There are five ferries that come to Oak Bluffs from different destinations: Steamship Authority, Island Queen, Martha’s Vineyard Fast Ferry, Hyline Cruises, and New England Fast Ferry Company

• Steamship Authority, Woods Hole MA, +1 508 477-8600. This is the main public car and passenger ferry between Martha's Vineyard and the mainland at Woods Hole. Round trip ticket prices: adults $16, children (age 5-12) $8.50, bikes/surfboards/windsurfers $8. Round-trip fare for cars ranges from $85 to $135 depending on season (to bring your car, be sure to book in advance). Operates year-round between Woods Hole and neighboring Vineyard Haven, but from May-Oct about half the scheduled routes are between Woods Hole and Oak Bluffs. The trip takes about 45 minutes one-way.
• Island Queen, 75 Falmouth Heights Rd, Falmouth MA, ☏ +1 508 548-4800, info@islandqueen.com. This ferry is a seasonal passenger that makes frequent trips between Falmouth (Massachusetts) and Oak Bluffs. Round trip ticket prices: adults $18, children $9, bikes $6 round trip (all include an additional $1 round trip fee). In operation from May to Oct (exact dates differ each year). The trip takes about 40 minutes one-way. 
• Rhode Island Martha’s Vineyard Fast Ferry, Quonset Point, North Kingstown, RI, info@vineyardfastferry.com, +1 401 295-4040. This ferry operates from May-Oct (exact dates vary). It takes trips from Quonset Point in North Kingstown (8 minutes from interstate 95) to Oak Bluffs. Dockside parking is $10 a day. Round trip ticket prices: $75 adults, $52 children (4-12), $6 infants (3 and under), $70 seniors, $12 bikes and surfboards, and $14 bike with trailer.
• Hyline Cruises, 220 Ocean St, Hyannis MA, +1 508 693-0112. This ferry has year round operation (with the exception of Christmas) of high speed and traditional ferries from Hyannis, MA to Oak Bluffs. There is another high speed ferry which travels from Nantucket to Oak Bluffs under the same company from mid-Jun-mid-Sept. Parking is $17 in-season. Round trip ticket prices: $69 adults, $48 children (age 5-12), free for children under 4, and $12 bikes.
• New England Fast Ferry Company^{[dead link]}, 49 State Pier, New Bedford MA, +1-866-453-6800. This ferry operates daily from May-Oct (exact dates vary yearly) from State Pier, New Bedford to Oak Bluffs. Round trip ticket prices: $70 adults, $40 children (3-12 years old), free trip for children under 3, $62 seniors, and $12 bikes.

Oak Bluffs is compact and you can easily walk off the ferry and spend the day on foot exploring the town or visiting the beach.

• Martha's Vineyard Regional Transit Authority (aka VTA), 11A Street, Airport Business Park, Edgartown, MA. +1 508 693-9440. This public transit system operates buses island-wide year round. One-way fares are $1 per town, including town of origin. Discounts are available in the form of 1-day, 3-day, 7-day, or longer passes. All VTA vehicles are handicap accessible.
• MV Tours operates private sightseeing bus tours.

Van-sized taxis are ubiquitous on Martha's Vineyard. There are taxi stands in Oak Bluffs near the Steamship Authority dock and near the base of Circuit Ave by the harbor. When picking up passengers from a ferry, the drivers will often group several parties going the same direction into one vehicle. Fares for parties of 1-2 people may range from $7 in-town, to as much as $75 to go from one end of the island to the other.

• AAA Island Auto Rental, 31 Circuit Ave (across from Island Queen and RI Fast Ferry Dock). +1 508 693-0011 or +1-800-696-0233. This auto rental has been in business for over 12 years. They rent Jeeps, convertibles, SUVs, and minivans (economy through full-size vehicles) for daily, weekly, or longer durations. They accept MasterCard, Visa, AMEX, and Discovercard and take reservations for vehicles.
• Budget Car Rental, 12 Circuit Ave, +1 508 693-1911 or +1-800-527-0700. This car rental has economy through full-sized vehicles with free customer pick-up from most locations on the island. Most major credit cards, such as MasterCard, Visa, and Discovercard, are accepted.

Most ferries to the island will let you bring your bicycle for an extra charge. There are several moped/scooter rental shops in town.

• Anderson’s Bike Rentals, Circuit Ave (between the Hy-line and Island Queen Ferry dockings), ☏ +1 508-693-9346. An excellent bike shop for its supply of rentable bikes, bike repairs, and bike sales. The shop is open from 8 AM–6PM daily from April 1-October 31.
• Sun 'N Fun Bike Rental, Lake Av., Oak Bluffs, ☏ +1 508-693-5457.
• King's Rental, Inc., for Mmpeds. Circuit Av. ☏ +1 508-693-1887.
• Vineyard Bike & Moped, Oak Bluffs Av. ☏ +1 508-693-6886.
• Vineyard Pedicab ^{[dead link]}, +1 978 270-6150. Rides are free. Profits donated to charity. Drivers work for tips. Also available for tours. Open Memorial Day through Columbus Day: noon-1AM.

• Pecoy Point Preserve, Pecoy Point (located off of County Road via Pulpit Rock Road). There are 14 acres of trails that can be accessed by car (6 parking spaces), foot, or bike. Trails include marshes, woodlands, and shoreline. Free to public.
• Farm Pond Preserve, Beach Road (before Hart Haven going towards Edgartown). Open all year, every day. Access this preserve by car, foot, or bike and enjoy 27 acres of marshlands and woodlands trails which all connect to Tradewind Field Preserve. Free to public.

The beaches in Oak Bluffs face into Vineyard Sound and usually have very minimal surf. This makes the water ideal for swimming, and for wading by small children. For real ocean waves on Martha's Vineyard, you need to visit beaches along the southern shore of the island, in Edgartown, West Tisbury, Chilmark or Aquinnah.

• Oak Bluffs Town Beach, Sea View Ave (runs along the eastern shore of the town between the harbor and the Farm Pond; adjacent to Steamship Authority dock and Ocean Park).
• The Inkwell, Sea View Ave (southernmost section of Oak Bluffs Town Beach, across from Waban Park). This historic traditionally African-American beach is today frequented by a diverse crowd.
• East Chop Beach, East Chop Drive (located west of Oak Bluffs harbor entrance). Open all year, every day from dawn to dusk. This beach has great views of Nantucket Sound and all of the boating activity in the area. Free to public.
• Joseph Silvia Beach, known locally as "State Beach", located from the first bridge after Hart Haven to the Edgartown town line. Open all year, every day from dawn to dusk to the public. Accessible by bike, car, bus, or foot. This beach is ideal for windsurfing and shell fishing (which is allowed by special permit only from the town hall on School Street). Free to public.

• Martha’s Vineyard Camp Meeting Association Tours, located at the Tabernacle, +1 508 693-0525, Tu or Th at 10AM in July and August. Take tours of the MVCMA grounds for approximately 1 ½ -2 hours and listen as they describe MSCMA’s historical background. Private tours can be arranged. Adults $10 and children under 12 are free, both include a free pass to the Cottage Museum.
• Martha’s Vineyard Sightseeing, Circuit Ave (behind Mad Martha’s Ice Cream), +1 508 693-0058/4681. Open May-Oct from 9AM-4PM. A fully narrated or private tour with professional guides and drivers. Tour takes route through all of the island’s towns and stops at Gay Head Cliffs for a ½ hour. Tour takes a total of 2 ½ hours.

• Ryan Family Amusements, 1 Trinity Park (near Tabernacle), ☏ +1 508 693-5163. Open daily in summer from 10AM-11PM. An arcade and game center with skeeball, air hockey, kid rides, and other games.