog loves shoes even more than I do. But what are a few teeth marks between friends, and anyway, the occasional mouthing from a fluffy white Samoyed can only add character.

    Jason N left a comment on 5/13/2010 at 9:52 PM:

    It’s a bit ironic to find this post the night before I go for my first sailing class tomorrow. I’ve - of course - thought about this quite a bit, but feel my first foray into the salty ocean blue needs a bit more research. Paul Theroux had to have written something about this at least once, right? 

    I’d inaugurate my Sperrys (and me for that matter) setting out from Manhattan and sail up the East Coast stopping occasionally for more beer and a chance to grab authentic Nantucket red GTH pants from, well, Nantucket.

    Kristine S. left a comment on 5/13/2010 at 8:30 PM:

    With my new iconic pair of Sperry’s I would sail to London, England, where I would first visit the Lock & Co. Hatters to purchase a matching and equally iconic hat.  I would then take my ultimately preppy boat shoe/bowler hat combo, find the chap who rides down the river in an Edwardian bath chair, ask him to take me to the nearest Garden Party, and feign flattery while all the yummy Mummy’s ask me where I ever got a pair of such fabulous boat shoes.

    Mariel Strouse left a comment on 5/13/2010 at 7:15 PM:

    Although there are so many exotic locations I would love to see by boat, there is something so lovely about just sailing the East coast of the US. From spicy Miami up to Maine, stopping in all my favorite seaside cities (Charleston, the Outer Banks, and Newport to name a few), I would have a ball. And where better to wear such quintessentially American shoes than some of our finest towns?

    TomMc left a comment on 5/13/2010 at 5:58 PM:

    Wearing my beloved Sperry boat shoes, I would sail back in time to be at Hyannis Port with John and Jackie, then back further to West Egg to enjoy the glow of Gatsby, Nick and Daisy. These shoes open doors.

    Hatzes left a comment on 5/13/2010 at 5:05 PM:

    Greece! My grandfather jumped ship illegally as a teenager while her was in the Greek navy to get to the U.S. Since I was a child I have wanted to go the islands, next year me and husband are going. My father has one survivng cousin in Athens that we will visit. What better way to break in a new pair of sperry’s then sailing the bluest waters, looking at the white stucco houses in memory of my sweet papou who was a sailor both there and here!

    Mike Dos Santos left a comment on 5/13/2010 at 3:32 PM:

    I’d take my Sperry’s and sail to Sydney Australia, which has one of the most beautiful cityscapes which complements its oceanic view. I’d be a real sailor with my Sperry® Topsiders. I’d cast the sail the only way real men know how to, and visit some of the most interesting sites to see on the country/continent. I’d check out some of the unique wildlife, food, and most importantly the women. Yes sir! I’d be an unabashedly prepped-out Crocodile Dundee with my new Sperrys and it would be all thanks to the good ol’ boys up at http://unabashedlyprep.com.

    Kristian Koschany left a comment on 5/13/2010 at 3:00 PM:

    I would love to follow in the footsteps of a family friend of mine who has sailed from Vancouver to Hawaii to New Zealand and back again at least once or twice. It would be an incredible adventure, and a chance to see some of the most beautiful parts of the world.

    Claire left a comment on 5/13/2010 at 1:29 PM:

    I’d sail to the Galapagos…I’ve wanted to go there ever since reading Vonnegut’s book in high school.  Of course, I’d also stop by Easter Island and maybe Peru.

    Ian O left a comment on 5/13/2010 at 1:15 PM:

    I would take my shoes and set sail for Lilliput, as it seems like a rather entertaining place to be. If I could, I’d try and find Laputa, as well, but I hear it’s a difficult place to find, what with it being in the air and all.

    Kate Noelle left a comment on 5/13/2010 at 1:06 PM:

    It’s always been a secret dream of mine to sail from San Diego all the way up the West Coast to Vancouver, Canada with a group of friends, and stop to camp on beaches the whole way up. It would be like a pirating/sailing/outdoors adventure .... whale watching, sunset fires in private coves, falling asleep to the sound of waves, feeling the wind in my hair as we sail up the coast…. sounds like an adventure…

    Williamsburgian Hipster left a comment on 5/13/2010 at 12:32 PM:

    I would wear my topsiders to the brooklyn flea market looking for bullet pencils, ratty pendleton flannels and overpriced industrial furniture (made in the US of course).  Afterwards, my ironic, topsider-wearing friends and I would go consume large amounts of artisanal BBQ at Fette Sau and finish up at a Dash Snow memorium art opening at an up and coming gallery in Red Hook.

    N left a comment on 5/13/2010 at 12:32 PM:

    I’d sail from Fremantle, WA to Rottnest Island, because those two places might be the best in the world.

    Aly M left a comment on 5/13/2010 at 12:03 PM:

    I would wear my new boat shoes to sail to the Cocos and dive with the hammerhead sharks. Being an avid sailor, nothing would be more adventurous and fun than to sail to the Cocos, dive in and look up to see hundreds of schooling hammerheads above me. Absolutely amazing.

    Laguna Beach Trad left a comment on 5/13/2010 at 10:12 AM:

    I would don my Sperry Top-Siders and sail to Mauritius, in the Indian Ocean, and then west to Madagascar and along the East African coast, stopping off at various islands such as Pemba and Zanzibar, and then east to Seychelles to see if a pirate’s life is all that it’s cracked up to be.

    Kud left a comment on 5/13/2010 at 9:31 AM:

    I would sail to the Arctic! May need to bring a pair of socks…

    Sam left a comment on 5/13/2010 at 8:55 AM:

    I’d sail to Alualu - the fictitious atoll set outside the Federated States of Micronesia where Christopher Moore’s 1996 book, Island of the Sequined Love Nun was based.  Why?  The Sequined Love Nun liked to walk around naked, and was referred to as the Sky Priestess as she resembled a pin-up painted on the nose of a WWII Bomber. How could that be bad?

    Sara K left a comment on 5/13/2010 at 7:57 AM:

    I would sail from Hainan off the coast of China all around South East Asia.  I love tea and exotic cuisines and would love to be able to enjoy the sea while making unplanned stops along the way to sample local flavors.

    Theresa N left a comment on 5/13/2010 at 7:08 AM:

    I’d sail the Hawaiian Islands forever and a day.

    Sophie left a comment on 5/13/2010 at 4:02 AM:

    I’d sail all around the Aegean with a crew of friends; our very own Odyssey.

    M.D. Cooley left a comment on 5/13/2010 at 2:24 AM:

    I would sail my boat into neverland, via peter pan and tinkerbelle.

    ryan left a comment on 5/13/2010 at 1:55 AM:

    Dear Sperry-Topsider giveaway,

    I’d sail every Finger Lake from heel of hand to fingertip. Move on to the Great Lakes, till I understood every facet of their greatness. And finally shed a single tear in remembrance as I sped across the dried up bed of Salt Lake.

    Or maybe just go to Nantucket.

    Jeremy left a comment on 5/13/2010 at 12:23 AM:

    Starting from my hometown of Virginia Beach, Va., I’d sail the old spice routes to Mumbai and travel along the coast of India.  From there, I’d go to Hong Kong where’d I enjoy their long history of tailoring

    mjl left a comment on 5/12/2010 at 11:24 PM:

    i don’t want new ones.  i like the ones i have.  they’re broken in after beating the snot out of them on the lake, the sand, the bars and all that lies between.

    if i were to sail in some new ones though, i’d do something funny.  like get a little catboat and sail a water hazard during a golf tournament.

    Ginger left a comment on 5/12/2010 at 10:58 PM:

    I would sail up and down the California coast.

    Jay left a comment on 5/12/2010 at 10:52 PM:

    I’d start in the cape, work my way down the coast and island hop till i cant hop no more!

    bunny left a comment on 5/12/2010 at 10:30 PM:

    bless prince’s heart. i’d never read the history behind the shoe before.

    Josh left a comment on 5/12/2010 at 10:28 PM:

    Easy, I’d sail out and not turn around until I ran out of food.

    Percy Chatsworth left a comment on 5/12/2010 at 10:19 PM:

    If I had a boat, I would sail away to the islands of Turks and Caicos (Down to Parrot Bay). I would play with the waves of the ocean and seas, stopping in ports in different countries from time to time for food, rest and note-taking. For my final destination would give me the perfect location to write my first novel. All while wearing my trusty pair of Sperrys.

    Andrea S left a comment on 5/12/2010 at 9:59 PM:

    I grew up sailing and - in college - I even set off on a few high-seas adventures.  The rose-colored plans were typically for exotic shores in the South Pacific, but our actual trips were to old Hemingway haunts in the Bahamas or the Keys.  It sounds terribly romantic to set sail with nothing but nautical charts, a GPS unit, and a few supplies.  Reality never quite lived up to the grand plans, but I know my next trip could make up for the past. 

    My topsiders and I would take off on a lovely trip down the East Coast.  I live in New York, but we would head away from the Northeast and make a number of stops along the way.  Highlights along the way would include windsurfing at Cape Hatteras, a leisurely afternoon lounging below the Spanish Moss on Hilton Head, and drinks on Palm Beach.  But, my final destination, would have to be the forbidden shores of Havana, Cuba where I would sip mojitos, relax in the sunshine, and admire the old-world ambiance.

    knitxcore left a comment on 5/12/2010 at 9:50 PM:

    i would sail to school. i have to take a summer course in order to graduate on time.

    AJ left a comment on 5/12/2010 at 9:39 PM:

    I am a single mother of 2, my oldest son has been sailing for 2 years now. If I could sail anywhere I would charter a bus for the 3 of us to sail from Annapolis to Africa. We would have quite an adventure exploring the open ocean and travelling around the coast of Africa. We would enjoy meeting people along Ghana and Sierra Leone, South Africa, and east Africa. It would be fabulous to have such an amazing experience with my kids—something that we would always remember.

    And, for the record, they both have Top-Siders but I do not. How crazy is that?!

    Ryan Waldron left a comment on 5/12/2010 at 9:21 PM:

    I’m pretty sure that I’d sail ou of New Orleans here and head to the Venetian Lagoon, with maybe a stop in Florida

    Mattias left a comment on 5/12/2010 at 9:06 PM:

    I’d set sail for the land of opportunities, no matter how horrible the weatherconditions were. I’d sail for a fortnight, or however long it would take me. I’m not talking about a pleasant ride, and nor am I expecting one. I’m talking about a trip with a goal - fueld by determination. Determination that there can be more to style and living than there is where I’m from. A place where the madras bleeds more colorfull than ever, and where the khakis are that much more khakier.

    I’d cross the Atlantic, no matter what - for the persiut of happieness, and excellent rep ties.

    Diane left a comment on 5/12/2010 at 9:03 PM:

    Hmm..I would sail to Boston (just because I’m currently craving that city) and then to Europe, where I’d end up in Paris. I went there in high school but didn’t get to see enough of it-and I can think of SO many outfits for sightseeing that would pair perfectly with Sperry’s and be comfortable as well.

    K. Nights left a comment on 5/12/2010 at 9:01 PM:

    I would take my 2 best friends, fill our boat with of necessities, and set sail toward the many small, unexplored islands scattered across the Pacific Ocean. Together we would explore, build huge bonfires on the beaches, and just live day-to-day with windswept hair, sunburned shoulders, and rumpled clothing.
    The thought of sailing somewhere where few people have been before appeals to me, and I would love terribly to have the kind of indian-summer adventure I’ve always fantasized about. I can hardly imagine what those topsiders would look like after such an adventure.

    Xavier Cadena left a comment on 5/12/2010 at 7:56 PM:

    I would start my trip in New Orleans and make a trek around the entire continent of South America . Starting in the gulf, even though the I dont know how the oil spill is currently affecting the third cost, I would sail along Mexico and cross the Panama Canal making stops at all the major South American coastal cities. Making sure to hit Lima in Peru, Valparaiso In Chile, crossing the famous Tierra Del Fuego like the explorers of old. Buenos Aires, Rio de Janeiro, everything along the coast till I reach the Caribbean and eventually hit home, Texas.

    Sam left a comment on 5/12/2010 at 7:45 PM:

    I would hit up the Great South Bay in my grandfather’s
    Sunfish and try to make it to Fire Island.

    Shawn G, left a comment on 5/12/2010 at 7:36 PM:

    Anywhere my love wanted. Many men say they’d go to the ends of the Earth for a their woman; too few actually do.

    claire left a comment on 5/12/2010 at 7:32 PM:

    I go to school in Bristol, RI and I would sail from Bristol, to Newport, to Block Island, to Martha’s Vineyard and end my tour in Nantucket. It’s a small East Coast journey, but there’s no where else I’d rather be but Nantucket. It’s small, quaint and comfortable, just like my Sperry’s.

    James P. A. left a comment on 5/12/2010 at 6:54 PM:

    The spirit of adventure is very prevalent in America and I also have that spirit as an American. My grandfather always told me of this small island that they would vacation on in New York.  It was only a few acres and had a couple houses on it and no bridge or anything.  They went out with another family in their sailboat and stay there for weeks and months in the summer. I don’t know where this island is or what it’s called. I’m honestly not even sure if it actually exists at all (my grandfather was always an amazing story-teller, but in his later life I knew he made up a lot of stuff). He told me all about the small outings and little adventures he would go on and the absolute freedom he could experience.  I don’t want to copy his experiences, but I want to be able to find my own experience based on the freedom to explore and the freedom to go own an adventure, no matter how big or small. So in conclusion, I would sail anywhere looking for my metaphorical island of freedom and adventure. It doesn’t matter where I’d be, where I’d be going, just as long as wherever I’m going promises me that. Hopefully someday we might all be able to experience the summer joy and excitement of exploration that my grandfather felt on his little island.

    Zak left a comment on 5/12/2010 at 6:36 PM:

    Anywhere my parents wanted. They wanted a cruise honeymoon; they gave us private school instead.

    Z left a comment on 5/12/2010 at 5:08 PM:

    As a young man my grandfather would sail to Holland and around Europe in his yacht. He would sail with friends and family; sometimes taking my mother, auntie and uncle on his travels. He has many great stories that are both captivating and exciting; he was a true adventurer. So as he is passed the age of intrepid adventuring and nonchalant decisions, I will take my new pair of Sperry Topsiders proudly on a voyage in my grandfather’s yacht; which he has been building for 25 years. Where will I go? I don’t know yet. It doesn’t matter, the world as they say is my oyster. I could meet tailors in Italy, taste wine in the south of France underneath the gentle sunset, watch bull fights in Spain, work my way round to the Greek islands and relax while watching the world pass me by through my wayfarers. My adventure will be based on spur of the moment planning and choices made on my desire. I can forget my brain because all I need is to be following my heart, just like my grandfather and sailing forebears. It will be a voyage to mark in my families history; I hope to tell my grandchildren similar great stories and inspire them to find their own. In their own Topsiders.

    Ryan F left a comment on 5/12/2010 at 4:22 PM:

    Manhattan in the summer, New Orleans in the winter

    Andy left a comment on 5/12/2010 at 4:18 PM:

    Like Yuriy, I’d do Croatia as well.  I spent much of my first European vacation a few summers ago with a good friend in Croatia.  While on the island of Hvar we met some great British guys who were sailing through the Adriatic on a small yacht.  Long story short we wound up staying on the sail boat for a couple nights with some more travelers drinking warm Croatian beer and diving into the gorgeous blue waters over and over.  I’d love to repeat that trip, but this time with a non-platonic girlfriend and with the extra time to sail to another island from there.  I’d never understood the desire to disappear from one’s normal day to day existence until I spent a few days on the sea there with my Blackberry turned off.  I hope to try it again.

    jacksonkkp left a comment on 5/12/2010 at 4:17 PM:

    I will set sail from Miami to the remote island of St. John, USVI with my Weimaraner, Lord.. Along the way, we would stop at St. Thomas and St. Marteen for a little B&B before staying at my summer home at our final destination. A fantastic new pair of Sperry topsiders would be the only shoes I’d wear on the boat, exploring the islands and on my way to the private, secluded beaches of St. John. The appropriate apparel packed for the trip would be a couple pairs of chino and some light linen and polos to go with my new footwear.

    maryn left a comment on 5/12/2010 at 4:15 PM:

    From Mystic, CT to Groton Long Point, CT - and back: repeat for the entire month of July.  :)))

    JMH left a comment on 5/12/2010 at 4:04 PM:

    My dad’s family went on a four-year sailing expedition when he was a teenager.  My grandfather still lives on his sailboat, and the very first pair of Sperrys I ever saw were on his feet.  With a new pair of Sperrys I would recreate my dad’s voyage.  He started in Nanaimo, Canada, went down the coast of the USA and Mexico, through the Panama Canal, and back up to New York city.  From there, he went across the Atlantic Ocean (great stories of a week without seeing land) to Britain and down the coast of France.  The best stories came from the year he spent tracing the coast of the Mediterranean, through Turkey, Israel, and North Africa.  From there, they went back across the Atlantic, spent the summer in the Caribbean, went down the coast of South America, and back up the west coast to Nanaimo where it all started.  I would love to take a few years and retrace his journey and see all the places he told me about as a child.

    Kara left a comment on 5/12/2010 at 3:43 PM:

    I would sail all the way to Italy to experience the cities, culture, people - everything.  I’ve never been but have always wanted to go, so why not make it even more memorable by sailing there.  I want to be able to experience the food and fashion and architecture first hand, not just by what i’ve read in magazines.  I also have family roots there and it would be amazing to be able to explore the destinations where distant family members once lived.  My new Sperry’s would always remind me of this fantasy trip.

    Jason H. left a comment on 5/12/2010 at 3:43 PM:

    I’ll probably start in Annapolis with my current pair of Sperry AOs on. I’m always in them. Before leaving I’ll have to get my fill of blue crab at The Crab Deck on Kent Island; it’s a great place. Having several former classmates who live along the Eastern Shore, I’ll sail southeast through the bay, stopping by Oxford and later Cambridge for a day or two of relaxing in the sun, fishing, crabbing, and catching up over a couple G&T’s. After leaving Cambridge, I’ll head on back to Annapolis. Having a new pair of shoes won’t change this… but it wouldn’t hurt.

    If I had a bigger boat and time and money weren’t an issue, well, I’ve always wanted to go to Tahiti…

    Yuriy left a comment on 5/12/2010 at 3:39 PM:

    My fiance and I are getting married in September and we’re planning on flying to Croatia for our honeymoon. We’re chartering a Sun Odyssey 34 sailboat and going to sail the beautiful islands of Croatia in the breathtaking Adriatic Sea for a week, just the two of us. We plan on making stops on beautiful uninhabited islands as well as Dubrovnik, which is one of the most beautiful cities I’ve ever seen (in photos). It sounds too good to be true.

    sarah left a comment on 5/12/2010 at 3:07 PM:

    well, i live in texas, but would no longer sail from the gulf….  wouldn’t want to soil the sperry’s with oil…. 
    i’m an architect, so i would love to set sail from the UK toward the Netherlands and Denmark.  there is so much to see in terms of design in those parts of the world.  after getting my fill of man-made beauty, i would then have to take a long tour to the south to Italy where i could relax with a bottle of wine in the tuscan countryside.

    N Ward IV left a comment on 5/12/2010 at 3:04 PM:

    I wouldn’t choose any place in particular. I would simply sail out one day and let the waves take me away like a message in a bottle. I think the sight of an endless sea would have to be the most wonderful experiences in the world. Live free and enjoy the serenity of the unknown.

    Merete left a comment on 5/12/2010 at 3:01 PM:

    I will set sail from the south coast of Spain - just off Almeria in August. I will sport my cutesy boat shoes as I glide through the Mediterranean’s Balearic Islands. However, my Sperry’s will need to navigate me through the streets of Madrid first.

    Josh left a comment on 5/12/2010 at 2:46 PM:

    Guadeloupe Islands
    From the research I’ve done it is a less traveled too island but still beautiful.

    Would love to sail there with the wife & our beautiful daughter & a nice medium format film camera and the old polaroid land camera I have for the need of immediate gratification! No pressure no worries other than enjoying the time with them and the comfort of my new Sperry boaters!

    Christian Bourasseau left a comment on 5/12/2010 at 2:44 PM:

    I would sail with those sperrys where my roots begin, France and the perfect place would be St. Tropez. My father, my brother, my sister and my best friends will have to come with me. With that team I’ll asure to win lots and lots of regatas and I’ll asure to have one of the most incredible moments in our lives full of the passion of sailing, adventure, danger and the most amazing experience that’s sailing in one of the most beautiful places on earth. We will do this for ever and bring our children to this adventure in St. Tropez, France.

    Jenae left a comment on 5/12/2010 at 2:44 PM:

    I would grab my closest friends and head to the open sea with only the clothes on our backs! I’d sail across the Pacific over to Papa New Guinea and the many islands along the coast over the Great Barrier Reef!  We’d stop do some snorkeling and visit many tribes on each island. We’d sit around a fire each night swapping stories from our native lands and we’d catch our own food and they’d teach us how to cook it! All while drinking out of a coconut.  Then we’d set sail for the next island making great memories all along the way!

    Ashley left a comment on 5/12/2010 at 2:41 PM:

    I would sail from the Gulf of Mexico to the Mentawai Islands.  They have the most perfect almond shape waves in the world.  I would never come home.

    V left a comment on 5/12/2010 at 2:27 PM:

    I’m a lady, and if I had my way, I’d sail from San Francisco across the Pacific to end in New Zealand. I’ve heard it’s the only place in the world comparable to where I grew up (Alaska), and it’s always been my dream to go. Having a sailboat while there would be even better for exploring the islands both around them and on them. And to be fair, I’d probably be swayed to sail over to Australia too.

    Grant S left a comment on 5/12/2010 at 2:19 PM:

    There’s something about the French Riviera that is calling me toward it, and I can’t think of a better accessory to bring along than a pair of Sperry’s. I’d set sail and make my way along the Cote d’Azur, making stops to all the beaches and touring Monaco, Saint-Tropez and Cannes. A great pair of Sperry topsiders are the perfect shoe to wear in the gorgeous Mediterranean world of the Riviera.

    Mia W left a comment on 5/12/2010 at 2:04 PM:

    I would set sail from my hometown of Seattle, make a quick stop in Hawaii, and then end up in Japan. I would where my Sperry boaters as I sailed to each of the Japanese Islands, eating only sushi and vibrantly colored Japanese candy.