This holiday season, gift an experience of a lifetime. These days, more and more people are choosing experiences over ‘things’. After all, memories are what last. So if you and your loved ones are seeking more relaxation, more romance, or more adventure in your lives, what better way to do so than in paradise? Here are the best Key West experiences and excursions to enjoy anytime of year.

[Holiday Events in Key West 2023]

Bed and Breakfast Stay in Key West: Bed and Breakfast Package

For hard-to-buy-for friends and family members, a gifted bed and breakfast stay never fails. When you book the Bed & Breakfast Package at The Gates Hotel, all guests enjoy a daily delicious full breakfast for only $5.

Our daily Resort Fee also provides guests with a host of amenities, like complimentary shuttle service to Old Town, an on-site ‘conch’cierge, daily live entertainment, 10% off at our on-site Starbucks, in-room coffee, tea, and bottled water, access to two swimming pools, our 24-hour fitness and business center, and so much more. So dig in, fuel up, and set the tone for a day exploring Key West.

Key West Bicycling Trip: Bike Around Key West Package

A cycling trip around Key West is a great way to explore our small island while getting in fresh air, movement, and a pass to indulge in guilt-free eating and drinking in between stops. When you book the Bike Around Key West Package, cruise the island with two bike rentals per day. Our location puts you within a 10 minute ride from Smathers Beach and 15 minute ride from Old Town. Your rental also includes helmets, a bike basket and light, lock, and keys.

Classic Key West Sunset Cruise and Snorkel Tour: Fury Watersports Package

If you think back to the holidays of your past, what do you remember most? Family, friends, and fun experiences always top the list. This holiday season, invite your guests on a water excursion like no other. Choose from two amazing Key West experiences with our Fury Watersports Package, a sunset sail with live music, eats, and drinks, or a snorkel excursion at North America’s only living coral reef.

Key West Diving Excursion: Dive Then Dream Package

Experience Key West’s stunning underwater world with the Dive and Dream Package. Save 20% on all dives and excursions at Southpoint Divers, get complimentary reef-friendly suntan lotion, and take our shuttle to be dropped off near their Old Town shop to begin your adventure. You and a guest will hop aboard the Phoenix and head to the Florida Keys National Marine Sanctuary, the only living coral barrier reef in the country and the site of the 520-ft Vandenburg wreck, the second largest artificial reef in the world. Night dives are also available!

Biggest Party of the Year: Book Direct and Save 25%

Get ready to say goodbye to the old year and welcome the new with a bang. The Gates Hotel is kicking the New Year off early with an epic party and fireworks celebration on Dec. 30 at the Sunset Green Event Lawn. Beginning at 6 p.m., there’s food, drinks, and a performance by The Marshall Morlock Band, followed by a dazzling fireworks show that will light up all of New Town. All ages are welcome. A portion of your food and beverage purchases will go straight to the Highgate Charitable Foundation. Stay steps from New Town’s biggest New Year’s Eve party with our Book Direct and Save 25% exclusive offer, plus get three free rewards, only when you click here.

[All Routes Lead to Key West: Direct (Non-stop) Flights to Key West]

The Gates Hotel also offers special packages for AAA members, seniors, government officials, educators, and healthcare workers.

Happy Holidays!

The Gates Hotel Key West is a Conde Nast award-winning hotel set in New Town that offers shuttle service to and from Old Town. At The Gates, guests can take a dip in our gorgeous pool or order a cocktail made with locally-distilled rum from the outdoor pool bar. Take a look at our specials.