Capt. Sean Flynn

USCG 100 GRT NC Master
Aux Sail Endorsement
Towing Endorsement
STCW Medical Certificate
CPR and 1st Aid Certification
Marine Radio Operator
Radar Unlimited
PADI Dive Master

Sean began his sailing career in Sausalito, California where he bought a boat to live aboard. He was quickly in awe with the lifestyle and realized that he wanted to be in the boating industry. Sean went to the east coast to be a deckhand on the tall ship S/V Liberty Clipper doing week-long charters for up to 24 guests in the Bahamas. After completing that journey, his next position was as deckhand on George Patton’s sailing yacht, S/V When and If, where he sailed from Quebec to the Florida Keys. He was quickly offered a position as Captain due to his variety of skills, attentive care for the ship and crew, as well as his captivating presence with guests. While Sean remains the relief captain for When and If, he has continued his sailing career joining M/Y OLOH transiting through the ICW and east coast as well as joining the educational vessels S/V Adventuress and SSV Geronimo. Sean enjoys every experience he has on the water watching a sunset and spotting marine and wildlife. He is drawn to continue his career in the USVI and BVI for the unique diving excursions and the opportunity to sail in one of the world’s most beautiful locations.

Chef Elizabeth Gugino

Basic Life Support
Registered Yoga Teacher

Elizabeth grew up as a competitive swimmer inspired by the healing benefits of water. She moved to Florida to be by the ocean and to be near her grandmother who passed away shortly thereafter from Alzheimer’s disease. Elizabeth enriched her life in Florida by achieving success for eight years in a career helping people with cognitive impairments as well as providing guidance to caregivers. Her compassion led her down a path as an Eldercare Advocate to help people in the hospital to ensure a safe discharge with a focus on their quality of life. Elizabeth developed a weekly yoga and meditation program to help relieve stress and enhance memory stimulation for both patients and their caregivers. She also led multiple yoga classes in the community that focused on holding a calm and safe space for beginner to advanced practitioners. She is on the next chapter of her career and wishes to connect with people through sailing to incorporate similar healing benefits that yoga embodies. Not only does Elizabeth want to show people a fun and memorable experience, she will create nourishing meals to satisfy your taste buds and enhance your vacation.

Sean and Elizabeth met while visiting mutual friends in Michigan for the fourth of July holiday in 2017. Their worlds collided as Sean worked as crew on the historic sailing yacht , When and If, making stops along the eastern coast of the United States in areas where Elizabeth coincidentally had travel plans to visit friends and family. Their connection was immediate, and while Sean's home base during the winter was Key West and Elizabeth lived in Jacksonville, Florida, they committed to traveling the distance to be together. When Sean joined the crew of the schooner Adventuress in Port Townsend, Washington, they were determined to make their long distance relationship work even though they would now be living in the most Northwestern and Southeastern regions of the United States. They spent vacations together on the west coast sailing and hiking around the Puget Sound, Vancouver and San Francisco. Both of them constantly curious and craving adventure, their relationship blossomed not over coffee and dinner dates, but by the trips they planned together to Paris, Rwanda, Uganda, and most recently the US and British Virgin Islands. Although every trip has been life changing for them, they felt a strong connection to the USVI and BVI while sailing there.

Sean's extensive sailing experience on vessels traversing the Atlantic, Pacific, Caribbean and Gulf of Mexico, his reputation as a beloved captain and crew mate, and his dedication to exploring and preserving the beautiful ecology of the oceans combined with Elizabeth's passion for creating holistic, zen experiences, her skill in hosting and her attention to detail make them the perfect captain and crew to share an incredible adventure with. You'll find them easy going with a great sense of humor, easy to talk to and dedicated to your experience.

Sean grew up in Arkansas with a passion for environmental science and navigating the local waterways in his small boat. Elizabeth grew up in Connecticut, turning her passion for nurturing into a successful career in social services. She's a foodie and believes food feeds both body and soul. As a talented yoga instructor she shares her passion for and love of this ancient spiritual, physical, and mental discipline. They now live in Orlando and continue to travel around the United States, Europe and the Caribbean.


Type Catamaran
Year Built2014
Size45.00 Ft
Beam27 Feet
Draft5 Feet

Boat Details

Cabins: 3
Queen: 3
Single Cabins: 1
Showers: -
Wash Basins: 3
Heads: -
Electric Heads: -

Pick Up Locations

Pref. Pick-up: -
Other Pick-up: -


Refit: -
Helipad: -
Jacuzzi: -
A/C: Full

Engine Details

Dual Yanmar 54hp's keep this baby cruising! ONAN 13kw keeps this baby charged up and cooled down!
Fuel Consumption: -
Cruising Speed: -
Max Speed: -


Winter Area: Caribbean Virgin Islands, Caribbean Leewards, Caribbean Windwards
Summer Area: Caribbean Virgin Islands, Caribbean Leewards, Caribbean Windwards


Salon Tv/VCR: -
Salon Stereo: -
Sat Tv: -
# of Videos: -
# DVDs/Movies: -
# CD's: -
Camcorder: -
Books: -
Board Games: -
Sun Awning: -
Deck Shower: Yes
Bimini: -
Water Maker: -
Special Diets: -
Kosher: -
BBQ: -
# Dine In: -
Minimum Age: -
Generator: -
Inverter: -
Voltages: -
Water Maker: -
Water Cap: -
Ice Maker: -
Sailing Instructions: -
Internet Access: Onboard WIFI
Gay Charters: -
Nude: -
Hairdryers: -
# Port Hatches: -
Guests Smokes: -
Crew Smokes: -
Pets Aboard: -
Pet Type: -
Guest Pets: -
Children Ok: -
Hammock: -
Windscoops: -

Water Sports

Dinghy size: -
Dinghy hp: -
Dinghy # pax: -
Water Skis Adult: -
Water Skis Kids: -
Jet Skis: -
Wave Runners: -
Kneeboard: -
Windsurfer: -
Snorkel Gear: -
Tube: -
Scurfer: -
Wake Board: -
Kayaks 1 Pax: -
Kayaks (2 Pax): -
Floating Mats: -
Swim Platform: -
Boarding Ladder (Loc/Type): -
Sailing Dinghy: -
Beach Games: -
Fishing Gear: -
Gear Type: -
Rods: -

Scuba Diving Details

Crew License Resort Course Full Course
- - -
Divers - Tanks - BCs - Regulators - Dive Lights -
Air Compressor - Wet Suits - Weight Sets - Dives/wk - Night Dives -
General Diving Info
Diving Costs information


Designed by Chef Elizabeth




Citrus and goat cheese stuffed crepes & Fresh pressed celery juice

Greek yogurt parfait with avocado toast and smoked trout

Melon and berries with homemade granola

Omelettes with crispy potatoes and peppers

Chilled overnight soaked oats with homemade almond milk

Wake up smoothie with blue cheese and mushroom frittata

Sweet potato pancakes with bacon cheddar deviled eggs

Poached eggs and sprouts on top of toast with melted cheddar





Cayenne-rubbed chicken with avocado salsa

Burrata, melon and prosciutto salad

Kale salad, honey mustard glazed turkey burgers and pineapple

Superfood salad with tuna and lemon yogurt dressing

Barbecue coated chicken with simple green salad

Green bean, tomato, corn salad with fresh feta

Baked falafel sandwiches topped with tzatziki sauce





Skirt steak fajitas with jalapeño cilantro salsa and sour cream

Salmon with a lemon mint crust

Zucchini and yellow squash gratin

Hamburgers topped with melted cheese,  roasted tomato, and fried onions

Rosemary meatballs and spaghetti

Chicken and basil stir fry

Butternut squash risotto with ricotta and tomatoes





Red wine lava chocolate cakes

Cinnamon crunch strudel with caramel and chocolate ganache

Ginger spiced chocolate cupcakes with a vanilla icing and coconut dusted fruit

Baked apple empanadas with cinnamon and molasses

Orange soufflé with a blackberry drizzle

Broiled apricots with fresh ginger whipped cream

Lemony butter cookies


2 Pax 3 Pax 4 Pax 5 Pax 6 Pax
Winter 2020 to 2021 $14,500 $15,250 $16,000 $16,750 $17,500
Summer 2021 $14,500 $15,250 $16,000 $16,750 $17,500
Winter 2021 to 2022 $14,500 $15,250 $16,000 $16,750 $17,500
Summer 2022 $14,500 $15,250 $16,000 $16,750 $17,500
Cruising Permits, Fees, and Taxes to be paid by the Charterer upon entry to Cruising Grounds or Ports for all locations.
Please inquire about rates and customary fees.

*6 Night Minimum* Inquire for short charters.


Christmas Flat Rate $20,000 St Thomas pick up and drop off. 7 night minimum. Charter must end on or before 12/26/2019
New Years Flat Rate $21,000 St Thomas pick up. 7 night minimum. Charter must start no earlier than 12/27/2019

Christmas Flat Rate $20,000 St Thomas pick up and drop off. 7 night minimum. Charter must end on or before 12/26/2019
New Years Flat Rate $21,000 St Thomas pick up. 7 night minimum. Charter must start no earlier than 12/27/2019

(7/4/3 BREAKFAST/LUNCH/DINNER): $150 off / person

***3 lunches and 4 dinners ashore at client expense*** 

***Does not combine with child discounts***

$250 off for each child age 15 and under. 
***Does not combine with half board options***

***Age is based on the charter date NOT the date of booking***

***Max discount - 4 children***

(Rate / 6 X #Nights)

***(Rate divided by 6N X number of nights*** For 6 nights divide rate by 7 X 6N.

$1,000 Sleep aboard the night before the charter departs
Guests arrive to the yacht at 5pm. Snacks and welcome drink served, this is not an open bar. Dinner is ashore on clients expense. Continental breakfast provided next morning. Vessel departs at noon.
Rate $15,000 plus all expenses
Includes: Captain, Linens/Towels, Dishes, Flatware, Cooking Utensils/Cookware, Toys

Not Included: Fuel, Water, Customs/Immigrations, Food/Liquor/Ice/Trash Disposal, Mooring/Dock Fees, *Diving, Gratuity

*Diving can be arranged
Provisioning can be arranged
MCA Compliant
All Inclusive.Cruising Permit: Paid by BoatLicenses: Paid by Boat

(15 December -30 April)
Caribbean Virgin Islands, Caribbean Leewards, Caribbean Windwards
(1 May - 14 December)
Caribbean Virgin Islands, Caribbean Leewards, Caribbean Windwards


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Great Adventure Catamaran

Great Adventure:

$1,000 off charters 6 nights or more
Valid for charters starting in November 2020, December 2020 and January 2021
Not including Christmas or New Years
Expires January 31st, 2021
New Charters Only

Check out our video on Great Adventure Catamaran