Saturday-to-Saturday Martha's Vineyard itinerary: rental logistics, day-by-day plan from Edgartown and Chappy to Aquinnah and Menemsha sunset, farmers markets, food experiences, and sunset sail. Everything verified for 2026.
A week on Martha's Vineyard is a different trip from a weekend or a 3-day visit. Seven days give you time to go to the farmers market twice, find a coffee shop where they start to recognize you, spend a morning deciding which beach to go back to, and do the things weekenders cannot: the Wednesday community sing, Orange Peel Pizza Night, a full food-experience day, and a final-evening sunset sail.
This Saturday-to-Saturday itinerary is built for a week of living on the island rather than racing around it. Every price, hour, and address verified for 2026. For shorter trips, see our 2-day weekend getaway, 3-day itinerary, or Trip Cost Calculator.
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A full week changes the trip. Nobody is racing the boat schedule.
Seven days, at a glance
The Saturday-to-Saturday cycle remains the dominant weekly rental standard on Martha's Vineyard during peak summer. Major agencies like Tea Lane Associates, Sandcastle Realty, Vacasa, and MVVR list properties with 7-night minimums aligned to Saturday changeover. Some properties require a 14-night minimum.
Arriving Friday night is a very common and practical strategy, especially for families driving from Boston. Saturday ferry traffic is heavy; arriving Friday takes the morning rush out of it. There are no chain hotels on MV; all lodging is independently owned.
| Hotel | Town | Peak Rate |
|---|---|---|
| Summercamp Hotel (Lark) | Oak Bluffs harbor | $350–$600+/night |
| Pequot Hotel | Oak Bluffs | $200–$350/night |
| Vineyard Harbor Motel | Vineyard Haven | $200–$350/night |
| Madison Inn | Oak Bluffs | $200–$350/night |
| Oak Bluffs Inn | Oak Bluffs | $275–$450/night |
Mainland alternative: Stay in Falmouth the night before (cheaper, more availability) and catch an early Saturday ferry.
Martha's Vineyard is larger than visitors expect (~100 square miles). A car provides maximum flexibility for up-island destinations like Menemsha, Chilmark, and Aquinnah. But the VTA bus system is good and currently fare-free, making car-free travel viable for down-island stays.
VTA Bus System (fare-free through June 30, 2027):
On-island car rentals (Budget MV, MV Auto Rental, A-A Island Auto, Hertz, Avis): weekly rate $700–$1,500+ depending on vehicle and season. Renting on-island is often easier and cheaper than bringing your own car on the ferry.
All companies offer free island-wide delivery with helmet, lock, and trail map.
| Bike Type | Daily | Weekly |
|---|---|---|
| Standard bike | $30 | $120–$150 |
| Road bike | $60 | $205 |
| E-bike | $70–$96 | $280–$500+ |
Key companies: RW Cutler (Edgartown, est. 1947), Rent Bikes MV (OB), Martha's Bike (VH), All Star MV (OB). The best strategy for a car-free week: bikes + VTA bus. Read our complete bike routes guide.
Weekly grocery budget for a couple: $250–$400/week. MV prices run 15–25% higher than mainland. Alcohol is sold retail ONLY in Edgartown and Oak Bluffs. Chilmark is the island's one fully dry town (its restaurants are BYOB: bring your own bottle, no liquor license, you carry in the wine), while West Tisbury and Aquinnah pour beer and wine with meals only. Stock up before heading up-island: Al's in Edgartown, or Jim's and Our Market in Oak Bluffs, and Our Market delivers island-wide.
Only two self-service options on the island:
MV Baby Rent (mvbabyrent.com) and Martha's Vineyard Linen and Rentals offer chairs, umbrellas, tents, wagons, coolers with delivery to all 6 towns. Many rentals include basic beach gear; check with your agency.
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Day one: unpacked, and watching the light go down over the harbor.
SSA Walk-on: $11 one-way / $22 round-trip adult. Child (5–12) $5.75. Bike $5.25. No reservation needed. 45-minute crossing.
SSA with car (peak summer): ~$127–$168 one-way depending on day. Vehicle reservations opened February 3, 2026 at 8:00 AM and peak Friday/Sunday slots filled within hours. Traditional vehicle standby has been suspended since November 2024 and had not returned as of September 2026 (a limited Blue Line exists only for SSA preferred and excursion account holders); you cannot show up without a reservation.
Best Saturday arrival: 6:00–7:00 AM ferry. Arrive at Woods Hole terminal area 1+ hour early. See our complete ferry guide.
Grocery shop at Stop and Shop (across from VH ferry) or Cronig's Market. Walk downtown Vineyard Haven (Main Street shops, Black Dog General Store, galleries) or Oak Bluffs (Circuit Avenue, Gingerbread Cottages, Flying Horses Carousel, America's oldest operating carousel, est. 1876).
Edgartown Harbor with the Edgartown Light in the distance; the On Time ferry to Chappaquiddick leaves from the foot of the harbor.
Edgartown Lighthouse (end of North Water Street): Grounds and Lighthouse Beach free year-round. Tower open for the season from late spring into mid-October, 7 days a week 10 AM–4 PM weather permitting. $5 adults, free for children 12 and under.
North Water Street: Grand 19th-century whaling captains' homes with widow's walks, built 1830s–1850s when Edgartown was one of America's wealthiest communities. The Harbor View Hotel (1891) is a landmark.
Main Street Edgartown: Upscale boutiques, galleries, bookstores. Old Whaling Church (Greek Revival, 1843). The Pagoda Tree on South Water Street was planted in 1837. See our complete Edgartown guide.
Chappy Ferry: Departs 53 Dock Street, Edgartown. Twin ferries carry 3 cars each plus passengers/bikes, running continuously. Summer hours: 6:30 AM to midnight.
Mytoi Japanese Garden: 14-acre Japanese-inspired stroll garden on Dike Road, 2.5 miles from ferry (15-min bike). Trustees of Reservations property. Open daily sunrise to sunset. $10 adults May–October (children 12 and under free); free for everyone November–April. Allow 20–60 minutes.
Cape Poge Wildlife Refuge: seven-mile barrier beach. Historic Cape Poge Lighthouse (first erected 1801). Trustees offer guided natural history tours via over-sand vehicles.
Wasque Point: Southeastern corner of Chappaquiddick. 200 acres, sandy beach, half-mile trails. Birdwatching. Seals more reliably seen October–April. $25 parking for non-members; free with library card pass from Edgartown, VH, West Tisbury, or Chilmark libraries.
Up-island is the wild end: the red clay cliffs at Aquinnah, then down to Menemsha for fish straight off the boat.
Take South Road for the drive: winding, hilly, stone walls and farm fields through West Tisbury and Chilmark. Return via North Road for variety. VTA Route 5 runs WT–Chilmark–Aquinnah (~45–60 min from VH). Route 4 serves Menemsha. In summer (through late August) the VTA Route 12 sunset shuttle runs from the Tabor House Road lot to Menemsha Beach.
Gay Head Cliffs: Multi-colored clay cliffs (red, orange, yellow, white, black), National Natural Landmark since 1975. Free from the overlook. The cliffs sit on trust land of the Wampanoag Tribe of Gay Head (Aquinnah), federally recognized in 1987, with about 1,360 enrolled citizens. Aquinnah means "land under the hill" in Wampanoag.
Gay Head Lighthouse: Reopened Memorial Day weekend 2026 after a year of restoration. The town of Aquinnah has owned the light since February 2015. Schedule: daily through Labor Day, then four days a week into the fall, 10 AM–4 PM. Admission: $6 for ages 13+, free for 12 and under, military/veterans, and Aquinnah residents. Current brick tower dates to 1856; original first-order Fresnel lens on display at MV Museum.
Moshup Beach: Boardwalk path from the overlook leads down to a rocky beach beneath the cliffs. Parking in the Moshup Beach town lot runs about $35 a day, card only; the overlook at the Circle has free 30-minute parking. Wear water shoes. Do NOT climb or touch the cliffs: protected Wampanoag tribal land. Faces southwest for sunset.
A 300-year-old working fishing village on Chilmark's northwest end. One of the last working fishing villages in New England. Filming location for Jaws (1975). Chilmark is a dry town: BYOB everywhere.
Menemsha Hills Reservation (Trustees): 211 acres, 3 miles of trails. Prospect Hill at 308 feet is MV's second-highest point. Views of Menemsha Harbor, the Elizabeth Islands, and Gay Head Lighthouse. Rocky north-shore beach with tide pools. Historic 19th-century brickworks ruins along Roaring Brook. Moderate, 1.5–2 hours.
Larsen's Fish Market (56 Basin Road, 508-645-2680): Open 9 AM–7 PM in season. Fresh fish, raw bar, cooked-to-order lobsters, chowder, lobster bisque, crab cakes. Pre-made cooler with lobster rolls (~$28–35), shrimp cocktail. Pre-order cooked lobsters early; they sell out by sunset. You can eat on the beach steps away. This is the classic Menemsha meal.
Menemsha Fish Market (54 Basin Road, 508-645-2282): Separate business right next to Larsen's. Some visitors prefer their lobster rolls.
The Bite closed. Iggy's Bread/Bakery occupies the former space at 29 Basin Road.
The Homeport Restaurant (512 North Road, 508-645-2679): Open for 2026 under new ownership. Since 1930. Famous for lobster dinners "served in the semi-rough." BYOB (glassware and mixers provided, corkage fee). Prix fixe ~$75–83/person. Reservations via OpenTable.
The Menemsha Galley (515 North Road, 508-645-9819): Casual takeout. Burgers, sandwiches, fried seafood. 11 AM–8 PM daily.
See our complete sunset guide for more spots.
A full beach day: South Beach for the Atlantic surf, a towel, and nowhere else you need to be.
Read our complete beach guide for every beach on MV.
Island Spirit Kayak (508-693-9727): Located at "Little Bridge"/Jaws Bridge area. ACA-certified. Book at islandspiritkayak.com.
| Tour | Duration | Price |
|---|---|---|
| 2-Hour Kayak Adventure | 2 hrs, daily | $75 adult / $55 kid |
| Sunset Kayak Tour | 2.5 hrs, Mon/Wed/Fri/Sat | $85 adult / $55 kid |
| Kayak Glow Tour | Evening, Mon/Wed/Fri/Sat | $120/person |
| Full Day Kayak Adventure | Daily at 9 AM | $175 (lunch included) |
Wind's Up (199 Beach Road, VH, 508-693-4252): Since 1985. Rentals: SUPs, kayaks, canoes, sailboats, windsurfers, surfboards. On-water rentals on Lagoon Pond. July/August: Mon–Sat 10 AM–5:30 PM, Sun 12–5 PM. Lessons available.
The Skipper (Slip #74, Oak Bluffs Harbor, 508-693-1238): MV's only shared party fishing boat. $100/person, ~4 hours, twice daily. All gear and fishing licenses included. Crew cleans and fillets your catch. BYOB cooler. Also partners with Felix Neck for Marine Life Cruises (Tuesdays in July/August, 5:30–7:30 PM).
5 Post Office Square, Oak Bluffs, 508-693-3688. Named #5 bakery in the country by USA Today. From 7 PM to midnight, the screen comes down and they sell hot, freshly made donuts right out of the fryer. The apple fritters are the signature item: 60,000+ sold in a recent year. Lines can be long; the line is part of it.
The slow day: the West Tisbury Farmers’ Market at the Grange Hall, a couple of galleries, no schedule at all.
This is the day that makes a week different from a long weekend.
Agricultural Hall, 35 Panhandle Road, West Tisbury. Founded 1934, revived 1974: MV's oldest and largest open-air market. Free admission and parking. SNAP/EBT accepted. No dogs.
| Day | Season | Hours |
|---|---|---|
| Saturdays | June–October | 9 AM–12 PM |
| Wednesdays | June–late August | 9 AM–12 PM |
40+ vendors: Morning Glory Farm, North Tabor Farm, Beetlebung Farm. Cottage City Oysters. Food trucks: Stoney Hill Pizza (mobile Neapolitan oven), Komorad Fried Chicken, Good Pierogi. Salt Rock Chocolates (go early; sells out). Chilmark Coffee Roasters. Live music. Presidents and celebrities have shopped here; mostly it is the town doing its weekly shopping.
The Field Gallery and Sculpture Garden (1050 State Road, West Tisbury, 508-693-5595): Mon–Sat 10 AM–4 PM, Sun 11 AM–4 PM. Free admission (outdoor sculptures always accessible; public land since 2011). The famous white sculptures by Tom Maley (1911–2000): dancing figures scattered across the field. Inside: rotating contemporary paintings, sculpture, photography by 25+ artists. Everyone photographs them.
Granary Gallery (636 Old County Road, West Tisbury, 508-693-0455): Oldest and largest gallery on MV (since 1954). Works by Alfred Eisenstaedt (LIFE photographer), Thomas Hart Benton, Roy Lichtenstein. 75+ artists. Free to browse. Friday evening artist premieres.
Featherstone Center for the Arts (30 Featherstone Lane, OB, 508-693-1850): Only year-round non-profit arts center on the island. 6+ acres with galleries and studios. Francine Kelly Gallery open daily 12–4 PM, free. Classes in pottery, jewelry, painting. Live music, outdoor movies, annual Empty Bowls fundraiser.
Other notable galleries: Cousen Rose (OB), Louisa Gould (VH), Alison Shaw (OB; the island's best-known photographer), Martha's Vineyard Glassworks (West Tisbury; watch glassblowing), Christina Gallery (Edgartown).
Weekly tradition for 100+ years, Wednesdays from early July through late August (in 2026: July 1 to August 26). Trinity Park Tabernacle, the 1879 open-air wrought-iron hall in the MVCMA Camp Ground, Oak Bluffs. Free (free-will offering). Arrive early for seats. If you do one thing only a week-long visitor can do, make it this.
L’Etoile in Edgartown in the evening, string lights on and the garden in bloom.
Open-ocean farm off East Chop, Oak Bluffs (508-299-7745). Book at cottagecityoysters.com. Dan and Greg Martino (since 2014).
Food-and-farm experience company run by Nevette Previd (508-687-9012; book by phone and confirm the current season, the old farmfieldsea.com site is offline).
Katama Farm, Edgartown. Trustees of Reservations. Hands-on cooking classes with local chefs: "Cooking From the Island" (harvest-to-dinner), Beach Plum Jelly Making, Farm Fresh Pasta. Thursday Farm Dinners (outdoors, summer). Book at thetrustees.org.
22 State Road, Aquinnah. Run by Juli Vanderhoop, Aquinnah native. Wood-burning stone oven. Pizza Night: Thursdays 5–8 PM in season, $35 per adult and $10 for kids 13 and under. The bakery's website was showing a closed notice in early September 2026, so confirm before you drive up. BYOT (Bring Your Own Toppings): bakery provides dough, sauce, cheese, and the oven. BYOB. Community atmosphere, picnic-style on the lawn. Check Instagram for the current schedule. Go if you can.
270 Upper Main Street, Edgartown. May–October, 11 AM–9 PM. 7-barrel brewing system, ~10 beers on tap (brewed with hand-picked wild grape leaves from MV). Artisan pizza, soft pretzels. Live music, outdoor games.
Sunset over Vineyard Haven Harbor, boats out on the water. The last night before the Saturday-morning boat home.
Schooner Alabama / Black Dog Tall Ships (20 Beach Street Extension, VH, 508-693-1699, theblackdogtallships.com): Historic 1926 100+ foot schooner. Departs from Black Dog Wharf, 2-minute walk from VH ferry.
| Sail | Duration | Price |
|---|---|---|
| Day/Sunset Sail | 3 hrs | $100 adult / $60 child (4–12) |
| Fireworks Cruises (July 4 Edgartown and the Oak Bluffs August show, when it runs) | 4 hrs | From $187.25/person |
Includes water, soda, chips, cheese platter. BYOB and picnic welcome. Passengers can help hoist sails and take turns at the wheel.
Mad Max Catamaran (25 Dock St, Edgartown): the 60-foot, 49-passenger catamaran that ran the cheapest shared sunset sail (about $60–$65 a person, bring your own food and drink) is not sailing in 2026 while a bigger boat is built. The marina says it returns in 2027 or 2028, so plan on the schooners this year.
Sail the Vineyard (S/V Phoenix) (VH, 508-493-8767): Ranked #1 on TripAdvisor for 6 consecutive years. Public Sunset Sail Mon and Thu, 2 hrs, $200/person (21+, 4-guest min). Private 2-hour sunset: $700 (up to 6).
Catboat Charters (1 Dock Street, Edgartown, 508-524-6903): Private only (up to 6 guests) on restored antique catboats "Dolphin" (1893) and "Tigress" (1927). Pure sailing: no motor.
Nomans Land is a 628-acre uninhabited island 3 miles southwest of MV. Access strictly prohibited: National Wildlife Refuge with unexploded ordnance from 1954–1996 Navy bombing range. In 1602, Bartholomew Gosnold originally named THIS island "Martha's Vineyard"; the name later transferred to the larger island.
Viewpoints from MV: Visible from Aquinnah/Gay Head Cliffs, a low, flat island on the horizon. Also from Squibnocket and Lobsterville Beaches. The waters around it are serious sport fishing grounds; charter with Captain Buddy Vanderhoop (Wampanoag tribal member) from Menemsha for striped bass, bluefish, bonito, tuna, sharks.
| Restaurant | Location | Status |
|---|---|---|
| State Road Restaurant | West Tisbury | Open (2026 James Beard semifinalist) |
| Nancy's Restaurant | Oak Bluffs | Open May 2026 |
| Nomans Restaurant | OB | Open (seventh season) |
| L'étoile | Edgartown | Open · 38th year |
| Alchemy | Edgartown | Open |
| The Homeport | Menemsha | Open for 2026 |
| Beach Plum Inn Restaurant | Chilmark | Pop-ups only July/August |
| Offshore Ale | OB | Open year-round |
| Art Cliff Temporarily closed Closed until further notice: the sign on the door and the diner's own website say temporarily closed as of 5 September 2026. No reopening date given. (through Oct 3) Diner | VH | Open |
| 7a Foods | West Tisbury | Open |
| Among the Flowers | Edgartown | Summer 2026 |
| Newes from America | Edgartown | Open daily |
| Tier | Weekly Cost | Notes |
|---|---|---|
| Budget | $2,000–$3,500 | Modest interior homes, no pool, OB or VH |
| Mid-range | $4,000–$7,000 | Nice 2BR in Edgartown or West Tisbury |
| High-end | $10,000–$25,000+ | Waterfront, pool, Chilmark/Edgartown premium |
Budget: $120–$180/day
Mid-range: $250–$350/day
Luxury: $500–$800/day
| SSA ferry walk-on (RT) | $22/adult |
| SSA ferry with car (peak RT) | ~$260–$320 |
| VTA bus | Free through June 30, 2027 |
| Standard bike rental (weekly) | $120–$150 |
| E-bike rental (weekly) | $280–$500 |
| Car rental on-island (weekly peak) | $700–$1,500+ |
| Casual lunch (lobster roll) | $28–$35 |
| Mid-range dinner entrée | $25–$45 |
| Fine dining entrée | $40–$75+ |
| Cottage City Oyster tour | ~$100–$150/person |
| Schooner Alabama sail | $100/adult |
| Mad Max sunset sail | not sailing in 2026 (was ~$60–$65/person) |
| The Skipper fishing trip | $100/person |
Use our Trip Cost Calculator for a personalized estimate.
Visitors can get library cards at any of MV's 6 town libraries (all part of the CLAMS network, 1.6 million+ items). Massachusetts libraries issue cards to anyone.
What a library card gets you:
Aalia’s Coffee sign over its yellow-trimmed window in Oak Bluffs.
Seven days allow what shorter visits cannot: visiting the farmers market twice, finding a favorite coffee shop where they start to recognize you, having unhurried unscheduled days, finding the places weekend visitors never see. The island slows you down on its own: no chain hotels or restaurants, and the early mornings belong to the people who live here. By midweek it stops feeling like a destination and starts feeling like a place you know.
Not strictly: the fare-free VTA bus reaches all six towns, and bikes handle the rest. But a car makes up-island dinners, sunset trips to Menemsha, and spontaneous exploration much easier. For families with kids, a car is usually worth it. See our car-free MV guide.
3–6 months ahead for peak summer (July/August). Peak weeks around July 4th and mid-August sell out first. Shoulder season (June, September) is much more flexible.
For traditional MV vacation homes through major agencies, yes: the Saturday changeover is standard. Airbnb and VRBO increasingly offer shorter stays, but weekly rentals are the norm for whole houses in peak summer.
The Wednesday Community Sing at the Tabernacle. It's been happening for over 100 years, it's free, and weekend visitors never see it. It runs Wednesdays from early July to late August.
Walk-on passengers, yes (no reservation needed). With a car, no: traditional vehicle standby has been suspended since November 2024 and had not returned as of September 2026. Book the moment reservations open (February 3 for summer 2026).
Same vendors roughly; Saturday is larger with more live music and a community feel. Wednesday is a calmer shopping experience. Go to both; that's the whole point of a week.
For longer trips, see our 3-day itinerary and 2-day weekend getaway guides.
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Edgartown Lighthouse is climbable daily in summer, roughly 10 AM–4 PM, with the shortest waits right at opening. Small admission ($5 at last check). Staff may close the door a few minutes early.
Where to play pickleball on Martha's Vineyard in 2026: the town courts in Oak Bluffs (Niantic Park), Vineyard Haven (Lake Street, $20 an hour) and Edgartown, the indoor option at Airport Fitness, fees, how the summer queue works, and why up-island has no public courts.
Which Martha's Vineyard tour is worth it, by the trip you are on: the Edgartown walking and Jaws tours, the three-hour island bus tour, private charters, the MV Skipper party boat, Felix Neck kayak tours and the all-in day trip from Boston, with 2026 prices from the operators.
Complete 2-day car-free Martha's Vineyard weekend itinerary: Friday ferry timing, where to stay, walk-in dining, Saturday beach + Aquinnah, Sunday departure. Three budget tiers. Verified for 2026.
50 genuinely free things to do on Martha's Vineyard: beaches, hikes, concerts, lighthouses, lantern festivals, and more. Every location verified, every price double-checked for 2026.
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