Sailing into the sunset on Chesapeake Bay

Captain Your Own Voyage into the Scenic US

Sailing into the sunset on Chesapeake Bay

Traveling by yacht sounds a bit like something most of us would only see in the movies. Now the dream of cruising in your own boat (at least yours for a week or two) has become a new travel trend. I checked out Annapolis Yacht Charters which operates on the Chesapeake Bay, the largest estuary in the contiguous United States. Our launching point was Annapolis, the capital of the state of Maryland. This is a central point for exploring many of the most historic areas of the eastern US.

How it Works

Boat charters work much like renting a condo in an exotic destination. Numerous styles and sizes of yacht are available so you can reserve a boat with the amenities and number of berths that would work best for your party. If you are already a seasoned sailor, you’ll review the operation of the boat and then sail away on adventure. Travelers who are new to sailing can rent a boat and hire an experienced sailor to managing the operation of the vessel. If you’ve sailed in the past but don’t feel completely comfortable captaining a new boat in an unfamiliar area, captains can be hired for a few hours or a few days of your journey to give you time to become comfortable.

Where to Sail

The Chesapeake Bay is famous for oysters and American history. From the arrival of the first European explorers in 1524, the bay became one of the most important areas for settling North America. Because boats were the primary mode of transportation in this region for hundreds of years, most of the major historic sites are conveniently located near the water. If you’re more interested in nature, the bay’s 24,299 square miles of waterway, fed by over 150 major rivers and streams, provides endless opportunities for exploring.

Why Sail

Boats can easily traverse the region providing scenic views as you go. Avoiding the heavily travels freeways in this busy northeast portion of the US allows you to spend your vacation exploring rather than fighting bump-to-bumper traffic. Sail to a new location each day or simply pace yourself as you enjoy the peaceful life aboard a yacht. No more dragging your suitcases into a new hotel room each evening. Stay unpacked aboard and enjoy the freedom of having 24/7 access to your own kitchen, lounging areas, and private quarters.

The sheltered waters of the Chesapeake Bay are perfect for both novice and experienced sailors. Dock at the Chesapeake Bay Maritime Museum to get an overview of the bay’s history. Kid-friendly activities and the large park-like setting to help any children in your party use up any excess energy. The historic cities and towns of Baltimore, Oxford, St. Michaels, Tilghman Island, and Cambridge all provide plenty of places to explore and easy boat access.

Smooth Sailing

The process for reserving a yacht was surprisingly simple. Information on the website made it easy to find a boat that would work best for our needs. Annapolis Bay Charters provided us with some suggested sample itineraries and they were able to answer whatever questions we threw their way. They put us in touch with an experienced boat captain able and willing to skipper our adventure. We were a little surprised when we arrived at the marina to see all the amenities there. We had full use of a swimming pool, picnic areas, and grills. A breakfast and sandwich shop was on the property and a water-taxi service was available to shuttle us to visit the shops and restaurants in downtown Annapolis. It was nice to know that this slip and other amenities at the marina would be available to us throughout our rental.

Water taxi crosses Baltimore’s historic Inner Harbor

There is something very special about sailing with the smell of the water and fresh breezes. Rather than a hectic rush to drive from one scenic point to another, the freedom to sail where we pleased, when we pleased was liberating. Online services like Snag-a-Slip and websites for the various docks in the area made it easy to customize our itinerary as we sailed along. Between docking locations there was always interesting scenery to view.

When we weren’t walking around scenic towns, our workout was waving to the other boats we passed along the way. It was like a road trip but without being stuck in one position all day. Being able to move around at our leisure while watching the scenery made the trip considerably more interesting and relaxing. We all took turns pitching in to help crew the boat. This gave us more interaction with each other and an opportunity to acquire sailing skills.

If you are interested in finding out more about how to channel your inner pirate, you’ll have plenty of help planning your boating adventure.

Andy Higgs
Andy Higgs

I know what it's like to go from being a crazy backpacker without a care in the world, via being a vaguely sensible parent to being an adventurer once more. In other words, evolving into a Grown-up Traveller.

Like everyone else, I love to travel, have visited a lot of countries and all that but my big thing is Africa.

I also own and run The Grown-up Travel Company as a travel designer creating personalised African itineraries for experienced adventurers

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