Pick Your Vacation Days

Ready to plan the perfect lowkey or action-packed vacation? Use the calendar below to see our next available voyage times.

Pick Your Vacation Days

Ready to plan the perfect lowkey or

action-packed vacation? Use the calendar below to see our next available voyage times.

Ready to Book Your Dates?

Reach out to Barefoot Cowboy now. While we can’t always guarantee a spot will be available, we have occasionally been able to move dates around to fit clients’ schedules.

Couple sunbathing

Ready to Book Your Dates?

Reach out to Barefoot Cowboy now. While we can’t always guarantee a spot will be available, we have occasionally been able to move dates around to fit clients’ schedules.

Couple sunbathing

View Available Dates

Booking FAQs

How much does a Barefoot Cowboy Charter cost?

Our charters are 8 days, 7 nights all inclusive. These are our rates.

Christmas flat rate of $43,000 and New Year's flat rate of $44,000.

5 PAX

$33,500

6 PAX

$34,000

7 PAX

$34,500

8 PAX

$35,000

9 PAX

$35,500

10 PAX

$36,000

How many people can be included in my trip?

Barefoot Cowboy can accommodate up to 10 guests, so bring your friends and family along!

How far in advance do I need to book my trip?

Barefoot Cowboy’s calendar fills up quickly. If you have a date in mind and it is open on the calendar, we recommend you book it immediately before someone else steals the spot.

How do I personalize my experience?

This vacation is all about you! When you select a date or contact us, you will receive a preference sheet to tell us your favorite foods and drinks. You can also tell us about any special occasions you may want to celebrate.

We will have an itinerary, but it is flexible and always able to be changed. If there is another beach or island you would rather visit, no problem! This can even apply to last minute changes or spur-of-the-moment ideas, within reason.

What happens if inclement weather occurs when I’m supposed to go on my trip?

If a named storm is predicted in our area before your charter, we will cancel the charter and re-book for a new date. This rarely happens because we do not book charters during Hurricane season.

Travel insurance is always recommended. We’ll tell you the details in your Charter Contract.

If something comes up and I need to cancel my trip, will I receive a refund?

You will only receive a refund if we are able to book another charter for your dates. We’ll explain our refund policy in depth in your Charter contract.

The date I want isn’t available! Is there anything that can

be done?

Maybe! Give us a call. We try to be as accommodating as possible while respecting the dates and times booked by other passengers.

Booking FAQs

How much does a Barefoot Cowboy Charter cost?

Our charters are 8 days, 7 nights all inclusive. These are our rates.

Christmas flat rate of $43,000 and New Year's flat rate of $44,000.

5 PAX

$33,500

6 PAX

$34,000

7 PAX

$34,500

8 PAX

$35,000

9 PAX

$35,500

10 PAX

$36,000

How many people can be included in my trip?

Barefoot Cowboy can accommodate up to 10 guests, so bring your friends and family along!

How far in advance do I need to book my trip?

Barefoot Cowboy’s calendar fills up quickly. If you have a date in mind and it is open on the calendar, we recommend you book it immediately before someone else steals the spot.

How do I personalize my experience?

This vacation is all about you! When you select a date or contact us, you will receive a preference sheet to tell us your favorite foods and drinks. You can also tell us about any special occasions you may want to celebrate.


We will have an itinerary, but it is flexible and always able to be changed. If there is another beach or island you would rather visit, no problem! This can even apply to last minute changes or spur-of-the-moment ideas, within reason.

What happens if inclement weather occurs when I’m supposed to go on my trip?

If a named storm is predicted in our area before your charter, we will cancel the charter and re-book for a new date. This rarely happens because we do not book charters during Hurricane season.


Travel insurance is always recommended. We’ll tell you the details in your Charter Contract.

If something comes up and I need to cancel my trip, will I receive a refund?

You will only receive a refund if we are able to book another charter for your dates. We’ll explain our refund policy in depth in your Charter contract.

The date I want isn’t available! Is there anything that can

be done?

Maybe! Give us a call. We try to be as accommodating as possible while respecting the dates and times booked by other passengers.

Unforgettable Memories Are Just

a Click (or Call) Away

After how stressful this year has been, you deserve a chance to get away and unwind. Barefoot Cowboy has your back. We’ll take care of the details, so you do not spend any time doing activities that don’t fit your preferences and all the time enjoying your voyage to the fullest.

man on a phone call

Unforgettable Memories Are Just

a Click (or Call) Away

man on a phone call

After how stressful this year has been, you deserve a chance to get away and unwind. Barefoot Cowboy has your back. We’ll take care of the details, so you do not spend any time doing activities that don’t fit your preferences and all the time enjoying your voyage to the fullest.

Life is too short to waste on overpriced cruise ships with predetermined activities, tight schedules, and crowded decks. Reach out to Barefoot Cowboy today and plan the trip you’ve always dreamed of.

Barefoot Cowboy logo

GO BAREFOOT!

Connect with US

All rights reserve | ©2024. | Powered by ROI Online | Privacy Policy