Key West Winter Getaway
A Boutique Solo Tour
February 8 - February 11, 2027
Key West Winter Getaway
February 8 - February 11, 2027Highlights
- Stay in a Lovely Waterside Resort
- Taste Your Way Around Key West on a Food Tour
- Enjoy a Sunset Sail
- Visit Hemingway House & Southernmost Point
- Boutique size - no more than 12 travelers
- Time to explore personal interests
- Suggestions for things to see and do
- And More... See itinerary for details
Your Hotel: Southernmost Beach Resort
Itinerary
Monday, 08 February 2027: Arrive Key West; Welcome Dinner (D)
Welcome to Key West! Schedule your arrival flight no later than 4:30pm. The tour begins in the hotel lobby at 6:00pm with a Welcome Meeting. After introductions we will have our Welcome Dinner to get better acquainted and discuss our upcoming adventures. Overnight Key West - 3 nights
Tuesday, 09 February 2027: Southernmost Point; Hemingway House; Food Tour (B,L)
Be prepared for a day of walking exploration of Old Town Key West. We begin with a visit to an iconic site. Take a step back in time as we visit the home and gardens of Nobel Prize-winner Ernest Hemingway, who spent time here in the 1930s. We take a stroll to see the Southernmost Point buoy (a must photo-op for all those visiting Key West!). A short walk away, we visit the delightful Butterfly and Nature Conservatory to walk among hundreds of colorful butterflies and birds. This afternoon, we're in a for a treat! We'll taste our way through Key West on a walking food tour where we'll do more than just fill our bellies, we'll learn about the culture of the island along the way. We'll cover a distance of about 1.5 miles. The remainder of the afternoon and evening are yours to enjoy as you wish.
Wednesday, 10 February 2027: Free Morning; Farewell Lunch; Sunset Sail (B,L,O)
Enjoy a leisurely morning at your own pace. Take care of some final shopping or enjoy the amenities at our hotel. We'll regroup for a lunch together. Late this afternoon, we're in for another treat as we set sail in a schooner where wine and hors d'oeuvres are included on board. Take in the sun set views while we recount our adventures of the week.
Thursday, 11 February 2027: Return Home from Key West (B)
Sadly, our time together has come to an end. Schedule your departing flight for any time that is convenient for you. The airport is about 15 minutes from the hotel. You should plan to arrive at least 2 hours prior to departure. If you wish to soak up Key West for an additional night, there is a post night optional available (excludes breakfast). See the reservation form for pricing.
Key West Winter Getaway
February 8 - February 11, 2027Pricing
Room Share
Not AvailbleSingle Room
$4,477.00Non-Members
ADD $50.00Status of this Tour
More than 1/2 Full
Tour Pricing Includes
- All meals and activities expressly listed in the itinerary, PLUS...
- Specialty hotel accommodations with waterfront rooms, single occupancy
- Resort fees paid on your behalf
- All tipping of local guides
- WTT Tour Leader to enhance the individual & group experience
- Travel Dollar credits (a benefit of WTT membership) toward future travel with WTT
Not Included In The Price
- Airfare or other transportation to and from the tour
- Airport transfers
- Meals and activities not specified in the itinerary
- Any personal expenses or expenditures
- Any pre- or post- tour arrangements
- Any gratuities for the WTT Tour Director
- Trip Cancellation / Trip Interruption Insurance
Payment Dates -and- Cancellation Terms for This Tour
You have 3 days to cancel and receive a refund. Thereafter, the amount required at time of reservation is non-refundable and the following cancellation penalties will be enforced.
Wednesday, 12 Aug 2026: Last day $500 deposit can be converted to a credit for use on a new reservation; thereafter the deposit is forfeited.
Tuesday, 10 Nov 2026: Balance Due. Cancellation after this date but before Friday, 25 Dec 2026 results in a cancellation penalty of 50% of your Total Tour Cost.
Friday, 25 Dec 2026: Cancellation on or after this date results in a cancellation penalty of 100% of your Total Tour Cost.
Using Parked Credits: If traveler cancels during the 3-day cancel without penalty period, used credits will be re-parked with the original expiration date(s). Thereafter, cancellation will result in forfeiture of the total amount of parked credits used. If applicable, additional cancellation penalties will be assessed based on date of cancellation.
To Cancel: Should you need to cancel after your space on this tour is confirmed, you must use the Cancellation Form. Cancellation penalties are based on the date we receive your cancellation form. No other method of communicating a cancellation will be accepted.
Insurance Reminder
WTT is not licensed to sell travel insurance. You can purchase travel insurance from any provider you choose. To get an idea of rates, please go to NTA Travel Protection Plan (Enter 206063 for the "Tour Operator Location #") or TravelGuard.
Key West Winter Getaway
February 8 - February 11, 2027Flights, Transfers & Lodging
Arrival & Departure Information
Travelers will make their own air arrangements as follows:
Arrival Airport: EYW - Key West, US (Key West International Airport)
Arrival Date: Monday, February 8. Arrive no later than 4:30pm.
Arrival Transfer: Use local shuttle or taxi. Details provided in Final Travel Instructions.
Departure Airport: EYW - Key West, US (Key West International Airport)
Departure Date: Thursday, February 11th. Depart at your convenience.
Departure Transfer: Use local shuttle or taxi. WTT Tour Leader can assist with ride-share coordination.
When to Book Your Air
Once you have booked your flights (or other transportation arrangements), use the Travel Arrangements Form to send WTT your flight details -AND- use this same form again to update your information should it change.
Airport Transfer Information
Getting from the airport to the hotel (i.e. the arrival transfer) can be a point of concern for some travelers. Locate the "Arrival and Departure Information" -OR- "Want to Arrive a Day Early?" on this page for arrival transfer information.
When arrival transfers are not included: WTT will provide suggestions to get to the hotel in your Final Travel Instructions about 2-3 weeks before the start of the tour. You'll also be able to see who else is arriving at the same time if you want to coordinate ride-sharing to the hotel.
Don't Worry. We're Expecting You: One of the reasons we ask for your travel arrangements is so we know when you're arriving and can approximate when you should be at the hotel. Your Final Travel Instructions will have instructions on what to do and who to contact if your flight is delayed.
Lodging / Hotels
Key West: Southernmost Beach Resort
The Southernmost Beach Resort is a 2022 Cones Nast Traveler readers' choice and 2024 TripAdvisor Traveler's Choice Award Winner, located at the end of Duval Street in the quieter section of historic Old Town. It is ideal for relaxation and convenience, featuring three heated pools, a private beach, four bars, and close proximity to the Southernmost buoy. Your private room provides a relaxing retreat from the cares of the world and easy access to the sun, surf and the planned activities and restaurants included in this tour.
In the unlikely event WTT is unable to provide the hotel accommodation(s) listed, for whatever reason, WTT will substitute similar quality accommodation(s) at no additional cost to the traveler.
Want to Arrive a Day Early?
Worried about possible flight delays? Consider arriving one day before the official tour start date. Many of our travelers choose this optional service. Your pre-tour package includes:
- The room (standard check-in times apply)
- Breakfast the following morning
- Optional activity suggestions prior to tour
$938.00 Single Occupancy
Early Arrival Hotel: This tour uses the same hotel used on the first night of the tour.
Optional Purchases For This Tour
In addition to the Early Arrival Optional Package - available on all WTT tours - this tour offers the following optional purchases.
- Late Departure, Single Occupancy (no breakfast) $938pp
CANCELLATION TERMS: Cancellation of Optional Purchases, which become part of your Total Tour Cost, are subject to the same cancellation terms as the main tour.
Key West Winter Getaway
February 8 - February 11, 2027Destination Information
What do others say about this tour and traveling with WTT?
How Active is this Tour?
- 70% Easy
- 30% Moderate (walking tours)
Your Responsibilities as a Solo Traveler
As a solo traveler you are responsible for yourself, your possessions, your physical fitness, and all other aspects related to participation in the WTT tour you have chosen. Be sure to read the itinerary closely to better understand the physical requirements necessary for the tour.
WTT tours are not suitable for anyone whose mobility is challenged or compromised. If you struggle with walking, standing or negotiating stairs or if you are in doubt as to your ability to meet the physical activity requirements, you should not sign up for this trip.
What is the Group Size?
You will be introduced to the WTT Tour Leader when you receive your Final Travel Instructions, about 2-3 weeks before the tour begins.
Learn about your fellow travelers after final payment by visiting MyWTT. Room sharing assignments will be listed in the Final Travel Instructions.
What meals are included and how are dietary restrictions accommodated?
Each day of the itinerary lists the included meals for that day (B,L,D,O). When a meal is not included, the WTT Tour Leader will have suggestions for where to eat.
You do not have to dine alone unless it is your personal choice. You'll most likely be dining with new acquaintances you've made, or you can join the Tour Leader.
Dietary Restrictions: Vegetarian and gluten-free dietary requests can be accommodated on this tour with limited selections.
What clothing and items should I pack for this trip?
In general this time of year, the average daily temperature is likely to be in the mid-70s, dropping to the mid-60s at night. Be sure to pack for cooler evenings. February is the month with the lowest amount of rainfall. We suggest you monitor weather apps leading up to the time you depart for more up-to-date information.
For this Tour You May Want—
- Comfortable walking shoes
- Smart-casual wear if you’d like to dress up a bit for dinners
- Warm jacket, best if also water-resistant
- Swimsuit and a coverup
- Hat or visor for sun protection
- Refillable water bottle
- Motion sickness medication/band for the sailboat
Good Packing Habits—
- Bring what you need to get a good night's sleep, such as ear plugs, white noise generator, sleeping aids, etc. Unfamiliar noises of all types can disrupt your rest.
- Pack a limited amount of comfortable, casual clothing that layer and coordinate. Your fellow travelers will not mind or even notice – seeing you in the same clothing.
- Bring only two pairs of everyday shoes: one pair of well-broken-in walking shoes, and a second pair that could do double-duty as a walking shoe or a slightly dressy shoe.
- Pare down your beauty regimen to the bare minimum and always pack travel-sized toiletries.
- Pack medication in your carry-on and pack only as much as needed for the duration of your tour plus a few extra days as a precaution.
What are the luggage restrictions for this tour?
- We strongly recommend you bring only one suitcase plus small shoulder bag/day pack/purse.
- You are responsible for managing your own belongings.
How much money should I bring on this tour?
What are the tipping guidelines for this tour?
- You are responsible for tipping waitstaff, porters, or other individuals who provide a service to you at the hotel, or other public locations.
- You may want to tip your WTT Tour Leader for an outstanding job. The amount is entirely a personal preference. If you'd like a guideline, consider $8-$10 per day.
Can I transfer my deposit to another tour?
To get off this tour and register for another tour, you must follow these steps - in the order shown:
2) WAIT before submitting your new reservation! You must receive the Cancellation Confirmation email before submitting your new reservation. This can take up to 2 business days. The Cancellation Confirmation email will list the amount of parked credits from this tour that are now available to use on a new reservation.
3) COMPLETE the new Reservation Form and USE the parked credits towards your deposit on the new tour.
Note: If you used Parked Credits to pay the deposit on this tour, these credits cannot be used a second time and are not eligible to be transferred.
What happens if I need to cancel this tour?
Key West Winter Getaway
February 8 - February 11, 2027SPACE RESERVATION REQUEST
If becoming a member and signing up for a tour at the same time, you only need to fill out this form.
Our Promise to You
It doesn’t matter which tour you choose.
You’ll find your people and make memories that last a lifetime.