The best way to experience Martha’s Vineyard is through its well-organized tours. The classic 3-hour island tour stands out as the most efficient introduction, covering major highlights while providing historical context. Private guided tours offer flexibility and personal attention – perfect for families or those wanting to set their own pace. Sailing trips around the island are especially worthwhile, combining stunning coastal views with local maritime stories.
I’m particularly fond of tours that include stops at Aquinnah Cliffs and East Chop Lighthouse – these natural wonders and historic sites truly capture the island’s essence. Most tours are reasonably priced and accommodate various mobility needs.
Let’s explore the top-rated Martha’s Vineyard tours worth your time and money.
Key Points
-
The 3-Hour Island Tour offers a comprehensive introduction to Martha’s Vineyard’s landscapes and history at an excellent value of $70 per person.
-
The Private Guided Tour provides a personalized 3-hour exploration of the island’s six distinct towns with customizable stops and luxury minivan comfort.
-
The Sailing Tours offer relaxation and scenic views, with options for 2-hour and 6-hour experiences on classic ketches, including a private Vineyard Haven Harbor tour.
-
The Luxury Tour is a 2-hour immersive experience focused on history and landscapes, featuring professional guides and small group sizes with a 5.0 overall rating.
-
The Audio Tour provides a self-guided exploration of Oak Bluffs with GPS-guided audio, allowing flexible sightseeing and offline functionality.
3-Hour Marthas Vineyard Island Tour From Oak Bluffs
The 3-Hour Martha’s Vineyard Island Tour from Oak Bluffs provides visitors with a comprehensive introduction to the island’s diverse landscapes and rich history. This highly-rated tour earns a Badge of Excellence, with 90% of travelers recommending it. Over 1,235 reviews attest to its quality, with guests praising the knowledgeable guides and intimate small-group experience.
The tour covers the island’s main attractions, including the charming towns of Oak Bluffs, Edgartown, and Vineyard Haven. Highlights include a stop at the iconic Aquinnah Cliffs, where visitors can admire the stunning ocean views. Other key stops include the Flying Horses Carousel, Edgartown Lighthouse, and Aquinnah Lighthouse.
The tour operates in all weather conditions, so guests can explore the island rain or shine. While the van may feel slightly cramped for some, and a few guests have noted communication issues with the guide, the overall experience is praised for its comprehensive island overview and beautiful sights.
At $70 per person, this 3-hour tour offers an excellent value for those seeking to discover the essence of Martha’s Vineyard.
Read our full review: 3-Hour Marthas Vineyard Island Tour From Oak Bluffs Review
Book now: Check availability
Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs)
This private, guided sightseeing tour of Martha’s Vineyard Island provides travelers a comprehensive 3-hour exploration of the island’s six distinct towns.
Operated by Laid Back Tours, the tour boasts an impressive 4.9 overall rating from 74 reviews, with 97% of travelers recommending the experience. Guests explore the island’s highlights from the comfort of a luxury minivan, led by a knowledgeable local guide who offers historical insights and engaging storytelling.
Photo stops and walking opportunities allow visitors to enjoy the island’s natural beauty and charming local culture. Optional stops for classic New England fare like lobster rolls and clam chowder add to the authentic experience.
The tour departs from the easily accessible Steamship Authority Vineyard Haven Terminal, with the flexibility to meet at selected locations. Travelers appreciate the tour’s small group size, bottled water, and customization options.
Read our full review: Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs) Review
Book now: Check availability
2 Hour Sailing Tour of Vineyard Haven Harbor and Sound
A 2-hour sailing tour of Vineyard Haven Harbor and Sound offers visitors a chance to experience the charm of this historic Massachusetts island from a unique vantage point.
Guests will sail on a classic 60-foot ketch, featured in the movie “Trading Places,” and enjoy views of the East and West Chop Lighthouses. The tour is designed for both first-time and returning visitors, with a maximum of six passengers.
Visitors can bring their own alcoholic beverages and meals, and complimentary bottled water, snacks, and soda are provided. Optional catered lunch and dinner are available for an additional cost.
The tour departs from the Black Dog Wharf in Vineyard Haven, with a $4 launch fee per person.
While infants must sit on laps, the tour isn’t recommended for travelers with back or heart problems. A moderate level of physical fitness is required, and children under 14 must wear life jackets.
With an overall rating of 4.6/5 based on 7 reviews, this sailing tour offers a memorable and relaxing experience on the waters around Martha’s Vineyard.
Read our full review: 2 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
6 Hour Sailing Tour of Vineyard Haven Harbor and Sound
Spanning a duration of 6 hours, this private sailing tour allows visitors to explore the picturesque Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound aboard a classic 60-foot (18-meter) ketch sailboat that previously appeared in the movie “Trading Places”.
Accommodating up to 12 people, the tour provides an intimate and customizable experience, with the itinerary tailored to the group’s interests. Complimentary water, sodas, and snacks are included, while lunch and alcoholic beverages can be purchased separately.
The tour departs and concludes at the Black Dog Wharf in Vineyard Haven, with access via the Vineyard Haven Launch dock. Operating daily from May 23 to September 20, 2025, between 9 AM and 3 PM, the tour requires advance confirmation of the start time.
Though not wheelchair accessible, this activity is suitable for moderately fit travelers, with infants and children under 5 not permitted, and those under 13 required to wear life jackets.
Read our full review: 6 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
Marthas Vineyard Luxury Tour (2hrs)
Operated by Laid Back Tours, the Marthas Vineyard Luxury Tour immerses visitors in the island’s rich history and picturesque landscapes over the course of 2 hours.
Travelers explore the island aboard a luxury mini-van with a professional driver/guide, who provides historic details about the island’s past and present. With a small group of up to 5 people, the tour offers a personalized experience and the opportunity for customizations. Bottled water is included, and the van is described as extremely clean.
The tour departs from the Steamship Authority Vineyard Haven Terminal, with the option for a private pickup location. It ends back at the meeting point.
Though not wheelchair accessible, the tour is suitable for most travelers, including infants who must sit on laps. Cancellation is free up to 24 hours before the experience, and a “Reserve Now and Pay Later” option is available.
With 100% of travelers recommending the tour and a Badge of Excellence, it’s no surprise the Marthas Vineyard Luxury Tour earns a 5.0 overall rating from 21 reviews.
Read our full review: Marthas Vineyard Luxury Tour (2hrs) Review
Book now: Check availability
3 Hour Sailing Tour of Vineyard Haven Harbor and Sound
Although the Marthas Vineyard Luxury Tour offers a rundown of the island’s history and scenery, the Hour Sailing Tour of Vineyard Haven Harbor and Sound provides a more immersive and personalized experience.
This 3-hour private tour aboard a classic 60-foot ketch sailboat allows visitors to explore the local landmarks and Nantucket Sound at their own pace. The customizable itinerary caters to the group’s interests, making it a truly unique adventure.
The tour includes water, sodas, and snacks, with a lunch option available for an additional $15. Alcoholic beverages can also be purchased.
Guests will meet at the Black Dog Wharf in Vineyard Haven, where they’ll access the launch dock for a small fee. The tour runs from May to September, with flexible scheduling from 9 AM to 5 PM.
While some reviewers felt the tour was overpriced, the vast majority praised the excellent service, food, and the overall experience with Captain Sequoia and the crew.
For those seeking a more intimate and customized sail around Marthas Vineyard, the Hour Sailing Tour is a compelling choice.
Read our full review: 3 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
Oak Bluffs, Marthas Vineyard Audio Tour
What better way to take in the charm of Oak Bluffs, Martha’s Vineyard than through a self-guided audio tour? The Oak Bluffs, Martha’s Vineyard Audio Tour offers a flexible and convenient way to explore this picturesque town at one’s own pace.
Lasting as long as desired, the tour can be commenced at any time and guides visitors through the town’s highlights, including the iconic Ocean Park and Circuit Avenue Extension.
While the tour has received some mixed reviews due to reported technical issues, the operator has committed to improving the experience for the 2023 season, with enhanced GPS triggers and turn-by-turn directions.
At $12.50 per person, the tour provides an affordable way to discover the town’s history and architecture, accessible through streaming or downloadable audio files on a smartphone.
Despite the occasional glitches, the tour remains a popular option for those seeking an immersive and self-paced exploration of Oak Bluffs’ charm.
Read our full review: Oak Bluffs, Marthas Vineyard Audio Tour Review
Book now: Check availability
Vineyard Haven Harbor Sailing Tour Review
For those seeking a quintessential Martha’s Vineyard sailing experience, the Vineyard Haven Harbor Sailing Tour is a must-consider option.
This 4-hour private tour offers the chance to sail aboard a classic 60-foot (18-meter) ketch sailboat, featured in the film “Trading Places.” With a capacity for up to six passengers, the tour allows you to sail around Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.
The tour includes water, soft drinks, and snacks, and guests are welcome to bring their own alcoholic beverages if they’re 21 or older. There’s also an option to arrange for a catered lunch or dinner for an additional cost.
The meeting point is at Black Dog Wharf in Vineyard Haven, and the tour concludes at the same location.
Available from May 23 to September 20, the tour operates daily from 10 AM to 5 PM.
Moderate physical fitness is required, and children under 5 aren’t allowed, while those under 14 must wear life jackets.
Read our full review: Vineyard Haven Harbor Sailing Tour Review Review
Book now: Check availability
Marthas Vineyard Driving & Walking GPS-Guided Audio Tour
The Martha’s Vineyard Driving & Walking GPS-Guided Audio Tour provides a comprehensive and flexible way to explore the island at one’s own pace. This self-guided audio tour offers offline functionality, hands-free operation, and GPS-guided audio, allowing users to access the content for an entire year.
The tour includes detailed maps, suggested itineraries, travel tips, narrated audio, videos, and hidden gems, ensuring a memorable and engaging experience. The app activates audio based on location, eliminating the need for constant cell service.
Compatible with iOS 14 or later and Android 9 or later, the tour can be easily accessed through Bluetooth, USB, or aux connections. Users can prepare for the trip by downloading the app and tour content using strong Wi-Fi, ensuring a smooth experience.
The tour starts at Katama Beach/South Beach in Edgartown, with the audio beginning automatically upon opening the app at the starting point. While reviews have been mixed, the tour offers a unique storytelling experience with a professional narrator and the flexibility to explore Martha’s Vineyard at one’s own pace.
Read our full review: Marthas Vineyard Driving & Walking GPS-Guided Audio Tour Review
Book now: Check availability
Sum Up
Martha’s Vineyard offers a variety of tours to suit different interests and budgets. From comprehensive island tours to sailing excursions and self-guided audio experiences, visitors can explore the island’s charming towns, historic sites, and scenic landscapes. Whether you’re looking for a quick overview or a more immersive experience, there are plenty of options to make the most of your time on Martha’s Vineyard.