Old Town Trolley Tours of Boston is the premier sightseeing company in New England. It is part of the largest family-owned heritage tour and attraction company in the United States, Historic Tours of America, Inc. Since its inception in 1980, Old Town Trolley Tours has expanded to 9 history-rich cities across the country and has been named one of the best “Hop-On, Hop-Off” tours in the world by Forbes.
For over 40 years, Old Town Trolley Tours of Boston has entertained visitors with its diverse team, which includes people from varied backgrounds, personalities, and talents. These elements make up our vibrant company culture. Our mission is threefold: to prioritize safety, be courteous, and help our guests relive history.
Visit us in our sister cities: Charleston, SC; Key West, FL; Nashville, TN; San Antonio, TX; San Diego, CA; Savannah, GA; St. Augustine, FL; and Washington, DC.
Are you ready to join the ranks of the funemployed?
We continually seek good, dependable, and enthusiastic people who are highly motivated and possess leadership skills. We are an exciting and dynamic company marked by constant expansion and change while maintaining a stable environment for daily support, empowerment, and career growth.
Our beautiful, open-air restaurant offers spectacular waterfront dining. Overlooking the Historic Seaport and the Key West Marina, the view and the atmosphere combine to bring you the finest restaurant in the Bight. The outside Brick Courtyard or Terrace Patio can seat groups from 30-200 people. If you prefer something a little more exclusive, our restaurant is available for completely private affairs with an all-inclusive menu and open bar package for up to 400 people.
Our top team of chefs have put together several suggested menus and will prepare and offer an eclectic mix of Caribbean influenced menu items. Ranging from a spectacular raw bar with oysters, clams, mussels, stone crab, and Key West pink and Royal Red shrimp to locally caught fresh Dolphin, Grouper and Tuna. For the meat lover we have Reserved Dry Aged Black Angus steaks, succulent pork medallions and mouthwatering chicken. We also offer new and exciting pasta dishes and our specials even include fresh lobster and surf and turf options. There is always something to please everyone.
Boasting the largest bar between Miami and Cuba and hosting over 80 different brands of rum our bar includes all premium well and call drinks, wines and beers from around the world, frozen tropical drinks, house specialty drinks, ice cream drinks, and cordials. Four spectacular 160-gallon saltwater tanks with marine life indigenous to the Florida Keys divide the Bar and Restaurant areas.
Key West Food Tours offers their signature "Southernmost Food Tour" where guests eat their way through Key West, trying some of the best and iconic dishes the on the island like Cuban roast pork and key lime pie. Come join us on a three hour food tasting and cultural walking tour in the historic district.
We also offer our Seafood Lover's Tour, a 'best-all-around' food tour of fresh local ingredients straight from our waters. Stops include fish tacos from a nationally acclaimed food truck, lobster mac and cheese and craft beer from a local brewery! Taste maritime history as we walk the historic seaport!