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Island Time: Turning Back the Clock in Bermuda

07/21/2013 11:20 EDT | Updated 09/20/2013 05:12 EDT

As this is my first blog for HuffPo, I feel I chose the right destination. Starting at the beginning in a way.

Although Toronto-based now, I was indeed born and raised on the island of Bermuda. As a '70s child, the place has changed much from my formative years spent schooling and scooter-ing through the '80s and '90s. However, after living away for some time, and recently attending my high school reunion, I am happy to report that a few things have remained the same. Despite the influx of corporate business, vacationers -- eager to escape the hustle of North American cities -- can take advantage of the variety of activities on offer, or cool their heels in the warm pink sand. And I recommend you block off plenty of time to do the latter.

Day One I arrive at L.F. Wade International Airport, and breeze through customs to meet family friends who had graciously offered to pick me up. I was to stay with Aunt Sandra in Shelley Bay for my first two nights, before checking into The Fairmont Southampton for the weekend. Sandra's daughter, Lynn, was doing the driving and suggests we hit up an old favourite, Portofino's, for dinner. Gladly. I was up for a spin along Bermuda's narrow, winding roads, and over to Hamilton.

The restaurant was exactly as I left it. Only they are on the gluten-free train (along with many other local restaurants) so they offer pastas for intolerant diners. I chose the seafood risotto, but wished I'd gone for a pizza. Perhaps my palette is a bit spoiled in Toronto, but I was surprised that the fish was not fresh.

In any case, it was a lovely evening out in a cozy spot.

Day Two After an early morning run around the bay, Lynn drives me into Hamilton. I decide to start the day at Rock Island Coffee on Reid Street. Delightful staff and delicious baked goods confirm this was a good idea. Although the single shot cappuccino rings in a bit high, I drink it down and remember this is Bermuda, everything is expensive.

But maybe not? My next stop, the National Gallery at City Hall, is a free dose of culture. Their collection of local and internationally acclaimed painters and photographers, including (former classmate) Meredith Andrews, is definitely worth checking out.

Lunchtime brings a few options. Settle in for a patio lunch at Lemontree Cafe on the edge of Par-La-Ville Park or, if you fancy a food truck there are a few to choose from; Little Mexico (corner of Church and Wellesley Streets), Winky Dinky Dog (on the opposite end of the park), and Smokin' Barrel (on Front Street, next to the ferry terminal).

The rest of the afternoon is spent gathering intel for those that want to cruise into downtown for some shopping. Front and Reid Streets are home to M.A.C and MaxMara, as well as island originals Goslings, Calypso, and A.S. Cooper & Sons. Other notable new-to-me stores include Gimi (Front Street), Perry Collection (great shoes and bags on Reid St) and Atelerie (in the Washington Mall).

After a full day, I easily hop on the bus back to Shelly Bay in time to enjoy the sunset with a glass of wine.

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Turning Back the Clock in Bermuda

Day Three I am dropped at Bermuda High School for a nostalgic visit and Lynn graciously offers to take my bags over to The Fairmont Southampton, as she had to go out that way. This was a real lifesaver as it starts to rain just as I set off post-tour to get to the Hamilton Princess. This grand landmark hotel (that I also worked at for a spell) is also a Fairmont property that's recently been acquired by the Green family. And while it may interest some readers that $50 million in hotel renovations are forecasted, my main concern was getting on the complimentary ferry that would take me to its sister property.

I check in on schedule and meet up with the lovely Carlita, who leads me on my second tour of the day. I realize there is a theme going, being that this is the hotel where I had my high school prom.

The place is just as stately as I remember it. My room is spacious and comfortable. Carlita tells me that all rooms are the same size, and that the only difference is the view. I like my northern vista, that sweeps across to Dockyard, very much.

We carry on discussing the rejuvenating treatments at the hotel's Willow Stream Spa, and how nice a twilight game of golf would be (if I played golf, that is) at Turtle Hill -- one of the world's top five par three courses.

Carlita treats me to a light lunch at Ocean Club where I sip the restaurant's signature cocktail, an original concoction of Tequila Silver, mint, blueberries, agave and fresh watermelon juice. After gobbling up fresh fish tacos, we chat with the two young dudes who had been providing the soundtrack. Chris Finsness and Oscar Deuss (yes, the billionaire's son) make up the band Crown & Anchor, and perform regularly around the island.

That evening I pull it together to join a raucous Irish wedding party at Elbow Beach, where dancing at the hotel's Deep Lounge goes on into the wee hours.

Day Four I've agreed to meet the aforementioned wedding party for a cruise out of Hamilton Harbour and into the Great Sound. The catamaran is to leave at 11 a.m. sharp. Miraculously I'm out of bed and organized enough to catch the bus into Hamilton, and even have time to grab a peanut butter/espresso/frappuccino type drink at Juice & Beans Café (61 Front Street). I declare it the best thing ever, but am even more impressed that the bride and groom showed up to get on this boat.

The Sally Bum Bum is chartered by Leon Raynor, who is affectionately known as Captain Crunch. I will leave that one with you. The swimming and antics end around 2 p.m. at the Ferry Terminal. I'm a bit hungry so I order juicy jerk chicken off the Smokin' Barrel truck, and then head to Gosling's as I remember I need to bring a bottle of wine to a Sunday night dinner.

Bussed it back to the hotel to ready myself and return to Hamilton for the reunion party. Luckily I'm able to share taxi with a couple staying at my hotel and I arrive at Harry's Bar on time. The establishment is usually very busy with the after-work crowd, but on a Saturday night we pretty much have the place (and patio) to ourselves. Good times, great wine, and Chef Bradley Clease whipped up some of the best cocktail snacks I've ever had. Enjoying the catch up with the Class of '93 so much that I am one of the last to leave. This taxi back to the hotel included a driver with exceptional vocal range. He sang Louis Armstrong ballads the entire journey. So sweet.

Day Five It's Sunday and I'm all about getting downstairs for brunch at Windows On The Sound. Among the endless array of choices, I'm thrilled to load my plate with codfish cakes and bananas -- something I've really missed (trust me, it's yum).

Faced with burning off my breakfast either by walking over to Gibb's Hill Lighthouse (the world's oldest cast iron beacon) or bussing it over to Dockyard, I decide to put on some snorkeling gear and get some under-the-sea action. For those that want to go deeper, the pros at Fairmont's Dive Centre will help you suit up right on their beach. Life is so easy here.

My day ends with family friends picking me up for a breezy dinner on the patio of a traditional home, nestled just off Harbour Road. Georgina lets me know she may need a house sitter for two weeks next July. Sign me up!

Day Six This is leaving day so I'm up in time to get to the gym, then swim and suntan at the spa's pool. All before check out. Arrange my ($15) airport transport, which I should have done the day prior, and zip down to the Ocean Club. I need to enjoy the scene of that pretty private beach one more time. I order a savory fish chowder and those tacos again, only wishing I'd be around for Happy Hour that would be kicking off at 3 p.m.

Essential Excursion: Taxi or bus it over to the Royal Naval Dockyard and cruise through the National Museum. A permanent exhibit tells the story of Bermuda's discovery and early settlement through a fascinating collection of artifacts salvaged from 16th and 17th Century shipwrecks. Pick up a few souvenirs, and a Bermuda Rum Cake, at the Clocktower Shops before your beach bumming begins at the Snorkel Park.

Head back over Somerset Bridge -- the smallest drawbridge in the world -- for more photo opportunities at Church and Cross Bay. These smaller beaches dot the south shore and are some of the best spots to soak up the scenery as the sun goes down.

When to Island Hop: As the heat and humidity are rather oppressive in July and August, I suggest booking your week/weekend jump April through June, or late September through December. American Airlines, AirTran, Delta, United, WestJet, US Airways, jetBlue and Air Canada Vacations all fly into Bermuda. Cruise in on Celebrity, Norwegian or Royal Caribbean. Look for super saver offers from many hotels in the off-season.