Ego Alley – the narrow Annapolis waterfront where boaters like to dock – was overflooding into nearby parking lots as I looked out of hotel room window after checking in on a rainy Friday afternoon. Ducks swam in the road, curious as to why cars were approaching, leaving large splashes of water in their wake. I was glad I’d brought my rain boots. And although the rain wasn’t exactly what I’d thought of for our 48-hours in Annapolis when I planned a water-based romantic weekend getaway with my husband, splashing in the puddles was a good way to start.

We’d wanted to play in the water. (Ok, I wanted.) My husband probably would have loved at least a few traditional Annapolis highlights like a tour of the United States Naval Academy. Beyond being the state capitol and home to the prestigious (and beautiful) military academy, the small city is rich in history as the place where George Washington resigned as General of the Continental Army following the Revolutionary War and where the Treaty of Paris (ending the Revolutionary War) was signed.

But I was looking for a way to combine adventure with a small town getaway, and all things water are a perfect fit when it comes to this nautical town. My goal for our romantic weekend getaway was simple. I wanted us to experience Annapolis from the water in as many ways as possible.

Rainy day in Annapolis

On our first afternoon, that meant getting wet. As in, playing in the puddles kind of wet. (Or trying to avoid the puddles and still getting splashed by oncoming cars.) We’d hoped to be in the water that evening, for a guided night LED SUP tour but stormy skies delayed our paddling dreams.

I’ve always loved this small town for its quaint streets and water views. Our typical visits were quick day trips that involved walking, shopping and eating. But to spend almost 48 hours in Annapolis for a weekend adventure? That felt like a gift.

ego alley in Annapolis

Walk around ego alley in Annapolis

Walking tour around ego alley in Annapolis

48 hours in Annapolis

48 hours in Annapolis

Drop anchor at the Annapolis Waterfront Hotel

Annapolis Waterfront Hotel room

You’ll want to book a room for your getaway at the centrally located Annapolis Waterfront Hotel, but you’ll want to stay for the nautical-inspired atmosphere and water views. Shades of blue line the halls and rooms alongside maps and photos from the nearby Naval Academy. While there are only 25 rooms with balconies overlooking the water and bay, all of the rooms offer a water, yacht club or city view – which made me want to keep the curtains open to take it all in.

What I loved about the hotel – other than the fabulous location (overlooking Ego Alley, and steps away from the many shops and restaurants) – was the staff. From the bell desk to reception to the housekeeping staff that we passed in the halls throughout the days, we encountered smiles and the feel of “exactly like nothing else” in every interaction. And? On a summer weekend when there isn’t a private event, guests can enjoy a leisurely morning or afternoon on a newly renovated rooftop patio overlooking the water (including ordering from room service while you are there).

Want to immerse yourself in the Naval Academy experience? Thanks to a partnership with the US Naval Academy, hotel guests can take advantage of dinner at the Officers’ Club or take a walking tour as part of your getaway. Admittedly, I passed on the Officer’s Club dinner experience not realizing what a rare honor this would have been. Next time I won’t make the same mistake. Guests can also inquire about special dining recommendations at local hotspots with special perks just for hotel patrons.

Get comfy on a SUP

Guided SUP tour in Annapolis

Kevin – our SUP guide – as we explored Spa Creek


Capital SUP guided history tour in Annapolis


I tend to think of stand up paddleboarding as a great fitness activity as opposed to a way to experience a new destination. But with Capital SUP, you can paddle and learn on a guided history tour through Spa Creek and Ego Alley. Although we’d first hoped to participate in the night LED paddling tour (offered on Friday and Saturday nights), seeing the quieter more residential side of Annapolis – and the beautiful houses that back up to the area known as Spa Creek – offered an immersion into local waterways and ways of life. Water is king in Annapolis, and paddling around anchored yachts and locals using their dingy to run errands around town was the perfect way to start the day. With local born Kevin Haigis as our guide, we even played with a few yoga poses in the small bay in front of St. Mary’s Church. Interestingly, although I thought I had a higher statistical chance of getting wet (by falling in) while on my SUP, it wasn’t until the next day when we rented kayaks from Capital SUP that I took a swim in Spa Creek after paying too much attention to a dreamy house in the distance. Want to try SUP yoga? Capital SUP offers that too!) Not sure you are ready for SUP? Take a lesson with Capital SUP or rent a kayak for self-guided exploration.

Become part of the crew on a Schooner Woodwind cruise

Annapolis Waterfront Hotel weekend getaway

The Schooner Woodwind docks right outside the Annapolis Waterfront Hotel.


Touristy sailing cruises often leaving docks, taking guests on sightseeing journeys. And while there is nothing wrong with a leisurely a cruise, setting sail with Schooner Woodwind offers much more than just beautiful views. The two schooners – the Woodwind and Woodwind II – are family-owned and run 74-foot-vessels that sail (and race) along the Chesapeake. Captain Ken and Captain Jen are the father-daughter duo who narrate the voyage alongside their personable crews with multiple sailings a day during the summer season, answering questions and entertaining us with easy banter and conversation as we made our way toward the Chesapeake Bay bridge.


Raising the sails on the Schooner Woodwind

Go sailing on the Schooner Woodwind Annapolis

sailing on the Schooner Woodwind in annapolis

I grew up with a grandfather who built his own catamaran, so although I would not call myself a skilled sailor – I feel comfortable on the water with the wind as the motor. So I wasn’t entirely surprised when I raised my hand when a crew member asked for volunteers to help raise the main sail during our sunset cruise. Or when I volunteered to take the helm (with the captain close at hand). Not sure you want to work while you sail? No problem. Feel free to find a seat on deck, enjoy a craft beer or glass of wine and watch the sails fill with Annapolis in the distance.

Take in the water views and atmosphere at Pusser’s Caribbean Grill

Afternoon at Pusser's Caribbean Grill Annapolis

Afternoon crowd at Pusser’s Caribbean Grille.


One of my favorite parts of Annapolis is the proximity to water. So any chance to partake in waterside dining is alway a highlight. What I hadn’t realized is that while the outside deck offers water views and an afternoon and evening social scene on the outdoor patio, even the inside seating at Pusser’s Caribbean Grille offers a trip back in time with memorabilia that is reminiscent of the British Royal Navy and beautiful wooden ships. Sitting at a table on the water for afternoon drinks or dinner with a jovial atmosphere that might just make you forget the rest of your plans for the day.

Walk, shop and stroll along Main Street and Maryland Avenue

shopping in Annapolis


I know. Shopping does not fit in with the water focus. But I cannot resist window shopping (or actually shopping) along the charming streets in Annapolis. Plus, you never know what you might find, like happening upon a hat store on a Friday night and trying on hats at Hats in the Belfry just because, or taking a turn with paint and color to show your creative side with an afternoon of pottery painting at the Clay Bakers. You might even decide to treat yourself like we did to a rich scoop of ice cream (or fudge). You are worth it after all.

shopping on Maryland Avenue Annapolis

Annapolis walking sights

Annapolis sights

Paint at Clay Bakers Annapolis

Date time at Clay Bakers

Afternoon at Clay Bakers Annapolis

Feed your inner foodie at Vida Taco Bar

Lunch at VidaTaco Bar

Eat at Vida Taco Bar

Have Lunch at VidaTaco Bar

I found Vida Taco Bar on Instagram before our trip to Annapolis. The more locals we met during our weekend, the more we heard about all the reasons to eat at Vida. I can’t remember the last time I’d spent an entire weekend looking forward to tacos. But I did. And yes, they were that good. Octopus, grouper and fried avocado are just some of the examples of types of tacos. And the guacamole? Yum.

Imagine living in your dream house while walking in historic neighborhoods

kayak on Spa Creek in Annapolis

My dream house. Also the house that caused me to lose my balance and fall into the water.


We’d seen the houses along Spa Creek from our paddleboards and kayaks, so we knew that there were cute neighborhoods with dreamy houses prime for exploration. The good news was that we were right. The streets that leave the historic downtown – emptying in Action Cove and Old Womans Cove – are full of charming row homes. The bad news was that with each new street, I kept finding houses that I’d like to live in one day.

Annapolis historic neighborhoods
Annapolis neighborhodds

Get up early for breakfast at Iron Rooster

French toast at Iron Rooster

Breakfast at Iron Rooster Annapolis

Iron Rooster breakfast Annapolis

In the mood for a decadent breakfast? Get up early and make your way to the Iron Rooster for a menu that challenged my decision-making skills. There are a few tables on the top level near the windows so you can even keep an eye on boats coming into Ego Alley while you fuel up with the most important meal of the day. When I first read the breakfast menu, I’d was inspired by rich and savory plates of eggs and bacon as well as the sweeter, more carb-rich pancake or french toast. In the end, I went for a simpler (and less decadent) egg scramble but did take a few forkfuls of my husband’s french toast. (Not a morning person? You are in luck. The Iron Rooster serves breakfast all day long.)

Enjoy dinner at Vin 909 Winecafe

dinner at vin 909 Winecafe in Eastport

flatbread at vin 909 cafe in Eastport

dessert at vin 909 cafe in Eastport

Ask a local about Vin 909 in the Eastport neighborhood, and they’ll tell you first that it is delicious and second that you need to get there early. Both are true. We’d read that the restaurant was small and knew to get there early on a Friday evening – with the expectation that we’d still need to wait. And yes, we waited (with a glass of wine). But once we sat down at our table, every bite proved worthy. Looking around the dining room, it was clear by the conversations, hugs and familiarity that the majority of diners were regulars – which always makes me more intrigued about a restaurant. I found myself wishing that we’d been eating with a larger group so that everyone could have ordered different dishes (for us all to share).

48 hours in annapolis maryland

I was a guest of the Annapolis Waterfront Hotel during my stay and sailed as a guest on the Schooner Woodwind. All opinions are my own. I cannot wait to go back to try the Capital SUP Night LED tour and take our daughter for a sail aboard the Schooner Woodwind. Maybe we’ll even take sailing lessons as a family on our next trip to Annapolis!


Written by Elena Sonnino

Elena Sonnino

Chaser of Dreams. Life coach, wellness and travel writer, yogini, former teacher, adventure seeker, hiker, foodie …and oh right, cancer survivor. Elena writes about finding everyday wellness in far-flung lands and in her own backyard in the Washington D.C. suburbs.


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