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:

Saturday

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

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.

Monday

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!