A Key West Christmas Adventure December 6-9, 2021


Spend 4 days 3 nights during the holiday season in the Southernmost City in the USA, Key West is an oasis surrounded by gorgeous crystal waters. It’s here that you’re invited to come as you are, kick back and let go of all the stresses of hectic day-to-day life.

This tour has a deposit option with final payment due October 9, 2021




Christmas in Key West

It’s the most wonderful time of the year! We may not get a white Christmas in Key West, but you’d be surprised just how festive the island can be. The holiday season at the Southernmost Point is as unique as all other Key West celebrations. From lighted bikes to boats decorated top to bottom, there’s no shortage of holiday cheer in the Conch Republic. Much in the same way Harry S. Truman retreated to his Little White House when things got a little too cool for comfort up in DC, Key West is where Santa comes to spread cheer and hang out in his Christmas-themed board shorts. This is one of the best places on Earth to celebrate the holiday season, just ask Conchy The Sandman and Rudy The Bottle-nosed Dolphin!

The southernmost city in the U.S. is filled with holiday lights, trimmed-trees, and cheer in December.

Visiting Key West during Christmas is filled with non-traditional ways of celebrating the holiday. No snowmen, hot cocoa or sledding here. It’s more like relaxing on the beach, palm trees with Christmas lights, historical homes decorated for the holiday season and touring the island in summer attire. Considering the fact that Key West still has weather in the high 70’s in December, they sure do know how to get into the holiday spirit. From decorating their charming bed and breakfasts, to Christmas light-lined sail boats there is no shortage of Floridian ways to celebrate the season.


Day 1: Miami-Key West – Tour Begins

Transfer from The Villages to Orlando International Airport. Direct non-stop flight to Miami. We will then board a deluxe motor-coach for a locally guided tour on our way down to Key West. A must see short (3) hour ride stopping in Islamorada for some local lunch. (on own)   Welcome to the “Conch Republic.”

Arrive in Key West ready to explore. Walk to many attractions and dining options upon arrival then gather again with your tour director to visit the Mel Fisher Museum. Artifacts and treasures from the Atocha and Margarita form the cornerstone of the museum’s collection. Among the items found on the wrecks are a fortune in gold and silver bars; coins destined for the coffers of Spain; a solid gold belt and necklace set with gems; a gold chalice; a gold chain that weighs more than seven pounds; a horde of contraband emeralds including an impressive 77.76 carat uncut hexagonal crystal experts have traced to the Muzo mine in Colombia and so much more. After checking into the Santa Maria Suites Resort for the next three nights your evening is free to explore the area on your own.

Day 2: Key West

After time for breakfast, gather with your tour director to walk to the Hemingway House. Nestled in the heart of Old Town Key West, this unique property was home to one of America’s most honored and respected authors. Ernest Hemingway lived and wrote here for more than ten years. Calling Key West home, he found solace in the turquoise waters that surround this tiny island.

Visit the rooms and gardens that witnessed the most prolific period of this Nobel Prize winner’s writing career. Be sure to stroll through the lush grounds and enjoy the whimsy of the more than forty cats that live and wander free here. The rest of the day is yours to explore with your two-day Conch/Trolley Tour Pass. Get a narrated tour and be able to hop on and off at many of the famous sites in the historic old town area. Included in your pass are admissions to the beautiful Butterfly House and Harry Truman’s Little White House.  This evening we will take the Old Town Trolley’s Holiday
Lights & Sights Tour. We will depart from  Mallory Square and board the Old Town Trolley. Sip cider and indulge with holiday cookies as the Holiday Trolley transports you through the city in search of the best holiday light displays. You’ll even be given special holiday lights glasses to ensure you enjoy all the sparkle.

Day 3: Key West

Today use your Trolley Pass to get further around the island. Your day is free to find many more Key West treasures, famous restaurants and wonderful attractions. Be sure to pose at the Southernmost Point of the United States! A trip to Key West would not be complete with a champagne cruise during sunset. We will depart on Fury’s Champagne Sunset Cruise aboard a spacious 45 ft power catamaran which offers guests a tranquil ocean setting in which to experience Key West’s world famous sunset.

Day 5: Key West – Tour Ends

Transfer to Miami International via luxury motor coach to fly back to OIA. Transfer to The Villages





Santa Maria Suites Resort

4 star resort


Discover a contemporary Key West resort tucked into the charm of Old Town. Steps from the beach, ocean, and Duval Street, Santa Maria Suites offers a tranquil oasis where you can relax and indulge. It all starts with a warm smile at check-in. Lounge by our two garden-enclosed heated pools with chilled towels, smoothies, bottled water and other items served poolside. Walk down to the beach and let our attendant pamper you with towels, umbrellas and chairs. Ease into our happy hour with wine and snacks, and savor creative Japanese cuisine and fresh sushi at Ambrosia. For anything else, from tours to dining, our concierge will help you explore. With its retro panache, beautiful gardens, and peaceful vibe, Santa Maria Suites Resort is your home on Key West. Discover luxury redefined.




Let’s Go! Walking is the best way to get to know a new place. I’m energetic and enjoy a good physical challenge, so I’m always ready to spend the day on the move. Whether it’s public transit, city streets or village cobblestones, I’m game.



  • You will receive a courtesy email reminder 3-5 days prior to the trip departure. A meet and greet will also be scheduled prior to tour.
  • Dining is not included unless specifically defined in the trip description
  • Prices are per person. Rates and space are subject to availability. A minimum of 24 people is required for the trip to commence. Specified inclusions i.e. hotels, restaurants, shows, etc. are subject to change. All trips require some walking. Cancellation penalties will apply. Bus driver gratuities are not included.
  • Lifestyle Venture Tours is not responsible for errors and omissions in our website, emails, or print descriptions.
  • Lifestyle Venture Tours recommends purchasing travel insurance with RoamRight® Travel Insurance. 
  • 24 guests required for this tour to commence.

Cancellations & Refunds

















Additional Information


PP Double Occupancy, PP Single Occupancy

Trip Includes

  • Round trip airfare from Orlando International Airport to Miami
  • Airfare taxes, fees & fuel surcharges
  • Ground transportation and transfers
  • Accommodations at Superior First Class hotels
  • Full buffet breakfast daily (B)
  • Comprehensive sightseeing tours as indicated in itinerary
  • Tour Director and local guides

Trip Excludes

  • Passport and visa fees
  • Excess baggage charges, baggage
  • Travel insurance
  • Gratuities
  • Optional tours, beverages, other items and expenses of personal nature

Air Services
Airfare purchased through Lifestyle Venture Tours for travel originating in the United States. By using Lifestyle Venture Tour's air services, you accept that Lifestyle Venture Tours is only acting as your agent and is not responsible for any accident, death, personal injury, illness, property damage, delay or other monetary loss or expense of any nature that may arise directly or indirectly out of any act of God, or any actions or default of any carrier. Lifestyle Venture Tours is not liable for, and does not assume responsibility or accept claims with regards to any losses incurred due to cancellation of flights or change in flight schedule resulting in additional expenses to you, even when the air services are purchased through Lifestyle Venture Tours.

Airline Security Measures
The Transportation Security Administration requires that travelers provide their name exactly to their airline as it appears on the passport or a government issued I.D.(such as a drivers license) to be used while traveling, along with their date of birth and gender when making reservations to fly within the U.S. When making your flight reservations through Lifestyle Venture Tours, you will be asked for this information by our staff. Due to airline security measures, your photo I.D. or passport must match your airline ticket name and your tour reservation name or you may be denied aircraft boarding.