Annapolis In 3 Days Itinerary: The Best Must-Sees And Dos

Annapolis is famous for its water activities and fun, and tons of people have fallen in love with its beauty… but what else does it have to offer? You don’t have to be out on the ocean or wandering around a dock to have an amazing time (although certainly, we’re going to be recommending those activities too). 

There’s a huge amount going on here and we don’t want you to miss out on a single thing! If you’re a bit limited on time and you’re only visiting this magical city for a few days… well, there are lots of fun things to do in Annapolis! Let’s “dive in” to the sailing capital and start crafting an Annapolis in 3 days itinerary.

Day 1 of Annapolis in 3 Days Itinerary: The Water Day

You can’t come to Annapolis in 3 days and not see the sea. It simply can’t be done! This ocean-side city is just waiting for you to get your water wings on and start checking out its aquatic beauty.

Morning

You might start your Annapolis in 3 days itinerary with a tour of the docks and the US Naval Academy, where you’ll learn tons about Annapolis’s important role in educating naval officers and sending the best of the best out into the world. It’s been doing that since 1845!

There’s also a beautiful crypt – yes, we do mean beautiful – where the father of the US Navy, John Paul Jones, rests. The chapel that contains it is more than worth a visit and the Academy Museum is also important to check out. It’s got two floors of incredible paintings and rare artifacts, plus a collection of model ships that will take your breath away.

And if you’re getting peckish? There’s the Naval Academy Club waiting to serve you an in-theme lunch, and several other spots you can choose from if that doesn’t take your fancy. Fuel up on some good lunch, because there’s a busy afternoon ahead!

Afternoon

Once you’ve had your fill of the history and got some food in your stomach, it’s time to continue your Annapolis in 3 days itinerary getting in touch with the present day… and what better way to do that than heading out onto the water yourself?

Here, you’ve got many different options! If you can’t fit them all in but you’re enthusiastic, try bumping one onto another day or extending your stay if you can. There’s just too much to choose from.

Firstly, what about a cruise or tour? This will take you around all the important sites, giving you information about the fascinating history Annapolis has enjoyed, and letting you understand more about its importance. 

Alternatively, if you’d like something a bit more active, you might choose to go for a paddle on Spa Creek. Simply rent yourself a kayak or canoe and spend the whole afternoon out on the water, soaking up the beauty, immersing yourself in nature… you won’t be sorry!

If that’s not quite your ticket either, how about checking out some parasailing and other water sports? Give yourself a true trip to remember by flying high above the waters in an adrenaline-fuelled rush. There’s nothing like it!

Another option? What about sailing? We’ve got sailing choices galore here! Short trip or full day – either way, you’re in for a great time. Bask in Chesapeake Bay’s beauty from the deck, the sea spray lashing against your face. This is Annapolis as it was meant to be seen.

Evening

Clubs or bars – whichever you fancy, you’ll find it. Grab yourself a delectable bite to fuel yourself up, and then hit the streets for an amazing night out!

Annapolis offers plenty in the way of concerts and evening events, so check out what’s on offer while you’re there. The Robert Kauffman Theater has some excellent productions, and the Rose Theater is also always worth a visit! Alternatively, Twain’s Tavern often has live music and combines that with great drinks… what more could you really want?

Day 2 of Annapolis in 3 Days Itinerary: Nature, History, And More Nature

It’s not only the water that Annapolis has to offer. No – there are some stunning natural spots to make the most of too, and that’s where we’re going to spend Day 2 in your Annapolis in 3 days itinerary!

Morning

First up, an activity for all the family. Let’s head over to William Paca House & Garden. There’s tons going on here! Guided tours that will tell you about the history of the place? Storytime to enchant the kids once a week? Yuletide Traditions (a December special)? Or how about just a self-guided tour around the breathtaking gardens – including a kitchenette garden and a wilderness garden?

The Yuletide tour is particularly interesting if you’re visiting at the right time of year; it’s an hour-long tour by candlelight, during which you’ll learn all about the Paca household and how they hosted Christmas, as well as other 18th-century traditions. There’s also a sweet treat to tempt visitors!

Afternoon

When you’ve stopped for a bite to eat, it’s time to check out the Maryland State House. This place has it all. It’s the oldest American state house that has always been in legislative use, and it was the Capitol from 1783 to 1784. Wander through amazing historic chambers and learn about the famous political figures who have graced this building. Check out where the Treaty of Paris – which ended the Revolutionary War – was signed… and then head to the National Underground Railroad Network and to Freedom site.

You could spend many an hour in Maryland State House, but if you’ve had your fill and you’ve still got energy going spare, it’s time to trot over to the Banneker-Douglass-Tubman Museum to slot in a bit more learning. This museum celebrates Frederick Douglass and Benjamin Banneker, as well as Harriet Tubman. Learn all you need to know about these three famous figures, who deserve all the accolades for their amazing contributions to shaping US history.

Evening

After a busy day, you might like a more chilled-out evening on your Annapolis in 3 days itinerary… so why not pick an amazing restaurant and simply soak up the atmosphere of Annapolis while enjoying some spectacular flavors? We’d recommend heading over to Cantler’s Riverside Inn for some tantalizing fresh seafood – what could be better in a harbor town? Here, you can enjoy:

• Crab cakes
• Shrimp
• Oysters
• Scallops
• Lobster
• Fish
• Maryland blue crabs

And with views across the waters of Mill Creek, it’s the perfect setting for a quiet evening meal, alone or with your family – whichever you prefer! Plus, the restaurant’s family has five generations of experience in the seafood industry and the restaurant has been open for almost four decades… so you know it’s going to be more than amazing!

Day 3 of Annapolis in 3 Days Itinerary: Shopping Shenanigans

Finally, the day of shopping arrives on your Annapolis in 3 days itinerary. After all, who wants to leave without a few souvenirs to take to their buddies or those family members who couldn’t come on the trip? Or perhaps mementos for yourself!

Annapolis has shops galore with anything and everything… so let’s plunge in!

Morning

If you’re thinking clothing, head over to The Pink Crab, where you’ll find a whole selection of casual, fun clothes in a lovely environment. The service is great, the store is organized, and the staff knows exactly how to help customers have an amazing time!

There’s also Helly Hansen Annapolis if you don’t find what you need at The Pink Crab – again, great staff and a wide range of quality clothing make this a fantastic option for many.

You can follow that by heading over to the Annapolis Mall, where you’ll find stores to suit every taste and need. Whatever you’re looking for, you should find it here, so souvenirs will soon be taken care of. There are also eateries aplenty, meaning that when you start to run out of steam, you can slow down and get some grub before you start on Shopping Adventure Part II.

Afternoon

Full of good food, why not head over to check out Annapolis Pottery, where you can get tons of unique handicrafts? You can even watch the staff crafting pottery – an amazing experience in itself – and the items on offer are gorgeous.

You can follow that up with a trip to the Annapolis Bookstore, where you’ll find titles old and new, plus some rare options, and very knowledgeable staff able to help you out with anything you want. Finding a great bookstore might sometimes be challenging these days… but not in Annapolis!

There are also some amazing markets in Annapolis, including the Annapolis Quiet Waters Park Farmers Market. Locally grown veggies and fruits? Handmade jewelry? Baking, crafts, and treats galore? Yes please to all – and all can be found at this market. It’s the perfect place to finish up your day and can lead beautifully into our final evening activity…

Evening

Stroll through Quiet Waters Park. Even after the market has closed, this place has so much to offer, with – as the name suggests – a very tranquil atmosphere. Trees, deer, and waterside views… what more could you want? It’s a wonderful way to finish a day of shopping, letting you unwind before you head back to your hotel. Definitely a win!

Annapolis in 3 Days Itinerary: FAQ

Annapolis in 3 Days Itinerary: Final Thoughts

Hopefully, you’ve had an amazing time virtually visiting Annapolis – now it’s time to do it for real. There’s nothing like travel to restore and renew you, and if you’re feeling enthused, why not also check out our 24-hours in New York City guide? You’ll have a blast!

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