The 10 Best Tours in Oak Bluffs, Massachusetts (MA)

January 24, 2022 Margarita Chappel

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. The population was 4,527 at the 2010 United States Census. It is one of the island's principal points of arrival for summer tourists, and is noted for its "gingerbread cottages" and other well-preserved mid- to late-nineteenth-century buildings.
Restaurants in Oak Bluffs

1. AFAM History Tour

1 Seaview Ave, Oak Bluffs, MA 02557, USA HomeGrown Tours
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 1 reviews

The af/am history tour is one of the most treasured tours here. We will visit most or all of the sites that have to do with af/am history and heritage. There are 27 sites to visit. We will see the Rebecca Amos farm, The Shearer Cottage, the Denniston House of worship, The Highlands, and many many others. We will also visit places that are not listed on the trail.... This tour can take 2 hours or up to 5 hours depending on what you would like to see...

Inclusions: Bottled water, Snacks, Air-conditioned vehicle, Private transportation, Screen to see what certain sites looked like in the 1800s

Exclusions:

Reviewed By Ebony3052404

Very informative but wish we could have time for more questions and answers. But she was thorough and enjoyed it. Can someone contact me so I can tip her? Unfortunately we didn't have cash and I couldn't find her in Venmo. Her tip is well deserved and I whirls really like to give it to her

2. Martha's Vineyard Private Sunset Sightseeing Cruises by Island Time Charters

Owen Park Way, Tisbury, MA 02568, USA Island Time Charters
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 13 reviews

Island Time Charters offers Martha's Vineyard sunset/cocktail cruises which are ideal for those who want to celebrate a special occasion such as bachelorette parties, proposals, first time island visitors or just want to celebrate life. We will pick you up by boat and take you on a private sightseeing harbor cruise while you comfortably enjoy the sunset sipping on your favorite cocktail. There are 3 different routes to choose from giving our guest the opportunity to experience different areas of Martha's Vineyard.

Inclusions: A fully fueled 26' Bennington Pontoon Boat, Soft drinks, towels, blankets ​

Exclusions: Can be arranged for an additional charge., Guest are encourage to their own snacks and BYO, Gratuities

Reviewed By Nina24k

This was the most memorable experience on the island. The boat was spectacular and our captain was incredible! I definitely would recommend this cruise. It was amazing! ????

3. Martha's Vineyard Sightseeing Cruises

Owen Park Way, Tisbury, MA 02568, USA Island Time Charters
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 15 reviews

Island Time Charters offers Martha's Vineyard sunset/cocktail cruises which are ideal for those who want to celebrate a special occasion such as bachelorette parties, proposals, first time island visitors or just want to celebrate life. We will pick you up by boat and take you on a sightseeing harbor cruise while you comfortably enjoy the sunset sipping on your favorite cocktail.

Inclusions: A fully fueled 26' Bennington Pontoon Boat, Soft drinks, towels, blankets ​

Exclusions: Can be arranged for an additional charge., Guest are encourage to their own snacks and BYO

Reviewed By briannaf403

Captain Joe made our time spent in Martha’s Vineyard both educational and fun. We had a blast cruising around the island 10/10 would recommend to anyone visiting for the first time or the hundredth!

4. Martha's Vineyard Leisure Sightseeing Cruise

Owen Park Way, Tisbury, MA 02568, USA Island Time Charters
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 5 reviews

Island Time Charters offers Martha's Vineyard Sightseeing cruises which are ideal for those who want to celebrate a special occasion such as bachelorette parties, proposals, first time island visitors or just want to celebrate life. We will pick you up by boat and take you on a sightseeing cruise while you comfortably enjoy breathtaking views sipping on your favorite beverage. There are 3 different routes to choose from giving our guest the opportunity to experience different areas of Martha's Vineyard.

Inclusions: A fully fueled 26' Bennington Pontoon Boat, towels, blankets ​

Exclusions: Guest are encourage to their own snacks and BYO, Can be arranged for an additional charge., Gratuities

Reviewed By Nina24k

This was the most memorable experience on the island. The boat was spectacular and our captain was incredible! I definitely would recommend this cruise. It was amazing! ????

5. Newport, RI Day trip to Martha's Vineyard

Newport, RI, USA Yes! We Van
Excellent
0%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
100%
Overall Ratings

4.8 based on 9 reviews

Enjoy a self-guided daytrip to Martha’s Vineyard! Do sightseeing, shopping, or have fresh "right-off-the-boat" seafood! We will pick you up in our comfortable, semi-private vans at your desired location in the Newport, RI area and take you to the historic seaport of New Bedford, Massachusetts. Your driver will say good-bye as you enjoy a luxurious cruise to Martha’s Vineyard on the SeaStreak Fast Ferry. The ferry glides through the waters between the islands ensuring a smooth, relaxing trip! When you arrive on the island, explore the sights that interest you at your leisure (self-guided). Follow the walking tour of Oak Bluffs including the Flying Horse Carousel, Ginger Bread Houses, and picturesque marina. Enjoy authentic New England seafood or just relax on one of the many beaches. Feeling adventurous? Take a shuttle over to the Aquinnah cliffs! At the end of the day, your driver will meet you in New Bedford for your return ride to the Newport, RI area.

Inclusions: Hotel pickup and drop-off, Round-trip shared transfer from Newport, RI to the ferry port at New Bedford, Round-trip ferry from New Bedford to Martha's Vineyard

Exclusions: Gratuities, Shuttle bus on Martha's Vineyard (approx. $10), Food and drinks, A Guided Tour

Reviewed By 346kimg

Wonderful experience! Great drivers. Very friendly and informative. Would definitely recommend. Have fun!

6. Martha's Vineyard Day Trip with Optional Island Tour from Boston

New England Excursions
Excellent
77%
Good
14%
Satisfactory
7%
Poor
2%
Terrible
0%
Overall Ratings

4.7 based on 59 reviews

New England Excursions is a veteran owned coach service to Martha's Vineyard. Our ease of booking, convenient pickup and drop-off locations and comfortable, air-conditioned coach will provide you with a memorable experience. You'll enjoy a short ride from Boston to Woods Hole where you will board the Steamship Authority with no lines or waiting in a holding area. With us, you will have time to enjoy breakfast, coffee or shopping before boarding. As always, round-trip ferry tickets, snacks, water, island maps, discount food cards and commentary are all free of charge.  Island tour option; You'll have a wonderful 4 hour, full island tour in one of our 14 passenger air-conditioned, high-top vans. Tour goes through all 6 towns with stops along the way for snacks and pictures. A one-hour lunch break in Edgartown is very pleasing. Our guides are the best in the business. Enjoy the intimate experience by asking questions and being part of the New England Excursions family.

Inclusions: Snacks, Bottled water, maps, Discount food card, Driver/guide, Live commentary on board, Hotel pick-up and drop-off, Ferry Tickets

Exclusions: Island tour only available as an add-on, Food and drinks on the ferry and the island are up to the traveler unless specified otherwise

Reviewed By MendyG_12

We were in Boston for my husband's 50th birthday. We booked a tour with New England Excursions. So glad we did! Matt, the owner and driver communicated with us the day before and verified the time he would arrive at our hotel to pick us up. Matt was punctual, professional, friendly, knowledgeable and enthusiastic about everything Boston and the surrounding areas. My hubby and I were extremely grateful with his help in securing two seats for a 2hour tour on Martha's Vineyard. I would definitely recommend this tour and will use this company when we visit Boston again. ???? Got our eyes on Kennebunkport Maine! ????

7. Providence, RI day trip to Martha's Vineyard

Providence, RI, USA Yes! We Van
Excellent
0%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
100%
Overall Ratings

4.6 based on 16 reviews

Enjoy a self-guided daytrip to Martha’s Vineyard! Do sightseeing, shopping, or have fresh "right-off-the-boat" seafood! We will pick you up in our comfortable, semi-private vans at your desired location in the Providence, RI area and take you to the historic seaport of New Bedford, Massachusetts. Your driver will say good-bye as you enjoy a luxurious cruise to Martha’s Vineyard on the SeaStreak Fast Ferry. The ferry glides through the waters between the islands ensuring a smooth, relaxing trip! When you arrive on the island, explore the sights that interest you at your leisure (self-guided). Follow the walking tour of Oak Bluffs including the Flying Horse Carousel, Ginger Bread Houses, and picturesque marina. Enjoy authentic New England seafood or just relax on one of the many beaches. Feeling adventurous? Take a shuttle over to the Aquinnah cliffs! At the end of the day, your driver will meet you in New Bedford for your return ride to the Providence, RI area.

Inclusions: Hotel pickup and drop-off, Round-trip shared transfer from Providence to ferry port at New Bedford, Round-trip ferry from New Bedford to Martha's Vineyard

Exclusions: Gratuities, Shuttle bus on Martha's Vineyard (approx. $10), Food and drinks, Guided tour on the island

Reviewed By JDM92012

We used Yes we van for our airport transfers for 6 adults. The process was very easy they were very prompt with responses and right on time to pick us up. They confirmed by text each day prior to our transfers. We had Sean take us to The airport and Dave bring us back, both were great! Will definitely use them again.

8. 3-Hour Martha's Vineyard Island Tour from Oak Bluffs

1 Seaview Ave, Oak Bluffs, MA 02557, USA Martha’s Vineyard Tours and Transportation
Excellent
0%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
100%
Overall Ratings

4.5 based on 171 reviews

Experience our famous 3-hour full Island tour for a budget friendly rate! 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 two 15-minute stops in Menemsha & Cliffs of Aquinnah. Top highlights on this tour include Oak Bluffs, Edgartown, Vineyard Haven, Aquinnah, West Tisbury, Chilmark, and Menemsha.

Inclusions: 3-Hour Island Tour of Martha's Vineyard from Oak Bluffs, Small-group tour for a more personalized experience, Professional Driver/Guide, Live commentary on board, Transportation via air-conditioned vehicle, Experience top Martha's Vineyard areas including Oak Bluffs, Vineyard Haven, and Aquinnah, 15-minute photo stop at Aquinnah (Gay Head Cliffs), 15-minute stop in Menemsha, an Idyllic fishing village

Exclusions: Gratuities, Snack & Water

Reviewed By 509fernt

Great way to see the Vineyard if you are visiting without a car. Interesting information about the island. Rich was very kind and friendly.

9. Martha's Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option

Boston Marriott Long Wharf, 296 State St, Boston, MA 02109, USA New England Trips
Excellent
0%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
100%
Overall Ratings

4.4 based on 862 reviews

Don't be fooled by copycats. We are Boston's ORIGINAL Martha's Vineyard day trip and Boston's #1 day trip service to the island since 2011. 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!

Inclusions: Boston to Martha's Vineyard Day-Trip Excursion, Round-Trip Transportation on Air-Conditioned Mini Coach Bus, Hotel Pick-Up/Drop-Off included at select Boston hotels, 3-Hour Narrated Martha's Vineyard Island Bus Tour (option available at checkout), 50-minute stop to explore downtown Edgartown at your leisure (Island Tour upgrade), 15-minute stop to view the Gay Head Cliffs in Aquinnah (Island Tour option), See all 6 Martha's Vineyard Towns during your island tour including Vineyard Haven & Aquinnah , Drive through charming downtown Falmouth and along the Cape Cod Canal on the way to the ferry, Scenic 35-45 min ferry cruise from Cape Cod to Oak Bluffs or Vineyard Haven (based on travel date), Bonus stop at Nobska Lighthouse in Falmouth in Cape Cod (based on travel date), Complimentary Bottled Water, Snacks and Island Guidebooks, Narration during Mini Coach Bus Ride, Restroom stop halfway between Boston and Cape Cod, 6 hours total time on the island

Exclusions: Gratuities, Lunch (dining options available on Martha's Vineyard)

Reviewed By Dwight A

Christine was a great tour guide and personal chauffeur. It was a very hot day and she made herself available for a quick pick-up when the heat got too much for anyone. It was a small group with Covid going on so she catered to our groups preferences and substituted other attractions for the advertized activities that where closed. Great job!

10. All Island Bus Tour

1 Seaview Ave, Oak Bluffs, MA 02557, USA HomeGrown Tours
Excellent
61%
Good
17%
Satisfactory
0%
Poor
0%
Terrible
22%
Overall Ratings

4.0 based on 21 reviews

Our All Island Bus tour is for those that want to get an overall idea of what Marthas Vineyard is and be able to do a little shopping, eating and sightseeing. Being narrated by a third generation Islander, we have loads of history to tell along with personal stories to highlight.

Inclusions: Bottled water, Lite snacks: pretzels, fritos, chips, crackers, cookies, Rain ponchos, Air-conditioned vehicle, Screen at front of bus shows what certain sites looked like in the 1800s, Feel the Vineyard thru items passed around: cedar shingles, quahog shells, wool, etc, Tshirts, homemade items (key chains, jewelry) available for sale, Charging station for your phones or tablets.... no computers., swag bags: Every passenger receives a swag bag: included are maps, guides, coupons and surprises

Exclusions:

Reviewed By Susan S

I spent three hours touring Martha's Vineyard in a private van with Donna as my driver/guide. It was a delightful afternoon, and I am so happy I took the tour today. The sun was shining the whole day, and Donna enhanced the trip by offering all kinds of historical information along the way and in all the places we visited. It was great to be with a long-time local, as Donna filled me in with details that perhaps I would not have experienced with someone else. Again, a delightful afternoon.....Thank you!

ThingsTodoPost © 2018 - 2024 All rights reserved.