Plan an Unforgettable Luxury Annapolis Getaway

Annapolis is a hot spot of culture, activity, history, and sightseeing. There are endless ways to fill the day—so many that it can be hard to pick and choose. Make this Annapolis getaway the most fun and comfortable you’ve ever taken by using this handy guide:

What to Do During Your Annapolis Getaway

Charter a fishing boat while you’re in town to enjoy the beautiful waters of the bay. You’ll want to see some of the famous museums while you’re here too, like the Annapolis Maritime Museum & Park, the U.S. Naval Academy, and the Maryland Federation of Art. For a breath of fresh air and nature, head down to Sandy Point State Park and the lovely Helen Avalynne Tawes Garden. If you really want to splurge, consider finishing out your trip with a helicopter tour on the very last day to see all the sights one last time. These are the top 5 tourist attractions in Annapolis!

Where to Eat

Treat yourself to some of the best fine dining experiences you’ll ever have for your Annapolis getaway. Have the best steak you’ll ever eat at Lewnes’ Steakhouse. Take a deep dive into French cuisine at Les Folies Brasserie where you can try dishes like ahi tuna, beignets, or venison in lingonberry sauce. Check out Osteria 177 for some high-end Italian. Try the Caprese, the Cioppino, or the Sacchetti di pasta ai Porcini! You really can’t go wrong at this restaurant, which is a big favorite among locals.

Where to Stay

For historic style, make your home-away-from-home at Submariner’s Gate. This property has a beautiful private courtyard, and a basement game room complete with a shuffleboard table, darts, and even a bar. For something even more spacious, consider the Magical Memories, which overlooks the breathtaking Chesapeake Bay. The yard is lush, the home is beautiful, and it’s only five miles from Historic Downtown Annapolis. If you’re coming with a really big group, you’re going to want to stay at the Ogleton Porticos. This luxury home is 6000 square feet, provides enough sleeping room for 17 people, and sits directly on the waterfront. With a built-in bar, a fireplace on every level, multiple porches and balconies, and a private pier on Lake Ogleton, this will without a doubt be the nicest home you’ve ever vacationed in. Check out our pet-friendly vacation rentals today!

How to Get Started

The most important step in planning any vacation is choosing your perfect place to stay, so when you’re planning a vacation of utmost luxury, you’ll want a rental property of utmost luxury to match! That’s where At Home Annapolis can help you. Get in touch with us today at 443-837-6870 to get started on planning the most unforgettable Annapolis getaway you’ve ever had!

Top 5 Pizza Places Locals Love in Annapolis

There are so many things we love about living in our city on the bay: the history, the views, the people, and crazy as it may sound, the pizza! Gooey and delicious, we’d wager that the pies served in Annapolis could compete with any in the world! And although pizza is a dish that people of all ages enjoy, living so close to the US Naval Academy and all it’s younger denizens who would rather order out than make a meal ensures that we have plenty of excellent choices for you to enjoy during your Maryland vacation.

Sammy’s Italian Pizza Kitchen, 1007 Bay Ridge Avenue A

Designed to feel as if you stepped into the dining room of your beloved Italian grandma’s home(with a few extra tables and chairs), Sammy’s Italian Pizza Kitchen offers a warm and welcoming ambiance that blends nicely with the meals they serve. And although they feature an extensive menu of your favorite Italian dishes, it’s the pizza that is the star of the show; hand tossed and offering a combination of New York and Chicago style pies, we won’t blame you if you choose to visit here more than once!

Annapolis Pizza at Vin 909 Wine Café, 909 Bay Ridge Avenue

The menu changes with the seasons, but the one thing that stays the same year-round is the divine taste of their diverse Annapolis pizza menu! Offering an innovative selection of toppings (including wild boar meatballs) that are locally-sourced and fresh from the farm, a visit to Vin and the charming cottage it’s housed in makes a romantic and memorable occasion!

Neo Pizza, 220 Harker PlaceSuite 145

Casual and chic, Neo Pizza is known throughout the state for its artisan pizzas and regional wines selections.also offering a large craft beer menu, if you’re looking for a place to hang and enjoy a slice, this 20-year-old establishment will fit the bill! And because they also offer delivery, depending on your location, you never have to leave the comfort of your vacation escape; they bring the best to you!

Mangia Italian Grill & Sports Bar, 81 Main Street

Sports fans will be thrilled to have their pizza and watch the big game at the same time! Annapolis is a hugely sports-oriented city, and the owners of Mangia have created a winning combination of pizza and sports about which we are not complaining one bit! Strategically-placed televisions throughout the restaurant do not clash with the Italian décor, and the hand-tossed pizzas topped with farm fresh ingredients add a savory element to the game on the big screen.

Rocco’s Pizzeria, 954 Bay Ridge Road

If it ain’t broke, don’t fix it seems to be the theme behind this classic pizzeria located inside a 1970s storefront. Walk inside and you’ll see a décor that probably hasn’t changed a bit since opening day; the aromas that greet your twitching nose will tell you that changes aren’t needed! Rocco’s also offers delivery of their classic New York-style pizzas, so on the nights you just want to lay around in your jammies and veg, call 410-263-9444 and wait for the delicacies to arrive at your front door!

Eating Out or Eating In

It doesn’t matter how you choose to eat your Annapolis pizza, all that matters is that you choose an At Home Annapolis home in which to enjoy the leftovers! Our homes are stylish, comfortable, and designed to make today’s travelers feel right at home. Reserve yours today!

Must See Attractions in Annapolis

One of America’s great historic cities, Annapolis is famous for its Georgian and beaux arts buildings, romantic cobblestone streets, and charming harbor district with shops, fine dining, and family-friendly attractions. This city by the bay is not shy about its love of the sea, from yachts to evening sails to decadent seafood, and that’s just how we like it. With so many historic sites, fascinating museums, and scenic waterways we know it can be daunting to plan your itinerary, but you won’t want to miss any of these must see attractions in Annapolis!

Sail On!

As the sailing capital of America, no trip to Annapolis is complete without a voyage out onto the charming waters of Chesapeake Bay. Take a romantic sunset cruise aboard a classic wooden schooner, learn to sail at Annapolis Sailing School, or simply hop aboard one of the water taxis linking all the points of interest along Annapolis’ shoreline. For a special treat check out Schooner Woodwind and indulge in one of their decadent dinner cruises, or stay overnight for their popular “Boat and Breakfast”, one of our favorite ways to catch a sunrise over the Bay (while enjoying a delicious breakfast, no less).

Historic Downtown and Other Must See Attractions in Annapolis

Founded around the confluence of the Severn River and the Chesapeake Bay, the historic downtown district is impossibly idyllic. Cobblestone streets intertwine around colonial-era architecture and historic builds. We love spending at least a morning here, though you can easily enjoy an entire day. Take in the manicured grounds of the U.S. Naval Academy and marvel at its classic Beaux Arts facades, visit the country’s oldest capital building, the Maryland State House (built in 1772), or grab a meal with a view at one of the many delicious restaurants lining the waterfront.

Ego Alley

The City Docks are also known as Ego Alley thanks to the penchant for captains of all classes to showcase their boats on this narrow waterway. Here the streets are lined with cafes, boutiques, gift shops, art galleries, and more. Nearly everywhere you go has splendid views of the river, harbor, and the bay, making it a perfect place to grab a meal any time of year but especially during the weekend sailboat races in May and the annual boat show in October. Which reminds us…

Eat Crab Cakes!

This one speaks for itself. Available in nearly every restaurant, this Maryland specialty is not to be missed! If your stay is over a first or third Sunday (July-Sept.), don’t miss the Annapolis Crab, Crash & Cruise at Chesapeake Brewing Co. of Annapolis. Eat your fill of steamed crabs, fried chicken, crab cakes, grilled corn, Maryland’s state cake (yeah, we have one), and of course, beer!

At Home Annapolis is proud to offer more than just the best selection of vacation rentals in Annapolis; we strive to provide you with the absolute best vacation possible. While you may have trouble deciding what to do when you visit, you can sleep easy knowing you made the right choice in your accommodations. Browse our wide selection of properties or contact our expert local guides to help you plan your trip, today!