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Key West Singles Weekend
40's, 50's, 60's + Florida Singles Vacations

January 21 - 25, 2021


Need a great way to kick-off this winter season, vacation with Best Single Travel in Key West, the southern most point of the United States. Jet ski in crystal blue waters, have a margarita while admiring a stunning sunset, discover history and party the night away with a great group of singles.

Experience Key West, a destination where there is always a good time going on.
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Key West Singles Weekend Itinerary
Doubletree Key West

Vacation Day 1: Arrive in Key West, Florida
You can fly directly to Key West (airport code - EYW) and take the provided hotel shuttle or fly into Miami (airport code - MIA) and take a shuttle or bus to Key West - see below for more informatiion.  The friendly staff of the DoubleTree Resort by Hilton Hotel Grand Key will be waiting to welcome us with a freshly baked chocolate chip cookie. Arrive early and spend the day poolside, where you can enjoy frozen specialty drinks and light fare at the Tiki Bar. 
Meet and greet with your singles host and fellow weekenders before the group travels to Old Town, for our Welcome Dinner.


Vacation Day 2: Key West Touring
key west trolleyToday we hop on and off the OldTown Trolley as we turn back the pages of time. Sit back as our trolley conductor narrates our tour with his own blend of trivia, anecdotes, and humorous stories. From the Southernmost Point to the quaint streets of Old town, we will see all the major areas and attractions.
At the Sails to Rails Museum we will journey through the Age of Sail, a time when tail ships plied the treacherous waters of the Caribbean, Gulf of Mexico and Florida Keys from the 1500 to early 1900’s. These waters were once filled with treasure-laden Spanish Galleons, dreaded Pirates, merchant ships and more as the New southernmost pointWorld made its riches known to all who sailed her waters. 
At Mile 0 it is selfie time in front of the iconic Southernmost point buoy marker. Photo stop by Ernest Hemingway's House, where he is rumored to have written A Farewell to Arms. Visit Papa's Pilar Distillery and discover how the Hemingway Rum Company makers craft their unique spirit, uncover the untold Tight rope MallorySquarestories of Hemingway and experience an adventure Papa would be proud of!
See you at Sunset in Mallory Square!  Beginning two hours before sunset, it’s a celebration and view that has captured the love and astonishment of iconic figures from Mark Twain in the 1800s to Tennessee Williams in the late 20th century! Join the group and watch the glowing pink and red sun sink into the Gulf of Mexico. Partake in the nightly festival of magicians, jugglers, clowns, psychics, local musicians, artists and food vendors for an incredible evening experience.

Vacation Day 3: Do it All Water Sports Day
watersport keyGet ready for the water adventure of a lifetime!  We will cruise out to the warm, tropical waters off the coast of Key West to enjoy a day of jet-skiing, snorkeling, banana boating, kayaking, sailing, windsurfing, waterskiing and parasailing for the ultimate watersports adventure. Try one or try them all. Use of all watersports equipment, plus a barbeque lunch, snacks, soft drinks and draft beer (afterward) are included. Soak up the Florida sun while sailing on a comfortable, sleek catamaran along the smooth waters to the Gulf of Mexico. With 12 watersports activities we will never have to wait to have fun.
key west haunted trolleyAfter time for dinner, climb aboard the Trolley of the Doomed for an experience unlike any other. Uncover Key West’s darkest secrets and hear the stories of those lost souls who many locals believe still wander the streets of this historic island town. Visit one of the island’s haunted Civil War forts, once a barracks that was quarantined for suffering soldiers left to die from yellow fever. See the Artist House, home to Robert the Doll. It has been said that this doll is possessed by spirits and has a reputation that can only be described as terrifying. Robert was the inspiration for Chucky, the character in the 1988 horror film Child’s Play.


Vacation Day 4: Day At Leisure & Sunset Dinner Cruise
TSunset dinner cruiseoday is your day to discover Key West at leisure. Spend the day at the beach, hotel pool or enjoy a round of golf. The choice is yours.
There is something amazing about a Key West sunset and no better view than from a sunset cruise. The panoramas are awe inspiring and the horizon endless, but the real bonus is to catch a glimpse of frolicking dolphins, leaping sailfish and curious sea turtles. Tonight our sunset farewell dinner cruise starts at Key West's historic seaport, where we'll board a 65-foot yacht and set off across the water. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as we take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere.


Day 5: Depart Key West
Enjoy breakfast before departing Key West for your flights home. Sad to say another wonderful singles weekend has come to an end.
Key West Arrow


Key West Singles Weekend 

Dates: January 21 - January 25, 2021

Price: $1595*

Singles Weekend Includes
* 4 Nights Accommodations
* 3 Breakfasts - Welcome & Farewell Dinner
* All Activites and Tours listed above
* Dedicated Group Leader
* All Taxes and Surcharges

* The price per person is for a double room. Best Single Travel provides free roommate matching on all our vacations, so there is never a need to pay a "single supplement". If you wish to room alone it is an additional $850


Not Included

* Airfare
* Pre-Night Hotel - Single Room
* Airport shuttles

Deposit $300
Balance Due November 13, 2020
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FAQ and Cancellation Policy

How to Get to Key West from Miami Airport

Miami to Key West Bus (departs 7:45am from Regency Airport Hotel - 3 mins from airport)  (305) 444-4666

Keys Shuttle - provides door-to-door service between the Keys and the Miami and Ft. Lauderdale-Hollywood International Airports. (305) 289-9997 or 1 (888) 765-9997

Greyhound Lines - Makes numerous scheduled stops between Miami International Airport and the Key  (800) 231-2222 or (305) 296-9072