Schooner Woodwind Sailing Cruises

Description

Picture this: You’re lounging on the deck of a beautiful 74-foot wooden schooner, the wind in your hair and the sparkling waters of the Chesapeake Bay stretching out before you. That’s exactly what you’ll experience aboard the Schooner Woodwind Sailing Cruises in Annapolis, Maryland. It’s not just a boat ride; it’s a full-on sailing adventure that’ll have you feeling like a seasoned sailor in no time.

Now, I’ve been on my fair share of boat tours, but let me tell you, this one’s something special. They’ve got two of these magnificent vessels, Woodwind and Woodwind II, and they’re not your average tourist trap boats. These are honest-to-goodness sailing schooners, the kind you’d imagine in a swashbuckling pirate movie (minus the plank-walking, of course).

You can hop aboard up to four times a day for their public sailing cruises. And let me tell you, there’s nothing quite like watching the Annapolis skyline fade into the distance as you set sail. It’s the perfect escape from the hustle and bustle of everyday life. You just sit back, relax, and let the crew do all the hard work. Speaking of which, the crew is top-notch – friendly, knowledgeable, and always ready with a fun fact or two about the bay and its history.

Now, let’s talk about the good stuff – the drinks! They’ve got a bar on board (because what’s a cruise without a little libation, right?), and it’s not your run-of-the-mill selection either. They’ve gone all out with a fantastic array of independent, craft brews from the local area. It’s like a floating beer festival! And if you’re not in the mood for alcohol, no worries. Every public cruise comes with a complimentary soft drink or water. Hydration is important, folks!

But wait, there’s more! If you’re feeling fancy and want the whole boat to yourself (and who wouldn’t?), they offer private events too. I’m talking corporate cruises, team building events, birthdays, reunions – you name it, they can probably do it. They even have catering options, so you can munch on some delicious grub while you sail. It’s like having your cake and eating it too, except you’re on a boat. And trust me, everything tastes better on a boat.

For the education enthusiasts out there (I see you, lifelong learners), they also offer student, scout, and group sails. These are more interactive and educational, perfect for those who want to learn a thing or two about sailing, the Chesapeake Bay, or just marine life in general. It’s like school, but way cooler because you’re on a boat.

One thing I really appreciate about Schooner Woodwind is their attention to detail. The boats are beautifully maintained, clean, and just oozing with that classic sailing charm. It’s clear they take pride in their vessels and the experience they provide.

Now, I’ll be honest, sailing isn’t always smooth… literally. If you’re prone to seasickness, you might want to come prepared. But don’t let that deter you! The gentle rocking of the boat is part of the charm, and for most people, it’s more relaxing than anything else.

All in all, Schooner Woodwind Sailing Cruises offers a unique way to experience Annapolis and the Chesapeake Bay. Whether you’re a sailing enthusiast, a casual tourist, or just someone looking for a fun day out, there’s something here for everyone. It’s the kind of experience that leaves you with a smile on your face and a story to tell. So why not give it a go? The bay is calling, and Schooner Woodwind is ready to answer!

Key Features

• Two 74-foot wooden schooners, Woodwind and Woodwind II, offering an authentic sailing experience
• Up to four daily public sailing cruises on the Chesapeake Bay
• On-board bar featuring a selection of local, independent craft brews
• Complimentary soft drink or water included with every public cruise
• Private event options available for corporate events, team building, birthdays, and reunions
• Catering services offered for private events
• Educational and interactive cruises for students, scouts, and groups
• Knowledgeable and friendly crew providing insights about the bay and sailing
• Stunning views of the Annapolis skyline and Chesapeake Bay
• Well-maintained, clean vessels with classic sailing charm
• Relaxing atmosphere perfect for unwinding and enjoying nature
• Opportunity to assist the crew and learn about sailing (if desired)
• Chance to spot local wildlife like ospreys, herons, and sometimes even dolphins
• Sunset cruises offering breathtaking views of the bay at dusk
• Themed cruises occasionally offered, such as beer tasting or music sails
• Convenient downtown Annapolis location for easy access
• Suitable for all ages, making it a great family activity
• Small group sizes ensuring a more personalized experience
• Option to purchase souvenir photos of your sailing adventure

Best Time to Visit

Alright, folks, let’s talk timing. When’s the best time to hop aboard one of these beautiful schooners? Well, like most things in life, it depends on what you’re after.

If you’re a sun-worshipper like me, you’ll want to aim for the summer months. From June to August, Annapolis is in its full glory. The weather’s warm, the days are long, and the bay is bustling with activity. It’s perfect for those who want to soak up some rays while they sail. Just remember to slather on that sunscreen – trust me, a lobster-red look is not the souvenir you want to bring home!

But here’s a little insider tip: May and September can be absolute gems. The weather’s still lovely, but you’ll dodge the peak tourist crowds. Plus, there’s something magical about sailing in May when the spring flowers are in full bloom along the shoreline. And September? Well, that’s when you might catch a glimpse of the stunning fall colors starting to appear.

Now, if you’re more of a “sweatshirt and hot cocoa” kind of sailor (no judgment here), you might want to consider an early fall cruise. October can be spectacular, with crisp air and stunning foliage. Just be prepared for a bit of a chill – it’s nothing a warm jacket can’t handle, though.

For the true adventurers out there, Schooner Woodwind does operate in April and early November too. It can be a bit nippy, but there’s something exhilarating about sailing in the cooler months. Plus, you’ll have bragging rights about being a hardy sailor!

One thing to keep in mind: summer weekends can get pretty busy. If you’re not a fan of crowds, consider a weekday sail. It’s usually a bit quieter, and you might even score a better deal.

Oh, and let’s not forget about those sunset cruises! They’re available throughout the sailing season, and let me tell you, there’s nothing quite like watching the sun dip below the horizon from the deck of a schooner. It’s the kind of moment that makes you forget all about your overflowing inbox and unanswered texts.

Ultimately, the best time to visit is whenever you can make it happen. Each season has its own charm, and the Chesapeake Bay is beautiful year-round. Just remember to check the weather forecast before you go. Mother Nature can be a fickle friend, especially on the water!

How to Get There

Alright, adventurers, let’s talk about how to get your sea legs over to the Schooner Woodwind. Trust me, it’s easier than finding buried treasure!

First things first, you’ll want to make your way to downtown Annapolis. It’s a charming little city, and half the fun is just wandering around before your sail. The schooners dock right in the heart of the action, so you won’t have to trek far once you’re in town.

If you’re driving in (which is probably the easiest option for most folks), you’ll find plenty of parking garages scattered around downtown. Just follow the signs – they’re usually pretty good about pointing you in the right direction. Word to the wise: bring some quarters for the meters if you’re planning on street parking. Nothing ruins a post-sail buzz quite like a parking ticket!

For those of you embracing the public transport life, you’ve got options too. There are buses that run into Annapolis from nearby cities like Baltimore and Washington D.C. It might take a bit longer, but hey, it’s all part of the adventure, right?

Now, if you’re feeling fancy (or just hate traffic), you could always fly into Baltimore/Washington International Airport or Reagan National Airport. From there, you can rent a car or catch a shuttle to Annapolis. It’s about a 30-minute drive from BWI or an hour from Reagan, depending on traffic. And let’s be real, there’s always traffic.

Once you’re in downtown Annapolis, finding the schooners is a breeze. They’re docked at the Annapolis Waterfront Hotel, right on Compromise Street. You can’t miss ’em – just look for the tall masts and the crowd of excited sailors-to-be.

If you’re like me and have a terrible sense of direction, don’t worry. The friendly locals are usually more than happy to point you in the right direction. Just ask for the “big sailboats” and they’ll know what you mean.

Oh, and here’s a pro tip: if you’re planning on enjoying some of those local craft brews on board (and why wouldn’t you?), consider using a ride-share service to get back to your lodging after the sail. Safety first, folks!

Remember, half the fun of a sailing adventure is getting there. So take your time, enjoy the journey, and maybe even stop for some of Annapolis’s famous crab cakes on your way. After all, you’ll need to fuel up for all that relaxing you’ll be doing on board!

Tips for Visiting

Alright, sailors-in-training, listen up! I’ve got some nuggets of wisdom to share that’ll help you make the most of your Schooner Woodwind adventure. Trust me, I’ve learned some of these the hard way!

First things first: dress for success. And by success, I mean comfort. You’re going to be on a boat, folks, not a fashion runway. Wear shoes with non-slip soles – the deck can get a bit slippery, and nobody wants to do the “deck slide” (although it can be pretty entertaining for the other passengers). Layers are your friend, especially for those evening sails. The temperature can drop faster than a seagull diving for a fish, so bring a light jacket or sweater.

Speaking of seagulls, let’s talk about sun protection. The sun reflects off the water like a giant mirror, so even on cloudy days, you can get more rays than you bargained for. Slather on that sunscreen, pop on a hat, and bring some shades. Trust me, lobster-red is not a good look on anyone.

Now, let’s address the elephant in the room – or should I say, the swell in the bay. If you’re prone to motion sickness, come prepared. Take your preferred motion sickness remedy before you board. There’s nothing worse than feeling green around the gills when you’re trying to enjoy those stunning bay views.

On the subject of green, bring some green – as in cash. While they do accept cards, it’s always good to have some cash on hand for tipping the crew (if you’re so inclined) or buying extra drinks. They work hard to make your experience amazing, so a little appreciation goes a long way.

Shutterbugs, rejoice! The photo ops on this trip are insane. Bring your camera or make sure your phone is charged. Just remember to live in the moment too – sometimes the best memories are the ones we don’t capture on film.

If you’re a planner (hello, kindred spirit!), consider booking in advance, especially for weekend sails or sunset cruises. These can fill up faster than a lifeboat on the Titanic. But if you’re more of a spontaneous soul, don’t worry – they often have space for walk-ups too.

For my fellow foodies out there, while they do offer some snacks on board, you might want to grab a bite before you sail. All that fresh air can work up an appetite! And hydrate, people. The complimentary water is there for a reason.

Now, here’s a fun tip: if you’re interested, ask the crew if you can help out with the sailing. They’re usually more than happy to show you the ropes (literally). It’s a great way to learn something new and feel like a real sailor.

Lastly, and most importantly: relax! This isn’t a cruise ship with a rigid schedule and endless activities. The beauty of Schooner Woodwind is in its simplicity. Take a deep breath, feel the wind in your hair, and let

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