Attractions & Things to Do
on Martha’s Vineyard
Hotelito Oso places you directly in the beating heart of Oak Bluffs — no Uber required, no itinerary necessary. Step outside your door onto Circuit Avenue and you’re immediately surrounded by the island’s best shopping, cafés, cocktail spots, galleries, live music, and late-night wanderings. Just steps away sits Ocean Park, the grand green lawn by the sea that may very well be the most beautiful public park in America — a place where kites fly, ferries drift into the harbor, and the Atlantic breeze somehow slows time down. A short stroll brings you to the legendary Flying Horses Carousel, the oldest operating platform carousel in the United States, where brass rings, painted horses, and summer nostalgia have been spinning since the 1800s.
Beyond Oak Bluffs
One of the great luxuries of Hotelito Oso is location. You are almost perfectly positioned between the Vineyard’s two other iconic harbor towns: historic Edgartown and charming Vineyard Haven — each roughly six miles away in opposite directions. Spend the afternoon in Edgartown among captain’s homes, yacht culture, fine dining, and polished New England elegance, or head toward Vineyard Haven for bookstores, cafés, galleries, and a slightly more laid-back island rhythm. In every direction, Martha’s Vineyard unfolds into beaches, cliff walks, lighthouses, bike trails, conservation land, and miles of coastal hiking that feel worlds away from the mainland. From the dramatic clay cliffs of Aquinnah to hidden trails through the island’s forests and shoreline, the Vineyard rewards people who wander slowly and stay curious. And at the end of it all, you return not to a resort packed with strangers — but to a single key waiting for you above Circuit Avenue.
Public Tours
Private Martha’s Vineyard Tours
$250 per hour (two-hour minimum)
Looking for a more personalized experience? Private tours are available for individuals, families, and groups at a rate of $250 per hour, plus gratuity for your driver-guide.
Our private tours are completely customizable and can be tailored to your interests, schedule, and pace. Whether you’re interested in history, architecture, the filming locations of Jaws, Island neighborhoods, or simply seeing the best sights Martha’s Vineyard has to offer, we’ll create an experience just for you.
Please note that a realistic driving tour of the entire Island, including Aquinnah and the up-Island communities, requires approximately three hours, even without extended stops.
The minimum private tour is two hours. Due to time constraints, a two-hour tour does not include Aquinnah or the Cliffs of Aquinnah.
Private tours may be booked for as many hours as you’d like, allowing plenty of time for sightseeing, shopping, photography, dining, or exploring at your own pace.
Advance reservations are recommended.
Island Tour – Martha’s Vineyard in 2½ Hours
$55 per person ($50 for hotel guests)
Join us daily at 11:00 AM and 2:00 PM for a fully narrated, 2½-hour journey around Martha’s Vineyard aboard our comfortable Ford Transit touring van. (14 passengers max)
Our signature tour circumnavigates the Island, showcasing the history, culture, and breathtaking scenery that make Martha’s Vineyard unlike anywhere else in America. Highlights include the colorful cottages of Oak Bluffs, the historic whaling village of Edgartown, rolling farmland, stone walls, coastal vistas, several lighthouses and a visit to the spectacular Cliffs of Aquinnah.
Your tour includes approximately 20 minutes in Aquinnah, where you’ll have time to explore the shops operated by members of the Wampanoag Tribe, photograph the iconic Gay Head Lighthouse, and take in some of the most dramatic ocean views in New England.
The Wampanoag people have called Martha’s Vineyard home for approximately 12,000 years. To put that into perspective, they were living here thousands of years before the Great Pyramid of Giza was completed and long before the rise of Ancient Rome. Few places in North America can claim such a continuous connection between a people and their homeland.
Whether it’s your first visit or your fiftieth, this tour provides the perfect introduction to the Island’s rich history, unique culture, and stunning natural beauty.
Reservations are recommended.