Two weeks in Annapolis almost felt like a vacation, with easy access to groceries, restaurants and civilization in general. Some people have referred to our adventures as vacation, but I assure you, it is not – it is a lifestyle. Some choose to live in a cottage on a lake, some a condo in Florida, and we choose to drop an anchor almost every night in a new location and keep exploring this beautiful world. However, it is not lost on me that we are blessed to be able to live this life.
Annapolis was also an education, and we learned some disturbing information from other Canadian boaters. Remember a few months ago I was impressed with how easy it was to check-in with US Customs when we entered Maine? Well, we just learned we made a huge mistake with no easy fix.

The CBP (Customs & Board Patrol) website provides a lot of information and boasts how it strives to make things easy for foreign vessels from certain countries (Canada is on the list) to cruise in US waters. The information provided is heavy on content, but is not well organized and can be easily misinterpreted. This is what we knew:
• A cruising decal must be purchased in advance for any boat over 35 feet
• CBP’s ROAM app should be used to check-in when crossing the border. If CBP determines you need a personal visit, they will notify you via the app.
• When you are cleared for entry into the United States, the App will send you a clearance number and you receive a “welcome to the USA” email.

We completed all the above, to the letter and received welcome notices by both App and email and assumed we were good to proceed. We were wrong. In Annapolis we learned this process applies only to people, not vessels, so Allen and I (and Cat Stevens) were cleared to enter the USA, but Meshuggana was not. Meshuggana requires her own “cruising permit” that must be obtained at the first point of entry in the US, and we were many, many ports beyond our initial entry point in Maine.
The risk of continuing our journey without the permit was great. If we were pulled over by the Coast Guard, we’d face huge fines up to confiscation of the boat. We needed to get compliant so we did the only thing we could do – go to the nearest CBP office in person and explain what has happened. We made our way back to the nearest office in Baltimore, received a humiliating berating by an officer with zero empathy, but finally emerged with a way to legally keep Meshuggana in the US. We now must go into a CPB office in each state, fill-out forms and pay $38 in fees. This process has been complicated (CBP offices are not easily accessible and require busses, taxis and trains) and frustrating, but at least we can rest assured that we are now compliant (until the next state) and we will not make this mistake again when returning from the Bahamas.



Now that we were “legal”, we set out to enjoy more of the spectacular Chesapeake region. Chesapeake Bay is huge, but shallow so strong winds can whip-up hazardous conditions in an instant; however, Mother Nature was smiling on us and gave us calm seas and fair winds. We visited several charming towns in Maryland (St. Michaels, Oxford, Solomons Island) and Virginia (Mill Creek, Yorktown and Hampton). These are beautiful, affluent towns, busy with tourists with souvenir shops, restaurants and spectacular Victorian homes.


While these charming towns have begun to blend together for me, one of our stops stands out due to its unique location and stark contrast to other Chesapeake towns: Tangier Island.



Tangier Island lies on the eastern side of Chesapeake Bay and is just a tiny spit of land that is slowly disappearing into the rising ocean. The town has about 400 permanent residents, a post office, a health station, an airstrip, a church, a general store, one working restaurant, but it looks like there may be one or two more that may be open during the peak summer season. As far as we could tell, they only access to the island is plane or personal boat as we did not see any indication of ferry service. The homes ranged from well-maintained cottages to decaying, abandoned houses. Fishing is the main and likely only industry, with dozens of fishing boats buzzing around a channel with docks in varying states of decay.



Tangier has an interesting history going back to a visit by Captain John Smith in 1606, then settled in 1686. In 1814 Tangier served as the headquarters for the British fleet as it attacked settlements on the Chesapeake. Many of the inhabitants are descendants of these early settlers and at times it felt like this was a place that time forgot. Despite several scientific reports showing that due to climate change and rising ocean levels, the island will disappear in the next 50 years, Tangier islanders prefer to believe Donald Trump’s prediction that the island will be around for hundreds more years (87% of its population voted for him). I likely won’t be around to see what happens, but the town’s streets already flood every day at high tide, so I’m betting on science.



We finished our Chesapeake adventures at anchor in Hampton, Virginia, awaiting our entrance to Norfolk and the beginning of the ICW, or Intercoastal Waterway – aka the Highway to Florida. We were one of hundreds of boats of all types and sizes waiting for the right weather window and the calendar to turn – many insurance companies do not provide hurricane coverage south of Norfolk before November 1. It really hit us then that we were part of huge pack of adventurers heading south and it was a little intimidating (will there be enough room in marinas and anchorages….enough space in the canals?) and a little exciting as we began to meet others on the same journey. Part 2 was about to begin.
But first, we had to check-in with the next CBP office – ughh!

These border officers are on such a power trip! Good luck on the rest of the journey 🙂
Glad you got it all sorted out, even if it is pain now to physically check in.
Lots of fun adventures ahead on the ICW!
We got lucky last week! Details in this week’s blog
Pictures are beautiful. Such history in these costal towns . I hope you don’t have any more difficulties with your access to states. I guess you would have to go out to international water to avoid this..which is not an option.
Oh well only 3 more states to go.
Just sitting here looking at the sideways rain and the howling wind as this storm passes through. We were lucky again and are basically on the fringe of the storm. Glad that we were not in the direct path. You guys take care as Nicole heads your way today.
Hugs
We’re glad you came through Ian and Nicole without damage – the steep price to pay for living in paradise. Hoping we may see you when we get to the “sunshine state”
Looking forward to it