Discover amazing Oyster Bay activities and premium in-home experiences.
Oyster Bay invites you to explore its rich tapestry of history and natural beauty, where charming streets meet serene waterfronts. Known for its vibrant maritime heritage and lush landscapes, this coastal gem offers a perfect blend of outdoor adventure and small-town warmth. Whether you're sailing the tranquil waters or discovering local lore at historic sites, Oyster Bay welcomes you with open arms to savor every moment.
See Westchester’s landmarks from the air on a quick, scenic flight
Fly privately from Westchester for sweeping Manhattan views in 30–45 minutes
Soar above Manhattan with narrated views on a 30–45 minute shared flight
Experience Madison Square's Gilded Age architecture and nightlife history
Unlock Midtown from Times Square to Rockefeller Center
Explore three floors and the veranda of this rare octagonal landmark with an expert docent
See Central Park's highlights on a guided 2-hour bike ride with photo stops
Explore hip hop's origins with pioneer guides across Harlem and the Bronx
Explore Harlem's hip-hop roots with legend guides on a 2-hour walk
Experience Niagara Falls in a day with guided coach transport from NYC and seasonal boat access
See D.C. and Philadelphia highlights in a single guided day with round-trip coach transport
Taste five award-winning NYC dishes on a guided 3-hour walk with skyline views
Taste diverse global bites in Midtown’s Hell’s Kitchen while hearing insider stories from your guide
Fly by private helicopter to East Hampton for a catered beach picnic
Enjoy a casual 4.7-mile run through Central Park's top sights with a guide in about 1.5 hours
Explore iconic immigration landmarks with an expert guide in a small group of no more than eight guests.
Explore The Met's highlights with an expert guide in a small group and skip the lines.
Explore The Met and Central Park with an expert guide in a small group of up to 8, with reserved entry included
Create your own street-style artwork with guidance from a local NYC graffiti artist in a Brooklyn studio.
Discover Bushwick's vibrant murals with a local street artist guide
Create a custom graffiti piece together with a local artist in a Bushwick studio
Private instruction in a Bushwick studio led by an NYC graffiti artist
Visit hidden speakeasies with rich Prohibition stories and preferred entry
Skip the lines and explore bars, speakeasies, and a rooftop with a local host
Enjoy free admission and express entry to bars, speakeasies, and a rooftop with your nightlife host
Discover Midtown speakeasies and Prohibition history with rich storytelling
See Central Park landmarks on a 40-minute horse-drawn carriage ride for all ages
Ride a private horse-drawn carriage through Central Park with drop-off at Tavern on the Green or the Loeb Boathouse
Ride a horse-drawn carriage from Central Park to Rockefeller and Times Square in 50 minutes
See Central Park’s top sights in 45–60 minutes with a comfortable pedicab and licensed guide
See Gaslamp, the Bay, and Balboa Park on a 2.5-hour guided eBike ride
Cover more of San Diego’s top sights with easy, pedal-assist eBikes and ride farther with less effort
Pedal the National Mall after dark when it’s cooler and less crowded with guided stops at major memorials.
Cycle past the Capitol, Supreme Court, and White House with an expert guide
Customize your route for an intimate, all-ages ride with 2–4 hour options
Flexible bike rentals from 2 hours to 1 month with helmet, map, and lock
Discover South Beach’s Art Deco and historic districts on a guided 2-hour ride
Explore Miami Beach at your pace on quality hybrid bikes to Ocean Drive, Espanola Way, and South Pointe Pier
Pedal Lower Manhattan and the Brooklyn Bridge with a private guide
Oyster Bay offers a delightful blend of history, nature, and small-town charm that sets it apart from its neighbors. This picturesque area is known for its rich maritime heritage and vibrant arts scene. Visitors can start their journey at Theodore Roosevelt's Sagamore Hill, where they can walk through the former president’s home and enjoy trails with sweeping views. In warmer months, Beekman Beach becomes a hub for kayaking enthusiasts looking to paddle along serene waters.
A stroll down Audrey Avenue reveals quaint shops and cozy cafes perfect for an afternoon break. The local farmers market is a must-visit on weekends, offering fresh produce alongside artisanal goods crafted by talented locals. For those interested in exploring further afield, nearby Planting Fields Arboretum provides stunning botanical gardens ideal for leisurely walks or picnics under ancient trees.
The town comes alive during annual events like the Oyster Festival each fall when seafood lovers gather to savor delicious shellfish dishes while enjoying live music performances. Whether you're hiking through lush preserves or attending cultural festivals that celebrate local traditions, Oyster Bay invites you to experience authentic Long Island life away from bustling city streets.