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Are you looking for someone to help you put together a group tour or plan a special event in Key West? Whether it is a family reunion, a company function, a conference or convention, or a simple get-together with old friends, we can help you arrange a customized itinerary that covers every detail needed to make your group’s time in Key West relaxing, fun, and memorable. Trust your reunion, group or corporate event with Cool Destinations.

  • Full-Service Planning — We create customized itineraries that cover every detail needed to make your group’s travel relaxing, fun, and memorable. We offer transportation, hotels, dining, activities and excursions for individuals and groups of all sizes.
  • Local Expertise — Years of local experience give us the insider connections needed to get the best choices, package rates and group discounts in Key West and beyond.
  • Exceptional Support — Our office is open 7AM-11PM EST, 365 days a year and is operated by a knowledgeable, professional and courteous staff. You can call or email us with your questions, including on the day of travel.

With years of local experience and all the insider connections needed to get the best choices and prices when it comes to transportation, hotels, meals, entertainment, attraction admissions, guide services and more, we offer some of the best group tour and event packages in Key West. Nearly anything is possible: day programs with tours and activities that can be booked for the whole group or individuals, nightlife packages with dining, parties, and pub crawls, outdoor or indoor programs, special locations or venues, or catered events at your hotel or other selected location.

Cool Destinations can meet all your transportation needs from getting to Key West to getting around once you get here. Regional air, rail, and motor coach arrangements, local ground transportation in buses, mini-buses, vans, or limos – we can provide whatever you need. We can also easily handle special requests. Do you need a dinner speaker, a multi-lingual guide or escort, a photographer, or convention staffing? No problem whatsoever. Everything will be arranged and taken care of in advance so your group can enjoy a well-organized, stress-free Key West visit.

From student groups to adult and senior groups, clubs, corporate employees, military groups, and international visitors, we have been successful in helping a broad variety of private individuals and professional tour operators put together the ultimate in Key West good times. Call today and our courteous and professional agents will help you plan and organize a unique and memorable group tour or special event.

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“The electric car we rented was clean and easy to drive. Shuttle picked us up quickly and was also clean and new. Driver was very informative and friendly. Great prices and a great time. No problems We will be back!”

Michael Darnall

“Capt Gary and first mate Justin were very sharp and effective getting us trained and setup in a couple solid spots on a windy morning. Great job and very friendly. I look forward to going again when I return.”

Joseph O'Brien

“I booked the wrong day, and the staff was helpful, friendly and polite about getting us a car on the spot. Thank you!”

Phil Polderdyke
Florida Travel


As the premier online concierge guide to Activities, Hotels, Things to do, and Tours, Cool Destinations is your one-stop hook up for all your travel information.

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