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One Month Living in Annapolis: How It’s Going

view of main street Annapolis with no cars on it and people walking and scootering down the street. Flags hang on the posts on each side of the street which is lined with businesses. a church steeple pokes up at the end of the street. the sky is blue with some clouds.

We’ve been in Annapolis for a month now and are enjoying the slower pace of movement (aka not going anywhere). Getting north quickly allowed us to stop for an extended period in Maryland to repair the watermaker and water heater, among other boat projects.

I’m sure you’re thinking, “What? The Bahamas was such a fast-paced, hectic life?” Heh. While that may seem like the implication, the truth is slightly different.

Cruising within a timeframe creates an urgency to see and experience as much as possible. What timeframe were we working in? The first was the 90-day cruising permit limit, which is extendable. The other driving factor in our timeline was hurricane season. We needed to get out of the insurance-defined-risk area by June 15, which meant going either north of latitude 36ยบN or south to Grenada or Trinidad, where hurricanes are less likely.ย 

Note that Hurricane Beryl just demonstrated the risk of spending hurricane season in Grenada. Consider donating to help Grenada rebuild.

Working Our Way North

We had to get north to get to this much-needed, extended stopping period. In mid-May, after a beautiful two-day passage from West End in the western Bahamas, we landed back in the US via Brunswick, GA. We worked our way up the ICW until a weather window opened for more coastal sailing out of Savannah, GA. By Memorial Day, we arrived in Beaufort, NC, and only a week later, we were back in the Chesapeake Bay.

In three weeks, we completed our northbound passage to Deale, MD, where we started in November 2023. For reference, the southbound journey from Deale to the Bahamas took three months. We were very pleased with our progression from overly cautious cruisers to slightly more confident cruisers.

We made the short hop from Deale to Annapolis, where Loka now sits in a comfortable slip in the Eastport neighborhood we love. We have been relishing the break from constant moving.

Northbound Stops

Lack of Timeline

And now we’re back to living outside of a timeline. Sure, there is the November 1 date when we can move south of 36ยบN again (an insurance-driven date). Though the 100ยบF heat index doesn’t indicate it, winter will be here before we know it, and we’ll want to head south to a warmer climate.

This summer, we plan to head north to New England, with eyes on Block Island and Martha’s Vineyard. We write those plans in the sand at low tide, which means our plans will change. So, we avoid getting attached to any of them. Detaching from solid plans is a considerable deviation from how we lived our career-focused, land-based life. This detachment is a challenge with the reward of exploring things we couldn’t imagine possible.

For example, if we had stuck to a rigid plan of getting boat projects and the boat cruising north to New England by the end of June, we would’ve missed out on spending the 4th of July with our family. Did we miss out on cruising some enjoyable places? Maybe. But what a treasured time we had with our family in the historic city of Annapolis.

boy standing in the middle of brick-laid street holding an orange beach ball. kids and adults sit and stand on the curb across the street, waiting on a parade. in the background, an ice cream store has people standing in line.
The older nephew got one of the beach balls that a vendor was handing out to kids before the parade.

4th of July in Annapolis

In the summer of 2023, we had just moved onto the boat in Deale, MD, only a 30-minute drive from Annapolis. We spent the holiday at the boat, too exhausted from the Great Downsizing of 2023, to drive anywhere or coordinate with anyone to hang out. It was a very low-key holiday last year. We’ve come a long way in that timeframe, sailing over 3000 nautical miles to the Bahamas and back.

My brother, sister-in-law, and their two boys (4 and 6) live only a 90-minute drive from Annapolis. We decided to spend the holiday together, so they booked a hotel and drove to Annapolis to enjoy all the festivities with us.

Together, we enjoyed breakfast at Miss Shirley’s Cafe and took a boat tour ride around Spa Creek. The Watermark Spa Creek cruise was a pleasant 45-minute boat ride in the sedate waters of Spa Creek. We ogled the fancy houses (including Cal Ripkin’s old place), marveled at the different boats, and learned a bit of history about the creek.

We expected Annapolis, the capital of Maryland, to put on a good show for Independence Day. They scheduled activities that promised to deliver.

a smiling family sits together on a boat with power boats in the background. there are 2 adult men and 2 adult women who have kids on their laps.
Spa Creek boat tour was a fun way to get out on the water with the family!

The Parade

The city closed several streets for the parade, which started around 6 p.m., followed by a large fireworks display shot from a barge in the harbor.

We could have had too high expectations for the parade, but it was slightly less than we had thought. It started strong, led by the Naval Academy’s marching band, and shortly after, there was a cool, historic, Revolutionary War-style band. The most surprising part of the parade was the large number (5-6 large groups) of political and religious organizations publicizing their message.

I’m all for free speech, so it wasn’t that they were political or religious. My main complaint is that they didn’t have a float (no creativity) or do much to make it fun for the kids (my 6- and 4-year-old nephews don’t care about a political sticker). In most cases, it was a group of people walking, holding signs, maybe chanting or singing. In those moments, it looked more like a march than a parade.ย 

Not to mention, if you disagree with the message of the politician or religious group, it’s hard to be excited about being at a parade. Parades are for kids. They don’t feel kid-like when we introduce adult themes without any playfulness.

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What was good about the parade? In addition to the marching bands, I loved its multicultural aspect. Apart from the political groups, there were lots of different cultures represented, including Native American, Mexican, and several others I couldn’t identify (due to my lack of knowledge). I felt particularly proud to be an American who can celebrate all the different types of people that make up this incredible, if flawed, country (yes, even the politicians and religious groups).

Was the parade perfect? No. Did we have fun? Yes. Hanging out in Main Street Annapolis while closed to traffic was a unique experience. My nephews got plenty of candy, and we spent quality time together.

The Fireworks ๐ŸŽ†

After dinner at O’Brien’s, we gathered with the masses in the streets to watch the fireworks. The boys were nearly done, but they hung in there. We got a spot near City Dock, which ended up farther from the display than we thought. The fireworks were good but less interesting than it would’ve been if we had been on the boat. We’re spoiled from years of lake living and watching big fireworks displays from the water. Next year, if we’re in Annapolis, we’ll watch the fireworks from the harbor.

We all went home tired from a full day of celebration activities. Thus, we did little besides lounging with the family the next day. The boys had never been on a boat like ours, so we showed them around and let them explore all the hidey holes (aka all the cabinets and access hatches they could open). We took the opportunity to start teaching them safety and boat etiquette. We had a blast.

boy sitting inside a boat on a blue settee holding a conch horn to his mouth.
The oldest nephew learns to blow the conch horn

What's Next For Us?

As I mentioned before, our plans for this summer originally included cruising up north to Long Island Sound, Block Island, and Martha’s Vineyard with an eye toward Maine. However, the boat projects in Annapolis are taking longer than we originally thought (it’s why we stay flexible), and Maine looks unlikely. And we’re looking at alternatives to following the cruising crowds. We will share more later once we have a better idea of the boat project timelines and our plans.

For now, we’re enjoying “being stuck” (aka living) in Annapolis and getting a taste of what life would be like if we lived here long. As a huge boating town, Annapolis is on our list of cities where we might settle when we’re ready to move back to land life. We’re soaking in all its aspects, positive and negative.

2 thoughts on “One Month Living in Annapolis: How It’s Going”

  1. Love reading your update! So glad you are getting some family time in Annapolis ๐Ÿ’› And wow yโ€™all have accomplished a lot of incredible sailing in year one! You will be getting a swallow tattoo before you know it!

  2. This is such a lovely post; Family time is wonderful, and you all certainly looked happy! I love when you post. XOX

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