When it comes to experiencing New York City, few tours manage to balance city sights and iconic landmarks quite like this combined 6-hour adventure. For just $160 per person, you’ll spend roughly three hours strolling through Manhattan’s most famous neighborhoods and landmarks, followed by a 90-minute sail on a historic tall ship that provides a fresh perspective on the city’s skyline and harbors. We’ll explore this tour’s highlights, what makes it stand out, and some points to consider before booking.
What we love most about this experience is the chance to get up-close views of the Statue of Liberty and Ellis Island from the deck of a tall ship, combined with the rich storytelling during the walking tour. The small group size and knowledgeable guides help keep the experience intimate and engaging. Also, the fact that it includes a sailing adventure—something quite rare in NYC—adds a dash of adventure that we find truly appealing.
A possible downside, however, is that the sailing portion is separate from the guided tour, with no guide accompanying you onboard. This means you’ll need to navigate independently during the cruise, which could be a consideration for travelers seeking a fully guided experience.
This tour is perfect for travelers who want a rundown of Manhattan’s most famous sights combined with a unique maritime perspective of New York Harbor. It suits those who enjoy walking, sightseeing, and a little adventure on the water, and who appreciate engaging guides and authentic local experiences.
Key Points

- Combination of city walking and sailing offers a well-rounded NYC experience.
- Knowledgeable guides enhance the storytelling and sightseeing.
- Small group size ensures personalized attention.
- The sailing cruise provides stunning views of the Statue of Liberty and NYC skyline.
- The itinerary covers iconic neighborhoods and landmarks with historical context.
- It’s a full-day experience, ideal for those wanting a thorough exploration.
This tour offers a detailed, balanced way to experience New York City’s most recognizable sights, blending history, culture, and scenic views. It’s designed to appeal to those who want both a walking tour of Manhattan and a sailing adventure on the harbor—two perspectives that reveal different facets of the city.
Starting Point: Wall Street and Lower Manhattan
.jpg)
The adventure kicks off at Federal Hall, 26 Wall St., located in the heart of the Financial District. From here, your guide, Jessica (or similar), will lead you through the bustling streets, pointing out how Wall Street’s iconic buildings like the New York Stock Exchange and landmarks such as the Charging Bull and Fearless Girl statues symbolize financial resilience and social progress.
What we love about this section is the insider storytelling—your guide will weave in tales about the district’s storied past, from the days of early commerce to the present-day finance hub. The one-hour walk gives you a chance to soak in the energetic atmosphere while snapping photos of the historic architecture.
If you're drawn to exploring New York City on foot, we've looked into these other walking experiences
Visiting Ground Zero and the 9/11 Memorial
.jpg)
Next, your group heads to Ground Zero, a place charged with emotion and significance. The 30-minute stop at the 9/11 Memorial offers an opportunity to pay respects and reflect on the city’s resilience. It’s a poignant moment, often described as moving and thoughtfully designed, allowing for personal contemplation amid the crowds.
If you’re interested in deeper engagement, the nearby 9/11 Museum can be visited separately, but this tour keeps it simple and respectful. The emotional impact of this site is undeniable, and it’s a key highlight that adds depth to the tour.
Exploring Little Italy, Chinatown, and Nearby Neighborhoods
.jpg)
From here, the tour ventures into Little Italy and Chinatown. We love the way these neighborhoods overflow with vivid sights, sounds, and smells. Your guide shares stories about the immigrant communities, local legends, and the historic gangsters and entrepreneurs who shaped the districts.
In Little Italy, you might see the historic Woolworth Building, featured in films like Fantastic Beasts, offering a tangible link to the city’s cinematic past. Chinatown provides vibrant street scenes, colorful signs, and a chance to pick up some snacks or souvenirs.
The Iconic Flatiron Building and Midtown
.jpg)
As you approach Midtown, the highlight is the Flatiron Building, an architectural marvel with its distinctive triangular shape. Perfect for a quick photo, this stop signals the end of the walking tour, which lasts about five minutes—enough time to admire and capture the moment.
Preparing for the Sailing Cruise
.jpg)
After the walking portion, it’s time to make your way to the South Street Seaport Historic District for the sailing adventure. The cruise lasts approximately 90 minutes, passing by The Statue of Liberty, Ellis Island, Governors Island, and various famous bridges like the Brooklyn Bridge.
Enjoy being on the water? Here are other boat experiences we've looked into in New York City
The Sailing Experience
.jpg)
The tall ship, the Clara, is a restored historic vessel, and sailing on it offers a different perspective on NYC’s waterways. You’ll enjoy stunning views of the skyline, especially with the wind in your hair and the city unfolding around you.
While your guide doesn’t accompany you onboard, the crew provides commentary, and the ship’s design ensures excellent viewing from multiple vantage points. Expect to see the Statue of Liberty up close, a moment many consider unforgettable. The cruise also offers fantastic photo opportunities, so bring your camera.
What’s Included and What’s Not
.jpg)
The tour includes the 3-hour walking tour, the sailing ticket, and a small group size—limiting to 20 participants—making it more intimate. You’ll want to bring your own food and drinks, as these aren’t included, and plan for about $5 for metro fares if you’re using public transportation to reach the meeting point.
At $160, this experience balances cost and value nicely. The combination of guided walking and sailing means you’re covering a lot of ground without feeling rushed or exhausted. The small group size ensures you get personalized insights, and the scenic cruise adds an element of adventure and spectacular views that can’t be matched by land-based tours.
The timing allows for a relaxed pace—three hours of walking with plenty of stops, followed by the cruise, which provides a fresh perspective on familiar sights. Many users mention the guides, like Jessica, as knowledgeable and engaging, adding layers of context that make the sights come alive.
Authentic Experiences and Unique Viewpoints
.jpg)
What sets this tour apart is the marriage of land and water experiences. Walking through historic neighborhoods allows you to absorb the city’s texture, while the sail on NYC Harbor offers an authentic maritime perspective—something you simply can’t get from a bus or a quick photo stop.
Travelers have commented on how the views from the ship are spectacular, especially with the city skyline as a backdrop. The chance to see Liberty Island and Ellis Island from the water at close range enhances the visit’s significance, making it more than just a sightseeing tour—it’s a memorable experience.
This experience appeals best to those who want a balanced exploration of Manhattan’s neighborhoods and the harbor’s maritime charm. It’s ideal for history enthusiasts, photographers, and adventurers who enjoy being on the water. If you prefer guided tours with detailed storytelling and authentic local flavor, this tour offers plenty of that.
However, if you’re looking for a completely guided experience, note that the sailing portion is self-guided, so you’ll need to be comfortable navigating independently during the cruise.
In essence, this combined walking and sailing tour offers an excellent value for anyone wanting to see Manhattan’s highlights with a maritime twist. It’s well-organized, with engaging guides who bring stories to life, and the scenic cruise provides a unique vantage point of NYC’s most famous sights.
Perfect for first-time visitors eager to tick off iconic landmarks and those who want a more intimate, authentic experience of New York’s harbor and neighborhoods. While it’s not a backpacker budget option, the combination of land and sea makes it a memorable way to spend a day exploring the Big Apple.
If you’re after a balanced, authentic, and scenic New York experience, this tour hits all the right notes.
How long does the entire tour last?
The full experience takes about 6 hours, including a 3-hour walking tour and a 90-minute sailing cruise, with some break time in between.
Where do we meet for the tour?
The tour begins at Federal Hall National Memorial, 26 Wall St., in Lower Manhattan.
Is transportation included?
No, transportation to the meeting point is not included. You’ll likely need around $5 for a Metro ride or plan to arrive on foot.
Does the tour guide stay with us during the sailing?
No, the guide does not accompany you on the boat. The cruise is self-guided, but crew members provide commentary during the sailing.
What sights are visible during the cruise?
You’ll see The Statue of Liberty, Ellis Island, Governors Island, and NYC’s famous bridges, with fantastic skyline views.
Are food and drinks included?
No, you’ll need to bring your own food and drinks if desired, as they are not provided.
How big are the tour groups?
The maximum group size is 20 travelers, ensuring a more personal experience.
Is this tour suitable for children?
Most travelers can participate, and the tour is family-friendly, but check individual needs for the sailing portion, especially if anyone has mobility issues.
This detailed review aims to help you decide whether this combined walking and sailing tour matches your interests and travel style. Whichever way you choose, exploring New York from both land and sea offers a memorable way to experience one of the world’s greatest cities.
More Walking Tours in New York City
- Highlights of Central Park New York City Guided Walking Tour
- Full Day Private Walking Tour in New York from New York hotels
- The Best of Midtown Manhattan Self-Guided Walking Tour
- Ultimate NYC Christmas Lights At Night Walking Tour
- New York Midtown self-guided walking tour & scavenger Hunt
- Rockefeller Center Walking Tour With Top of the Rock
More Tours in New York City
- Boho Greenwich Village: A Self-Guided Audio Tour
- Highlights of Central Park New York City Guided Walking Tour
- Central Park Scandal and Vice Tour
- Secrets of the Statue of Liberty and Ellis Island Guided Tour
- Full Day Private Walking Tour in New York from New York hotels
- Street Art & Graffiti Tour in NYC Private Tour
More Tour Reviews in New York City
- Boho Greenwich Village: A Self-Guided Audio Tour
- Highlights of Central Park New York City Guided Walking Tour
- Central Park Scandal and Vice Tour
- Secrets of the Statue of Liberty and Ellis Island Guided Tour
- Full Day Private Walking Tour in New York from New York hotels
- Street Art & Graffiti Tour in NYC Private Tour
More New York City experiences we've covered
- Highlights of Central Park New York City Guided Walking Tour
- Central Park Scandal and Vice Tour
- Secrets of the Statue of Liberty and Ellis Island Guided Tour
- Full Day Private Walking Tour in New York from New York hotels
- Street Art & Graffiti Tour in NYC Private Tour
- Manhattan Helicopter Sightseeing Tour
- Full-Day Luxury Long Island Private Winery Tour
- The Best of Midtown Manhattan Self-Guided Walking Tour
- NYC Adventure Pass – Edge Observation Deck, The Beast and RiseNY
- Official Audio Tour of St. Patrick’s Cathedral
- Ultimate NYC Christmas Lights At Night Walking Tour
- 2-hour Private Luxury New York City Sunset Boat Tour
