Sail in luxury on a 44-ft catamaran yacht! We are one of the only sailing catamaran charters in Maine, and our luxurious yacht makes for a relaxing and fun experience. Our catamaran is stable and does not bounce in waves, providin... More

Come join us aboard a Lowcountry Lunch Cruise with the Dolphins departing from Harbour Town aboard the Spirit of Harbour Town! This cruise combines the beauty of the Lowcountry scenery with the excitement of spotting dolphins in t... More

Your Tripshepherd Tours Guide will greet you at either your downtown Miami or South Beach accommodations and begin your fully guided tour in the comfort of one of our complimentary vehicles, passing by the Venetian Bridge. Next, ... More

Take in the views on this award-winning 90-minute Architectural Tour, a jaw-dropping excursion through a city that defies all expectations!... More

Embark on the ultimate Miami adventure with our Best Miami Boat Tour, cruising the tropical waters and gliding past the lavish homes of celebrities. Let our Captain guide you on a thrilling 90-minute sightseeing voyage across Bisc... More

Experience the ultimate Miami adventure with the best Miami Celebrity Homes Boat Tour. Cruise the tropical waters, glide past the opulent residences of celebrities, and let our Captain lead you on an exhilarating 90-minute sightse... More

Hop aboard our 2-hour Private Miami Sunset Boat Tour, setting sail from our Miami Beach marina. Our friendly Captain will greet you with a warm welcome, making sure your sunset adventure is the highlight of your trip. Sit back, re... More

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome. Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to discover the... More

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic Boston tall ship! We depart Fan Pier Marina and raise the sails, then it’s time to just chill out and relax. Get a... More

Discover the beautiful views of the ocean, local wildlife, and the iconic east side of Oahu as you join me on a private catamaran cruise in Waikiki. We’ll depart from Kewalo Basin Harbor located in Honolulu and make our way up t... More

Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides a... More

Our Independence Day Premier Dinner Cruise on Lake Michigan is an unforgettable way to celebrate and experience the city from the water. While onboard, you’ll enjoy chef-prepared menus, creative cocktails, beer, wine, and Chicag... More

Come aboard for the ultimate sightseeing experience. Float along the Hudson and take in amazing views with light narration by our pianist of notable New York City sights like the Statue of Liberty, Brooklyn Bridge, One World Trade... More

Enjoy a festive Christmas cruise aboard a classic yacht decorated for the holidays and cruise into an evening of skyline views, holiday music and some tasty beverages. Get into the holiday spirit with close friends and family. ... More

Beach Weekend offers not only a unique adventure but educates on the love and respect for a marine life and natural habitats. You enter Beach Weekend as a guest and leave as family.... More

Discover the beautiful views of the ocean, local wildlife, the iconic east side of Oahu, and the sun dipping into the sea as you join me on a private catamaran cruise in Waikiki. We’ll depart from Kewalo Basin Harbor located in ... More

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Climb aboard the ‘Dutch Apple II’ for a 90-minute ride along the Hudson River. A Hudson River Narration is given along the way, sharing historical anecdotes and recalling interesting facts about the history of Albany and surro... More

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline... More

Step aboard a historic sailing ship and cruise around New York Harbor, taking in magnificent views of this grand city by day. You will enjoy breathtaking views of New York City and see the Statue of Liberty, Ellis Island, the Manh... More