Oak Bluffs Boat Tours
The best out of 32 boat tours in Oak Bluffs - enter dates to check availability
42 ft
Up to 6 people
Martha’s Vineyard Charter Company
5.0
/5
(6 reviews)
Martha's Vineyard (9 min drive from Oak Bluffs)
Set sail around the scenic waters of Martha’s Vineyard aboard Our Passion, a beautifully maintained 1983 Pearson 422 Sailing Yacht operated by Martha’s Vineyard Charter Company.
"My wife and I booked a last minute sunset sail and were pleasantly surprised to get a confirmation so quickly." — Michael,
"My wife and I booked a last minute sunset sail and were pleasantly surprised to get a confirmation so quickly." — Michael,
+3
trips from
US $945
60 ft
Up to 6 people
Island Sailing Tours
Martha's Vineyard (7 min drive from Oak Bluffs)
Set sail on the beautifully restored 1980 Nautical Development 56 Sailing yacht, refreshed in 2024, and based out of picturesque Martha's Vineyard.
trips from
US $600
30 ft
Up to 6 people
Bounty Hunter Shark Adventures
Martha's Vineyard (16 min drive from Oak Bluffs)
Our shark dive adventures are the culmination of many years in the waters we operate. We currently sail from S. Yarmouth, Martha’s Vineyard, and Nantucket. Our vessel Fins has been outfitted to run at speed with our super-strong, custom-built cage.
trips from
US $750
27 ft
Up to 6 people
Vineyard Boat Charters with Capt. John Hobby
New
5.0
/5
(24 external reviews)
Martha's Vineyard (3.1 miles from Oak Bluffs)
A fun time to cruise up and down the north shore of the Vineyard and see the island from a water view. We leave from Tahmoo Harbor and cruise down the North shore coast or over the the Elizabeth Islands.
trips from
US $450
25 ft
Up to 6 people
Popponesset Bay Tours & Sunset Cruises
5.0
/5
(2 reviews)
•
27 external reviews
Mashpee (1 hr 29 min drive from Oak Bluffs)
Experience the beauty of Cape Cod from the water with our scenic boat tours and sunset cruises through the pristine waters of Popponesset Bay in Mashpee, Massachusetts.
"Chris and his colleague were absolutely amazing! I arrived later than expected, and Chris was incredibly accommodating and understanding." — Jorlyna,
"Chris and his colleague were absolutely amazing! I arrived later than expected, and Chris was incredibly accommodating and understanding." — Jorlyna,
+1
trips from
US $300
32 ft
Up to 6 people
Obsession Tours – Martha's Vineyard
New
Martha's Vineyard
Obsession Tours is a beautifully restored 1989 Blackfin 1 Sportfishing (refitted in 2011), operating out of Falmouth and offering an unforgettable private boating experience for up to 6 guests.
trips from
US $450
25 ft
Up to 6 people
In The Net Sportfishing
New
5.0
/5
(2 reviews)
•
41 external reviews
Barnstable (15.3 miles from Oak Bluffs)
Step aboard In The Net Sportfishing, a 2021 Grady-White Fisherman 257 center console designed for speed, comfort, and serious on-the-water adventure out of Barnstable.
"We had a non-fishing expedition with Captain Benjamin, and he did a wonderful job keeping my non-water-friendly mother happy and calm as we toured the bay." — Susanna,
"We had a non-fishing expedition with Captain Benjamin, and he did a wonderful job keeping my non-water-friendly mother happy and calm as we toured the bay." — Susanna,
+3
trips from
US $400
26 ft
Up to 6 people
Fishon Boat Tours
Wareham (22.3 miles from Oak Bluffs)
Discover the beauty of the Cape with Fishon Boat Tours aboard a sleek 2018 Cobia 261 Center Console, departing from Wareham.
+2
trips from
US $300
21 ft
Up to 6 people
Waquoit Bay & Washburn Island Boat Cruises
New
5.0
/5
(27 external reviews)
Mashpee (11.2 miles from Oak Bluffs)
Discover the natural beauty and rich coastal heritage of Waquoit Bay on one of our relaxing boat tours and sunset cruises in Mashpee, Massachusetts.
+1
trips from
US $300
25 ft
Up to 5 people
Fishy Business Sportfishing
New
4.8
/5
(42 external reviews)
Plymouth (35.6 miles from Oak Bluffs)
Summers on Cape Cod and in Plymouth, MA, are made for unforgettable days on the water with family and friends. Join Fishy Business Sportfishing for a fully customizable private boating experience designed around your ideal day at sea.
+5
trips from
US $400