The Best Boat Rentals Near Martha's Vineyard

Most private captained outings on the island run about $200–$350 per hour for classic sailboats, $250–$400 per hour for center-console or fishing boats, and $500–$1,000+ per hour for larger motor yachts, with half-day trips often totaling $800–$1,500 and full-day trips $1,500–$3,000+. Fishing charters commonly advertise around $600–$900 for a half day and $1,200–$1,600 for a full day. Prices typically include the boat, captain, standard safety gear, and basic fuel for slower cruising; faster powerboat trips and specialty itineraries may add fuel surcharges, gratuity, or extras like catering. (getmyboat.com, menemshabluescharters.com, bassnblue.com, bassnblue.com)

You’ll find classic sailing yachts for scenic cruises, center consoles for fishing and exploring, and motor yachts for celebrations or longer day trips. These are the most common categories offered locally, so it’s easy to match the boat style to your group size and vibe.

Most visitors choose a captained trip so a local skipper handles navigation, anchoring, and weather calls while you relax. Self-operated (“bareboat”) options are more limited and typically require strong experience, plus the owner’s approval based on your boating background. If you’re unsure, request a captain—it's the lowest-stress path to a great day.

The most common departure points are Edgartown Harbor near North Wharf and the mooring field, Oak Bluffs Marina right in Oak Bluffs Harbor, Vineyard Haven (Tisbury) with access to Vineyard Haven Harbor and Lake Tashmoo, and Menemsha Harbor in Chilmark. Your captain will confirm the exact pickup spot based on the day’s wind and sea state. (edgartownharbor.com, oakbluffsma.gov, tisburyma.gov, chilmarkma.gov)

Expect postcard views of Edgartown Harbor Light and East Chop Light, the dramatic Gay Head (Aquinnah) Cliffs and lighthouse on the island’s western tip, and the wild barrier beaches and Cape Poge Light off Chappaquiddick. Many trips also swing by quiet coves, osprey nests, and working harbors like Menemsha for a classic Vineyard sunset. (mvmuseum.org, gayheadlight.org, thetrustees.org)

As of the 2025 season, adults are not yet required to hold a general Massachusetts boater safety certificate, but youth rules apply: ages 12–15 need an approved course to operate a motorboat without adult supervision, and PWC operation is restricted to ages 16–17 with a certificate. A new statewide requirement to carry a boater safety certificate for operating motorboats and PWCs begins April 1, 2026 (with phased deadlines), so captained trips remain the simplest option for most visitors.

Yes—family trips are very popular. Every charter carries U.S. Coast Guard–approved life jackets; Massachusetts law requires children under 12 to wear a PFD while above deck on a boat underway, and all passengers must have a properly fitted life jacket available. Let your captain know your child’s ages so the right sizes are ready when you board. (boat-ed.com, uscgboating.org)

Most private charters welcome BYO snacks and beverages, and many provide coolers with ice; lightweight, non-glass containers are preferred. Passengers of legal drinking age may enjoy beer or wine at the captain’s discretion, but the operator may not be under the influence—Massachusetts enforces strict boating under the influence laws. If you plan to celebrate with drinks, keep it moderate and follow your captain’s rules.

Many captains are pet-friendly on private trips if your dog is calm and you bring a canine life jacket and waste bags. Always ask in your booking message so your captain can confirm and prepare a safe spot on deck for your pup.

Your captain watches local marine forecasts and will reschedule or cancel if conditions are unsafe. On Getmyboat, weather-related changes follow each owner’s cancellation policy; most hosts try to rebook you or offer refunds when the forecast doesn’t allow a safe trip. If skies are gray but conditions are still safe, normal policies apply.

Absolutely. Private charters are a stress-free way to celebrate, and many boats can host small groups comfortably. Note that many U.S. charters operate under the Coast Guard’s “six-pack” rules, which cap uninspected passenger vessels at six paying guests; larger groups should request an inspected vessel early to ensure availability.

The peak boating season runs June through early September, with the warmest water in late July and August. Weekdays are less crowded, and mornings are usually smoother before the afternoon sea breeze builds. Holiday weekends—Memorial Day, July 4, and Labor Day—book up far in advance; popular local highlights include Edgartown’s July 4th parade and fireworks over the harbor, Oak Bluffs’ Grand Illumination Night and the town’s Fireworks in late August, the Vineyard Cup Regatta in mid-July, and the Martha’s Vineyard Agricultural Fair in late August. Shoulder-season September days are gorgeous and quieter, especially if you’re boating around the island during the Striped Bass & Bluefish Derby. (seatemperature.info, weatherspark.com, harborviewhotel.com, mvcma.org, oakbluffsma.gov, sailmv.org, marthasvineyardagriculturalsociety.org, gomarthasvineyard.com)

Mornings are typically favored for smoother seas and easier dock access, while afternoons can bring a steady southwest breeze that’s great for sailing but choppier for small powerboats. If you prefer calmer water for swimming or photos, choose a morning start; for lively sailing, plan for the afternoon wind.

Yes. Captained trips often include Chappaquiddick’s Cape Poge beaches and lighthouse, or a full-day cruise along the Elizabeth Islands to Cuttyhunk for raw bars and harbor walks. Your captain will time the route to tides and weather and can advise on moorings or short dock stops. (thetrustees.org, mvleisurecharters.com)