Key West, the southernmost point in the United States, is famous for its beaches, watersports, lively nightlife, fabulous restaurants and bistros, historic sites and its pastel, conch-style architecture. We can’t wait to show you this unique city!

HIGHLIGHTS INCLUDE:

Florida Keys ~ Key West City Tour ~ Mallory Square ~ Duval Street Sunset Cruise ~ Hop-on/Hop-off Trolley

TOUR INCLUDES:

*Four nights’ accommodations

*Five meals- 4 Breakfast & 1 Dinner

*Key West City Tour

*Sunset Cruise

*Trolley Pass

ACCOMMODATIONS: Blue Flamingo Resort Key West

ITINERARY:

Day 1: The Villages ~ The Keys ~ Key West, Florida ~ Welcome Dinner

Depart 761 Hoopfer Way in The Villages (located off Rolling Acres Rd) - You may leave your car here. Travel aboard luxury motor coach for southern Florida.  Rest and meal stops will be made periodically.  Travel the Road That Went to the Sea, which ends in the southernmost city in the continental United States, Key West.  Enjoy four nights at the Blue Flamingo Resort Key West.  Later today we transfer into downtown Key West for a delightful dinner at a local restaurant - included.

Day 2: Historic Trolley Tour ~ Hop-on/Hop-off Trolley Passes

Enjoy breakfast at the hotel – included.  This morning, we embark on a guided Trolley Tour which features Old Town, Mallory Square, Duval Street, Southernmost Point and the scenic waterfront.  Blessed with a delightful subtropical climate, Key West is known for its rocky shores, sandy beaches and weathered homes reminiscent of a coastal New England town. Continue exploring Key West with hop-on/hop-off trolley passes for the balance of the day.  Be sure to take advantage of Key West’s most popular natural attraction – its sunsets!  Each night street vendors and performers entertain spectators gathered at Mallory Square Dock in Old Town.

Day 3: Key West at Leisure ~ Sunset Cruise

Breakfast is included at the hotel.  Enjoy the day shopping and sightseeing in historic Key West.  Along Duval Street, imaginative cafes and open-air restaurants serve Caribbean cuisine ranging from gourmet specialties to ethnic snacks.  Stroll through the quaint shops, boutiques and museums of Old Town.   Later today we gather for a memorable evening sunset cruise on the glistening seas.  The two-hour excursion includes alcoholic and non-alcoholic beverages, tasty appetizers, live music and spectacular views.

Day 4:Key West at Leisure

Breakfast is included at the hotel.  Enjoy the day in Key West.  Key West offers a wide selection of optional attractions including Ernest Hemmingway Home, a lighthouse and maritime museum, butterfly and nature conservatory, shipwreck museum and aquarium.  A scenic glass-bottom boat cruise out to nearby coral reefs provides a panoramic view of the reef and its colorful and exotic sea life. You may choose to visit the Little White House Museum. Built in the 1940’s this home served as a vacation retreat for several presidents.

Day 5:  Key West ~ Journey Home

Enjoy breakfast at the hotel – included.  Today we depart Key West and begin our journey home.

PRICING:

$1,398.00 per person -Double Occupancy

$1,289.00 per person - Triple Occupancy

$1,799.00 per person - Single Occupancy

A $600 deposit (per person) is required upon booking. Deposit is refundable until February 27, 2026, less a $150.00 per person cancellation fee.

Final payment is due Friday, February 27, 2026. Entire cost is non-refundable after this date.

Travel Insurance is strongly recommended and can be purchased through Travel Insured. To purchase, click here: TRAVEL INSURED / WORKMAN TRAVEL INSURANCE| or call, 1-855-752-8303. Our agency # is 53258. Mention our Agency Name & Number to receive the best rate.

Meet & Greet: TBA- Wildwood Community Center at 2:00 pm.

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Workman Transportation uses their own deluxe motor coaches. They are driven by drivers certified and licensed for motor coach transportation. Our motor coaches are air conditioned, equipped with Wi-Fi, video monitors, on-board restroom, and reclining seats.

Our hosts are experienced and will help make your trip enjoyable. They will give you lots of information along the way to make the traveling time fun and interesting. We will strive to keep you comfortable by having rest stops every two to two and 1/2 hours in the schedule.

All tours require some walking and the ability to embark/disembark a motor-coach without assistance. Advance notice is required for special dietary requests and handicap seating.

Prices are per person. Rates and space are subject to availability. A minimum number of people is required for the trip to commence. Specified inclusions i.e. hotels, restaurants, shows, etc. are subject to change. Cancellation penalties will apply. Bus Driver and Host gratuities are not included. Itinerary subject to modification based on host discretion and unforeseeable circumstances such as inclement weather.

Workman Transportation / Workman Travel is not responsible for errors and omissions in our print ads.