Savvy travelers know the best way to explore Martha’s Vineyard is through its excellent guided tours. The island’s top experiences include well-orchestrated bus tours that efficiently cover the main highlights and sailing excursions perfect for experiencing the island’s rich maritime culture. I’m especially fond of the private guided tours – they let you set the pace and dodge the crowds while visiting the iconic gingerbread cottages and pristine beaches. For newcomers, the 3-hour overview tours provide great value, while seafaring types will appreciate the 6-hour sailing adventures along the coast. Let’s explore the island’s most worthwhile tours.
Good To Know
The 3-Hour Martha’s Vineyard Island Tour offers a highly-rated small-group experience visiting key towns and scenic viewpoints on the island.
The Private Guided Sightseeing Tour provides a customizable luxury minivan experience with engaging storytelling and optional stops for local cuisine.
The All Island Bus Tour is a comprehensive 3-hour tour with interactive experiences and knowledgeable guides, accommodating up to 28 passengers.
Sailing tours on Martha’s Vineyard range from 2 to 6 hours, offering stunning views, customizable itineraries, and opportunities for relaxation.
The Private Tour features a full-day exploration of the island’s natural beauty, history, and culture, with personalized experiences and catered meals.
3-Hour Marthas Vineyard Island Tour From Oak Bluffs
For those seeking an immersive introduction to the charming island of Martha’s Vineyard, the 3-Hour Martha’s Vineyard Island Tour from Oak Bluffs is a must-consider option.
This highly-rated tour, with a Badge of Excellence and 90% traveler recommendation, takes visitors on a comprehensive journey through the island’s key highlights.
The small-group tour, limited to just 14 people, ensures a personalized experience led by a knowledgeable professional driver/guide.
Travelers will visit the picturesque towns of Oak Bluffs, Edgartown, and Aquinnah Cliffs, encountering iconic sites like the Flying Horses Carousel, Old Whaling Church, and Edgartown Lighthouse.
A 15-minute stop at the stunning Aquinnah Cliffs provides an opportunity to take in the island’s natural beauty.
Throughout the tour, the guide delivers live commentary, sharing local stories and historical insights.
Convenience is another draw, with the tour departing near the Oak Bluffs Ferry Terminal and including snacks and water.
With flexible booking and cancellation policies, this 3-hour excursion is an excellent way to explore the highlights 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 offers travelers a comprehensive 3-hour exploration of the island’s highlights.
Operated by Laid Back Tours, the tour boasts a 97% traveler recommendation based on 74 reviews and a Badge of Excellence. Passengers will travel in a comfortable luxury minivan with a professional driver/guide, who provides historical insights and customizes the itinerary to group preferences.
The tour hits all six island towns, allowing participants to capture scenic photo opportunities. Bottled water is provided, and there are optional stops for lobster rolls and clam chowder at an additional cost.
With a maximum group size of 5, the tour provides an intimate and personalized experience. While not wheelchair accessible, infants can join the tour by sitting on laps.
Overwhelmingly positive reviews praise the knowledgeable and friendly guides, engaging storytelling, and comfortable transportation, making this an excellent choice for discovering Martha’s Vineyard.
Read our full review: Private, Guided Sightseeing Tour of Marthas Vineyard Island(3hrs) Review
Book now: Check availability
All Island Bus Tour
Travelers seeking a rundown of Martha’s Vineyard will find the All Island Bus Tour an excellent choice. Covering the island’s key highlights, this 3-hour tour provides first-time visitors with a well-rounded experience.
Departing from Oak Bluffs, the tour takes guests to the iconic Aquinnah Cliffs and the Martha’s Vineyard Camp Meeting Association, offering insights into the island’s history and culture. Along the way, travelers can enjoy interactive experiences, such as handling shells and wool, while listening to captivating local stories from the knowledgeable guides.
With a maximum capacity of 28 passengers, the tour ensures a personalized and intimate experience. While some reviewers felt the duration was too long, the majority praised the guides’ expertise and the balanced mix of stops for photos and exploration.
With convenient meeting points, accessibility, and flexible booking options, the All Island Bus Tour is an excellent way to discover the charms of Martha’s Vineyard.
Read our full review: All Island Bus Tour Review
Book now: Check availability
Private, Guided Sightseeing Tour of Marthas Vineyard Island(2hrs)
Though the All Island Bus Tour offers a comprehensive exploration of Martha’s Vineyard, those seeking a more personalized and flexible experience may opt for the Martha’s Vineyard Luxury Tour.
This 2-hour small group or private tour provides an intimate and well-researched look at the island’s highlights. Guests are transported in a luxury mini-van with a professional driver-guide who offers historic details and context.
The tour covers popular attractions and natural scenery, with the flexibility to customize the itinerary to individual interests. Travelers consistently praise the guide’s knowledge and pleasant demeanor, as well as the comfortable transportation, despite some wishing for more photo stops.
At €514.14 per group, the tour is on the pricier side, but the 100% recommendation rate and 5-star reviews suggest it delivers a unique and worthwhile experience.
For those seeking a more tailored sightseeing adventure on Martha’s Vineyard, the Martha’s Vineyard Luxury Tour is an excellent option.
Read our full review: Private, Guided Sightseeing Tour of Marthas Vineyard Island(2hrs) Review
Book now: Check availability
2 Hour Sailing Tour of Vineyard Haven Harbor and Sound
For those seeking a more leisurely and immersive way to experience the scenic waterways of Martha’s Vineyard, the 2-Hour Sailing Tour of Vineyard Haven Harbor and Sound offers a captivating option.
Aboard a classic 60-foot (18-meter) ketch, made famous in the movie “Trading Places,” guests can enjoy stunning views of the West and East Chop Lighthouses as they sail through Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.
Suitable for first-time and returning visitors, the tour accommodates up to six passengers and allows them to bring their own alcoholic beverages and meals. Infants must sit on laps, and children under 14 must wear life jackets.
While not recommended for those with back problems or serious medical conditions, the tour requires a moderate level of physical fitness. Inclusive of bottled water, snacks, and soda/pop, the tour also offers the option to arrange for catered lunch or dinner at an additional cost.
The tour operates daily from May 23 to September 20, 2025, with positive reviews highlighting the relaxing experience, friendly captain, and beautiful sunsets.
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
The 6-Hour Sailing Tour of Vineyard Haven Harbor and Sound offers a captivating way for visitors to enjoy the rich nautical tradition of Martha’s Vineyard. Aboard a classic 60-foot (18-meter) ketch sailboat, up to 12 people can sail around the picturesque Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound.
The tour provides a customizable itinerary that caters to the group’s interests, ensuring an unforgettable experience. Included in the tour are water, sodas, and snacks, with the option to purchase lunch and alcoholic beverages.
The meeting point is at the Black Dog Wharf in Vineyard Haven, with access via the Vineyard Haven Launch dock. The tour operates daily from May 23 to September 20, 2025, with a confirmed start time between 9:00 AM and 3:00 PM.
Guests must meet a moderate physical fitness level, and children under 13 are required to wear life jackets. With a 5-star rating and positive reviews, this sailing tour promises to deliver an authentic taste of Martha’s Vineyard’s maritime heritage.
Read our full review: 6 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
3 Hour Sailing Tour of Vineyard Haven Harbor and Sound
How does the 3-Hour Sailing Tour of Vineyard Haven Harbor and Sound offer visitors an intimate glimpse into Martha’s Vineyard’s rich maritime heritage? This private half-day tour aboard a classic 1980 60-foot ketch sailboat provides guests with a relaxing outdoor adventure.
Participants can explore Nantucket Sound and local landmarks while customizing the itinerary based on their interests. The tour includes water, sodas, and snacks, with a lunch option available for an additional $15. Alcoholic beverages can be ordered as well.
Guests meet at the Black Dog Wharf in Vineyard Haven and access the tour via the Vineyard Haven Launch dock, with a $4 per adult and $2 per child fee. The tour operates from May 23 to September 20, with flexible scheduling from 9 AM to 5 PM.
While not recommended for travelers with back problems or serious medical conditions, the tour offers a unique opportunity to experience the island’s coastal beauty and maritime traditions.
Read our full review: 3 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
4 Hour Sailing Tour of Vineyard Haven Harbor and Sound
Providing visitors an intimate glimpse into Martha’s Vineyard’s rich maritime heritage, the 4-hour Sailing Tour of Vineyard Haven Harbor and Sound aboard a classic 60-foot ketch sailboat offers a private, relaxing outdoor adventure.
Suitable for groups of up to six, the tour explores Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound, allowing guests to soak in the stunning coastal vistas.
Complimentary water, soft drinks, and snacks are provided, and adults can bring their own alcoholic beverages. Guests have the option to arrange for a catered lunch or dinner at an additional cost.
The tour departs and returns to the Black Dog Wharf, with access via the Vineyard Haven Launch dock. Operating from late May to mid-September, the tour isn’t recommended for travelers with back problems or serious medical conditions, as moderate physical fitness is required.
Though the overall rating is 3.0, the unique experience of sailing on a featured movie boat provides an unforgettable way to discover Martha’s Vineyard’s maritime wonders.
Read our full review: 4 Hour Sailing Tour of Vineyard Haven Harbor and Sound Review
Book now: Check availability
Private Tour of Marthas Vineyard With Lunch Included
Offering a comprehensive exploration of Martha’s Vineyard, this private tour provides visitors with an immersive experience that showcases the island’s natural beauty, rich history, and vibrant culture.
Boasting a convenient pickup from either your hotel or the Woods Hole area, the tour includes a delightful lunch, refreshing bottled water, and soothing coffee or tea, ensuring a comfortable and enjoyable journey.
The tour begins at 9:00 am and lasts for the entire day, allowing ample time to explore the island’s highlights. While the tour isn’t wheelchair accessible, it’s suitable for most travelers, including infants who can sit on laps.
Guests should note that the tour isn’t recommended for those with heart problems or serious medical conditions.
With a total of one review and a one-star rating, this private tour may not have the highest accolades, but the authenticity of the reviews has been verified.
Ultimately, the tour offers a personalized and enriching way to discover the charms of Martha’s Vineyard.
Read our full review: Private Tour of Marthas Vineyard With Lunch Included Review
Book now: Check availability
Frequently Asked Questions
Can I Bring My Pet on the Tour?
Most tour providers don’t allow pets on their tours, as they can disrupt the experience for other guests. However, some may make exceptions for service animals. It’s best to check with the tour company beforehand to understand their pet policy.
Is There a Discount for Seniors or Students?
Many tour operators offer discounts for seniors and students. It’s best to inquire about specific policies when booking a tour. Some companies may provide reduced rates or special packages for these groups.
How Do I Get to the Starting Point of the Tour?
Visitors can typically reach the starting point of the tour either by public transportation, such as a bus or ferry, or by driving and parking nearby. Many tour companies provide detailed information on their website about getting to the departure location.
Can I Customize the Tour Itinerary?
Customers can often customize tour itineraries to suit their preferences. Many tour providers are willing to adjust the schedule or activities to accommodate special requests, ensuring a personalized experience that meets the traveler’s needs and interests.
What Is the Cancellation Policy for the Tours?
The cancellation policy for tours typically allows customers to cancel or change their reservations up to 24-48 hours prior to the tour date without penalty. However, some tours may have stricter policies, so it’s best to check with the tour provider for their specific terms.
The Sum Up
Martha’s Vineyard offers a variety of tours to suit different interests and budgets. From island sightseeing to sailing adventures, visitors can explore the island’s natural beauty, historic sites, and charming towns. Whether you prefer a group tour or a private excursion, Martha’s Vineyard provides an opportunity to experience the unique character of this New England destination.