Skip to content

Key West, Florida - The Southernmost Point

Key West, Florida - The Southernmost Point

Enjoy the sun and sand of Key West!

Book Now

Click the DEPARTURE DATES TAB to begin your reservation!


$1,299 per person (Double Occupancy)




Welcome to Key West, Florida!  If you have never been to Key West before, and even if you have, you are in for a real treat! You will find attractions to suit everyone. Some of the most popular Key West tourist activities on the water include dolphin encounters, kayaking the backcountry, diving and snorkeling at Ft. Jefferson and the Dry Tortugas, or renting a boat at a Key West marina to explore on your own. On land, shopping, museums, art galleries, tours, theaters and more await you. Or simply relax in the sand at one of our Key West beaches, by the pool at your beautiful Key West hotel, or on Duval Street with a cocktail in hand.  There’s limited seating on this tour, so don’t delay and make your reservations today!


EARLY BIRD DISCOUNT:  Book & Pay in full by January 23, 2022 and receive $65 off per person! (Be sure to mention this discount as it is not an automatic deduction.)


PLEASE NOTE: This tour requires walking/standing. Those with mobility concerns are cautioned to carefully evaluate their personal level of stamina and ability. Weather appropriate clothing and cap are recommended, as well as flat comfortable shoes.

Monday, March 6:

Join Yankee Trails as we set our sights on warmer weather and we head to the Southernmost point of the US. Key West, Florida. We will depart Yankee Trails in Lady Lake, making one restroom / meal break before arriving in Coconut Creek FL for a visit to Butterfly World with lunch (included). Next we will continue on to Miami for one last restroom break at the Snapper Creek Service Plaza, prior to the final leg to Key West. Upon our arrival we will check into our accommodations for the next three nights at Fairfield By. Marriott - Key West at the Keys Collection (305-320-0910). Offering an outdoor pool and a convenient location near local hotspots like Duval Street, Old Town and Mallory Square. Included with your stay is the Old Town shuttle service, bottled water replenished daily, a frozen treat poolside daily, and two daily drinks redeemable at Barefoot Bar & Brew or at the Market. Your evening is free.

Tuesday, March 7:

A deluxe continental breakfast is included at the hotel each morning. Today you will be on your own to enjoy fabulous Key West at your leisure. Explore local hotspots, enjoy a workout in the fitness center or take a dip in the outdoor pool. Option A (+$50) is the One Day Key West Tour w/Old Town Trolley. There’s no better way to see all of Key West than with Old Town Trolley Tours.The island of Key West is full of fun and exciting things to do and see. From the Southernmost Point to the quaint streets of Old Town, our tour takes you to all the major areas and attractions. See Key West’s first tourist attraction, the Key West Aquarium, which was also the world’s first open air aquarium. Cross the street and you’ll find yourself back in the 1800s at the Key West Shipwreck Treasure Museum, learning about how Key West became one of the richest cities in the US. The Oldest House Museum is also nearby; it is one of the many beautifully restored homes that are open to the public in Key West. Stop by the Ernest Hemingway House Museum where he is rumored to have written A Farewell to Arms — and don’t forget to look for the 6 or 7 toed cats! Marvel at the beautiful species of butterflies in the Key West Butterfly and Nature Conservatory, and wander next door to the Southernmost House Mansion and Museum, known for its 19th century architecture and tropical gardens. Cool off with a drink at the famous Sloppy Joe’s Bar or Jimmy Buffet’s Margaritaville in the Old Town area. But don’t leave Key West until you’ve watched the sunset from Mallory Square, a truly memorable experience! The one day pass includes 1 day of unlimited re-boarding, Open-air sightseeing perfect for taking pictures, more than 100 points of interest, colorful anecdotes and well-researched historical facts, exclusive stops and Key West attraction discounts. If you prefer to spread your touring over 2 days, you can purchase the 2 day Key West Tour with Old Town Trolley (Opt B +$75).

Wednesday, March 8:

Enjoy breakfast at your hotel. Today you will be on your own to take advantage of local dining, shopping, beaches, museums, art galleries and theaters. Add the OPT C (+$75) "Commotion on the Ocean Sunset Sail excursion" for your last night at the Keys. Included in the excursion will be Live music, World-famous Key West Sunset, Hot & Cold Appetizers, Ice Cold Margaritas, Champagne, Draft Fury Lager, Bud light, & seasonal beer, Wine, Soda and water.

Thurday, March 9:

Breakfast is included at the hotel before we depart and head home. With so many wonderful experiences, you will have plenty to discuss along the way with new friends and old. Stops will be made on route home with an approximate arrival at 5PM in The Villages FL.

Tour Includes:

  • Round-Trip Motorcoach Transportation

  • Hotel Accommodations at Fairfield by Marriott - Key West

  • Baggage Handling & Taxes

  • Old Town Shuttle Service

  • Two Daily Drinks (redeemable at Barefoot Bar & Brew at the hotel)

  • 3 Breakfasts

  • 800 Travel Points


Optional Tours:

Option A: One-Day Key West w/Old Town Trolley - $50pp

Option B: Two-Day Key West w/Old Town Trolley - $75pp

Option C: Commotion on the Ocean Sunset Sail - $75pp

Below is a list of pick-up points available on this tour.

Below is a list of pick-up points available on this tour.

Name Address Contact Details
Yankee Trails on 441 Yankee Trails, 13731 U.S. 441
Lady Lake, FL 32159

Please select the number of passengers that will be traveling:

From Price Book Now Call Back Telephone Favorites

Availability Search

Keyword Search