Luxury Boat Rentals & Private Charters near Chilmark, Massachusetts

This full-day private charter is built for small groups who want a seamless, elevated day on the water. Running 9 AM to 5 PM, the operator uses a 32' Pursuit DC with comfortable seating and a seasoned captain; the listing emphasizes a personalized itinerary around Cape and Islands sea lanes. The experience is private to your party, includes a cooler stocked with ice, water and soft drinks, and leaves pickup flexible from one of three locations. Expect expansive coastal views, quiet anchorages for a swim or picnic, and the ability to tailor stops—ideal for guests who prize privacy and a captain-led local route.

Practical notes: fuel surcharges are calculated at the end of the trip and gratuities are not included. The experience accommodates up to six guests and provides the vessel and professional crew; for longer-range crossings or special requests discuss routing and any temporary docking fees with the operator before you travel.

For energetic gatherings—family reunions, bachelor parties or milestone celebrations—this Nantucket-based group package packs high-intensity watersports into a three-hour session. The operator stages demos, safety briefings and coached runs for wakeboarding and eFoiling, with tubing for guests who prefer a lower-skill thrill. Packages scale by group size and equipment, enabling events from intimate groups up to larger parties with multiple boats and eFoils. The listing notes a 23% service fee on completion of the event and that pricing examples are provided by the operator; direct coordination with their booking manager will yield a tailored plan.

This format works best when you want action and variety in a compact window. Bring sun protection, towels and a light jacket if the wind picks up. The operator furnishes required equipment and coaches; confirm age minimums and exact inclusions at booking.

When your schedule calls for a concise but memorable coastal outing, the four-hour half-day charter delivers a concentrated taste of Martha’s Vineyard and the Elizabeth Islands. These cruises emphasize scenic runs, photo-ready anchorages and time for a swim or short shore stop. The operator runs the same 32' Pursuit DC used for longer trips, includes a professional captain, and supplies a cooler with beverages for comfort aboard. With a maximum of six passengers, the format keeps the outing intimate while still allowing guests to experience multiple turns of coastline in a single block of time.

Half-day options are a practical fit for travelers based in Chilmark who want to combine a morning at the beach or an afternoon winery visit with a short, polished boat excursion. Check with the operator about meeting-point choices and any fuel surcharges that may apply for longer routing beyond standard harbor limits.

Newport’s full-day charter offers a slightly shorter but still substantial private cruising day—seven hours of exclusive use with the freedom to BYOB and bring your own food. Soft drinks, ice and a cooler are typically provided by the operator; the operator also notes that charters are private and that standard charters include boat, fuel and captain’s fee, while some longer trips may incur additional fuel surcharges. The model suits guests who prefer to self-cater or who want the convenience of a single, consistent pickup point in Newport harbor.

If you’re connecting through Newport or prefer the area’s different nautical flavor, this charter gives you flexibility without sacrificing privacy: no outside guests are added, and the operator flags customary practices around transient dockage and gratuities so travelers can plan accordingly.

For travelers who want to graduate from passenger to competent helm, the ASA 101 basic keelboat course provides concentrated, hands-on instruction across a 15-hour weekend format (typically Friday–Sunday mornings). Completing the course equips students with foundational skills to helm a keelboat and makes many future private rentals more comfortable and independent. The operator lists a typical tuition and offers clear scheduling across consecutive mornings, making it an efficient way to add a credential to your travel skill set.

This option is particularly compelling for couples or small groups who plan multiple days on the water or who intend to charter self-skippered vessels in future trips. Confirm enrollment limits, exact meeting points and any prerequisites with the provider before booking; the course price is set per student by the operator.

This wakeboarding program is designed to deliver rapid progression in a single three-hour session, accommodating both beginners and more experienced riders. The operator runs single and double-group formats—up to six participants for single lessons and larger capacity for double sessions—and includes all required equipment. Instruction is tailored to the group's goals, from getting up on the board to learning to jump the wake or surf behind the boat, and the provider emphasizes family-friendly coaching.

For travelers based in Chilmark, a wake session on nearby Nantucket sound is an energetic counterpoint to calmer charter days. The experience recommends essentials—sunscreen, water and towels—and flags a service fee applied on event completion for certain package formats. Confirm exact participant limits and any additional fees at booking.