Founded in 2008, Emerald Sail has crafted hundreds of unforgettable private yacht vacations across the Caribbean’s most iconic destinations.
We specialize exclusively in fully-crewed, all-inclusive charters, partnering with elite yacht owners and seasoned crews to deliver world-class service, comfort, and effortless luxury.
We specialize exclusively in fully-crewed, all-inclusive charters, partnering with elite yacht owners and seasoned crews to deliver world-class service, comfort, and effortless luxury.
Sail the Caribbean your way - with a luxury crewed yacht, chef-prepared dining, curated adventures, and every detail handled for you
about EMERALD SAIL
Your Private All-Inclusive Yacht Vacation Begins Here
Find Your Perfect Yacht in 2 Minutes
Answer a few quick questions to receive:
A custom itinerary designed for your preferred travel dates
One recommended yacht tailored to your group and goals
Estimated pricing for that yacht
One recommended yacht tailored to your group and goals
Estimated pricing for that yacht
No commitments — just a clear picture of what your private yacht escape could look like.
A selection of our most requested yachts
$29 000/per week
Soul Mates
4 suites · 8 guests · 48 ft length · 2024 year built
5 suites · 10 guests · 54 ft length · 2024 year built
$20 000/per week
Southern Queen
$28 000/per week
Southern Queen
5 suites · 10 guests
$51 000/per week
Tryst (Coral moon)
6 suites · 11 guests · 65 ft length · 2024 year built
$21 000/per week
Boatox
3 suites · 6 guests · 50 ft length · 2024 year built
A selection of our most requested yachts
$29 000/per week
Soul Mates
4 suites · 8 guests · 48 ft length · 2024 year built
5 suites · 10 guests · 54 ft length · 2024 year built
$20 000/per week
Southern Queen
$28 000/per week
Southern Queen
5 suites · 10 guests
$51 000/per week
Tryst (Coral moon)
6 suites · 11 guests · 65 ft length · 2024 year built
$21 000/per week
Boatox
3 suites · 6 guests · 50 ft length · 2024 year built
Where Your Journey Can Take You
St. Maarten & St. Barts
Chic marinas, fine dining, world-class shopping, and cosmopolitan island flair.
Bahamas
Shallow turquoise waters, untouched sandbars, exotic wildlife, laid-back anchorages.
USVI
Calm bays, vibrant culture, pristine beaches and upscale comforts.
BVI
Iconic island hopping, protected sailing routes, effortless relaxation.
Where Your Journey Can Take You
St. Maarten & St. Barts
Chic marinas, fine dining, world-class shopping, and cosmopolitan island flair.
Bahamas
Shallow turquoise waters, untouched sandbars, exotic wildlife, laid-back anchorages.
USVI
Calm bays, vibrant culture, pristine beaches and upscale comforts.
BVI
Iconic island hopping, protected sailing routes, effortless relaxation.
TEAM & EXPERTISE
Our dedicated team of 14 charter specialists manages every step of your trip — from yacht selection and itinerary design to onboard support and concierge services.
We partner exclusively with highly experienced, carefully selected captains and professional crews to ensure exceptional hospitality, expert navigation, and unwavering safety standards.
We partner exclusively with highly experienced, carefully selected captains and professional crews to ensure exceptional hospitality, expert navigation, and unwavering safety standards.
Truly all-inclusive pricing
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all-inclusive
Fully personalized trip planning
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personalized
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03
02
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Experienced professional crews
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professional
Curated fleet of premium yachts
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premium
20
1000
14
16
At a Glance
Years veteran captain on our team
Curated voyages
Charter specialists
Years experience since 2008
WHAT’S INCLUDED
08 Fully tailored itinerary
Every day is shaped around your preferences with a custom itinerary designed for your pace, interests, and style of travel.
06 All cabin amenities
Your cabin includes comfortable bedding, toiletries, and essential amenities to make your stay feel naturally restful.
04 Premium open bar
A well-stocked open bar offers a curated selection of premium spirits, wines, and cocktails available anytime.
02 Gourmet chef
A private chef prepares thoughtfully crafted meals tailored to your tastes, using fresh, high-quality ingredients each day.
01 Private captain and crew
Your dedicated captain and crew ensure a smooth, comfortable journey with attentive, professional service throughout your trip.
07 All fuel and mooring fees
All operational costs — including fuel, mooring, and dock fees — are covered, ensuring a truly all-inclusive experience.
05 Water toys (snorkel gear, paddleboards, floats)
High-quality water toys are available whenever you choose — perfect for snorkeling, paddleboarding, and relaxed time in the water.
03 All meals and beverages
Enjoy fully included daily meals, snacks, and refreshments prepared and served to match your preferred schedule.
A Day Onboard
Morning
Wake to calm waters and enjoy chef-prepared breakfast as you sail toward your first secluded bay.
Midday
Snorkel vibrant reefs, paddleboard across crystal shallows, or simply swim and unwind. A fresh, beautifully prepared lunch awaits.
Afternoon
Sail between islands, relax on deck, or enjoy quiet time in the shade — the itinerary adapts to your pace.
Evening
Sip cocktails at sunset, followed by a multi-course dinner beneath the stars. You end the day anchored in a peaceful bay. A day designed to feel effortless and entirely your own.
A Day Onboard
Evening
Sip cocktails at sunset, followed by a multi-course dinner beneath the stars. You end the day anchored in a peaceful bay. A day designed to feel effortless and entirely your own.
Afternoon
Sail between islands, relax on deck, or enjoy quiet time in the shade — the itinerary adapts to your pace.
Midday
Snorkel vibrant reefs, paddleboard across crystal shallows, or simply swim and unwind. A fresh, beautifully prepared lunch awaits.
Morning
Wake to calm waters and enjoy chef-prepared breakfast as you sail toward your first secluded bay.
what our guests say
Brenda Blackmon
The Do More crew - Adrian, Emma, and Georgina were the most amazing crew we could have asked for. They were all so polite, kind, patient, and friendly. Adrian was able to maneuver the catamaran with such ease and finesse, plus we loved his knowledge of the islands! Emma is one of the most amazing chefs we have ever encountered. Every meal was above any expectations, so flavorful, delicious, and thoughtful. She went out of her way to make sure every person in our group was taken care of!
Dorothy Crowder
We had an absolutely incredible all-inclusive charter in the Virgin Islands! From start to finish, everything exceeded our expectations. Chef Anna was amazing and prepared outstanding meals every single day and customized the menu perfectly to our group’s preferences — we miss her already! Captain Steven was fantastic as well, taking us to stunning spots like the Baths, Saba Rock, and even planning our itinerary to get us to various places at the best times.
Sally Mogonye
We have used Emerald Sail for our summer vacations the past three years. Each year surpasses the last. Philip is extremely knowledgeable in his field, he went above and beyond to make sure every single detail was taken care of. Excellent service and communication through the entire process. We can’t wait to book our trip with Emerald Sail next year!
Corey Hannon
My girlfriend found Emerald Sail on Facebook and it was great to work with them. They sent us on the perfect vacation and considering that it was our first time chartering, they walked us through exactly what a yacht charter vacation would look like, found the perfect vessel for us, and made the booking process beyond easy. Not even going to say much about the BVIs, since it’s just heaven on earth down there. Looking to do this every other year with our friends instead of all inclusive resorts and going to explore new destinations too. Highly recommend!
Kathy Senter
This vacation was so nice and relaxing! We’d love to do it again (and maybe even treat ourselves to a bigger boat next time). The crew of Big Nauti were so accommodating and curated a wonderful trip for us. We took our infant granddaughter with us and the crew was so wonderful to her as well. After Emerald Sail sent the crew our preference form, we had a zoom call with them and they ran through all of their ideas for us. Highly recommend this kind of trip.
Chris Tollefsen
The trip was great, we loved it. It was a 10 out of 10 experience and we just wish we had more time down there! The captain and chef were awesome and paid attention to everything we wanted, were very communicative, made reservations for us, and were so fun that we even took them to dinner with us. This trip was beyond relaxing a perfect vacation! We’ll happily work with Emerald Sail for our next one.
Start Planning Your Private Yacht Vacation
Receive your personalized proposal with recommended yachts, real-time availability & pricing tailored to your travel style.
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