LISTEN, I’m not one to namedrop. But I’ve just been on — ahem — Vince Vaughn and Owen Wilson’s boat.
Yip, those are the kind of circles you can move and shake in when you’re in this part of the U.S. Specifically: Annapolis, Maryland.
OK, so I admit the two superstar actors weren’t personally taking me on a tour of the glittering blue waters of Chesapeake Bay. And, fine, it’s not really THEIR yacht. But, hey, it’s as close to Hollywood as I can get.
It was the schooner Woodwind II and it was used in their movie The Wedding Crashers.
You can board it for a cruise out of the pretty little harbour in Annapolis and skim the surf for a wonderful two hours.
Even get a wee shot at the wheel. Well, that’s showbiz for you.
Water was the theme of this American road trip.
We’d started with a couple of nights in Washington DC. But, in less than an hour’s drive, you’re transported from America’s bustling capital to an entirely more rural and sedate landscape.
Over bridges, along coastlines — and, oh boy, are you in for a treat.
This is known as the Chesapeake Bay loop — a circuit that would, eventually, take us back to the capital via surely some of America’s most beautiful and diverse landscapes.
And, even with the July weather pushing into the ’90s, the Chesapeake seemed to always whisper a cooling breath.
It all comes under the umbrella of Capital Region USA (capitalregionusa.org).
Anyway, hire car picked up a short trip away from our Washington hotel. Let the adventure begin.
The journey took us over the Chesapeake Bay Bridge and gave us a taste of what to expect as the sun sparkle-danced on the waters which, at 64,000 square miles and spanning six states, is the largest estuary in the US.
We were heading for historic Annapolis — Maryland’s state capital and, for a few months in the late 18th Century, capital of the whole country.
When we arrived, we parked the car, walked up the street, round a corner and — wow — the diamond shimmer of the sea at the bottom of the road.
This must be one of the prettiest Main Streets in the world!
We had a date with that aforementioned Hollywood yacht.
Ivy Roost Cottage in the New Forest is the perfect place to relax in the lap of luxury
But first, had to squeeze a week’s worth of Annapolis — you could easily spend that here — into just one day.
There’s real American history here in what is the seat of Anne Arundel County — from the domed 1700s State House to the 18th Century higgledy-piggledy brick houses.
It’s known as the ‘sailing capital of the world’ because it’s so popular with serious sailors — and landlubbers with a fancy for the ocean. But it’s also home to the United States Naval Academy which occupies a sprawling waterfront site.
The town centre is a charming mix of hotels, bars, restaurants and boutiques. But it’s the eating we’ll remember — enough food to sink any ship.
We had lunch at the Iron Rooster (ironroosterallday.com) before heading for our sail.
After polishing off a mound of chicken, biscuits and gravy we were urged to try the home-made pop tarts. It was big enough to go for a sail on. Yummy, but made me worry I’d capsize the Woodwind II!
Fortunately, despite the extra ballast, we survived our sail on the celebrity boat (theschoonerwoodwind.com) — even, ahem, helping steer it home. Just call me Cap’n Al.
We weren’t on dry land for long. A quick hop on a water taxi (they skip around the bay like our black Hacks) took us to the neighbouring town of Eastport — which residents have declared an independent maritime state.
What costs what?
A two-hour weekday cruise on the Woodwind II costs around £34.
DO: get tucked into the seafood and Smith Island Cake.
DON’T: leave home without pills if you suffer from seasickness
A very cool, Boho community and home to the Annapolis Maritime Museum (Amaritime.org) — in the former McNasby oyster processing and canning factory. Learning about the area’s strong shell-fishing heritage is a pearl in the necklace of activities here.
After dinner at Boatyardbarandgrill.com (now barely able to move!) we waddled back to our hotel (westinannapolis.com).
It was a Wednesday, and every midweek night from July to September the restaurants take over some of the streets. The place is abuzz with couples, friends and families eating, drinking and dancing the night away to live bands.
There’s a strong sense of community along these coastlines — each with a distinct pride in their maritime heritage. Where they live really matters to them — its past, present and the responsibility of protecting their futures. That’s a message underpinning the work at Chesapeake Bay Environmental Center (bayrestoration.org).
We visited on our way to quaint St Michaels on Maryland’s eastern shore — and our stunning room at the Five Gables Inn and Spa (fivegables.com).
We’d just had lunch at Bridges Restaurant (bridgesrestaurant.net) in the Kent Narrows at a table overlooking — you guessed it — the water.
After the shrimp salad and fried crab cakes, we really needed a walk at the non-profit, non-political Environmental Center.
Assistant director Vicki Paulas oozes passion in the quest to restore and preserve the bay area for future generations.
GO: CAPITAL REGION
GETTING/STAYING THERE: A five-night stay in Chesapeake Bay costs from £1,015pp, two sharing, including return flights from Edinburgh to Washington Dulles with Aer Lingus, fully inclusive car hire, three nights’ room-only at the Westin Annapolis and two nights’ bed and breakfast at the Five Gables Inn and Spa, St Michael’s. See americaasyoulikeit.com
MORE INFO: For more on visiting the various areas see
visitmaryland.org, visitannapolis.org and talbotcountymd.gov. For more on the region as a whole see capitalregionusa.org
The 500 acres — including a man-made lake and woodland — is full of wild birds, including ospreys, woodpeckers and blue herons. We enjoyed it so much we took out membership.
Later, we found ourselves driving down a pretty, old-fashioned street where storefronts and restaurants nestled together —- tiny glimpses of a harbour and water captured between them.
St Michael’s, just across the border in Talbot County, is a town to fall in love with immediately. Our inn had Victorian balconies and shutters. The room was decorated in Americana style with original brick walls and a patchwork-quilted bed.
Local tourism boss Cassandra Vanhooser reinforced what we had already knew — this was all about eating and the sea.
She — erm — forced me to try their famous pudding after a hefty meal at the Tidewater Inn in neighbouring Easton. Smith Island Cake — marbled in layers with chocolate filling and chocolate frosting — almost killed me.
Luckily, we had another tour to walk it off. This time at St Michael’s Chesapeake Bay Maritime Museum (CBMM.org) — a glimpse into the history of the bay, with its ship-building, oyster and crab industries.
Highlights: The 1879 Hooper Strait Lighthouse rescued from the scrapyard and now a walk-through exhibit. Plus, oyster catching the old-fashioned way with tongs.
This leg of our tour finished the way it had begun. A cruise on Captain Iris’s Selina II — a wooden beauty from the days of the Great Gatsby.
MOST READ IN TRAVEL
We sipped drinks as the boat scythed through the waves and the sun fell into the bay, sky and sea merging in a deep, dark blue.
In this peace-filled cocoon you easily forget that Washington is just a couple of hours away.
So, get out of the city. The great outdoors of land and sea awaits. And it’s a Chesapeakey Blinder!
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