Frequently Asked Questions

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Boats are typically 45’ – 55’ late model monohulls—sloops—with a sleeping capacity of 8 - 12. We charter from reputable charter companies. See the photo Gallery for typical examples.

We typically spend each night at a different harbor. We depart each morning with breakfast and lunch onboard and sail to the next destination. There is no open ocean sailing or night sailing—we are required to be moored or docked before sunset. While sailing between islands we will always be in sight of land. After mooring, you will be free to swim, snorkel, relax, or explore the islands. Scuba diving can be arranged. We usually go ashore for dinner, but you are free to have dinner onboard, if you prefer. The actual itinerary will depend on the preferences of the crewmembers.

The cost of the boat is split amongst crewmembers and typically varies from $1,000 to $1,500, per week, depending on the boat, the number of crewmembers, the location, the season and other factors. See Crewmembers and Organizer/Skipper below for cost sharing information. Travel, provisioning for breakfast and lunch aboard, dinners ashore, moorings, fuel, etc. are personal expenses—see below. It’s a vacation for less than the cost of a hotel. All payments should be to the trip Organizer, preferably via PayPal. 

CAUTION:To avoid fees, when paying via PayPal, be sure 1) the funds come from a bank account and 2) select paying to Friends and Family.

Your participation is reserved when we receive your deposit. Payments are fully refundable before the boat is booked. Once the Organizer has a charter contract in hand, payments are nonrefundable. In case of cancellation, it is each person’s responsibility to find a replacement crewmember to receive a refund. In such case we would attempt to secure a replacement crewmember, but we cannot guarantee success. The Organizer has full discretion in selecting crewmembers.

Do not make travel arrangements until notified by the Organizer that a signed charter agreement has been executed. It is best to wait until the Organizer gives the go-ahead before booking flights.

Crewmembers should consider purchasing trip insurance for unforeseen events. Some providers: www.insubuy.com, www.insuremytrip.com, www.allianztravelinsurance.comor www.travelguard.com.

Food, drinks, cleaning and kitchen supplies. The list of food and drink items and quantities will be determined based on crewmembers’ preferences. On the day of arrival, we will shop together for provisioning. Budget approximately $150/week for provisioning and incidentals.

There are many tips online for what to pack for a sailing trip. A soft duffel bag or a backpack is preferred. Avoid suitcases. Some items to consider: passport, sunscreen, sunglasses, hats, swim suits, shorts, tee-shirts, a light jacket, boat shoes, wet shoes and a few Ziploc bags or a waterproof dry bag. If you think you may suffer from sea sickness, medication is advised. Don’t forget sunscreen! Pack light—it’s casual dress.

Snorkeling gear is usually provided on the boat and there will be opportunities to snorkel. Crewmembers may arrange to scuba dive individually but must do so in coordination with the Organizer.

The estimated cost is based on having some double occupancies—more crewmembers, lower cost per person. Singles may cost more per person. TBD during booking.

Everyone engaged by the Organizer is a crewmember. During the trip, in recognition of the fact that we will be together 24/7 in a relatively confined space, each crewmember will be expected to bring his/her positive energy and spirit and pitch in with food preparation, dishwashing and tidiness of the common areas.

Sailing experience is not required, but the assumption is that there is willingness to learn and help with raising sails, mooring, docking, tacking, jibing. Crewmembers are encouraged to share the helm and to participate in the sailing experience. Newbies are especially encouraged to look upon the trip as a learning experience. See YouTube videos for basic training.

The Organizer/Skipper (as distinct from crewmembers) is uncompensated—he gets to go sailing for his considerable efforts and expense in arranging these excursions. The Skipper is in charge and is responsible for the safety of the boat. The Skipper makes all decisions in relation to the boat, sailing route and navigation based on the weather and other local conditions, in collaboration with crewmembers. We always include at least one experienced crewmember as a backup. Safety first—everything else comes next.

Organizer/Skipper Ed Thompson has been sailing for decades and is experienced on sloop-rigged, auxiliary powered sailboats up to 55 ft. He has chartered in the BVI, Newport, RI, Long Island Sound and the Mediterranean. Ed is American Sailing Association 101, 103, 104 and 105 certified, which includes instruction in inland/coastal waters in moderate/heavy winds and sea conditions, provisioning, boat systems, auxiliary engines, advanced sail trim, coastal navigation, anchoring/mooring, docking, emergency operations, weather, and more.

Crewmembers participate at their own risk. As in any sport, there is the possibility of incurring bodily harm. The Skipper is responsible for the boat. Crewmembers are responsible for their own safety. This is not a commercial venture. It should be thought of as joining with friends on a cost-sharing basis. By participating, crewmembers agree to hold the Organizer/Skipper harmless for loss or injury. You must sign and return to the Organizer a waiver of liability.

All charter companies require the Organizer to provide a credit card guarantee against the deductible amount for hull insurance. Your exposure is limited. Refer to the liability waiver.

1) Fly direct to EIS (Tortola) from Miami (MIA) on American Airlines.

2) Fly to St. Thomas, US Virgin Islands (STT) and take the Road Town Fast Ferry to Road Town, BVI.

3) Fly to San Juan, Puerto Rico (SJU) with a connection to Beef Island (EIS), Tortola. Hint: Book a round-trip to SJU and a second round-trip SJU to EIS. It costs less than a single RT ticket.

There will be a safety review before departure. Every crewmember is required to observe the rules. Those who are uncomfortable with their swimming skills should so indicate.

Certain things are not allowed: consumption of alcoholic beverages while underway, smoking onboard and drugs. Drug usage will be reported to the appropriate authorities, with offenders disembarked.