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.

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At a Glance

Celebrate Christmas as you never have before — Florida Keys-style! Spend five 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. Top off your adventure with a visit to Dry Tortugas National Park.
Activity Level
Varies by date
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.

What You'll Learn

  • Visit Dry Tortugas National Park aboard the Yankee Freedom ferry.
  • 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

We are unable to accommodate roommate matching for solo travelers on this program. Almost all rooms have one bed. There are a limited number of rooms with one bed and one sofa bed.
Featured Expert
All trip experts
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Howell Geib
Originally from New England, Howell Geib is trained as an architect, having graduated 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, Howie practices water sports like paddling.

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

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Howell Geib View biography
Originally from New England, Howell Geib is trained as an architect, having graduated 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, Howie practices water sports like paddling.
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You can find many of the books we recommend at the Road Scholar store on bookshop.org, a website that supports local bookstores.
While we make every effort to ensure the accuracy of our published materials, programs are typically advertised more than a year prior to their start date. As a result, some program activities, schedules, accommodations, personnel, and other logistics occasionally change due to local conditions or circumstances. Should a major change occur, we will make every effort to alert you. For less significant changes, we will update you during orientation. Thank you for your understanding.
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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
Kimpton Fitch Lodge

Activity note: Hotel check-in available from 4:00 p.m. Remember to bring your nametag (sent previously).

Afternoon: Program Registration: 5:30 p.m. After you check in and have your room assignment, join us in the breakfast area of the hotel to register with the program staff, get any updated information, and confirm the time and location of the Orientation session. If you arrive late, please locate your Group Leader and let them know you have arrived. Orientation. The Group Leader will greet everyone and lead introductions. We will review the up-to-date program schedule, discuss roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer questions. 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. Periods in the schedule designated as “Free time” and “At leisure” offer opportunities to do what you like and make your experience even more meaningful and memorable according to your personal preferences. The Group Leader will be happy to offer suggestions. Program activities, schedules, personnel, and indicated distances or times may change due to local circumstances/current conditions. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding.

Dinner: At a local restaurant.

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

DAY
2
Key West Trolley, Railway Historeum, Custom House, Free Time
Key West Florida
B,L
Kimpton Fitch Lodge

Activity note: Walking about 2-2.5 miles throughout the day; paved sidewalks. Walking and other free time activities according to personal choice.

Breakfast: By the hotel pool.

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.

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
Kimpton Fitch Lodge

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; riding approximately 2.5 hours. Walking about 2 miles, approximately 1 hour throughout the day on group activities with some periods of standing; some uneven terrain and boardwalks.

Breakfast: Aboard the ferry.

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.

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 the hotel, take some time to freshen up before dinner.

Dinner: We will walk to a local restaurant.

Evening: At leisure.

DAY
4
Lighthouse, Hemingway Home & Museum, Holiday Trolley
Key West Florida
B,L,D
Kimpton Fitch Lodge

Activity note: Walking about 2-2.5 miles throughout the day; paved sidewalks. Getting on/off a trolley. Elective: 88 stairs up to the top of the lighthouse.

Breakfast: By the hotel pool.

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. While here, those with both stamina and a sense of adventure can take the stairs to the top of the lighthouse.

Lunch: At a local restaurant.

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.

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
Kimpton Fitch Lodge

Activity note: Walking and other free time activities according to personal choice. Walking to marina.

Breakfast: By the hotel pool.

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 a local restaurant.

Evening: At leisure. Prepare for check-out and departure 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






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