What happens when vacations aren’t easy?

A good vacation can take a lot of planning; a lot of comparing, a lot of decisions, and a lot of traveling, even after you’ve “arrived.”

If you’re a charts and lists king of person, this might be as much fun as your “vacation.” For the rest of us, there’s windjamming. You book, you board and off you go. Everything is taken care of.

On a typical vacation, you’ll spend a lot of time figuring out where to eat. And it needs to be close to whatever you’ve planned to do for the day. That means you’ll be doing a lot of driving. But you already did a lot driving to get to Maine, now you’ve got to drive more, every day? How about not?

That doesn’t sound easy. It doesn’t sound fun. And it doesn’t sound much like much of a vacation. Our trips put more vacation in your vacation. More There and Less There Yet?

Here are a few other typical vacation problems we solve easily on our trips along the coast of Maine.

Activities?

Taken care of. We visit island villages, national parks, nature preserves and completely uninhabited islands. Everywhere we go is special, because most people can’t get to where we go.

We are a small group. We are always warmly welcomed wherever we go. Our schooner adds to the scenery and cherished simplicity of Maine. Arriving aboard an active, antique schooner (over 150 years old!) is a scene in itself. We do not crowd up places when we visit. We go ashore with our 21 ft yawl boat.

We do not fill the docks with shuttles like locally controversial big, cruise ships. We do not change the character of where visit by flooding the charm and solace of a place with a packing crowd.

More strategically, we can sail into harbors and islands where large vessels cannot go. Many spots are only accessible by boats like ours. Maine is great. Maine by sail is special. You will enjoy places that few others even know about or can get to.

MidCoast Maine has so many islands. Even though the wind sets our path, we know we’ll always find wonderful places to explore and experience.

How do you figure out where to eat?

We bring our favorite restaurant with us. And you’ll always have a seat with a great view. Have you ever waited to get into a chosen restaurant only to end up seated away from a great view? That’ll never happen on schooner Stephen Taber.

Aboard Taber, the food is part of the scenery.

Whatever it is, the way you tell your story online can make all the difference.

And the food?! Everything is freshly made, everything is cooked with a wood-fired stove. Just like you’d hope it would be on a schooner from the Golden Age of Sail. Also, we are lauded for our wine and cheese indulgences. Jane worked in the wine industry for twenty years and eagerly shares her discoveries and favorites. Meanwhile Noah, answers the call of Cheese in pairing with Jane’s sharings. It’s an endearing dovetail of their marriage.

When it’s not easy, it’s not fun.

Windjamming is both easy and fun. It’s as easy as stepping aboard and it’s as fun as being an explorer.

There are plenty of good Maine, summer vacations. Maine is called “Vacationland” for a reason. With that moniker, comes an obvious problem. Maine can get crowded in the Summer.

You know where it’s never crowded? On the water.

Many of the scenes you’ll see, you can’t see from land.

The more boats the better. It’s a lovely scene to see other fleet members dancing the wind with us and weaving the island archipelago of our bay area. You’d think it was a rule to wave to all other passing vessels. It’s not, but nobody can help themselves. Happiness is best when shared.

You know where else it’s never crowded? Our boutique vintage 1871 schooner that only carries 22 guests on each trip. This is where you’ll really begin to feel the difference that our Maine sailing vacations offer. That a Taber trip is known for.

A windjamming trip along Maine’s MidCoast is one of the few that actually feels different. Which is funny really, because a Maine windjamming trip aboard Stephen Taber has so much in common with other vacations - Yet it is still so, so different.

We are a ship that cruises, but we are not a “cruise ship.”

If you’re looking to float around on an office building / amusement park with thousands (and thousands) of your new, closest friends, then this is not the trip for you. The personal scale of a windjamming vacation enables and enhances so much of what we can do. Because we’re small - relatively.

It’s worth understanding what makes our area special. MidCoast Maine—think Camden, Rockland, and Penobscot Bay—is the only place in the United States where traditional multi-day windjamming vacations still operate as an authentic travel experience. These aren’t cheesy replicas or tourist gimmicks. They’re working schooners—many over a century old—sailing a coastline that hasn’t been overbuilt or commercialized.

That alone puts it in a different category than your typical summer trip. As for all this talk about sailing. You won’t get seasick. We do not sail in the open ocean where the seas can be full of waves. We sail what are called “protected waters.” Along the many islands along the coast. They block the waves and keep things calm.

You’re not just visiting—you’re participating

Most vacations are passive: you check in, sit down, get served. On a windjammer, you’re part of the rhythm of the boat.

Help hoist the sails, or - just take a picture.

You can help raise sails, learn basic navigation, or just watch the crew work with cheery precision. The experience has a tactile, almost meditative quality that can’t be replicated at a resort or on a cruise ship.

No crowds, no noise, no artificial pace

Compare it to a Caribbean cruise or a packed national park in July. Windjammers carry a small number of passengers—often 20 to 30—and once you leave harbor, there’s no traffic, no lines, no background music. Just wind, water, and the creak of rigging.

Even the “destinations” are understated: hidden coves, spruce-lined islands, quiet anchorages. You’re not checking off landmarks—you’re inhabiting a landscape. You’re travelling the roads less taken.

The coastline is built for this kind of travel

The geography of Penobscot Bay—hundreds of islands, shifting light, protected waters—creates constantly changing scenery without long, monotonous stretches. You might wake up to fog rolling through the islands and end the day anchored off a sunlit granite shoreline.

It’s dynamic in a quiet way, which is uncommon.

Food that matches the place

Windjammer meals are deeply tied to the fresh and local options of Maine itself: fresh lobster bakes on a beach, homemade meals, and hearty, impressive cooking. It’s memorable and delicious in a way that buffet lines and overpriced resort menus are not.

It’s one of the last “analog” adventures

There’s a reason people come back from these trips talking about how it felt, not just what they saw. A windjamming vacation isn’t optimized for efficiency or entertainment—it’s built around wind, weather, time and nature. That unpredictability is part of the appeal. You read more, sleep better, and actually notice your surroundings. The days stretch out in a way that feels almost pre-digital. The days tingle like your days of summer camp and adventures with friends.

How it compares to other summer vacations

Versus a beach resort:
Resorts are easy, but interchangeable. A windjammer trip is immersive and specific to MidCoast Maine —you couldn’t drop it into another coastline and get the same experience.
Versus a cruise:
Cruises are about scale and amenities. Windjamming is about intimacy and authenticity. One gives you manufactured options; the other gives you the best of Maine, authentically and intimately.
Versus a road trip:
Road trips still keep you busy and controlling —planning, navigating, deciding. On our schooner, you surrender that control, which is exactly what many people don’t realize they need. People want to be taken care of, taken care of by people that care in a place that’s cared for.
Versus a national park:
Parks are spectacular but often crowded in summer. Windjamming offers a similar connection to nature without the congestion.

The bottom line

A windjamming vacation in MidCoast Maine isn’t better because it’s more luxurious or more convenient—it’s better because it’s rare. It offers a kind of travel that hasn’t been overproduced or diluted.

If you want a trip that feels like a real break from typical vacations —not just a change of scenery—this is one of the few options in the U.S. that genuinely delivers that. Our trips aren’t just a prettier version of something you’ve already done, they’re a way of taking what you think you know about vacationing and making it authentically emotional and freshly unforgettable.

Why should your Maine vacation be a Stephen Taber vacation?