What are the best things to do in Annapolis?

Hayley Bosch

The port city Annapolis has endless nooks and crannies to explore. Don’t let the city’s compact size — it’s about seven square miles — fool you, it is brimming with things to do and see. Forbes Travel Guide editors pick the five best:

1. Tour the United States Naval Academy. Founded in 1845, the U.S. Naval Academy occupies 338 acres at the junction of the Severn River and Chesapeake Bay, Tours of the campus are available through the academy’s Armel-Leftwich Visitor Center. See the tomb of John Paul Jones, the majestic chapel, the midshipmen’s living quarters and the naval museum.

2. Stroll Main Street. A stroll along the brick roads of Main Street reveals more than 300 years of history. From Church Circle, a picturesque roundabout at the top of the lane where St. Anne’s Church was founded in 1858, visitors can see straight to the harbor at the base of Main Street. You’ll also find shops and restaurants — each with its own unique personality — along this charming street.

3. Take a colonial tour. Guides in colonial garb lead walking tours through the Colonial Annapolis Historic District. Visitors can find a number of operators to take them through the Maryland State House and St. John’s College, as well as historical mansions and more.

4. Chow down at a crab feast. Annapolis is known for its crab feasts — the blue crabs from the Chesapeake Bay are a true Maryland delicacy. At Jimmy Cantler’s Riverside Inn, the sweet crabmeat is best savored with a heavy helping of seasoning and a splash vinegar.

5. Go on a sailing tour. If you want to set sail on the Chesapeake Bay, hop onto a narrated two-hour trip by Schooner Woodwind Annapolis Sailing Cruises. While aboard the 74-foot sailing yacht Woodwind, you can help raise the sails or steer the boat. It departs from Pusser’s Landing restaurant at the Annapolis Marriott Waterfront.

  • On July 31, 2012
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    When is the best time to visit Annapolis?

    Annapolis comes alive in the summertime, when the Chesapeake Bay is warm enough to swim in and crabs are hauled in on a daily basis. Outside of historical tours, most of the activities throughout the city are water-dependent, whether you’re into boating or crab feasts. On any given day throughout the summer, the Chesapeake Bay and the Severn and Magothy Rivers are teeming with sailboats and yachts. Sailors flock to the city to watch 150 crews compete in Wednesday Night Races at the Annapolis Yacht Club, and parents can send their children to any number of sailing schools in the area. The weather is warm, usually in the 80s or 90s, making Annapolis a great summer destination.
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    What is the best thing to bring home from Annapolis?

    Annapolis revolves around the Chesapeake Bay and its rivers, so you’ll want to bring home something to remember the Annapolitan way of life. If you indulge in a crab feast you’ll likely get a taste of Old Bay seasoning, the requisite spice for Maryland’s blue crabs. Locals swear by the seafood blend, going so far as to season popcorn, chips and Bloody Marys with it. Pick it up at any grocery store and most souvenir shops — you may even want to buy it in bulk.
     
    You may also want to consider packing some crab cakes on ice and bringing them home. Real Maryland crab cakes don’t have much filler because they don’t need it — the sweet lump crabmeat from the backfin makes for a rich, succulent cake without many extras. Hop in the car and head to one of Annapolis Seafood Markets’ three locations for some killer cakes.
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    What are the best Annapolis food experiences?

    Annapolis is known for its fantastic seafood as well as a few other local specialties. Here are Forbes Travel Guide’s picks for must-try eats in Annapolis:
     
    1. Crabs at Jimmy Cantler’s Riverside Inn. This spot’s specialty is local all the way — Chesapeake Bay blue crabs are served in abundance. Sit at the long picnic tables on the patio overlooking Mill Creek and order a dozen of “number one jimmies” and a cold beer. Get ready to get messy.
     
    2. Pledge allegiance at Chick and Ruth’s Delly. Every morning, diners in the Jewish delicatessen get to their feet to recite the Pledge of Allegiance. A variety of sandwiches here are named for locals. Try the “Governor of Maryland,” the “Martin O’Malley,” or the “St. Johnnies.”
     
    3. Have a lager at McGarvey’s Saloon & Oyster Bar. This saloon is a legend among Annapolitans and its dimly lit interior is a go-to spot for locals and tourists alike. Try the crab dip, one of the best in the city, the oyster shooters or the house Aviator Lager. McGarvey’s transforms into a bar and skews younger at night, filling up with Navy midshipmen, college students and local twentysomethings.
     
    4. Get crab cakes at Davis’ Pub. Located across the bridge in Annapolis’ rival town Eastport, Davis’ Pub is where locals will send you for great crab cakes. With barely any filler, the cakes are pure backfin (the sweetest part of the crab). Go during the summer and enjoy your classic Maryland meal at an outdoor picnic table.
     
    5. Get a scoop at Annapolis Ice Cream Company. Since it opened in 2004, the Main Street creamery has been a hit. The homemade ice cream flavors include blackberry cobbler, salted caramel and coffee Oreo.
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  • On July 31, 2012
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    Where is the best nightlife in Annapolis?

    If you’re looking to have a wild night at the clubs, Annapolis is not the place to do it. Rather, this small town is home to great low-key pubs and bars. Forbes Travel Guide editors suggest you head to downtown Annapolis — affectionately known by Annapolitans as DTA — where just about every restaurant doubles as a bar and fills with Navy midshipmen come nightfall.
     
    At the base of Main Street, surrounding City Dock, you’ll find several Forbes Travel Guide favorites. Make your way to McGarvey’s Saloon & Oyster Bar for its very own craft beer, Aviator Lager. College kids abound, thanks to themed nights like “Tiki Tuesday” and “Big Beer Night” Wednesdays. Find an older crowd in the front room of McGarveys and next door at Middleton Tavern.
     
    The Sly Fox Pub sits at the top of Main Street along Church Circle. It’s great in the summer when the patio is open and it offers weekly specials and live entertainment Thursday through Saturday. Another lively place is West Street, which is just a few blocks away from Main Street. Rams Head Tavern is known for its craft beer and its small concert venue, while Tsunami serves up eclectic sushi and sophisticated cocktails.

    Across the bridge in Eastport, you’ll find crowds of sailors at most bars around town, which include The Rockfish restaurant and Boatyard Bar & Grill.
  • On July 31, 2012
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    What is the best way to see Annapolis in one day?

    Local families are proud of their deep Annapolis roots and welcome visitors to share in their heritage. Forbes Travel Guide editors discovered a way for you take advantage of the warm locals and get the essence of city in just one day.
     
    Start the morning with eggs, delly potatoes and a giant milkshake at local favorite Chick and Ruth’s Delly. Check out the photos covering the walls — you may recognize some famous faces. Beware: If it’s a weekend, there will be a line out the door.
     
    Annapolis is the self-proclaimed sailing capital of the world and visitors need to get out on Chesapeake Bay to really experience Annapolitan life. Hop aboard the Woodwind yacht for a two-hour narrated cruise, or arrange for a private charter on the Woodwind II. Once you’ve had your sailing fix, it’s time to eat some crabs. Head to local hotspot, Jimmy Cantler’s Riverside Inn for Chesapeake Bay blue crabs. Cantler’s overlooks a creek off the Magothy River and is a great outdoor spot to pick a few crabs. Locals will tell you the best way to eat ’em is with vinegar, Old Bay seasoning and a beer in hand.
     
    After washing up, head to downtown Annapolis for a dose of history. Try an organized stroll with Annapolis Tours in which the guides are dressed in full colonial garb and usually speak with a British accent. The two-hour-plus Four Centuries walking tour from Watermark includes a visit to the Old Senate Chamber where George Washington resigned as commander in chief in 1783.
     
    When your history lesson is over, head to McGarvey’s Saloon & Oyster Bar for some in-season oysters on the half shell — only in the months with an ‘r’ in them — and an Aviator Lager from the restaurant’s microbrewery. If you’re still hungry, order one of the juicy charbroiled burgers.
  • On July 31, 2012
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    Where are the best places to eat in Annapolis?

    In Annapolis, life revolves around the water and from rockfish to blue crabs, you’ll be hard pressed to find a restaurant without fresh seafood on the menu. And for a town of less than 40,000 people, Annapolis has an outsized number of delicious dining options. Here are Forbes Travel Guide’s favorite places to eat in Annapolis:
     
    1. Joss Café & Sushi Bar. You won’t find many tourists here because the locals try to keep this place to themselves. Order up a soft shell crab roll or a Chesapeake roll for local flavor and sit at the sushi bar to watch the chefs work. Know that Joss doesn’t take reservations and tends to fill up quickly on the weekends with a wait time of up to an hour.
     
    2. Lewnes’ Steak House. The Lewnes family opened their fabulous steakhouse in 1921 and business has been booming ever since. One of the local gems of the city, Lewnes’ has a very intimate atmosphere. Although steak is the focus here, the seafood is a great choice too — it’s local and fresh, fished from the waters just one block away.
     
    3. Severn Inn. Located next to the Naval Academy Bridge, this waterfront restaurant serves great food that matches its amazing views of the Unites States Naval Academy and the Severn River. Seafood dominates the menu with dishes like the jumbo lump crab cake sandwich and the grilled fish taco. On a warm day, opt for a spot on the patio to watch the boats cruise the river.
     
    4. O’Learys Seafood. This place is owned by locals and loved by locals. Just a stone’s throw from the water, the cheery yellow building houses a seafood lover’s haven. Pick any fish on the menu, tell your waiter how you want it cooked and enjoy.
     
    5. Osteria 177. The tavern is run by Italian restaurateurs from Italy and serves fresh Italian coastal cuisine with a sexy atmosphere. Ask about the risotto of the day, always a phenomenal choice, and start with the memorable beef carpaccio.
  • On July 31, 2012
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    What are the best places to stay in Annapolis?

    With hotels scattered around the city and enough bed and breakfasts to house an army, Annapolis has a slew of hotel options from which to choose. Our Forbes Travel Guide editors picked the five best places to stay in Annapolis:
     
    1. The Westin Annapolis. Opened in 2007, this modern hotel and its signature Heavenly Beds boosted the popularity of Uptown Annapolis. It’s located within the Park Place development, which has everything from residences and restaurants to salons and shops, and it’s still within walking distance from downtown.
     
    2. O’Callaghan Annapolis Hotel. The Dublin-inspired boutique hotel comes with a healthy dose of Irish hospitality. Just a few minutes from City Dock and the rest of the attractions in historic downtown, O’Callaghan Annapolis Hotel is a comfortable retreat with imported furniture and spacious rooms.
     
    3. The Inn at Perry Cabin. If you don’t mind a little distance between you and Old Annapolis, book at room at this gorgeous manor house, located about an hour away in St. Michaels. The rural, genteel resort is run by luxury hotel group Orient-Express and is oozing with East Coast, blue-blood charm with a spa, restaurant and Adirondack chairs lining the shore of the Miles River.
     
    4. Marriott Annapolis Waterfront. True to its name, many of the rooms at this hotel offer waterfront views of the Chesapeake Bay and Annapolis Harbor. Guest rooms are decorated in nautical themes with sea blue hues and comfortable furnishings. The hotel is also at the hub of everything in downtown — from Main Street to the United States Naval Academy.
     
    5. The Annapolis Inn. One of the most charming things about Annapolis is its plethora of bed and breakfasts. The Annapolis Inn is a historic landmark townhouse located within a residential area of historic Annapolis, and offers three impeccably decorated rooms. This quaint bed and breakfast is near to downtown but removed enough to feel private.
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    Where is the best shopping in Annapolis?

    Over the past 10 years, Annapolis’s shopping options have grown with the introduction of several upscale shopping areas and further development of the historic area. Forbes Travel Guide editors suggest starting on Main Street, which bustles with boutique shopping ranging from Helly Hansen (top-notch sailing gear) to Laurance Clothing (classic preppy menswear). There are a slew of good souvenir shops downtown, including Pepper’s and A.L. Goodies General Store. West Street, in Annapolis’ up-and-coming Uptown neighborhood, has its own share of boutiques and restaurants.
     
    The Parole neighborhood’s Westfield Annapolis Shopping Mall has department stores like Macy’s and Nordstrom, as well as specialty spots like the Apple Store and Sony. You’ll also find the Under Armour store — it is a Maryland company after all — and a movie theater. Across the way is the city’s most recent addition, Annapolis Towne Centre at Parole. Here you’ll find hip shops like Lululemon Athletica, Anthropologie and boutiques like Urban Chic.
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    What are the best things to do with kids in Annapolis?

    From sailing on the Chesapeake Bay to playing pirate, this city has a knack for keeping kids entertained. Here are Forbes Travel Guide’s picks for the five best things to do with children in Annapolis:
     
    1. Discover Chesapeake Bay. Take one of the several different sightseeing cruises and learn about the culture of Annapolis. Choose from a selection of narrated boat tours that sail around Annapolis Harbor, the United States Naval Academy, the Old Annapolis neighborhood and the Thomas Point Lighthouse.
     
    2. Feast on blue crabs. You and the kids will enjoy eating on this local delicacy. Grab a table at Jimmy Cantler’s Riverside Inn for some steamed crabs in a setting that doesn’t get much more Annapolis — Cantler’s overlooks a creek off the Magothy River.
     
    3. Sail a pirate ship. Aboard the Sea Gypsy, Pirate Adventures on the Chesapeake sends your kids on a treasure hunt set off by a mysterious message in a bottle. Face painting, water-squirting canons and costumes are part of the fun, too.
     
    4. Explore Quiet Waters Park. Whether the weather is warm or chilly, kids can play at this greenbelt overlooking an inlet of Chesapeake Bay. Ice skate on the park’s outdoor rink in wintertime, or enjoy the giant playground and woods in summer. On a nice day, pack a picnic and head to the promenade that overlooks the South River.
     
    5. Take a colonial tour. Annapolis is teeming with history and there’s no better way to learn about it than a tour with a guide who speaks in a British accent and is clad in authentic colonial garb. You’ll walk through the United States Naval Academy and the historic downtown, passing storied historical homes along the way.
  • On July 31, 2012
    Forbes Travel Guide Inspector answered the question: Forbes Travel Guide Inspector

    What are the best things to do in Annapolis?

    The port city Annapolis has endless nooks and crannies to explore. Don’t let the city’s compact size — it’s about seven square miles — fool you, it is brimming with things to do and see. Forbes Travel Guide editors pick the five best:

    1. Tour the United States Naval Academy. Founded in 1845, the U.S. Naval Academy occupies 338 acres at the junction of the Severn River and Chesapeake Bay, Tours of the campus are available through the academy’s Armel-Leftwich Visitor Center. See the tomb of John Paul Jones, the majestic chapel, the midshipmen’s living quarters and the naval museum.

    2. Stroll Main Street. A stroll along the brick roads of Main Street reveals more than 300 years of history. From Church Circle, a picturesque roundabout at the top of the lane where St. Anne’s Church was founded in 1858, visitors can see straight to the harbor at the base of Main Street. You’ll also find shops and restaurants — each with its own unique personality – along this charming street.

    3. Take a colonial tour. Guides in colonial garb lead walking tours through the Colonial Annapolis Historic District. Visitors can find a number of operators to take them through the Maryland State House and St. John’s College, as well as historical mansions and more.

    4. Chow down at a crab feast. Annapolis is known for its crab feasts — the blue crabs from the Chesapeake Bay are a true Maryland delicacy. At Jimmy Cantler’s Riverside Inn, the sweet crabmeat is best savored with a heavy helping of seasoning and a splash vinegar.

    5. Go on a sailing tour. If you want to set sail on the Chesapeake Bay, hop onto a narrated two-hour trip by Schooner Woodwind Annapolis Sailing Cruises. While aboard the 74-foot sailing yacht Woodwind, you can help raise the sails or steer the boat. It departs from Pusser’s Landing restaurant at the Annapolis Marriott Waterfront.