How to Find the Most Scenic Spots in Annapolis

Our lovely city of Annapolis truly has it all—18th century historic buildings rich with American history, sprawling waterfronts on the Chesapeake Bay, and beautifully maintained city parks—not to mention excellent local dining and expertly prepared seafood! We’ve compiled a list of some of the most scenic places to see in Annapolis that aren’t to be missed, and unique ways for you to enjoy them!

Take a Cruise Around Annapolis Harbor

If a city is surrounded by water, often one of the best ways to see some of the most iconic places to see in Annapolis all at once is by boat, and Annapolis is no different! With Cruises On the Bay by Watermark, you can take a 40-minute ride through the harbor that serves as a perfect introduction to the city, and will take you on a narrated tour and past sights such as the U.S. Naval Academy and Chesapeake Bay Bridge from a distance. They also offer a number of other excursions, such as the Spa Creek Tour, the Severn River Cruise, and the Chesapeake Bay Bridge tour that’ll take you directly under the massive architectural feat. You can find Cruises on the Bay by Watermark at City Dock at 1 Dock St, Annapolis, MD 21401.

Picnic at Quiet Waters Park, One of the Best Places to See in Annapolis

If you’re looking for a serene way to enjoy the outdoors, stop by Quiet Waters Park for the afternoon. This 340-acre park has it all—miles of paved paths for biking, a striking sculpture garden, play areas for children, and formal gardens with fountains where you can stop for an unhurried picnic lunch.  There’s also a Reading and Butterfly Garden, and in the summer, you can rent a kayak to take out onto the cove. The park also hosts seasonal events like outdoor concerts and ice-skating in the winter. You can find Quiet Waters Park at 600 Quiet Waters Park Rd, Annapolis, MD 21403.

Take a Walking Tour Through Historic Annapolis

Pay a visit to downtown Annapolis for a vibrant, bustling neighborhood with four hundred years of historic architecture, carefully preserved buildings, and scenery around every corner. The Main Street area is not to be missed, and is brimming with 18th-century buildings, boutique shops, and outstanding local restaurants. Stop by the Historic Annapolis Museum Store for tips on a self-guided walking tour or sign up for a guided journey with Annapolis Tours. When you’re done taking in the sights, stop by a top-rated restaurant like Preserve or the Iron Rooster for comfort food and cocktails. For an easy starting point, you can find the Historic Annapolis Museum Store at 77 Main St, Annapolis, MD 21401.

With so much to do in Annapolis, our expert reservation specialists can assist you in finding a vacation home tailored with what you’d like to do the most while you’re here, whether it’s hitting all the historic sites or relaxing against the beautiful backdrop of Chesapeake Bay. Contact us to learn more today!

Outdoor Things to Do in Annapolis

Annapolis is a thriving city full of art and culture but thriving even more is the natural landscape that surrounds us. From the sparkling waters to the rich flora, this climate is one where you’ll want to spend a great deal of time outdoors. Here are some ideas for outdoor things to do in Annapolis you can take to make the most of each day:

Visit Quiet Waters Park

This is a great way to get your fill of the outdoors on a quiet afternoon where you just want to hang out. Take a picnic here, or go on a peaceful walk, and enjoy the winding paths and the local wildlife that you’re sure to see. You can even bring your dog along on this adventure and let him run free in the dog park.

Go Kayaking with the Family

One of the most exciting ways you can explore the outdoors is to hit the water in a kayak. Take the entire family with you on this adventure! With Kayak Annapolis LLC you’ll get the best gear, and the water here always makes for a serene day trip. It’s a fun way to get a good work out with all that paddling, but also existentially relaxing at the same time. Take some snacks and kick back far away from the shore, simply enjoying the sunshine and the sound of the water splashing around you.

Take a Ride Down B&A Trail

This is a long and flat trail that’s easy to ride and stretches from Boulters Way in Annapolis all the way to Dorsey Road in Glen Burnie. That’s a lot of road to cover, and you can ride however much of it as you like, depending on how much of the gorgeous, forested area you want to see.

Cast a Line with the Experts

Chesapeake Bay is rich with sea life, and it’s the perfect place for sportfishing. Head out onto the water with Captain Frank through Down Time Charters, and you’ll get the opportunity to catch all manner of fish in the best sportfishing areas, like Kent Island and Poplar Island. Fish with the best of the best and go back to your rental home at the end of the night with more than a few prizes in tow.

Start Your Adventure with At Home Annapolis

There are so many different adventures to be had in Annapolis, but without a doubt, the place to start is right here with At Home Annapolis. Give us a call today at (888) 508-9661 or (435) 571-0024 to get started on finding your rental home!

Your Annapolis Labor Day Weekend Vacation

Annapolis is a hotspot of beautiful sights to see and wildly fun activities. There is so much to do here, and September is a great time of year to visit. The long weekend that Labor Day provides gives you the perfect amount of time to see the best Annapolis has to offer. Here are some ideas for what to do each day to get the most out of your Annapolis Labor Day Weekend visit:


Do something crazy on the first day that will get the entire family excited about the three-day weekend in Annapolis, like a family-friendly pirate cruise with Pirate Adventures on the Chesapeake! Afterward, you can check out some of the amazing museums in town, like the Annapolis Maritime Museum. Keeping with the sailing theme, you can grab some dinner at the Boatyard Bar & Grill, a proudly nautical-themed seafood joint with an amazing vibe and even more amazing food.


Sunday is a great day to plan some peak relaxation and sight-seeing. Head to the aptly named Quiet Waters Park, where you can explore hiking trails on foot or on a bike, and even rent a kayak if you want to head out onto the water. If you pack a picnic, you can grab a shady spot under a tree and have your lunch there while you soak in the lovely weather and the scenery. Later on, head to Sandy Point State Park for one of the most gorgeous views you’ll ever lay eyes on. You can see the bridge from there, and the ocean in all its glory. Lay out some towels and chill out with some music on.


Since you’ve thoroughly enjoyed the waters, on Monday, you’ll want to enjoy the city itself! Check out local favorites like the Maryland Federation of Art for some culture, the Historic Annapolis Museum for some history, and the Old Fox Books & Coffeehouse for some afternoon coffee and a nice quiet look around a good old-fashioned bookstore. Pick up some fancy teas and spices from The Spice & Tea Exchange to take home with and maybe give out to friends as souvenirs! Top off your trip with an ice-cold craft beer from The Brass Tap on your last night in town.

Where Do I Start?

The first thing you’ll want to do is find an awesome place to stay, so you can make the most of your weekend getaway! Here at At Home Annapolis, that’s the most important thing to us. Just give us a call today at (443) 837-6870, and we’ll help you get started.

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!