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We want to make sure that each and every one of our customers has the best experience possible sailing with us, whether as a passenger on a leisurely cruise set against the breathtaking Boston skyline, taking a private lesson to try sailing out, or enrolling in one of our highly acclaimed keelboat courses. The details of each option are outlined below so that you can learn precisely what we're offering, and how and when you can redeem!

Weekends and evenings will book up quickly and all time slots are first come, first serve.

How to book

  •  You will use the online schedule to reserve your spot. Have your code ready.

  • Enter your unique voucher code at the top of the page, by clicking on the Promotion code button.

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  • You should see a number 1 on the left if the code is accepted. 

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  • Click the Book button for the deal you are redeeming. 

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  • Follow the instructions to schedule your course. If you selected the same course that your voucher is valid for, you will not be asked for any additional payment. 

To reserve your course now and get on the water, follow the button for your course below!

 


 

 

2-hour Private Lesson or Harbor Cruise for up to 4 people

This deal gets you one of our Rhodes-19 sailboats with an instructor for 2 hours. The R-19 can fit 3 adult passengers easily, or 4 if you don't mind a squeeze. Our instructor can teach you and your friends some sailing skills if you want a lesson, or she can simply skipper the boat while you enjoy the ride for the harbor cruise option - it's up to you!

Specific times and availability may vary. You may reschedule freely up to one week before your scheduled appointment. We will charge a $30 fee for rescheduling within one week of the scheduled appointment. Voucher is subject to forfeiture for cancellations within 24 hours or no-shows.

Redeem + Schedule

 

2-hour Sailing Lesson or Harbor Cruise for One

This deal gets you in one of our Rhodes-19 sailboats with an instructor and up to two other guests for 2 hours. The R-19 can fit 3 adult passengers easily. Our instructor can teach you and your friends some sailing skills if you want a lesson, or she can simply skipper the boat while you enjoy the ride for the harbor cruise option - it's up to you!

Specific times and availability may vary. You may reschedule freely up to one week before your scheduled appointment. We will charge a $30 fee for rescheduling within one week of the scheduled appointment. Voucher is subject to forfeiture for cancellations within 24 hours or no-shows.

Redeem + Schedule

 

12-hour Keelboat Course

Our Basic Keelboat courses are the best way to learn to sail on Boston Harbor! We recommend purchasing two of the LivingSocial vouchers for the full experience of our 24-hour Basic Keelboat Complete course, bundled with two months of membership.

One voucher will allow one adult(aged 18+) to take our introductory 12-hour Basic Keelboat Part 1 course OR our 12-hour Basic Keelboat Part 2 course, and is bundled with one month of membership.

Reedeem + Schedule

 

 


 

More answers to more questions

When is the best time to sail on Boston Harbor?

Some of the best sailing of the year is in May, June, and September. The hotter months in July and August are great, too, but are more prone to light wind and thunderstorms.
 

What if there's bad weather?

Well, that depends on what you mean by bad weather.  Sailing is fun even when the weather isn't perfect, and we cannot guarantee sunny days for everyone.  So if it's overcast or just a raining a little, we will sail.   In the event of unsafe weather conditions, heavy rain, or heavy winds, we will reschedule the two-hour sails free of charge.  We very rarely cancel our Keelboat courses, as there are plenty of onshore materials in the curriculum, and we can often use the nicer parts of a day for on-the-water activities and then have lunch or shore-school while a storm passes through.  If the weather is looking bad, it's best to give us a call before heading to Charlestown if we haven't already contacted you.
 

What if I need to reschedule my reservation?

As long as you give us a week's notice, it is no problem at all.  Please refer to the deal descriptions above.  We cannot guarantee availability for rescheduled appointments.
 

What should I bring with me? How should I dress?

Make sure the bring a printout of you voucher!
Cameras are welcome - we love to see photos from sailors posted to our facebook page!
Depending on the deal you purchased, you'll be outside for 2 to 6 hours.  Prepare accordingly, and check the weather!  We recommend a water bottle, sunblock, sunglasses, clothing suitable to any regular outdoor activity, and a hat.  If it looks like rain, pack a rainjacket.  Sneakers or athletic shoes are fine, but no flip flops or dress shoes.   If you're taking Basic Keelboat, you can either bring a lunch or visit a nearby sandwich shop.  You will be able to bring a bag on-board with you and stash it under the deck, where it will remain dry. 
 

Can I bring children? 

You may bring children on the 2 hour lesson or cruise.  There must be one responsible adult per child under the age of 12 who can oversee their movement on the boat (and the instructor doesn't count!).  Please let us know in advance if there will be children on board.  If bringing a child under 50 lbs, the customer is responsible for providing a U.S. Coast Guard approved personal flotation device for the child.
 

When should I arrive at Courageous Sailing?

Please arrive at Courageous 10-15 minutes early so that you can get your full two hours on the water.  If you are running late, please call ahead to let us know!  If you arrive late for your appointment, we will not be able to give you the full two hours.
 

Where is Courageous Sailing? How do I get there?

Courageous Sailing is located on Pier 4 of the Charlestown Navy Yard.  Various GPS and map services have a hard time finding us, so please us our Parking and Directions page so you don't get lost!  
 

What kind of boat will I sail on? Do they capsize? Will I get wet?

You'll be sailing in one of our Rhodes 19s.  R-19s are keelboats, which means there is a big heavy metal fin and bulb on the bottom that prevents the boat from capsizing.  On windy days, you may get a bit wet from spray as water breaks over the bow or sides of the boat, but there is a compartment where you can stow items and keep them dry.
 

I loved my two hour sail! How do I keep sailing ?

Courageous makes it easy.  If, after your sail, you decide to sign up for a course, you'll receive a $45 discount off one of our 12-hour courses or $95 off of one our 24-hour courses.  Check out our great lesson and membership options!
 

 

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We want to make sure that each and every one of our customers has the best experience possible sailing with us, whether as a passenger on a leisurely cruise set against the breathtaking Boston skyline, taking a private lesson to try sailing out, or enrolling in one of our highly acclaimed keelboat courses. The details of each option are outlined below so that you can learn precisely what we're offering, and how and when you can redeem!

Weekends and evenings will book up quickly and all time slots are first come, first serve.

How to book

online-deal-1 online-deal-2 

 

Please allow 48 hours from purchase to schedule your deal as we process the new voucher codes.

 

Scroll down to find the deal you purchased. Use the online schedule to reserve your spot. Have your code ready.

 

 

2-hour Private Lesson or Harbor Cruise for up to 4 people

This deal gets you one of our Rhodes-19 sailboats with an instructor for 2 hours. The R-19 can fit 3 adult passengers easily, or 4 if you don't mind a squeeze. Our instructor can teach you and your friends some sailing skills if you want a lesson, or she can simply skipper the boat while you enjoy the ride for the harbor cruise option - it's up to you!

Specific times and availability may vary. You may reschedule freely up to one week before your scheduled appointment. We will charge a $30 fee for rescheduling within one week of the scheduled appointment. Voucher is subject to forfeiture for cancellations within 24 hours or no-shows.

Redeem + Schedule

 

2-hour Sailing Lesson or Harbor Cruise for One

This deal gets you in one of our Rhodes-19 sailboats with an instructor and up to two other guests for 2 hours. The R-19 can fit 3 adult passengers easily. Our instructor can teach you and your friends some sailing skills if you want a lesson, or she can simply skipper the boat while you enjoy the ride for the harbor cruise option - it's up to you!

Specific times and availability may vary. You may reschedule freely up to one week before your scheduled appointment. We will charge a $30 fee for rescheduling within one week of the scheduled appointment. Voucher is subject to forfeiture for cancellations within 24 hours or no-shows.

Redeem + Schedule

 

12-hour Keelboat Course + 1 Month Membership

Our Basic Keelboat courses are the best way to learn to sail on Boston Harbor! One voucher will allow one adult(aged 18+) to take our introductory 12-hour Basic Keelboat Part 1 course OR our 12-hour Basic Keelboat Part 2 course, and is bundled with one month of membership.

Reedeem + Schedule

 

 


 

More answers to more questions

When is the best time to sail on Boston Harbor?

Some of the best sailing of the year is in May, June, and September. The hotter months in July and August are great, too, but are more prone to light wind and thunderstorms.
 

What if there's bad weather?

Well, that depends on what you mean by bad weather.  Sailing is fun even when the weather isn't perfect, and we cannot guarantee sunny days for everyone.  So if it's overcast or just a raining a little, we will sail.   In the event of unsafe weather conditions, heavy rain, or heavy winds, we will reschedule the two-hour sails free of charge.  We very rarely cancel our Keelboat courses, as there are plenty of onshore materials in the curriculum, and we can often use the nicer parts of a day for on-the-water activities and then have lunch or shore-school while a storm passes through.  If the weather is looking bad, it's best to give us a call before heading to Charlestown if we haven't already contacted you.
 

What if I need to reschedule my reservation?

As long as you give us a week's notice, it is no problem at all.  Please refer to the deal descriptions above.  We cannot guarantee availability for rescheduled appointments.
 

What should I bring with me? How should I dress?

Make sure the bring a printout of you voucher!
Cameras are welcome - we love to see photos from sailors posted to our facebook page!
Depending on the deal you purchased, you'll be outside for 2 to 6 hours.  Prepare accordingly, and check the weather!  We recommend a water bottle, sunblock, sunglasses, clothing suitable to any regular outdoor activity, and a hat.  If it looks like rain, pack a rainjacket.  Sneakers or athletic shoes are fine, but no flip flops or dress shoes.   If you're taking Basic Keelboat, you can either bring a lunch or visit a nearby sandwich shop.  You will be able to bring a bag on-board with you and stash it under the deck, where it will remain dry. 
 

Can I bring children? 

You may bring children on the 2 hour lesson or cruise.  There must be one responsible adult per child under the age of 12 who can oversee their movement on the boat (and the instructor doesn't count!).  Please let us know in advance if there will be children on board.  If bringing a child under 50 lbs, the customer is responsible for providing a U.S. Coast Guard approved personal flotation device for the child.
 

When should I arrive at Courageous Sailing?

Please arrive at Courageous 10-15 minutes early so that you can get your full two hours on the water.  If you are running late, please call ahead to let us know!  If you arrive late for your appointment, we will not be able to give you the full two hours.
 

Where is Courageous Sailing? How do I get there?

Courageous Sailing is located on Pier 4 of the Charlestown Navy Yard.  Various GPS and map services have a hard time finding us, so please us our parking and directions page so you don't get lost!  
 

What kind of boat will I sail on? Do they capsize? Will I get wet?

You'll be sailing in one of our Rhodes 19s.  R-19s are keelboats, which means there is a big heavy metal fin and bulb on the bottom that prevents the boat from capsizing.  On windy days, you may get a bit wet from spray as water breaks over the bow or sides of the boat, but there is a compartment where you can stow items and keep them dry.
 

I loved my two hour sail! How do I keep sailing ?

Courageous makes it easy.  If, after your sail, you decide to sign up for a course, you'll receive a $45 discount off one of our 12-hour courses or $95 off of one our 24-hour courses.  Check out our great course and membership options!