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- Length
- 27.4m
- Beam
- 6.5m
- Guests
- 6 sleep · 12 cruising
- Cabins
- 3
- Crew
- 4
- From / Week
- €33,600
Caribbean Breezes, Unfettered Freedom
WINDWARD yacht available for charter. Built in 2006 with a charter price from $39,000 for up to 6 guests in 3 suites with a crew of 4.
Step aboard WINDWARD, the elegant 27.4-meter Cheoy Lee motor yacht, and discover a sanctuary where the Caribbean’s embrace feels uniquely personal. Her Tom Fexas design ensures sleek passage across turquoise waters, while the 2017 refit guarantees every comfort for guests. With a dedicated crew of four attending to every detail, and an array of amenities from a beach club to big game fishing gear, this vessel offers a bespoke escape for those seeking genuine connection with the ocean's rhythm, all at a serene 12-knot cruise.
“WINDWARD is a 27.4m · Cheoy Lee · built 2006 charter yacht in the Blue Ocean Club fleet. Published specifications list accommodation for up to 6 guests. Current charter planning can be discussed for Caribbean, subject to the yacht's live availability and cruising permissions.”

A closer look

The Aft Deck Retreat
The aft deck serves as a sophisticated open-air lounge, where the scent of warm sea air mingles with the subtle aroma of morning coffee. Gather around the polished teak table for al fresco breakfasts as islands drift by, or simply recline with a book, the gentle hum of the engines a soothing backdrop to the endless horizon. This space effortlessly transitions from a casual dining area to a tranquil observation point, perfect for watching sunsets paint the sky.

Sun-Drenched Foredeck
Ascend to the foredeck and find an expansive stretch of sun loungers, beckoning relaxation under the tropical sun. Here, the ocean breeze is at its most invigorating, carrying the faint tang of salt. It’s an ideal spot for quiet contemplation, with uninterrupted views across the bow, or for soaking up the warmth after a refreshing dip from the swim platform. An outdoor shower is conveniently close for rinsing off the salt and sun.

The Saloon's Embrace
The main saloon offers a cool, inviting respite from the midday sun. Plush seating arrangements in muted tones create an atmosphere of understated elegance, perfect for intimate conversations or enjoying a film night. Large windows frame the passing seascape, bringing the outside in without compromising comfort. It’s a space designed for quiet repose, a sophisticated hub for guests to gather and unwind.

Beach Club Access
At the stern, the dedicated beach club unfolds, transforming the yacht into your private aquatic playground. This versatile area provides direct, effortless access to the water, making it simple to transition from lounging to swimming or launching water toys. With the water maker ensuring fresh water is always available and an ice maker for refreshing drinks, it’s the ultimate extension of your yachting experience into the azure Caribbean.

Bridge Deck Barbecue
The bridge deck is home to a superb BBQ setup, inviting casual evening gatherings under a canopy of stars. Imagine the sizzle of freshly caught fish or succulent grilled delicacies, prepared right before your eyes. This elevated vantage point offers panoramic views as you dine, making every meal an occasion. It’s a wonderfully unpretentious space for relaxed entertaining, complemented by the gentle Caribbean night.
Accommodation
Below deck, three beautifully appointed cabins provide sanctuaries of peace for up to six guests. The master suite offers a private haven, thoughtfully designed with a focus on serene comfort and ample storage. Each cabin is an exercise in quiet luxury, featuring tasteful finishes and individual climate control. The layout ensures privacy and tranquility, allowing guests to retreat and recharge after exhilarating days exploring the Caribbean, waking refreshed to another day of adventure on the water.



The culinary journey aboard is an integral part of the charter experience, with a dedicated chef crafting bespoke menus to your preferences. From gourmet breakfasts served al fresco on the aft deck, to elegant dinners in the saloon, every meal is an event. Expect vibrant, fresh ingredients, often locally sourced, presented with flair. The convenience of a coffee machine and ice maker ensures refreshments are always at hand, perfectly complementing the delightful array of dishes.
While not a dedicated spa vessel, WINDWARD offers a holistic sense of wellbeing through its connection to the sea. The expansive swim platform provides easy access for invigorating dips, and the sun loungers on the foredeck invite profound relaxation under the warm Caribbean sun. The outdoor shower offers a refreshing rinse after a swim, ensuring guests feel revitalised and connected to their surroundings, embodying a natural, unforced wellness.
The ocean becomes your playground with an exciting collection of water toys. Dive into adventure with inflatable water toys, or challenge friends to beach games on a secluded shore. The inflatable floating island offers a unique spot for lounging on the water, whilst kayaks and paddleboards provide silent exploration of hidden coves. For more active pursuits, a towable tube promises exhilarating rides, ensuring endless aquatic fun for all ages.
Equipment & Amenities
21 items reported by CharterIndex.




The Crew
A professional crew of 4 dedicated to your charter. Working language: English.
Mitch Armstrong
United States · English
Captain Mitch Armstrong has a 1600-ton masters license and has worked as a professional captain for 30 years. He has over 20 years charter experience in Florida and the Bahamas. He takes pride along with his crew in offering his guests a memorable and enjoyable trip. Captain Mitch has a Big Game fishing background from early in his career and enjoys sharing that knowledge with his guests. He also possesses a make it happen attitude to incorporate a fun filled adventure that will not be soon forgotten.
Edgar Morales
United States · English
Edgar has a deep passion for all things Water and Marine, he is 21 years old and has already received his 100 ton captains license, he is personable and loves to take his guests on aquatic excursions fishing, Snorkeling, and Spearfishing are his passion. Edgar looks forward to having you aboard for your next big adventure.
Video Tour
WINDWARD Charter Yacht - 2006 Cheoy Lee
via Vimeo
Cruising Areas
WINDWARD is available for charter in the following destinations and sub-regions.
- Bahamas
- British Virgin Islands
- Cayman Islands
- Greater Antilles
- Leeward Antilles
- Leeward Islands
- Trinidad & Tobago
- Turks Caicos
- U.S. Virgin Islands
- Windward Islands
- Carolinas
- Florida - East Coast
- Florida - West Coast
- Florida Keys
- Georgia
- Great Lakes
- Middle Atlantic
- New England
- Western Gulf
Full Specifications
- Designer
- Tom Fexas
- Refit
- 2017
- Beam
- 6.5 m
- Draft
- 1.68 m
- Cruising speed
- 12 kts
- Flag
- United States
- MCA
- None
- VAT
- Not registered
- Smoking
- No smoking
- Crew language
- English
- Captain
- Mitch Armstrong
- Prior name
- TALON
Diving
Diving by arrangement · Snorkeling Equipment · Spearfishing gear
Rates & Availability
| Season | Period | Weekly Rate |
|---|---|---|
| Published weekly rate | Dates and season terms to be confirmed | €33,600 |
Live data via CharterIndex · taxes, operating expenses and other charges are confirmed for the specific charter
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Suggested Itineraries
Enhance your charter with Blue Ocean Concierge.
Every booking includes a dedicated concierge manager. Add any of the following — or anything else you can imagine — to shape a truly bespoke week.
- Private jet & helicopter transfers
- Michelin-trained private chef
- Sommelier-curated wine provisioning
- On-board yoga & spa therapists
- VIP beach club & restaurant access
- Photographer & videographer
- Bespoke shore excursions
- Live musicians & DJs
- Anniversary, proposal & celebration staging
- Chauffeured cars & discreet security
- Marine biologist for the children
- 24/7 personal concierge manager
Gallery















WINDWARD: your questions, answered
The most common questions we receive about chartering WINDWARD. For anything specific to your dates, guest list or itinerary, message us directly.
What a yacht like WINDWARD costs to own — not just to charter
A charter week on WINDWARD is a fixed, all-in number. Ownership of a 27m yacht in this class is a five-year commitment — crew payroll, insurance, class and refit reserves, berthing and depreciation. Our yacht ownership vs charter vs fractional ownership study runs the real five-year cost of a €15 million yacht against the equivalent charter spend, and the most profitable yachts for owners ranking shows how much of that stack charter revenue actually recovers.
Plan a charter aboard WINDWARD
Destinations → Yachts → Experiences → Events → Costs — every step of the brief, in the order our brokers work through it.
- Honeymoon charterTwo of you. A private crew. One unrepeatable week.
- Family charterOne floating villa. Six bays a week. Zero hotel breakfasts.
- Gastronomy charterTwo-star kitchens ashore. A tasting menu on board. Six markets in seven days.
- Celebration & birthdayThe party doesn't end at the dock — it follows you to the next bay.
Compare destinations, itineraries & seasonal guides
Continue with the destinations, itineraries, marinas and practical guides that are most closely related to this page.
Knowledge graph
WINDWARD inside the Blue Ocean Club ecosystem
Every link below exists for a stated operational reason — berthing, cruising range, route fit or a like-for-like alternative.
Home port
Where the yacht is berthed — the start of every charter
- Nanny Cay Marina
Deepest superyacht berthing in the yacht's primary destination
Cruising grounds
The cruising grounds the yacht is chartered in
- St Barths Yacht Charter
Flagship destination inside the yacht's declared cruising region
- Tortola Yacht Charter
Flagship destination inside the yacht's declared cruising region
- Jost Van Dyke Yacht Charter
Flagship destination inside the yacht's declared cruising region
Ecosystem
Parent ecosystem for the yacht's season
- Caribbean
Cruising region declared on the yacht record
Itineraries this yacht can run
Routes this yacht can run
- The Grenadines
Route runs inside this yacht's cruising region
- British Virgin Islands
Route runs inside this yacht's cruising region
Comparable yachts
Comparable yachts for the same brief
- MAKE BIG HAPPEN
Comparable length in the same cruising region
- INDULGE II
Comparable length in the same cruising region
- 1LORENA
Comparable length in the same cruising region
Also berths at
Additional marinas able to berth this yacht
- Great Harbour, Jost Van Dyke
Marina able to berth this yacht inside its operating area
- Port de Gustavia outer / Public
Marina able to berth this yacht inside its operating area
- Village Cay Marina, Tortola
Marina able to berth this yacht inside its operating area









