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Florida

The Holidays in Key West: A Sunny Take on Christmas Traditions

Program No. 21671RJ
Discover unique Christmas traditions in the Florida Keys, where you’ll visit historic sites, enjoy traditional cuisine and revel in the famous lights of the Sunset Celebration.
Length
6 days
Rating (4.5)
Activity Level
Starts at
2,999

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Prices displayed below are based on per person,doubleoccupancy.

DATES & PRICES

Standard 1 Dbl Bed 2 Dbl Beds
Accommodation Details

Standard

Accommodation Details

Comfortable accommodations with one double bed.

Accommodation Details

Comfortable accommodations with two double beds.

Dec 21 - Dec 26, 2023
 
1 Double Bed 2,999
2 Double Beds 2,999

DATES & PRICES

Standard 2 Double Beds
Accommodation Details

Standard

Accommodation Details

Comfortable accommodations with two double beds.

Dec 21 - Dec 27, 2022
SOLD OUT
Standard 4,749
 

At a Glance

Celebrate Christmas as you never have before — Florida Keys-style! Spend four nights in Key West learning about its fascinating history of railroads, navy ships, art and literature and reveling in its unique, sun-soaked variety of holiday traditions. Start and end your adventure with a night in Miami and hop from one island to the next as you study Florida Keys ecology and history with a local expert on the Keys.
Activity Level
Keep the Pace
Walk 1.5 miles on pavement, boardwalks, uneven surfaces such as mulched paths, cobblestone, a few stairs. Some standing on field trips and museum visits.
Small Group
Small Group
Love to learn and explore in a small-group setting? These adventures offer small, personal experiences with groups of 13 to 24 participants.

Best of all, you’ll…

  • Experience the protected natural areas of the Keys, including a visit to John Pennekamp Coral Reef State Park, the country’s first undersea park.
  • Key West’s colorful history comes alive on visits to the Overseas Railroad Museum, the Custom House and Ernest Hemingway’s home.
  • Enjoy the unique artistic and holiday traditions of sunny Key West, including an expert-led walk through Mallory Square.

General Notes

All transfers by van.
Featured Expert
All Experts
Profile Image
Heather L Hamilton
Florida native Heather Hamilton has been exploring the beaches, lakes and forests of Florida’s wilderness since she was a little girl. As an experienced camper, hiker, biker, kayaker, fisher and photographer, Heather has seen Florida in just about every light on her extensive travels throughout the state. She studied culinary arts at the Art Institute in Fort Lauderdale and became a cook and pastry chef, but she changed careers several times before embracing her passion. She became a Master Naturalist and full-time Florida guide.

Please note: This expert may not be available for every date of this program.

Profile Image of Heather Hamilton
Heather L Hamilton View biography
Florida native Heather Hamilton has been exploring the beaches, lakes and forests of Florida’s wilderness since she was a little girl. As an experienced camper, hiker, biker, kayaker, fisher and photographer, Heather has seen Florida in just about every light on her extensive travels throughout the state. She studied culinary arts at the Art Institute in Fort Lauderdale and became a cook and pastry chef, but she changed careers several times before embracing her passion. She became a Master Naturalist and full-time Florida guide.
Profile Image of Alberto J Melendez
Alberto J Melendez View biography
Alberto Melendez is a certified educational excursion, a certified Advance Open Water Scuba Diver and a Florida master naturalist. He has been leading kayak and snorkeling explorations in the Orlando area for over eight years. A 'tree-hugger' since the term became popular, he enjoys introducing folks to the inside story of the critters, salt marsh and history of the area.
Profile Image of Howell Geib
Howell Geib View biography
Originally from New England, Howell Geib is trained as an Architect from Tulane University and works to pursue his passion for the intersection of the natural world and the built environment. He continued his education in Sustainable Development and International Relations, pursuing development programs in Africa, the Caribbean and Western Europe. Throughout his career, he has lived in France, Hawaii and Haiti. When not introducing Road Scholars to the natural world, Howell lives on a Biodynamic farm in Upstate New York.
Visit the Road Scholar Bookshop
You can find many of the books we recommend at the Road Scholar store on bookshop.org, a website that supports local bookstores.
National Audubon Field Guide to Florida
by Alden / Cech / Nelson
A Land Remembered
by Patrick Smith
Key West
by Gerald Sprayregen
Eco-Touring the Florida Keys
by Matthew Landau Larry Gates
Insiders Guide Florida Keys and Key West
by Victoria Shearer and Janet Ware
Hidden Florida Keys & Everglades
by Candace Leslie Ana Boese
Everglades Nat. Park & Surrounding
by Roger Hammer
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6 days
5 nights
12 meals
5 B 3 L 4 D
DAY
1
Check-in, Registration, Orientation, Welcome Dinner
Key West Florida
D
Westwinds Inn

Activity note: Hotel check-in 4:00 p.m.

Afternoon: Program Registration: After you have your room assignment, come over at 5:30 pm to the breakfast area of the hotel to register with the program staff and get your welcome packet containing your name-tag up-to-date schedule that reflects any last-minute changes. If your arrival is delayed, please ask for your packet when you check in. Orientation. The Group Leader will greet everyone with a warm welcome and lead introductions. We will review the up-to-date program schedule and any changes, discuss roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer any questions you may have. Our Group Leader will lead all field trips unless otherwise noted. Evenings will often include a review of the day’s sightings and an introduction to the activities for the following day with the remainder of the night at leisure. Meals at local restaurants will have plated table service of regional dishes from a select menu with soft drinks, coffee, tea and water included; other beverages available for purchase. Free time is reserved for your personal independent exploration. Evenings at leisure offer opportunities to make the program more meaningful and memorable through personal independent exploration, engaging in available activities on your own, or simply relaxing and making new friends among fellow participants. The Group Leader will always be happy to offer suggestions. Program activities, schedules, personnel, and indicated distances or times may change due to local conditions/circumstances. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding.

Dinner: At a local restaurant, we’ll have a plated meal with soda, coffee, tea, water included; other beverages available for purchase.

Evening: At leisure. Continue getting to know your fellow Road Scholars, settle in, and get a good night’s rest for the day ahead. Prepare for check-out and transfer in the morning.

DAY
2
Key West Trolley, Railway Historeum, Custom House, Free Time
Key West Florida
B,L
Westwinds Inn

Activity note: Walking a total of approximately 2 to 2.5 miles throughout the day; paved sidewalks.

Breakfast: By the hotel pool, the breakfast buffet offers choices such as eggs, cereal, fruit, bagels, pastries, eggs, milk, juice, coffee, tea, water.

Morning: We’ll take a field trip via trolley with narration to learn about the city’s history and some of its attractions. At the Overseas Railroad Museum, we’ll imagine the thrill of riding down the Florida Keys in 1929 aboard the “railway that went to the sea.” We’ll learn about the Key West Extension, and the tragic demise of Flagler’s dream in the devastating Labor Day hurricane of 1935. The Custom House, built in 1891, served as a post office, court house and government center when wrecking made Key West the richest city.

Lunch: At a local restaurant, we’ll have a plated meal with soda, coffee, tea, water included; other beverages available for purchase.

Afternoon: Free time. Take this opportunity for personal independent exploration to see and do what interests you most. Please refer to the list of Free Time Opportunities. The Group Leader will be happy to offer suggestions.

Dinner: This meal has been excluded from the program cost and is on your own to enjoy what you like. The Group Leader will be happy to offer suggestions.

Evening: At leisure. It’s an old cliché that Key West is enticing in a raffish sort of way. If you’d like to see for yourself, you might like to explore the lively night life and visit (or re-visit) one of the popular watering holes on Duval Street; take in a cabaret show or jazz venue; walk through some quieter neighborhoods on a Ghost Walk; stroll down to the marina or Old Seaport to gawk at visiting luxury yachts; or just relax and watch the always colorful people parade.

DAY
3
Yankee Freedom, Dry Tortugas National Park & Fort Jefferson
Key West Florida
B,L,D
Westwinds Inn

Activity note: Early departure from the hotel for a short walk to the dock to board the Dry Tortugas National Park Ferry, a large 150 passenger catamaran with an air conditioned lower deck and an open air top deck; restrooms on board. Getting on/off the boat; the ride is about 2.5 hours. Walking about 2 miles, about 1 hour, throughout the day on group activities with some periods of standing; some uneven terrain and boardwalks.

Breakfast: Aboard the ferry, we’ll have a breakfast buffet featuring choices including bagels, cereal, yogurt, fruit, juices, coffee and water.

Morning: En route to Dry Tortugas National Park, our onboard naturalist will provide an orientation about the area and the national park's surroundings. During our voyage, we will enjoy the beautiful scenery of the Marquesa Islands, Boca Grande, have an opportunity to see turtles and dolphins, and listen to pirate legends. Upon our arrival to the Park, we’ll enjoy a walking field trip through Ft. Jefferson led by a Park Ranger while learning about its role in U.S. history.

Lunch: Aboard the ferry, we’ll have a buffet lunch

Afternoon: We’ll then enjoy some free time on the island. You may wish to go on a walk around Ft. Jefferson’s moat with a naturalist, snorkeling, bird watching, or just relax on the sandy beach. Birders, be aware that beginning in late February the adjoining Bush Key is closed to visitors to enable the sooty terns and other unique birds to nest undisturbed. However, activity can often be viewed through volunteer rangers’ spotting scopes. We’ll then board the boat and, after returning to hotel, take some time to freshen up before dinner.

Dinner: We will walk to a local restaurant, soft drinks, coffee and water included.

DAY
4
Lighthouse, Hemingway Home & Museum, Holiday Trolley
Key West Florida
B,L,D
Westwinds Inn

Activity note: Walking a total of approximately 2 to 2.5 miles throughout the day; paved sidewalks.

Breakfast: Poolside buffet.

Morning: We’ll visit the historic Lighthouse Tower & Keeper’s Quarters for an expert-led exploration. Built in 1848, the lighthouse was de-commissioned in 1969 and has since been turned into a museum dedicated to Key West’s maritime history and heritage and the lives of those who kept the light shining out to sea. We’ll see belongings, photographs, and words of lighthouse leepers and their families. Elective: Those with both stamina and a sense of adventure can climb the 88 steps to the top of the light.

Lunch: At a local restaurant, we’ll have a plated meal with coffee, tea, water included; other beverages available for purchase.

Afternoon: We’ll visit The Ernest Hemingway Home & Museum in the heart of Old Town Key West. Hemingway visited Key West for the first time in 1928. He and his wife Pauline grew to love the place and a rich uncle bought this house for them in 1931. After writing in the early morning, “Papa” would go fishing or hang out with local friends in his favorite bars. The Hemingways lived here with their two sons until divorcing in 1940 when he left for Cuba. Today, the house looks much as it did during their residence. We’ll learn about the Hemingway era in Key West, his life, and work during some of his most productive days. We may also catch a glimpse of one or more descendants of his original six-toed cat. Docents will be happy to provide information and answer questions.

Dinner: At a local restaurant, we’ll have a plated meal with coffee, tea, water included; other beverages available for purchase.

Evening: What semi-tropical Key West lacks in snow and other trappings of winter holidays, it makes up for with bright lights. We’ll take a trolley ride to see some of the most colorful displays. Plus, we’ll have special holographic glasses that enhance and transform what we see. And, we’ll sing carols along the way! There are Christmas Eve services at a number of local churches. The Group Leader will be happy to offer suggestions.

DAY
5
Christmas Day Free Time, Christmas Dinner
Key West Florida
B,D
Westwinds Inn

Breakfast: Poolside buffet.

Morning: Free Time. Sleep late, take a walk, open a gift under a palm tree, attend a service, celebrate the day as you like. The average high temperature at this time of year is 76F. The average low is 67F!

Lunch: On your own to enjoy what you like.

Afternoon: With our Group Leader, we’ll set out on a relaxed walk to the Marina to see decorated boats and more of Old Town decked out.

Dinner: At local restaurant; soda, coffee, tea, water included.

Evening: At leisure. Prepare for check-out and transfer in the morning.

DAY
6
Program Concludes
Key West Florida
B

Activity note: Hotel check-out by 11:00 a.m. Independent Depatures

Breakfast: At a local restaurant, we’ll have a plated meal with juice, coffee, tea, water included.

Morning: Independent Departure






Important registration tip:
If you want to attend the live lecture, please do not wait until the last minute to enroll.
If you enroll after a lecture is complete, we’ll send you a recording of the event.