Rent a paddleboard for 24 hours at State Beach in Oak Bluffs
Rent a kayak or paddle board for 1–3 months with free delivery
Rent top-tier carbon or aluminum road bikes to explore the island.
Cover more ground effortlessly with pedal-assist power on colorful cruisers.
Cruise to town or the beach on a comfy 7-speed Townie
Cruise comfortably on a hybrid commuter bike with helmet and lock included
Cruise the island on a Specialized Como e-bike with pedal assist
Rent a premium dual sport bike for smooth riding on dirt roads and pavement
Ride Martha’s Vineyard trails on a Trek hardtail mountain bike
Rent a carbon fiber hybrid bike for smooth rides and fitness-focused comfort
Spend half a day sailing Cape Cod Bay with a private crew and optional swim stop.
Sail Provincetown Harbor and Cape Cod Bay on a private 6-hour charter
Sail Provincetown Harbor on a private, captained 2-hour charter for up to six guests
Customize a 4-hour private drive to historic towns, lighthouses, beaches, and scenic cliffs with a local guide
Tour Martha’s Vineyard’s 6 towns in 3 hours, with a stop at Aquinnah cliffs
Tour all 6 Martha’s Vineyard towns in 3 hours, with time for photos and a Menemsha stop
Sail a restored 1925 schooner at sunset with drinks and charcuterie

Search for whales on Stellwagen Bank aboard a boat reserved exclusively for your group.
Discover feeding and nursing whales at Stellwagen Bank on an intimate boat tour
Explore interactive exhibits and learn about Great White Sharks during a self-guided visit.
Track Cape Cod great whites with a captain and spotter pilot on a private 3-hour tour
Watch a Cape Cod sunset from the water with an ACA-certified guide
Paddle Scorton Creek, then make your own glass piece in Sandwich