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Prepare for your trip by reviewing our checklist of helpful information


Frequently Asked Questions

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Trip Planning
Plugged In

Staying Plugged In

  • Can I power my CPAP machine?

Yes, we can accommodate your machine. Even if you sleep on deck. 

  • Will my phone work?

Generally, yes. Note though that there may be areas with weak or no signal. We are always within sight of land, and so generally have signal, but depending on your carrier, there may be dead areas.  Sometimes we anchor in very secluded coves. Secluded even from cell phone signals. Have your phone ready for pictures though, they're beautiful. ​

  • Can I charge my phone on the boat?

Yes! Each cabin will have USB-A ports to charge your devices. USB-A are the ones with the rectangular plug, not the smaller USB-C plugs that most European phones and newer iPhones have. 


Note that the cabins DO NOT have AC plugs. So, you will not be able to plug in a hair dryer, waffle iron or karaoke machine. You'll have to sing a cappella and - who brings a waffle iron anyway? 

  • What is the Cancellation Policy?

We are a small business and each cancellation means a great deal to us. To offset any potential loss for either party, we sincerely recommend travel insurance. Allianz Travel Service was ranked best by Forbes, but feel completely free to explore your own options to be fully at ease with your choice. 


Once a deposit is made, the balance is due six weeks before sailing. You may cancel your trip up until 6 weeks before your boarding date and receive a refund, minus a handling fee that is 10% of the full cost. If you choose to cancel your trip within six weeks of the boarding date for any reason, we will issue a refund, minus a handling fee that is 10% of the full cost - only if we are able to rebook the berths.

Trip Planning

  • Is it a problem that I have dietary restrictions or allergies?

It is not a problem at all. Our chef is happy to accommodate any food allergies or dietary restrictions. Just make sure to let us know when you're booking. ​

  • ​Are children allowed?

Our age limit recommendation is generally 12 and up, but there may be some younger children who are specially suited for the trip. Just remember, this is an adult experience so we will ultimately leave this decision up to the parents to determine whether or not their own child will enjoy it. 

  • ​Do we know where we are going ahead of time?

No. One of the most unique parts of our trips is that we do not know where we are going before we depart Rockland, or from day to day! The coastal winds of Maine can change every day. The tides are different for each departure. We play the hand we're dealt to best win the day. Some trips have set stops included but, even then, we strive for variety to and from those places. Every trip is different, even if we've done it before. 

  • ​Can I charter the whole boat?

Yes, we arrange private charters that can be tailored directly to your needs. It is a wonderful way to enjoy special occasions with family, friends or colleagues.  We arrange memorable, tailored excursions. Click here to go to the Private Charter page. 

  • What is your COVID Policy?

We require proof of vaccination or a negative test 72 hours before departure. 


  • I'm excited for my trip! How do I get there to Rockland, Maine?

By Car:

If you put Captain Spear Drive, Rockland, Maine into your GPS, it'll bring you to the Windjammer Wharf sign shown below. At that sign, the road directly to the right of it, is Captain Spear Drive. Drive down that and park on your right. GRACE BAILEY will be the schooner all the way to the right. 


Upon arrival, park where you can on Captain Spear Drive. Once we have your luggage onboard, we will lead you to our private parking ($25 cash fee ) where your car will be safe for the duration of your cruise. 

By Bus:

The best, and most pleasant, bus company to travel with, from Portland or Boston, is

Concord Coach Lines 1-800)-639-3317.

  • In Boston you can get the bus straight from Logan airport or from South Station.

  • In Portland you can catch the bus at the Portland Transportation Center

100 Thompson Point,

Portland ME, 04102


By Air

Local Airport:

  • Owls Head ~ 10 mins away

Cape Air  (1-800- 227-3247) offers direct flights between Boston and the Knox County Regional Airport (207-594-4131)

Local Taxi:

If you need a taxi from the local airport, make a reservation for a taxi the day before you travel! They can get busy in the summer and not be quickly available for pickups.

They'll take you right to the Windjammer Wharf, where the schooner is docked, or to your local accommodations before you board. You can also get a rental car when you land. 

Regional / International Airport:

These international terminals allow you to be a quick rental ride away, from Europe or the lower 48 states. That said, the nearest large-scale airport, with more frequent int'l landings is

Regional Shuttle - From Portland or Bangor:

Sterling Elite (Midcoast Shuttle) (207) 785-3100

Contact them for pricing. They highly recommend that you make reservations in advance during the busy summer months. 

Life Aboard

  • What is "windjamming?"  

Windjamming is a way of staying connected to the spirit, ships and methods that helped build so much of this country. It began in 1936, in Maine, with Frank Swift of Bucksport. The sailing industry was waning, but the ships were still strong. Frank thought to repurpose them for passengers and pleasure trips. It's still a great idea today. Ol' Frank was pretty Swift. Read More

  • Where do we sail?

We sail the waters of Midcoast Maine. Now, where exactly is that? Here's a fun map to give you an idea. 

  • Will I get seasick?

It is doubtful, but everyone has different levels of sensitivity. The sheltered coastal waters we sail are much shallower than the open ocean. They are much calmer. These waters are world-renowned as one of the best and most beautiful places to sail. If you are very sensitive, then Dramamine or the like will put you at ease. 

  • When is Boarding time?

Boarding time is from 5pm to 6pm, on the start date of your trip. At 6pm there will be a Captain's Call where he will welcome and address all guests. For dinner that night, you are on your own to try any of the numerous, nearby town restaurants.

  • Can I bring my own wine and spirits?

Yes​! You are completely welcome to bring your own favorites. We have a large cooler on deck to chill your wine and beer.  Someone brought a batch of rum that they'd spiced themselves once. Tasty. 

  • When do we get back?

We arrive back in Rockland before noon on the end date of your trip. 

  • Will we be going ashore?

Yes, that's another fun part of our adventures! We visit island nature preserves, deserted islands, quaint Maine coastal villages, rustic harbors, bustling island towns. We even have trips that can visit Acadia National Park. We stopped once at a bird sanctuary island that we happened upon. Our trips aren't only about seeing the best of Secret Maine, but connecting with it, up close in a special way that you can only do on a windjamming trip.  

  • What should I tip for the crew?

10-15% of the cost of the trip. 

  • What are the cabins like?

We've added sinks, lights and USB charging ports. Take a look! The diagram below shows the cabin layout. 

Packing List: 

  • $25 Cash for parking in a lot right nearby. 

  • Sneakers and soft-soled shoes are best on deck and for walkabouts on shore.

  • Best to have layers, along with shorts and long pants to be comfortable as temperature fluctuates. 

  • 10% (of your trip cost) cash gratuity is customary for our devoted crew. 

  • Sun stuff: sunhat, sunglasses, sunscreen. Remember, there are no trees at sea for shade.

  • Rain jacket and rain pants if you're the type to want to watch a steely sea in the rain. Or you can hunker down in the galley with a book, cards or a game with fellow guests. 

  • Swimsuit: summer splashdowns can be great fun!

  • Earplugs: if you're a light sleeper, consider bringing a pair, the crew gets up early to get ready for the day, and sound travels easily in a wooden ship - it's like a big guitar sometimes!

  • Camera: of course a camera! Maine is too beautiful to just commit to memory. Do it for the 'gram! We post all the time!

  • Sleeping bag: this is only if you want to sleep on deck, which is a neat thing to do.

  • You do not need to bring any towels or washcloths. We have shampoo and soap in the shower, but you're welcome to bring your own such things if you prefer. 

  • BYOB: We've got a big cooler on deck. You're welcome to bring all your favorite beers, wines or spirits to punctuate your trip and celebrate your vacation choice. 

  • What if I forget something?

No worries, the morning we leave, you'll have a chance to walk into town to stores right nearby. ​

  • Can I bring my own beverages?

Yes! We've got a big cooler on deck to keep them chilled. Bring your favorites. Accentuate your day with a welcome "fsst," a cork-popping "foop!" or a hearty "cheers" of celebration for choosing the right vacation. 


Note that because the vessel is Federally inspected, and so under Federal jurisdiction, marijuana, though newly legal on the state level, and here in Maine, is still illegal federally and so not allowed aboard GRACE BAILEY. Sorry to harsh your mellow. 

  • What do I pack?

It's always cooler on the water, and we're powered by the wind - so make sure to have some sweaters and layers.

On top of that, at either end of the season, June in the beginning, and September & October towards the end, can be brisk. Above all, be comfortable and be prepared.​​