
Introduction
Martha’s Vineyard, an enchanting island off the coast of Massachusetts, is famed for its quaint villages, sandy beaches, and scenic lighthouses. With a storied past as a whaling hub and a summer retreat for artists and presidents alike, the island radiates charm and laid-back sophistication.
In late August, you’ll enjoy warm, gentle breezes and sunny days perfect for beach walks or vineyard picnics. Couples can indulge in fresh seafood at waterfront restaurants, take sunset sails, and explore the colorful gingerbread cottages in Oak Bluffs—all while savoring the island’s romantic, relaxed atmosphere without breaking the bank.

Itinerary for Martha's Vineyard · August 2025
Itinerary
Martha's Vineyard · August 2025
Viewing Day 1 · Thu 28 Aug. Numbered pins match today's itinerary stops; purple markers are recommended experiences. Click a pin for details.Pins match today's stops. Purple pins are experiences.
- 1Begin your getaway by wandering tree-lined streets and exploring beautiful whaling-era homes in Edgartown. Take in the charming shops and quaint cafes that showcase the town's rich heritage and relaxed coastal vibe.
- 2
Browse Local Art Galleries in Oak Bluffs
Experience Martha's Vineyard’s artistic spirit at galleries like Alison Shaw Gallery and Featherstone Center for the Arts. Enjoy diverse works from local artists and consider picking up a creative keepsake. - 3
Sunset Cocktails on the Harbor
Relax with a pre-dinner drink at a waterfront bar, such as The Atlantic or The Port Hunter in Edgartown. Toast to your romantic escape while watching the sun set over the sailboats in the harbor.
Recommended experience

#1 Best 3hr Martha's Vineyard shared Island Tour from Oak Bluffs
4.6 (1,625 reviews)
3 hours
Experience our famous 3-hour full Island tour for a budget friendly rate! Our tour drivers - native Islanders & long-time "wash-a-shores" have years of tour driving experience and the best reviews to show it! This 3-hour tour will introduce you to our 100 square mile island by giving you the history, both past and present, of our 6 unique towns. In all, 2 ½ hours of the tour is narrated, and you'll have a stop at the beautiful Cliffs of Aquinnah. Top highlights on this tour include Oak Bluffs, Edgartown, Vineyard Haven, Aquinnah, West Tisbury, Chilmark, and Menemsha. So join us in our comfortable air-conditioned vans & get ready to make memories for a lifetime - your Martha's Vineyard tour! (Children under 10 excluded from this tour.)
From $70 USD
per person
Key Facts
Location
Dukes County, Massachusetts
Currency
United States Dollar (USD)
Religion
Christianity (various)
Population
20,000
Language
English, some Spanish
Electricity
120V, 60Hz, Type A/B plugs
Time zone
UTCEastern Time (UTC-5)
Country code
+1
Internet access
Broadband widely available, high-speed
Climate
Oceanic, mild summers, cool winters
Logistics
To reach Martha’s Vineyard, most travelers take a ferry from Woods Hole or New Bedford in Massachusetts. Ferries accommodate both passengers and vehicles, though bringing a car can be expensive and requires advance reservations—perfect for a romantic getaway on foot or by bike. Allow extra time for potential weather-related delays, as ferries may be affected by storms between August 28 and September 1.
Alternatively, you can fly directly into Martha’s Vineyard Airport from major cities like Boston or New York. Train and bus services are available to ferry ports, making it easy to combine scenic rail or bus travel with the boat ride. If you’re traveling light, skipping the car lets you enjoy quaint local taxis, bike rentals, and classic inns while exploring the island’s charm.
Weather
Martha’s Vineyard has a mild, coastal climate with warm summers and cool, brisk winters. Spring and fall offer comfortable temperatures, vibrant foliage, and fewer crowds, making them ideal for sightseeing and exploring arts-and-culture or festivals. Summer days are typically sunny and warm, perfect for beach trips, fresh seafood, and outdoor entertainment.
From August 28 to September 1, expect pleasantly warm days near 75°F (24°C) and cooler nights. It’s generally dry, but the period falls in hurricane season, so brief rain or windy conditions are possible, though major storms are rare. This time is great for festivals, lively nightlife, and sampling seasonal gastronomy at local markets and restaurants.
Food & Drink
Martha’s Vineyard is famous for its fresh seafood—especially oysters, lobster rolls, and clam chowder. You’ll also find local farm produce, artisan cheeses, and memorable ice cream. For drinks, try local wines or craft beers from island breweries; sunset cocktails are a must at waterfront bars.
For a romantic evening, dine at The Seafood Shanty with harbor views or Alchemy in Edgartown for upscale American cuisine. Enjoy breakfast at ArtCliff Diner or dessert at Back Door Donuts. Most restaurants expect a 15–20% tip. Reservations are recommended in peak season, especially for waterfront dining.
Vegan, vegetarian, and gluten-free options are available at many venues, but calling ahead is wise. Dress is mostly casual-chic, and many spots showcase live music or cozy outdoor seating in warm months.

Hamburger
The classic American hamburger is a grilled beef patty served in a soft bun, often topped with lettuce,...

Barbecue Ribs
Barbecue ribs are slow-cooked, tender cuts of pork or beef that are generously seasoned with a flavorful dry...

Macaroni and Cheese
Macaroni and cheese is a creamy, indulgent dish made with elbow macaroni pasta and a rich, cheesy sauce....

New York-style Pizza
New York-style pizza is characterized by its thin, hand-tossed crust, generous cheese topping, and a variety of classic...

Southern Fried Chicken
Southern fried chicken consists of juicy, tender pieces of chicken that are coated in a seasoned batter and...
Accommodation
For a romantic getaway on Martha’s Vineyard, consider staying in Edgartown, known for its elegant harborfront and charming hotels like Harbor View Hotel and The Sydney. Oak Bluffs is another great option, offering boutique accommodations such as Summercamp Hotel with colorful architecture and lively surroundings.
Book your stay via reliable sites like Booking.com or Expedia, and reserve well in advance, especially for dates around August 28 to September 1, as late summer sees high demand. Most hotels offer cozy rooms with easy access to beaches and quaint downtowns, but expect prices to rise during this peak period.
For a more intimate ambiance, look for inns or boutique hotels that cater to couples. Vineyard Haven also features romantic lodgings and is conveniently located for exploring the island. Avoid last-minute booking, as availability can be limited.
Attractions

Marthas Vineyard Luxury Tour (2hrs)
Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. Relax and enjoy this narrated tour as we drive along the scenic coast, stop for photos, talk about famous people, learn about local history, all while passing through the 3 down-island towns. For those travelers coming over for the day with limited time, who would like to see the down Island towns, this is the perfect tour.
From $450 USD

Electric Bike Tours on Martha Vineyard
Explore the beauty of Martha's Vineyard on an electric bike tour designed just for you. It offers unique experiences tailored to your interests: secluded beaches, historic farms, the iconic Gingerbread Houses, and more. Let us take you there. Choose 4-6 hour private tour, where every detail is curated to ensure you see a few of the island's gems: lighthouses, Downtown Edgartown, Oak Bluffs, Chappaquiddick. Or call us and inquire about our 3-day Tour De L'ile for an in-depth adventure across the island's six towns. All tours include e-bike use, helmet, water, snacks, and admission to select attractions. - Explore top attractions like the Campground Cottages in Oak Bluffs and Chappaquiddick Island. - Private tours available for groups up to six riders, ensuring a personalized experience. If you have more riders, give us call a week in advance and we will try to accommodate you.
From $250 USD

Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs)
-Offering private tours of beautiful Marthas' Vineyard Island specifically for small groups of people (5 max) looking for a truly unique experience. -Relax and enjoy this narrated tour as we drive along the scenic coast, stop for photos, talk about famous people, learn about local history, all while passing through the 6 island towns. -For those travelers coming over for the day with limited time, who would like to see the whole island, this is the perfect tour.
From $550 USD

Martha Vineyard Bus Tour
Please Note: During the summer of 2026, our family experienced a devastating medical emergency involving multiple immediate family members. A small number of tours were canceled on very short notice while we handled those circumstances. We sincerely apologize to those affected and are deeply grateful for the kindness and understanding shown by so many guests during this incredibly difficult time. We are, the only ones have four stops to get off the bus. We also offer a lot of amenities that no other tour offers. The tours keep you fully engaged and all we require is for you to be curious! We will not disappoint, what makes us entirely different is that we have a screen at the front of the bus that shows what certain sites looked like in the days of yore. The All Island Bus Tour takes you on an adventure you will never forget. Capture the beautiful vistas, the quaint little cottages, the amazing clay cliffs and everything in between.
From $75 USD

Historical Tour of Nantucket
We are unique as we are the oldest tour company on the historic island of Nantucket. From the early days when Chester Barrett founded the company and drove a horse and buggy, to today, we are ready to give you a great truthful and historical view of Nantucket. We are you premier choice for bus tours, van tours, and wedding transportation in Nantucket, MA You will see a narrated tour where we show you old lighthouses, the village of Siasconset on the East end of the island, rose cover cottages, as well as the old railroad and either the oldest or 2nd oldest house on island. You will really enjoy seeing the island from this perspective. The 1.5 hour time is just enough time to see the sights and plan where to spend the rest of your visit on island. We can also do private and large group tours, inquire by calling.
From $57 USD

Boston to Martha's Vineyard Day Trip with Optional Island Tour
We are proud to offer Boston's ORIGINAL Martha's Vineyard Day trip. Since 2011 we have been Boston's #1 day trip service to the island. Our professional guides, approved Boston Hotel pickups and newer air-conditioned mini-coaches will help provide you with the personalized passenger experience that our guests truly deserve. Transportation to the island has never been this easy! You will also receive complimentary snacks, bottled water, island guidebooks and a discount card with some island perks! Once on the island, explore on your own or upgrade with our 3 hour fully narrated island tour. Let us help you Discover Martha's Vineyard!
From $129 USD

Boston: Martha's Vineyard ICONIC Small Group Day Escape w/Ferry
Leave Boston behind and set out on a full-day journey to Martha's Vineyard, one of New England's most beloved islands. This experience blends a scenic ferry crossing, historic seaside villages, and the laid-back charm of island life. Board the Island Queen ferry in Falmouth and cruise across Nantucket Sound to Oak Bluffs, where colorful gingerbread cottages surround the historic Tabernacle at the Martha's Vineyard Camp Meeting Association. Enjoy time to explore the island's most iconic spots, with an optional sightseeing bus tour covering the Flying Horses Carousel, the refined harbor town of Edgartown, Gay Head Light atop the dramatic Aquinnah cliffs, and Nobska Point Lighthouse. Return via the Steamship Authority ferry from Woods Hole, rounding out a full day of coastal views, ocean breezes, and authentic New England island character.
From $108 USD

Fall Foliage Scenic Day Trip to Vermont and Western MA with Stops
Discover the vibrant colors of autumn on a Fall Foliage Day Trip from Boston through Southern Vermont and Western Massachusetts. Your journey begins in Western Massachusetts with scenic stops at the French King Bridge, Mineral Road Bridge, and historic Cabot Camp—each offering sweeping views of brilliant foliage along the Connecticut River. From there, we’ll head north into Southern Vermont, where the season’s beauty unfolds at the charming Creamery Covered Bridge and the Hogback Mountain General Store and Scenic Overlook. Along the way, enjoy a relaxing lunch and time to take in the crisp mountain air. On the return trip to Boston, we’ll visit the Yankee Candle Flagship Store, where you can explore its signature scents and seasonal displays—an aromatic highlight to end the day. Don’t miss this unforgettable autumn escape from Boston, filled with breathtaking views, charming stops, and the very best of New England’s fall foliage.
From $149 USD

Boston to Newport Trip with Breakers and Marble House Admission
Escape to the lovely coastal city of Newport, Rhode Island, on this day trip that includes both a guided tour and free time. Explore The Breakers Mansion (the summer home of Cornelius Vanderbilt II's family), as well as The Marble House (as seen in the movie The Great Gatsby). See top Newport attractions such as St Mary's Parish, Ocean Drive and the Naval War College on a narrated tour. Then discover this quaint and historic city further on your own. This small-group tour is limited to 20 people for a more intimate experience.
From $155 USD

Newport, Marble House, The Breakers Full-Day Tour from Boston
Spend a relaxing day exploring the historic coastal city of Newport, Rhode Island. Departing from Boston in the morning, your first stop will be The Breakers Mansion, a grand Vanderbilt family summer home filled with Gilded Age elegance. Afterward, visit the beautiful Marble House, another luxurious mansion known for its stunning architecture and opulent interiors. Enjoy scenic views of the Atlantic coastline along the way before returning to Boston in the evening. Optional admission to both mansions allows you to customize your experience. Itinerary: Boston → Newport → The Breakers Mansion (120 mins) → Marble House ( 90 mins) → Boston Staying on the Same Bus To avoid being assigned to a different bus, please provide all confirmation numbers if you have multiple bookings once they are complete.
From $184 USD
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