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Quick Details

From :
$ 23,333


This elegant 58’ Leopard catamaran offers the best in large open decks and spaces for lounging, including a comfortable indoor salon, a breeze-filled fly-bridge with a dance floor and seating for 12, and the fun forward netted space to experience sailing firsthand in the day and star gazing at night. All 3 guest staterooms include en-suite bathrooms, air conditioning, and everything you would need to create sailing memories with families and friends. Guests will never forget their charter experience on Leeway!

TOYS: 5 x 10′ Floating Dock, Towable Tube, 2 Sea Scooters, e-Foil, 2 Stand Up Paddle Boards, Snorkeling Gear, (1) 2-Person Kayak, Subwing, 2 Fishing Rods, Yoga Mats, Onshore games

DIVING: Offered onboard at $65/per person per day dive, $90/per person per night dive. Gear not included.

TURN AROUND TIME: We prefer 48 hours in between charter drop off and pick ups, but feel free to inquire for 24. We will do our best to accommodate.

CRUISING GROUNDS: British Virgin Islands & U.S. Virgin Islands. BVI customs & cruising permit fees are included in the rate.


*To book a charter we have a 5-night minimum, but feel free to inquire for less.


Includes 7 breakfasts, 7 lunches and 7 dinners, happy hour canapes, standard ships bar and snacks. Meals ashore are additional.

2@$28,000 |

3@$28,500 |

4@$29,000 |

5@$29,500 |



7 night minimum

Full-board option only

Guests: 1-6 @ $37,500

Must end on or before 12/27

Please contact us for more information.


7 night minimum

Full-board option only

Guests: 1-6 @ $40,000

May not start prior to 12/28

Please contact us for more information.


Sleep aboard the night before charter dates. Available for half of the daily rate. Includes boarding after 4pm, snacks, welcome cocktails & continental breakfast. Dinner ashore is additional. Select option upon booking.

EXCLUDES: Christmas and New Year’s weeks.


Enjoy all that this yacht has to offer with a detailed and guided walkthrough of the vessel and a ‘float around’ video of the exterior.



Rob Hyson

Captain Rob Hyson was born and raised in a small coastal town in Maine and as such spent a large portion of his youth on the water, on small fishing boats sailing schooners and everything in between. After graduation high school Rob served in the US Marine Corps as a presidential guard in Washington DC and at Camp David. Soon after ending his service in the Marine corps Rob moved to The Great Lakes area where his love for sailing was born. When Rob moved to his home state of Maine again he bought, and completely refit a Pearson sailing yacht and sailed her all over the New England coast until he decided to find warmer weather and sailed south the the US Virgin Islands. Where he cruised for a year before deciding to turn his love for the ocean and sailing into a career. Now Rob spends his days on the water and even gets paid to do it. He is truly happy to be “living the dream”!

a man wearing a blue shirt
a person smiling for the camera

Jody Oles

Chef Jody is a native Californian, but has loved chartering in the islands for the last 17 years. She holds a US Coast Guard Masters License, and is a PADI Scuba Instructor, as well as an accomplished charter chef. Her passion for beautiful food equals her passion for the ocean. Before moving to the islands, Jody was an educator for several zoos and aquariums on each coast. She fell in love with the Caribbean waters working as an Aquarist at Coral World Marine park in St Thomas. Her knowledge of marine life gives her guests an experience they won’t forget! From the galley, her fresh breads, pastries, decadent desserts, and everything in between will present you with an array of goodies to tempt your taste buds. Her culinary style incorporates fresh local ingredients with culinary favorites for amazing meals that guests love. Her greatest pleasure is your smile of satisfaction!


 Jody can adapt the menu to any dietary need or allergy. 

Dietary restrictions are always considered.

Standard Ships Bar

Soft drinks, sodas, water, beers and well drinks, cocktails are available for your enjoyment.

Vodka brands: Tito’s, Stoli, Smirnoff
Whiskey brands: Johnny Walker, Dewars, Jack Daniels
Tequila brands: Souza, Milagro
Rum brand: Cruzan
Gin brands: Gordans, Tanqueray
Assortment of liqueurs.

Red and White Wines
Pino Grigio, Sauvignon Blanc, Chardonnay, Cabernet Sauvignon, Red Blend, Pinot Noir, Proseco

Bud, Coors, Corona, Miller, Caribe, Presidente

Please let your broker know your preferred brand.

If you require premium wines or spirits of your choice, please notify your broker and we will be happy to source it for you and have them onboard when you arrive.
These would be at an additional cost to you.


Dessert is served with coffee, wine, or liqueur of your choice.

Key Lime Pie Parfait with Lime Zest and Fresh Whipped Cream

Sticky Toffee Pudding with Warm Toffee Sauce and Fresh Whipped Cream

Poached Pears with a Vanilla Rum Sabayon garnished with Cinnamon Infused Chocolate “Leaves”

Rich Chocolate Mousse with Fresh Whipped Cream and Shaved Chocolate

Hot Grand Marnier Souffles with Powdered Sugar

Chocolate Cheesecake with Caramel Sauce, Melted Chocolate and Fresh Whipped Cream

Fourless Chocolate Torte served with Fresh Berries and Vanilla Ice Cream


Dinner is served with a specialty selected wine, cocktail, or drink of your choice


Caprese Salad with Burrata, Nectarines, and Heirloom Tomatoes

Asian Styled Steak Salad over Local Greens

Watermelon, Feta, and Mint Salad with a Lime Vinaigrette

Cream of Brie Soup with Crumbled Bacon and Fresh Chives

Homemade Crab Cake with Two Sauces, served over Mesculan Greens

Roasted Garlic Bisque with a Toasted Fresh Baguette Slice


Marinated and Grilled Pork Tenderloin served with a Merlot Mushroom Sauce, Potato Au Gratin Timbales, and Sauteed Asparagus

Jumbo Shrimp Scampi served over Angel Hair Pasta with Fresh Shaved Parmesan, served with Savory Herbed Beer Bread

Crab, Parmesan, and Herb Crusted Grouper served with a Wild Rice Blend and Roasted Vegetable Medley

Hand Cut Filet Mignon grilled and drizzled with Demi Glace, served with Mushroom Risotto and Roasted Vegetables

Cajun Spiced Red Snapper served over Zoodles in a Lemon Butter Sauce, and Seasoned Rice

Spinach and Mushroom Lasagna Rotini smothered in Homemade Marina with shaved Parmesan and Fresh Basil

Red Wine Braised Beef Short Ribs with Creamed Potatoes and Rosemary Brussel Sprouts

Hors d' Oeuvres

Served with wine, your favorite cocktail, or the special cocktail of the day

Warm Spinach and Artichoke Dip served with Tortilla Chips and Herbed Crackers

Tomato Bruchetta on Fresh French Bread Toasts with Mozzarella Cheese and Local Basil

Local Conch Ceviche with Mango and Peppers, served with Crudites and Lettuce Wraps

Mediterranean Platter with Fresh Made Hummus, Tzatziki, Pita Toasts, Fresh Vegetables, and a Feta/Olive Spread

Mini Lobster Cakes with a Creole Tartar Sauce

Ahi Tuna Nachos with fresh Wonton Crisps, Wasabi Aioli, and a Seaweed Salad

Baked Crab Stuffed Mushrooms with a drizzle of Warm Garlic Butter


Lunch is served with beer, wine, or favorite drink of your choice. Fresh made brownies or cookies are available for dessert.

Margarita Chicken Salad with Tropical Fruit and a Margarita-style dressing, served with a pitcher of Jody’s Margaritas

Build-Your-Own Blackened Mahi Mahi Tacos with Pineapple Salsa, Kicked Up Rice and a Cool and Creamy Avocado Sauce with Corn or Flour Tortillas

Loaded Beef or Chicken Taco Salad served in Handmade Tortilla Bowls with Chips, Salsa Roja and Guacamole

Ahi Tuna Nicoise Salad served on Fresh Local Greens with Fingerling Potatoes and a House Made French Vinaigrette

Blackened Jumbo Shrimp over a Greek Salad with Local Greens, served with fresh made Hummus and Pita Points

The Great State of California Chicken Sandwiches served Mile High with Swiss Cheese, Bacon, Avocado, Lettuce and Tomato and a Creamy Mustard Sauce on Brioche Rolls, with House Made Slaw


Breakfast is served with fresh fruit, yogurt, granola, cereal, coffee or tea, and juice of your choice. For the adventurous, Mimosas and Jody’s Famous Bloody Marys are available.

Fluffy Buttermilk Pancakes with real Maple Syrup or Jody’s Homemade Syrup, served with Crispy Bacon

Chef’s Choice Eggs Benedict with House Made Hollandaise Sauce
(examples : Southwestern, Traditional, Seafood, Florentine)

Ham, Havarti and Thyme Quiche with Toasted English Muffins and Homemade Jam

Rise N’ Shine Breakfast Sandwiches on a large, flaky Croissant with your choice of fillings

Large New York Style Bagels with Herbed Cream Cheese, Smoked Salmon and Capers, served with Tomato and Onion slices

Thick Sliced Praline Pecan French Toast garnished with Orange Zest and Confectioner’s Sugar

Three Cheese Italian Baked Eggs with Grilled House Made French Bread


April 2023

Captain Troy and Chef Jody are a great team and made sure every wish came true and then some. The sailing upon the Black Tortuga was extraordinary. Captain Troy knew just where to go and what cay or cove to anchor for the night. WE all had the time of our lives from the first night with a camp fire on the beach to the last night singing our hearts out to Kenny Chesney and pointing to his house .Limeout and the pizza boat all added to the fun.Chef Jodi ‘s incredible meals were second to none from breakfast to lunch and dinner all superb and delicious!

March 2023

Dear Troy and Jodi - The word that all eight of us consistently used this week was "epic". And it was truly epic - gorgeous daytime sails, colorful snorkeling and scuba, paddle boarding, making the whole days of a 60th birthday extra special, a midnight paddle board trip to a beach bonfire, and saving a lobster tail shell for a second grade ocean lesson. All wrapped up in Jodi's phenomenal food and for Troys fascinating ocean knowledge. Thanks doesn't cut it -it was epic!

February 2023

We can't thank you enough for such a lovely week. Private cruising with fabulous snorkeling, super fun sailing, kayaking, - the list goes on and to keep us going for all our adventures. Chef Jodi's food was outstanding! Thank you for accommodating all our different tastes and wowing us at every delicious meal. Such gracious hosts. Happy sailing!

February 2023

Dear Troy and Jodi, thank you for such an awesome trip! Traveling with multiple sclerosis is challenging and get pretty anxious and a bit scared, but you guys ensured I had nothing to worry about. The swim platform and donut were game changers! You were always ready to lend a hand, help me and always with a smile. You are the best team ever! Jodi, you meals were fabulous! Thanks for everything, you guys rock!

January 2023

Words can't even begin to describe the fun and amazing memories that we made on this trip. We truly had the best time. The food was awesome and so were all of the stops along the way. We will be back! Thank you so much for hospitality! Bill and Colleen Biggs

January 2023

Thank you for the most amazing vacation we've ever experienced. We will cherish these memories forever. Your kindness, hospitality, and knowledge truly made this a “Dream Vacation”!

January 2023

This was truly a trip of a lifetime. We've been dreaming of doing this for a long time and it was better than we ever imagined! Thank you Jodi and Troy for such an amazing experience! You guys are the best!

December 2022

Thank you Troy and Jody for a week we will never forget and hope to recreate again and again. The food, the itinerary, the music, the weather and the company were absolutely perfect! Much love, until next time!

November 2022

The best family time!! A fabulous experience for all of us. Exceeded all expectations. Jodi and Troy were the perfect personalities for their positions as chef and captain..and everything in between: tour guides, foodie advice, card players, and game hosts. We'll never be able to top this adventure and hospitality. Will miss you - your memories are the best of possessions and you have given us a 2022 Christmas trees' north. Thank you, Mark.