7 Days in Annapolis


Being able to spend any time at all in Annapolis is an exciting adventure, but if you really want to get to know the ins and outs of our city on the bay, you’ll need to stay here for a minimum of seven days. You still won’t see it all, but you’ll leave feeling you had a really great start! Of course, not knowing what to see is a downfall, but since you’re staying in a vacation rental from At Home Annapolis, you have our great team on your side. so, when you visit Maryland, check out this guide to spending seven days in Annapolis to help!

Visit Maryland – Day 1: Starting Out Slow

Traveling takes a lot out of you, so on this first day in beautiful Annapolis, during your visit to Maryland, we’re going to take it slow. Once you’ve unpacked and explored the amenities of your At Home Annapolis vacation escape, why not head over to Chesapeake Bay for a quiet walk and some quality people watching? Stretch out muscles cramped from sitting in an airplane seat designed for children, ooh and ahh over the sight of sailboats skimming across the bay, and when you’re ready, linger over dinner at Sam’s on the Waterfront, located at 2020 Chesapeake Harbour Dr E. Grab a waterfront table and watch the sun set over the bay as you enjoy one of the best crab cakes you’ve ever tasted!

Day 2: Rested and Refreshed

Our cloud-soft beds ensure your first night in town will be spent in a deep and dreamless sleep, allowing you to wake up rested, refreshed, and raring to go! Today is going to be a busy one, so be sure to start with a hearty breakfast at Eggcellence, located at 2625 Housley Road. Then, with bellies full, it’s time to explore the beauty of Annapolis. The best way to do so is with a walking tour of the historic district. Today, we may not do much more than look from the outside, but it’s the perfect way to get a feel as to what you want to explore more in-depth. Enjoy the architecture of buildings built before America was a free nation, walking in the footsteps of those courageous men who fought for our right to be free, and of course, stopping in to do a little shopping at the Historic Annapolis Museum Store to buy a little trinket to remind you of your stay in this historic city!

Day 3: Now That You Have an Idea About What Interests You

Your 3rd day will begin the in-depth exploration of our fair city—perhaps at the US Naval Academy museum, for example. Military buffs won’t be able to get enough of the exhibits, artifacts, and displays that tell the history of the Navy and the venerable institution that turns green young men and women into experienced seamen, ready to fight for our freedom. History buffs may want to spend some time exploring the home and gardens of William Paca, a signer of the Declaration of Independence. If you have a wedding planned in the future and want to do something unique, the Paca House can be rented for weddings as well! Dinner at Soul, 509 S Cherry Grove Avenue, finishes up this day quite nicely. If you’re here during the winter, try the Steak Chili for some quick warmth!

Day 4: Ready for a Road Trip?

Vacations can be expensive, so how would you like a chance to earn back some (or ALL!) of what you spent? A road trip to Hanover, just 35 minutes away, and Live! Casino is on the schedule for today, and we wish you all the luck in the world! Spend most of the day Vegas-style, playing blackjack, poker, or simply feeding coins into the slot machines, and when you get hungry, you don’t have to go far; there are 11 restaurants in the casino! From Chinese to Italian to good old-fashioned steak, there’s sure to be a meal that appeals to everyone in your traveling party. If you’re not in a hurry to get back to your Annapolis hideaway, you can finish up with a show. Live! has a variety of shows and sporting events going on all the time, all of which make for a memorable way to spend an evening.

Day 5: Row, Row, Row Your Kayak

During your warm weather visit, day five will entail going back to the bay, where all our adventures are going to be on the water! After another hearty breakfast, this time at Eastport Kitchen, which is close to most of today’s activities, we’ll mosey on over to Annapolis Canoe & Kayak on 311 Third Street. Offering kayaks, canoes, and SUP equipment, they also have a floating dock from which you can launch your water “vessel” of choice and spend your day exploring the city from the Chesapeake Bay. Take your time and enjoy the feel of the breeze against your skin and the sight of Mother Nature’s creatures flying high above you and swimming below your paddles. The only limit is your budget, and if you were successful at the casino yesterday, today won’t cost a thing!

Day 6: Free Day?

There’s nothing we dislike more than bossy tour guides who won’t let you have any free time, so on your last full day in town, we’re backing off with the suggestions—except for these last two! After that, you’re on your own to explore any places that have caught your fancy during your daily expeditions, we promise! First, we recommend a visit to the Kunta Kinte-Alex Haley Memorial found at City Dock. This moving memorial serves as a reminder to how far we have come in the last couple of hundred years, and maybe of how far we still have to go when it comes to race relations. For dinner, we hope that you will explore the culinary creations at the Federal House Bar & Grille; this iconic restaurant inside a building constructed in 1830 has long been a tradition for travelers and residents alike.

Day 7: We’re So Glad to Have Met You!

The last day of an excellent vacation is always a sad time, but we hope you have enjoyed your visit to Maryland! As you pack up your clothes and the souvenirs you picked up during your adventures, we also hope that you have had a chance to spend some time at home enjoying the comfort and style of your At Home Annapolis vacation escape. Reserve yours today for your next visit to our city on the bay! Click here and learn more about us!

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