Annapolis is the capital of Maryland, and it was right in the heart of the American Revolution over 240 years ago. Since then, it’s become a bustling center for the arts and entertainment on the East Coast, providing both oceanic adventures and metropolitan excitement.

The History of Annapolis, Maryland

Annapolis was, briefly, the Nation’s capital from 1783-1784. It was founded in 1609 and incorporated in 1708. Over the past 200 years, Annapolis has been the home to world-renowned writers (Barbara Kingslover), fashion designers (Christian Siriano), actors (Robert Duvall), professional athletes, photographers, scientists, and, of course, many, many politicians.

Annapolis is known, at least in part, for being the home of the United States Naval Academy, founded in 1845.  

Climate and Weather

Annapolis has warm summers. Throughout the 20th century, summer temperatures have ranged from as low as 33 degrees Fahrenheit– just a smidge above freezing!– to 103 degrees. But, in general, the average summer temperatures stick around 80-90 degrees.

In the winter, Annapolis is pretty temperate. While the winter temperature range sweeps from -8 degrees Fahrenheit all the way to a sizzling 81 degrees, the general temperature in the winter months stays in the 30-to-50-degree range. As a result, while it can get chilly, Annapolis rarely deals with serious snowstorms.

Annapolis is a touch rainier than the Midwest, although it doesn’t have a particularly rainy season. Each month’s precipitation hovers around 3.5 inches of rain, with only slight variation. As far as the wind goes, it tends to range from 9 to 16 miles per hour, with can make ideal weather for kiting and sailing. That being said, make sure to pay attention to wind gusts, which can get up to 30 miles per hour, and stay indoors during storms.

Places to Stay in Annapolis, Maryland

Annapolis, Maryland has many elegant, historically architectural homes and apartments, some of which were built over three hundred years ago. For this reason, it is highly recommended to use apps and sites like Airbnb and HomeAway when traveling to Annapolis, so that you might have a more authentic experience, rather than opt for some generic chain hotel.

Airbnb & HomeAway

Airbnb lists some extraordinary highlights: for $94 per night, three beds are available in an old bay bungalow, complete with a cozy sitting room fireplace and expansive kitchen, just a block away from the Magothy river; a newly renovated carriage house with two bedrooms, a private yard, and ample parking is yours for only $199 per night; and for $175 per night, a three bedroom house, gas grill, and private patio is ready to rent in downtown Annapolis.

If you’re up for something a bit fancier, HomeAway lists an $800-per-night rental house that’s got marble countertops, a wrap-around deck, four flat-screen televisions, four-and-a-half baths, four bedrooms (accommodating up to twelve people), a game room with foosball and air hockey, and a jacuzzi.

On the other end of the spectrum, a small, private bedroom and bathroom can be rented in downtown Annapolis for a mere $55 per night through Airbnb. This particular host, John, has garnered 86 five-star reviews and no reviews under four stars.

Historic Hotels

But, let’s say you’d rather pursue the grandeur that comes with historic hotels, rather than go the family home route; in that case, three overnight spots– The Governor Calvert House, the Robert Johnson House, and the Maryland Inn– have got you covered. Each of these stays are across the street from the state house and feature king rooms, double queen rooms, popular amenities and free Wi-Fi. Rates range from $102 to $181 per night.

Popular Chain Hotels

All that said, Annapolis does have a fine variety of traditional hotels from recognizable brands, including Holiday Inn & Suites, Comfort Inn, Crowne Plaza, Country Inn & Suites by Carlson, Doubletree by Hilton Hotel, Residence Inn by Marriott, Best Western, and Extended Stay America. Prices range from $76 per night to $256 per night, according to TripAdvisor.

Things to Do in Annapolis, Maryland

Everyone’s got their own tune to follow when it comes to adventuring in Annapolis. There’s plenty to explore no matter what you enjoy.

Dining

There are a lot of places to dine out when visiting Annapolis, so this list is just a sampler to get you started. Being right near the Chesapeake Bay area, many of the best restaurants in Annapolis feature fresh-caught crab and other seafood. But even if cooked crustaceans aren’t your jam, there’s something enjoyable to eat in the city for anyone.

Drummer’s Lot Pub

58 State Cir, Annapolis, MD

Drummer’s Lot Pub dates back to the 18th century, and it’s got a classic vibe. Entrees range from $20-$30, and the menu is revitalized each season as the chef takes on new challenges. Expect fresh seafood, cheeses, and salads to be at play on the plate.

Treaty of Paris

16 Church Cir, Annapolis, MD

According to reviewers for the DC Gazette, “Treaty of Paris serves innovative cuisine using fresh, local ingredients and Chesapeake Bay seafood…the restaurant at the Maryland Inn offers a unique mix of historic charm with creative and contemporary foods.” Dinner entrees range in price from $19-$38, but any meal of the day could be had there, be it breakfast, brunch, or dessert.

Galway Bar

63 Maryland Ave, Annapolis, MD

Galway Bar is a family-friendly restaurant named after a seaside town in Ireland. Serving authentic Irish food, Galway Bar aims to be a place of old-fashioned Irish hospitality, without any modern distractions like televisions getting in the way of conversation. The oysters and calamari are a good bet for a good meal, but so is the corned beef and cabbage or the Chesapeake bangers and mash. Dinner entrees range from $10-$25.

Vin 909

909 Bay Ridge Ave, Annapolis, MD

Vin 909 is known for their top-notch pizza. It’s brick-oven baked, all the ingredients are fresh, and the pizza dough is made by hand. The rest of their menu is also popular. It’s changed up seasonally, although staples like seared shrimp and polenta never go out of style. Dinner entrees range from $13-$18

Preserve

164 Main St. Annapolis, MD

In their own words, “Preserve is a casual American restaurant with a focus on fermentation and pickling.” Whether you’re looking for farmstead cheeses, hot honey chicken skins with pickle dip, or glazed and braised catfish, Preserve has a unique take on cuisine Americans might take for granted.  Dinner entrees range from $22-$32

Sin Fronteras Cafe

2129 Forest Dr, Annapolis, MD

Sin Fronteras Cafe is a Mexican-Latin American restaurant with authentic flavors rarely found north of Texas. With ingredients like sweet cream imported from Honduras, fresh salmon, plantain chips, and chipotle raspberry vinaigrette dressing, this diner is brimming with style. Dinner entrees range from $10-$20.

Kittens in Cups

177 Defense Hwy, Annapolis, MD

Kittens in Cups is a new kind of restaurant in Annapolis: the city’s first ever cat cafe! Kittens in Cups is a place where visitors can purchase tickets to hang out in a lounge with friendly, well-trained, adoptable cats while drinking coffee and tea and eating snacks. Snacks and drinks are in the $1-$5, and a half-hour walk-in ticket is $7.

Arts & Culture

There are over twenty-five art galleries in downtown Annapolis which host curated shows in paintings, sculpture, glasswork, and mixed media. Beyond the visual arts, Annapolis supports an opera, a symphony orchestra, a Shakespearean theatrical company, and a ballet company. That all meets some incredible contemporary performance right in the very same square, with groups like The Colonial Players innovating in a theatre in the round.

Nightlife

Ram’s Head On Stage ranks as one of the top small music venues in the world; meanwhile, Middletown Tavern features a piano bar upstairs and exciting live music downstairs every weekend. Nightlife is certainly lively in Annapolis, and while some are dancing the night away, others are dancing with lady luck: Annapolis now features two vibrant casinos– Live! Casino & Hotel and the Chesapeake Beach Resort & Spa.  

History

The history of the American Revolution vibrates throughout Annapolis. Visitors can stand in the exact spot the Treaty of Paris was ratified and then, on the same day, check out the Maryland State House for a peek into the room where George Washington resigned his military commission to the Continental Congress.

Outdoor Fun

Who wants to be cooped up indoors for their whole vacation? In Annapolis, spend an afternoon under the open sky while fishing, paddleboarding, sailing, or kite-surfing by checking out Annapolis Harbor’s Ego Alley. Or, gather up the kids and play pirate on the mock pirate ship Sea Gypsy. Or, for lower-speed fun, try renting a kayak from Terrapin Adventures so you might explore the harbor at your own pace.

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