Yacht Charter Vacations

By Yacht Charters Guru

Monohulls and More!

Our hearts will always be in love with traditional sailing yachts...we spent almost 20 years as an owner/operator of an Irwin monohull in the charter fleet. 


Sailing Vacations in the Virgin Islands on Sailboat ErosEROS - 115' 1938 Brooks Motor Craft Sailboat
Guests: up to 8 | Cabins: 4 | Showers: 4 | Crew: 5

Sailing a large classic like Eros is pure joy for veteran and novice sailors alike. Under a warm, tropical breeze, she heels gently and accelerates to ten knots or more, easily keeping pace with lighter and newer yachts. Guests can hoist sails, grind winches, take the wheel, or sit back and watch the crew at their positions; all once-in-a-lifetime experiences. Experienced sailors are welcome to charter Eros for one of the several classic yacht regattas she participates in during the year. Over the course of nearly 50 years, Eros changed ownership only three times before anchoring with her current owners. 

Eros has undergone a complete interior redecoration, seamlessly marrying the style and comfort of sophisticated luxury travel with the thrill of sailing aboard this historical masterpiece. Onboard you'll experience a step back in time and distinctly modern innovative touring vessel. 

RATES: 8 Days/ 7 Nights $39,00 - $48,000                 Sailing Yacht Eros Crewed Yacht Charter Vacation Video


VIEW Eros Details


Ree Sailing Crewed Yacht Charter BoatRee – 115′ Sailboat
Guests: up to 10 | Crew: 6 | Cabins: 5 | Showers: 5

S/Y REE formerly Parsifal II is a luxury sailing yacht that offers the comfort and superb facilities. Built in 1996 by Valdettaro Shipyard, Italy, she was designed  specifically for luxury charters. The yacht is equipped with all the very latest technology, from state-of-the-art sail handling to worldwide communications. She is the perfect combination of power under sail and luxury; able to sail at 10-12 knots with ease. Offering the ultimate experience for the most discerning sailors, REE features copious amounts of deck space. The very large covered cockpit seats 12 for al fresco dining in addition to  lovely seating areas. 

Having been on board s/y REE since May 2013, Captain Ottley takes pride in his excellent crew management skills & maintaining the vessel to the highest possible standards in order to ensure owners and guests experience the fullest enjoyment wherever they cruise. 

Yacht Charters Guru was invited to have an exceptionally delicious lunch onboard REE recently during the Antigua Yacht Show. Chef Akané’s cuisine is the meeting or the clash between the French terroir and Japanese artesian delicacy. Her talent shines with innovation & perfect presentation. We highly recommend this smooth & highly professional crew of six for a vacation of a lifetime!

RATES: 8 Days/ 7 Nights $55,000 - $65,000



Marae Sailing Crewed Yacht Charter BoatMARAE – 108′ Sailboat
Guests: 6| Cabins: 3 | Showers: 3|Crew 4

MARAE, pronounced ‘Mar-eye’ 108' Pilothouse Sloop, "Best Sailing Yacht", International Superyacht Design Award, 2004. The name Marae has origins from the native Maori tribe in New Zealand meaning a "special meeting place for family and friends"to enjoy life in harmony with the sea. This Ted Fontaine design captures the essence of a classic sailing yacht with timeless lines while incorporating the spaciousness and the engineering of a much larger yacht, delivering the whole with superb guest areas and sailing performance that enraptures and excites in equal measure. From her elegant interior to her inviting deck spaces, and from her vast array of water toys to the unparalleled service from her experienced crew, she provides the ultimate getaway to share with family and friends.

While Marae is a joy to sail, her shoal draft allows her to get closer to shore than almost any other yacht of her size, meaning you and your guests can enjoy the tranquillity of quiet anchorages that others cannot reach. Once there, a world of opportunities awaits. Her extensive toy store includes towed inflatables, two Laser dinghies, wakeboarding, waterskiing, fishing, snorkelling and even your own private island with built-in cooler and sound system, while her all-new entertainment system – controlled by iPads and iPod Touch remotes – allows for watching TV or movies, listening to music, or reviewing your own photos of your day from your own Apple gear almost anywhere on board.

Better than the best luxury hotel. Finer than the finest full service villa. Your private paradise awaits.

RATES: 8 Days/ 7 Nights $59,000 - $65,000
Sleeps 6 Guests in 1 Queen Cabin, 1 Double Cabin, 1 Twin, 1 Pullman


VIEW Additional Marae Details


Sailing Monohull Jupiter Crewed Yacht Charter VacationJUPITER - 100' Ferri Cantieri Sailboat
Guests: up to 8 | Cabins: 4 | Showers: 4| Crew: 4

Built by Italian yard Cantiere Ferri to a design by Giorgetti & Magrini and launched in 1989, luxury sailing yacht Jupiter has a modern design; open, clean, spacious and bright. All cabins feature natural light and ventilation from deck hatches and unique port-lights. The Main Salon provides entertainment system, lounging sofa and formal dining table seating 8 while the main cockpit table comfortably seats 10. A large sun deck & space for deck lounge chairs. Galley & crews quarters are completely separate from all guest areas. The spacious aft Master cabin includes two large double berths, copious storage, entertainment system and large head with double sinks and stall shower.

There are three guest cabins, one VIP double & two lower twin cabins all feature abundant storage and heads with stall showers. All cabins feature natural light & ventilation from deck hatches and unique port lights. There is state of the art soundproofing for a quiet and enjoyable cruise. Sailing Vacations on Yacht Monohull Jupiter Virgin Islands

RATE: 8 Days/ 7 Nights / $29,500 - 39,500


VIEW Jupiter Details


Sailing Monohull Lush 89 Crewed Yacht Charter Vacation Virgin IslandsLUSH -89' Oyster Marine Sailboat

Guests: Up to 8 | Cabins 4 | Crew 3

The Oyster 885 Lush is one of the newest models to be designed by Oyster. Among her many attractions are the spacious cockpit perfect for outside dining and relaxation on charter with open deck areas, and a large flip-down bathing platform.  The guest accommodation benefits from tall triple seascape windows that give these rooms a bright and spacious feel. The aft cabin offers a queen sized bed, desk and couch. Forward of the master cabin are two guest double cabins, one either side of the corridor. Each has en-suite bathrooms and a hanging locker with ample drawers under the berths. A fourth guest cabin is forward of the main salon. All cabins an integrated entertainment system with Apple TV.  

Captain Angus Wood started sailing at a very early age on the South coast of England. He discovered a love for skiing and worked in Canada as an instructor before going back to yachting. Today, he is always on the hunt for a new place to kite surf or a hidden reef to surf. With his love for water sports & passion for teaching, he is very happy to help you out trying new sports - be it wake boarding, water skiing, paddle boarding. Chef Iona Iona grew up in Scotland within a family of chefs and trained at Leiths in London. The two met in Majorca and have been working, sailing, kite surfing and traveling together ever since. They love working together as a team, their relaxed and friendly personalities are sure to make you feel welcome on board Lush. Join them for a relaxing holiday, or a more active adventure, and you are sure to have a memorable time.

RATES: 8 Days/ 7 Nights $45,000 - $49,500


View Additional Details


Sailing Yacht Charter Monohull AquilaAQUILA - 82' 2002 Swan Monohull

Guests: 6-8 | Ensuite Cabins: 4 | Crew: 2

AQUILA, the ever timeless SWAN 77, as the perfect getaway for your dream vacation. With spacious layouts, warm interiors and race-like hull design it offers everything in one package. It accommodates 6 guests and 2 crew. Composed wood, spacious layout, made-to-measure furniture, the warm interior with wood finishes and handmade furniture will give You a feel of home and life at sea. Each of three guest cabins is equipped with an ensuite head, shower, AC, and a flat screen TV, and the smart and simple deck is designed to offer the most use of space and storage, as well as numerous private spots for sunbathing, cocktail sipping and enjoying a dinner with Your friends and family.

Capt. Drew Donald grew up in Annapolis, Maryland, as a third generation yacht racer. For decades he’s been Captain on Grand Prix racing yachts, performance cruisers, and mega yachts. He has logged over 200,000 ocean miles in the Mediterranean, North Atlantic, Caribbean and the East Coast of the U.S. After many years of captaining mega yachts, Drew has returned to the helm of a beautiful Swan 77. Chef: Anne Parry-A native of Philadelphia, Pennsylvania, Anne grew up boating in Maine, Lake Winnipesaukee, and Barnegat Bay. After several years of living in France, Central Asia, Boston & Cape Cod, and five years in the Pacific Islands, her interests in cuisine, sailing and international travel evolved. Culinary school in Colorado & Oregon introduced her to the wonders of organic farm-to-table heirloom tomatoes and herb-roasted free-range lamb. Classically trained in French Mediterranean cuisine with a healthy twist, Anne also loves cooking for vegans, vegetarians, and those looking for the “cleansing spa experience” with healthy local farmers market produce, while also spoiling charter guests with vintage cocktails, her mother’s Hollandaise, her aunt’s chocolate fudge & madeleines, as well as her grandmother’s corn fritters. Outside of the galley, her favorite things are sunrises, sunsets, yoga, windsurfing, triathlons, organic farming, and philanthropic community projects. Anne joins AQUILA after 8 years as a freelance chef on private motor and sailing yachts in New England, the Bahamas and the Caribbean, and looks forward to treating guests to a 5-star luxury sailing experience.

RATES: $24,000 - $25,875 / Sleeps 6 Guests in 1 Queen(s), 1 Double(s), 2 Single(s), 2 Pullman (for children)


Additional Aquila Details

Affordable Yacht Vacation Collection

Pacific Wave

Pacific Wave Sailing Crewed Yacht Charter BoatPacific Wave – 72′ Sailboat – Crewed Charter
Guests: up to 6 | Crew: 2 | Cabins: 3 | Showers: 3

Pacific Wave is a successful blend of power and elegance as a stylish 72ft Italian custom built Sloop. Extremely easy to handle and ideal for both non-sailors & sailors; she is built of aluminum and is extremely refined, stable & safe with all lines running outside of her huge cockpit. Her on-deck and below-deck layout provides spacious comfortable living ideal for honeymooners and families; her simple but sophisticated decor is an exquisite blend of practicality and elegance that only a designer of the fame of Gae Aulenti could achieve. Pacific Wave won 2nd place as Best Monohull at The Tortola Charter Yacht Show & Chef Mark Miles took 1st place in the Chef Competition at The St. Thomas Charter Yacht Show. Mark also took 2nd place at the Antigua Charter Yacht Show Concourse du Chef. 

RATES: 8 Days/ 7 Nights $14,000 - $18,000


VIEW Pacific Wave Details                       LEARN about Scuba Diving Aboard Pacific Wave


Stargazer Sailing Crewed Yacht Charter BoatStargazer– 75′ Sailboat
Guests: up to 6 | Crew: 3 | Cabins: 3 | Showers: 3

Stargazer is crew owned. It is not our job to operate charters, it is our passion! We have a vested interest in making your vacation the safest and most enjoyable experience you could wish for. Working as a compatible team with a remarkable track record, we look forward to sharing our knowledge and love of the Virgin Islands with each and every one of our guests. 

RATES: 8 Days/ 7 Nights $13,450 - $18,875

VIEW Stargazer Details         LEARN About Scuba Diving Aboard Stargazer


Sailing Yacht Ocean Star Charter Vacations 2018OCEAN STAR - 60' 2015 Beneteau

Guests: up to 6 | Crew: 3 | Cabins: 3 | Showers: 3

This Award-winning yacht offers a luxurious ensuite Master King Suite forward and two Queen Suites aft, one of which may convert to a twin-berth suite. Capt. Hugh started competitive sailing and ocean racing in the UK & France in 1987 (30 years experience). He completed the intensive Royal Yachting Association (RYA) Yachtmaster 300 Ton Sail & Power Commercial License in 2002, and worked as a Captain & Chef in commercial yachting in the Cayman Islands, Virgin Islands, USA & Asia. Fabulous cuisine a big part of being onboard this yacht. Hugh attended culinary classes in Europe, Japan & France, and specializes in Mediterranean and Asian fresh food dishes with premium ingredients.

Ellen began her career in the cruise ship industry and later continued to work on yachts, support maintenance services and yacht deliveries around the Bahamas. Ashore in St Augustine she also worked in the hospitality & restaurant industry alongside the yacht business Ellen is an avid Wellness & Yoga enthusuiast and licensed Cosmetologist plus current Safety Training Certificate of Watchkeeping (STCW) holder for yachts. She is responsible for hosting guests on Ocean Star and ensuring they have both a fun and a relaxed charter including leading snorkel trips, yoga sessions, brewing up "wellness smoothies" and various incremental services such as facials, pedicures, head and shoulder massages. Capt. Hugh & Ellen have a zeal for sharing their love of the ocean, great cuisine as well as a great talent for making their guests feel at home aboard s/v Ocean Star! 

RATES: 8 Days/ 7 Nights $15,000 - $18,000


Additional Details About Ocean Star

Sea Witch

Sea Witch Sailing ChartersSea Witch– 58′ Sailboat – Crewed Charter and Day Sail
Guests: up to 4 | Crew: 2 | Cabins: 3 | Showers: 2

Sea Witch is a nationally recognized yacht from her annual travels along the American coastline between Cape Cod and the Caribbean. She is a luxurious 58' Pearson Ketch & is stunningly beautiful when all four of her sails are set. Her 37 ton weight & deep draft keel provide a very smooth sail. Sea Witch was built in 1981 in Portsmouth, Rhode Island. She is a comfortable cruising yacht and has circumnavigated the world.

Located in St Thomas, VI from mid-November to the end of March offering Daily, four nights to maximum of 2 weeks sailing charters. From mid-June to mid-September, you'll find the yacht Martha's Vineyard, offering 2, 4 or 8 hour daily charters, or term charters from 2 nights to weekly charters.

Experience the ultimate sailing adventure aboard the Sea Witch. Relax and experience the tranquil breezes that fill the sails as you glide through the beautiful blue waters of the Caribbean, watching for whales, turtles or just the gorgeous views of these tropical hideaways. If you want a little more action, you can help Capt. John & Susan Stephenson in hoisting the sails and navigating or just kick back, relax and soak in the Caribbean sun! They'll sail you to unique secluded destinations and romantic coves, with options for swimming, snorkeling, diving, fishing, kayaking or just basking in the sun during a glorious day. 

RATES: 8 Days/ 7 Nights $8,200 - $10,200



Mojecka Sailing Crewed Yacht Charter BoatMOJECKA - 56' Sailboat Charter

Guests: up to 6 | Crew: 2 | Cabins: 3 | Showers: 3

If you’ve already “been there, done that” in the U.S. & British Virgin Islands, you might want to consider the monohull MOJEKA. This 56.1' yacht, taking up to 6 guests will arrive in the Caribbean in December and be available for charters with Captain Dave Buller & Chef Emma White. She’ll be based in Antigua in the first half of the year and Grenada in the second half, and will be available from the Virgins to the Grenadines. MOJEKA introduces a new concept in monohull design with the salon and cockpit on the same level - referred to as “one level living”. With skylights that flood the main salon with light, panoramic views all-around, and a huge comfortable cockpit with convertible sunning bed, she offers unparalleled luxury and comfort in a yacht of her size.

RATES: 8 Days/ 7 Nights $13,250 - $15,750


VIEW Mojecka Details                                       MOJECKA VIDEO                            


Scorpio Sailing Crewed Yacht Charter BoatScorpio – 52′ Sailboat – Crewed Charter
Guests: up to 3 | Crew: 2 | Cabins: 2 | Showers: 2

Whether you cruise the BVI’s or head south to The Grenadines, Captain Richard and Jan know the territory. They’re also patient teachers for those wishing to learn more about sailing or SCUBA diving, or both. Richard is a certified ASA Sailing Instructor. With full scuba diving and snorkeling gear on board, you are free to explore the fantastic sights under the waves as well as sail the warm Trade Winds of the Caribbean. Scorpio is perfect for both sailors and divers, honeymooners or a small family of up to 3 (there is a single berth sharing a bath with the master cabin). The use of space is exceptional for a yacht of this size. 

RATES: 8 Days/ 7 Nights $5,750 - $7,150


VIEW Scorpio Details                        LEARN About Scuba Diving Aboard Scorpio

Tilly Mint

Tilly Mint Sailing Crewed Yacht Charter BoatTilly Mint– 68.2′ Sailboat – Crewed Charter
Guests: up to 7 | Crew: 2 | Cabins: 3 | Showers: 3

Tilly Mint is a semi-custom, handcrafted 67ft sailboat built in England by Discovery Yachts, a boatyard renowned for innovative and award winning sailboats. She is the largest model offered by Discovery, and like her little sister the Discovery 55’, she was designed by the most prominent naval architect of this century, Ron Holland. Since being launched in 2009, Tilly Mint has been lightly used by her private owner. Chartering in the Caribbean and Mediterranean. 

RATES: 8 Days/ 7 Nights $19,500 - $24,725


VIEW Tilly Mint Details


XIMERA 57.5′ Hanse Sailboat – Crewed Charter
Guests: up to 6 |Crew: 2 |Cabins: 3 |Showers: 3

XIMERA (pronounced Shimmerer) is a beautiful Hanse 575 that launched in 2014. Charter guests will embark on their sailing adventure in style and luxury. XIMERA is an ideal option for those who appreciate cruising in a high-performance sailing machine that is spacious and comfortable.  Ximera's Captain, William James Downing says, “I have sailed for over 40 years and am only truly at home in or on the water.” He always seems to have a sparkle in his eye, a few good jokes up his sleeve, some new stories and classic tales to share. Chef Michelle Weeks decided to take up sailing when she was 48 years old. She took a four-month, unpaid leave of absence and traveled to Gibraltar to take a 14 week Yachtmaster course. “I loved it” she said, “I went home and handed in my notice. I have been sailing professionally ever since! She met Capt. Will while they were working for the same company and together they taught sailing in Greece and Croatia. This past summer, while sailing XIMERA in the Balearics, Michelle had the honor of cooking for a Duke of Spain who was so impressed with her culinary skills he was ready to help finance her restaurant. But she prefers cooking at sea. 

RATES: $14,000 - $16,000


Not Finding the Right Yacht? Try YACHT SEARCH

This is a great tool for searching a worldwide inventory of charter yachts - whether you want a sailing yacht, a catamaran, a motor yacht, a mega yacht or a super yacht, you'll find it here!

A few things to keep in mind:

  1. All yachts look great on the web - find some you like, but then ask us for our expert and firsthand opinion about them. We know what the yachts look like from real life day to day experience,not just on the photo shoot. Want to know what the crew will be like when you are spending 24/7 together? We can help! 
  2. This is an industry search engine - for quality reasons, we may not recommend all of the yachts in your search results.
  3.  We have many more yachts available that are not featured here.


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