PORT TO VINO Samana 59 CY

Jeff and Caitlin have been working together since they met on the job at a dive shop in coastal North Carolina in 2010. Employment opportunities have taken them around the globe and back, settling in the BVI in 2012. They transitioned to crewed sailing charters from running dive boats in 2014 and haven’t looked back, logging over 150 charters with many happy guests who often return to make more memories. Their specialty is active, adventurous groups who want to explore all that the BVI has to offer above and below the water and love introducing kids to the ocean, so bring on the families! The BVI has been home for Jeff and Caitlin for many years but will always hold a special place as it’s where they were married on a beach in Virgin Gorda.

Captain Jeff holds a USCG 200 ton Near-Coastal Masters license and has been operating boats commercially for over 15 years. Hailing from Mississippi, Jeff cultivated his love for boats and the water in his adult life and can’t imagine doing anything else. He is originally trained as a high level dive instructor and naturally progressed to earning a captain’s license to operate the boats he’d previously worked on as crew. Running crewed charters allows for a more relaxed pace and the ability to tailor charters to each guest’s preferences, something that was more difficult to accomplish on dive boats. Jeff is a wealth of knowledge about the BVI, so make sure you listen in for “story time with Captain Jeff” while on charter.

Chef Caitlin also comes to chartering from a professional diving and marine research background but has been cooking since she was a small child and has the photos to prove it. She grew up in Pennsylvania and spent her formative years in the kitchen with her mom and Italian grandmother. Most of her menu items are cultivated through family recipes and world travels, bolstered by training at Ashburton Chefs Academy. She loves incorporating fresh, local ingredients with Mediterranean and Asian influences. Virtually everything Caitlin cooks is assembled from scratch, including an assortment of breads and pastas. She’s happy to accommodate a range of allergies and specialty diets. When her schedule allows, Caitlin loves getting in the water for guided snorkel tours with the guests, dusting off her marine science degree to talk about fish behavior and biology.
In the off season, Jeff and Caitlin spend time in the mountains of Western North Carolina where Jeff enjoys riding his motorcycle through all the twisting, scenic roads and Caitlin spends time volunteering at the local animal shelter. No better way to recharge after a busy charter season than with mountain views, crisp air, and not a large body of water in sight. They’re not able to have a dog on board during the charter season, so they “rent” as many as possible through the foster program at the shelter and take them out camping and hiking as frequently as they can!
Jeff and Caitlin are fully vaccinated for Covid-19.

Start date: Apr 12, 2024, End date: Apr 28, 2024 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: May 02, 2024, End date: May 09, 2024 - Booked: Tortola - Nanny Cay to Tortola - Nanny Cay

Start date: May 11, 2024, End date: May 18, 2024 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: May 24, 2024, End date: Jun 01, 2024 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Jun 05, 2024, End date: Jun 12, 2024 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Jun 15, 2024, End date: Jun 21, 2024 - Hold: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Jun 23, 2024, End date: Jun 30, 2024 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Jul 06, 2024, End date: Oct 25, 2024 - Unavailable: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Nov 03, 2024, End date: Nov 09, 2024 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Nov 16, 2024, End date: Nov 23, 2024 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Dec 02, 2024, End date: Dec 18, 2024 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Dec 20, 2024, End date: Dec 27, 2024 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Dec 28, 2024, End date: Jan 04, 2025 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Jan 06, 2025, End date: Jan 13, 2025 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Jan 18, 2025, End date: Jan 25, 2025 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Jan 29, 2025, End date: Feb 04, 2025 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Feb 07, 2025, End date: Feb 23, 2025 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Feb 26, 2025, End date: Mar 05, 2025 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Mar 15, 2025, End date: Mar 20, 2025 - Hold: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Mar 21, 2025, End date: Apr 06, 2025 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Apr 22, 2025, End date: Apr 30, 2025 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: May 04, 2025, End date: May 10, 2025 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: May 24, 2025, End date: May 31, 2025 - Hold: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI

Start date: Dec 03, 2025, End date: Dec 17, 2025 - Booked: Tortola, Nanny Cay, BVI to Tortola, Nanny Cay, BVI