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Annapolis, A Must-Stop Between The Hamptons And Palm Beach

Originally Posted: September 12, 2012

Douglas MacKaye Harrington

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The view up Main Street from the harbor in charming and historic Annapolis, Maryland. (Photo: Douglas Harrington)

Annapolis, MD - By land or by sea, Annapolis is a must-stop for any Hamptonian en route from the Hamptons to Palm Beach at season's end...or any time of the year for that matter.

Known as the "Sailing Capital of America," Annapolis, Maryland is truly one of the most charming and inviting harbor towns in the country. It is, of course, a small city not a town, but with a population of barely 40,000 and a historical architectural preservation that immediately transports any visitor to colonial America, it is hard to call this quaint seaside village a city.

The Reynolds Tavern has excellent accommodations, a great location, fine dining, charming service and the historic ambience and pedigree that any traveler to this iconic American landmark city should seek out and embrace. (Photo: Douglas Harrington)
That said, as the state's capital, Annapolis has all the amenities necessary for even the most discriminating urban traveler. Great restaurants, first class hotels, spa and salon services, attractions, museums, live theatre and shopping, but thankfully when it comes to retail, Annapolis is not populated by the usual high-end name brands found in similar vacation destinations, but independent small retail and service businesses vested in the community where they live.

Our first stop in Annapolis was check-in at The Reynolds Tavern, a full service Bed & Breakfast that has been providing respite for visitors, including our Founding Fathers, since 1747. Located on Church Circle across from historic Saint Anne's Episcopal Church, The Reynolds Tavern is perfectly situated within walking distance of everything Annapolis has to offer. If you are not a walker, the free Circulator Trolley Bus stops a block away from the tavern and it will take you anywhere you need to go in Annapolis.

Perfectly preserved and maintained, this absolutely beautiful inn was constructed in 1737, registered as a National Historic Landmark and is run hands-on by its charming and attentive Innkeepers, Wes and Marilyn Lynch. Stepping through the archway is like stepping into history with a curio-cabinet filled with historic artifacts accumulated over the nearly three centuries of its existence. When visiting a small city as historic as Annapolis, briefly our nation's first capital, I cannot imagine why a traveler would prefer a large modern hotel chain over a small traditional inn that is so indelibly connected to the city's colonial ambiance and pedigree.

A partial view of the spacious sitting room of the Washington Suite at the Reynolds Tavern. (Photo: Douglas Harrington)

Our guest room, one of only three in the tavern, was the beautifully antique appointed Washington Suite with a spacious sitting room facing Church Circle that contained two wing-backed leather Windsor chairs, original wide-beamed wood floors covered with oriental rugs, a large sleeper couch and a 19th century writing table that was bathed in luminous morning and afternoon sunlight. Our bedroom was equally well appointed, with a thick luxurious king poster bed that was as comfortable as any I have slept on in all my travels with linens and down quilts that were first class. A large antique armoire and dresser provided all the storage necessary for an extended stay.

The bathroom was small, but more than adequate with a full, deep granite bath, massage shower head, and well stocked with Crabtree & Evelyn personal grooming products. I must note, although I failed to identify the line, the bath towels were absolutely the thickest, largest and most luxurious I have ever experienced, as were the bath robes. All the rooms have hi-speed wireless Internet access, cable TV and individual climate controls.

The Reynolds Tavern provides complimentary breakfast in one of two warm and inviting dining rooms for its guests and the morning fare was outstanding and changed daily. My personal favorite was the Crab Cake Benedict...simply scrumptious! French Press coffee, juice and fresh fruit bathed in hand-whipped cream is also part of the daily breakfast menu. The Reynolds also offers Annapolis' most popular and authentic Afternoon British Tea, called Mary Reynolds' Tea in honor of the 18th Century proprietress of the property. Lunch and tea are served daily from 11:00 a.m. - 5:00 p.m. and dinner is served Wednesday through Sunday until 9:00 p.m.

One of two warm and inviting Reynolds Tavern dining rooms being set for dinner by waiter Nick Hanson. (Photo: Douglas Harrington)

We dined at the Reynolds with friends on our last night in Annapolis and it was absolutely superb! Our main course choices from their eclectic, mostly French inspired menu included Pecan Crusted Tilapia, Rockfish a la Chef and Stuffed Salmon, all delicious and fresh as could be. I opted for one of four British inspired entrees on the menu and experienced a true lamb Shepherd Pie that would have made my Scottish Grandmother jealous. I also had my first taste of Crab Chowder, outstanding!

The Reynolds Tavern has excellent accommodations, a great location, fine dining, charming service and the historic ambience and pedigree that any traveler to this iconic American landmark city should seek out and embrace. I cannot imagine my next visit to Annapolis without another stay at the Reynolds Tavern. (http://www.reynoldstavern.org)

On the Reynolds' property is the Sly Fox Pub located in the grotto like 18th Century cellar kitchen of the tavern revealing the original foundation walls of the Reynolds, a large open fireplace and the Rumford Broiler. British pub style lunch and dinner fare is offered, but the real appeal of the Sly Fox Pub is the large outdoor patio and bar, the largest alfresco gathering place in Historic Annapolis. Dog and smoker friendly with live music most nights, the Sly Fox is definitely a stop for a fun evening under the stars.

The ambience at Crush is chic and comfortable with a combination of traditional seating and dining on comfy couches. (Photo: Douglas Harrington)


Our first night's dining experience was hosted by Robert Laggini, proprietor of the Crush Kitchen & Winehouse, one of Annapolis' hottest restaurants. The ambience is chic and comfortable with a combination of traditional seating and dining on comfy couches. High ceiling, rich hued walls covered in interesting caricature art make for an atmosphere that is warm, casual and convivial.

The main appeal of Crush is their wine list, an ever-evolving and rotating selection of 70 wines specializing in small independent wineries from around the world that offer exceptional taste at superb value. Laggini literally tastes every wine selected and his passion as a vinophile is infectious. I expected a fine wine bar, but I did not expect the high quality and creative cuisine that Crush is sending through its kitchen doors.

I left it to Laggini to select our tasting menu and pair the wines, there was not a single miss along the way. We started with Proscuitto Wrapped Dates stuffed with Goat Cheese that was paired with a 2011 Fritz Sauvignon Blanc (Sonoma). Lily is not usually enamored of Goat Cheese, but she absolutely loved this appetizer and the wine literally danced with the dish. The Tuna Tartare was an equally wining opener and was matched beautifully with another Sonoma, a 2010 Vino Valpredo Bianca Mia.

Crush owner Bob Laggini explaining the Enomatic wine dispensing station to lily Kessler and Cindy Robinson. (Photo: Douglas Harrington)

Laggini took us European for our main courses with a delicious Grilled Salmon paired with a stunning 2010 Domaine Les Vieux Murs Pouilly-Fuisse and a melt-in-your-mouth, fall off the bone Pork Osso Bucco perfectly matched with a 2009 Donati Teroldego Rotalino. Familiar with Donati from my annual visit to the New York Wine Expo, we absolutely loved this bold Italian red.

Red and white were the choices for dessert as a 2009 Fritz Late Harvest Zinfandel and a 2009 Domaine de Beaumalric Muscat de Beaumes were paired with our combination of Double Chocolate and Strawberry Cream plates of Petit Fours. Rich and luscious all around, these were the perfect finish to an absolutely outstanding tasting dinner. Special thanks to our hostess Lydia Booz and sever Claire Copertino, the service was perfect!

Any visit to Annapolis should include a dinner reservation at Crush Kitchen & Winehouse and while there make sure you get Bob to explain to you the stunning modern art sculpture in the middle of the room that is actually the Enomatic wine server. A state-of-the-art wine dispensing and aeration station made in Italy, the only one in Annapolis! (http://www.crushwinehouse.com)

Both synonymous and eponymous with Annapolis is the United States Naval Academy (USNA) and we set out on our second day for a late morning tour of our country's second oldest of five Military Academies. Founded on 10 acres in 1845 as the Navel School at Fort Severn with 50 students it was renamed in 1850 and now boasts a 338 acre campus with 4,500 midshipmen.

The assembling of the Midshipmen Brigades in front of Bancroft Hall, the largest dormitory in America, for lunch call.(Photo: Douglas Harrington)


The Naval Academy tour is a must for any visitor to Annapolis. Both historically illuminating and emotionally touching, one would need to have a hole in their soul not to feel pride and patriotism while walking the beautiful and hallowed grounds.

Standouts on the tour for us were the cavernous Dahlgren Hall where we had the opportunity to see first-year midshipmen and women taking drill practice, a visit to the Main Chapel with stained glass windows, including Tiffany, as beautiful as in any cathedral in the world, the Naval Academy Museum in Preble Hall with a visually stunning and highly informative first floor exhibition of the history of the U.S. Navy and the USNA and an outstanding collection of antique ship models on the second floor. Particularly entertaining was the assembling of the Midshipmen Brigades in front of Bancroft Hall, the largest dormitory in America, for lunch call. This is a combination of drill, study, and pecking order affirmation of upper classmen over the first-year Plebes.

The crypt of Revolutionary War hero and Scotsman John Paul Jones beneath the Main Chapel.(Photo: Douglas Harrington)

I was most impressed with the crypt of Revolutionary War hero and fellow Scotsman John Paul Jones beneath the Main Chapel. After 113 years of obscurity in a Parisian cemetery, his body was located and verified by General Horace Porter, U.S. Ambassador to France, and returned to America in 1905. It is absolutely fascinating how Porter and his team were able to identify the body as Jones, but I will not spill the beans...go to Annapolis and take the USNA tour! (http://www.usna.org)

Leaving the USNA we headed down to the docks for a water tour of Annapolis Harbor aboard the Harbor Queen of the Watermark Tours, Charters, Cruises Company. Informative and fun, we had a chance to see the USNA and the harbor front from a Maryland Crab's perspective. The tour takes 40 minutes and the boat has all the amenities for a late afternoon cruise including snacks and a full service bar. (http://www.watermarkcruises.com)

A view of Market Square and the Annapolis docks from the Watermark Tours Harbor Queen. (Photo: Douglas Harrington)


Speaking of bars, Annapolis has plenty to choose from and we decided to join the TGIF crowd at the city's popular harbor front haunt Pusser's Caribbean Grill. This place seems busy every night, but Fridays are definitely SRO at the long outdoor bar that, like the Sly Fox, is smoker and dog friendly. Folks in Annapolis love to gather and party along the water, as our new friend Peter Oshana, accompanied by his Golden Retriever, noted, "Annapolis is either a sailing town that loves to drink or a drinking town that loves to sail." (http://www.pussersusa,com)

On the harbor but not waterside, The Middleton Tavern, founded in 1750, is another very popular gathering place in Annapolis for both locals and tourists alike. There is live music nightly including a piano bar every Friday and Saturday. Along with a full menu, there is a raw bar with the best oysters I have tasted in years. (http://www.middletontavern.com) A half a block away from Middleton's on Dock Street is the Dock Street Bar & Grill and here we had the best crab cakes of our visit. It is a small understated pub with a great beer list. (http://www.dockstreetbar.net) East across from the harbor one can enjoy waterfront fine dining and cocktails at the Severn Inn along the Severn River which feeds Annapolis Harbor and the Chesapeake Bay. A great view of the USNA at night! (http://www.severninn.com)

The gardens of the William Paca House Museum. (Photo: Douglas Harrington)

Saturday started with another Watermark Tour, but this time on foot as we set out on the "Four Centuries Walking Tour" highlighting historical landmarks throughout the city. Our colonial costumed guide was informative and passionate in his descriptions of the sites, events and the impact of Annapolis on our nation's history. Not only briefly America's first capital, Annapolis was the site of George Washington's resignation of his commission as Commander-and-Chief of the Continental Army and the signing of the Treaty of Paris, which ended the Revolutionary War. The tour of the State House was particularly inspiring as we stood in the footprints of the founders of our nation. Any visit to Annapolis should include this tour which sets off from the Annapolis and Anne Arundel County Conference and Visitors Bureau on 26 West Street, who's Communications Manger Sarah Todd-Evans was so helpful in arranging my visit to this beautiful city. (http://www.visitannapolis.org)

Several other historical museum tours highlighted our trip to Annapolis. A visit to Declaration of Independence signer William Paca's House and Garden (http://www.annapolis.org), the Banneker-Douglass Museum of African American History, as in Frederick Douglass (http://www.bdmuseum.com) and the Annapolis Maritime Museum (http://www.amaritime.org) should be bucket list visits on anyone's Annapolis itinerary. While wandering Annapolis, be sure to make a stop at the Annapolis Ice Cream Company for the finest boutique ice cream in the city (http://www.annapolisicecream.com) and if not staying at the Reynolds Tavern with their great breakfast, start your day at Miss Shirley's Café, believe me, lunch will be an afterthought! (http://www.missshirleys.com)

One cannot go to Annapolis without an evening's dining devoted to crabs and Cantler's is probably the most iconic crab house in the city. (Photo: Douglas Harrington)

One cannot go to Annapolis without an evening's dining devoted to crabs. Maryland is known for its crabs and there is no more iconic crab house in Annapolis than Jimmy Cantler's Riverside Inn. Simply known as Cantler's, everyone I know in New York who has ever visited Annapolis told me I had to schedule a visit to this landmark restaurant across the USNA Bridge and on the Mill Creek east of the city. The local crabbers, if that is what they are called, literally pull up to the dock at Cantler's and sell their catch by the hour daily. Unfortunately for us, joined by Annapolis friends and Maryland natives Cindy Robinson and Mike Trevisan, the Colossal and Jumbo sizes of crabs were sold out and the "Large" crabs, frankly, were a bit of a disappointment. That said, if you are planning for dinner at Cantler's at 5:00 p.m. get on the car line at 4:00 p.m. Yes, there is not only a wait at the door for a table, there is a wait to get your car into the parking lot that, at least on a weekend, can be as long as an hour. Inconvenient yes, but it is indeed a testament to the reputation of this Annapolis institution. (http://www.cantlers.com)

We ended our stay in Annapolis with a visit to our friend Cindy's resident condo's bar and restaurant Sam's Waterfront Café. As if planned, while I sipped my martini a sixty-foot yacht from Britain, making its way south from the Hamptons to Palm Beach, curled up to the dock. A bit of a drive out of downtown, but a great marina bar with live music and great bites, our bartender Kevin was outstanding. (http://www.samsonthewaterfront.com)

Brooks Brothers Blue Blazer wearing Hamptons' cliché that I am, if I have my way we will probably retire to Palm Beach one day, but I know Lily's choice is Annapolis. Frankly, she would not have a hard time convincing me. Annapolis is a diverse, cultured, historic and exciting city, with as friendly a populous and as engaging a social atmosphere as one will find anywhere. Again, Annapolis is a must stop-over on the way to Palm Beach and worth a visit any time of the year!

A view of the Annapolis Harbor from Main Street. (Photo: Douglas Harrington)


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Frequently mistaken for the "Most Interesting Man in the World" from the Dos Equis commercials and the iconic gray-bearded Sean Connery, DMH is the Senior Contributing Editor at Hamptons.com. www.hamptons.com Hamptons HamptonsOnline HamptonsOnline




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Guest (Sarah E.) from Annapolis, MD says::
Our unofficial motto is "A drinking town with a sailing problem." :)
Sep 14, 2012 1:24 pm

Guest (Eye On Annapolis) from Annapolis says::
Plus, we do have a BB here too! Just sayin' Nice article!
Sep 14, 2012 11:54 am

 

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