Let’s face it, we all get the call to go down to the sea at some point in our life. For some, like myself, it happens daily. For others, only every couple of years. No matter what though, if you’re hearing the call, it’s time to answer. One of my all-time favorite nautical cities is Boston. A town so rich in maritime history that you feel the urge to speak like a pirate the whole time. While attending the Sea Education Association in Woods Hole, Massachusetts. my cohorts and I took every opportunity to go to Boston and enjoy the bounty of one of America’s oldest ports.

In my opinion, one of the coolest hotels in Boston is The Liberty. It’s a former jail house and the bar still has the iron doors on each cell. The food, too, is worthy of a last meal. Don’t fret though, you won’t feel trapped, just incarcerated by fun. The atrium alone is worth the visit. It is the old center for the prison and all of the rooms still face out like the cells once did. Even better, it’s pet-friendly.

A major draw of Boston that often goes unspoken is its allures as a town for sailors. A licensed captain myself, some of the best sailing courses I’ve taken have been in the Boston area. It affords you the opportunity to learn to sail and to literally drink in some history. I personally got to sail on board the Spirit of Massachusetts (well I mostly scraped paint and sea-life off the hull, but we sailed too). The Spirit of Massachusetts is a beautiful tall ship modeled after an 1889 schooner named Fredonia. Today she is an ocean classroom for hopeful sailors to be. If you want something a little more leisurely to get your sea legs and see if you have a taste for the seafaring life, why not try a day sail? The Liberty Fleet offers tall ship tours of the harbor or you can take a tour of the USS Constitution, America’s most famous tall ship. The museum is more than worth it. Essentially being a full-grown child, I was never bored for a second, as we toured the hands on museum.

Viewfinder Tip: Try a celestial navigation class, it’s a great way to learn about stars and to use a sextant.

At this point you’re either fired up for more or you’re green around the gills. For the lubbers in the group, hoist the white flag and head over to the Green Dragon Tavern or Jo’s Nautical Bar. I don’t even know how you choose between these two bars. In fact, I don’t think I ever have. The Green Dragon is one of the Boston taverns that claims to be the oldest in the nation. While there is some discrepancy on the truth of that claim, it is undeniable that a great number of the founding fathers not only drank there, but also hatched plots against the British there. Jo’s is an unassuming local joint in the basement of an unassuming building on the harbor. Not only does it have great beer and free Wi-Fi, but it has one of the few entrances to the historic tunnels under the Boston Harbor. You’ll have to contact them, because on occasion they open it up and host tours.

Whether you came for the sailing or just to look (and drink) like a sailor, you’ll be pleased with all Boston has to offer.

What would you rather do in Boston: sail or bar hop?