January in Key West: Best Things to Do, Events, Weather & Travel Tips (2026)
January is one of the best times to visit Key West, offering warm winter weather, fewer crowds, and a full calendar of iconic island events. Visitors can enjoy boat races, food and wine festivals, waterfront races, art shows, and unforgettable days on the water—from sandbar trips to sunset cruises. Whether you’re planning a New Year’s getaway, escaping cold weather, or building the perfect Florida Keys itinerary, January in Key West combines outdoor adventure, cultural events, and laid-back island fun in one unforgettable vacation.
Quick Answer: January is one of the best months to visit Key West thanks to warm weather, major festivals, outdoor activities, and ideal boating conditions.
January in Key West at a Glance
- Ideal winter escape: Warm, dry January weather makes Key West perfect for outdoor activities and time on the water.
- Full event calendar: Enjoy food and wine festivals, boat races, art shows, and iconic island events throughout the month.
- Great for first-time visitors: Fewer crowds than spring and summer make it easier to explore at a relaxed pace.
- Excellent boating conditions: January is popular for boat tours, sandbar trips, and sightseeing cruises on cooler days.
- Family-friendly travel month: Comfortable temperatures and walkable attractions suit travelers of all ages.
- Easy island transportation: Scooters, golf carts, and compact distances make getting around simple for visitors.
Key West Food & Wine Festival
Flip Flops Required. Top chefs and restaurateurs display culinary creativity and the Keys’ indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively “Old Town Uncorked,” neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting. Learn more
Annual Wrecker’s Cup Race
This fun race series recalls the tradition of the wreckers in the Key West of the 1800’s. Vessels with rich cargoes from Gulf and Caribbean ports often became victims of the unmarked reefs 7 miles off Key West. The first wrecker to reach the site had the responsibility to save the passengers and crew, but they also won the right to salvage the cargoes.
Key West Sandbar Trips & Boat Rentals in January
Spend your vacation like a local, at the sandbar!
Explore the turquoise blue waters of Key West on your own boat rental. Stop at remote sandbars or just tour the island. There’s no better way to see Key West.
Be your own captain with a boat rental or let us do the driving and take one of our sandbar charters.
Annual Florida Keys Seafood Festival
The 2 day Seafood Festival celebrates our community by bringing families and friends together in a joyful and fun environment to sample the local catch. This family-friendly event at Bayview Park features local fresh Key’s seafood, drinks, chef demonstrations, marine-related crafts, youth activities, and live local music. Enjoy some local stone crab. Learn more
Try a New Restaurant or Bar
Looking to try a new Key West bar or restaurant since your last visit? We’ve got your covered. Checkout the Square Grouper location in Key West on Caroline Street.
Key West Half Marathon & 5K
Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. Learn more
Key West Art and Craft Festival
The Key West Craft Show, which attracts buyers from locals, cruise boats and tourists, was rated by Sunshine Artists in the top 100 shows, most recently at #45. The 2017 show had attendance estimated over 25,000 visitors. This show is popular with locals and tourists alike and is only one block from the popular Duval Street. Learn more
Annual Master Chef’s Classic
Local restaurants vie for top honors in appetizer, entrée and dessert categories. Attendees sample the culinary treats while judges pick the winners. The show is held from 4-7 p.m. at the Margaritaville Resort & Marina pier, 245 Front St. Event proceeds benefit the nonprofit Monroe Association for ReMARCable Citizens. Learn more
Annual Key West House & Garden Tours
Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs. Learn more
Scooter & Golf Cart in Key West – Explore the Island with Ease
With perfect November weather, scooters are the easiest and most fun way to explore Key West on your own time.
Cruise around Key West, island-style, with eco-friendly electric golf carts, Scooter Rentals, or gas-powered Golf Cart rentals. Embark on an exhilarating journey with our roadworthy rentals, meticulously crafted to effortlessly transport you from one dream destination to the next. These vehicles promise a smooth and secure ride, elevating your vacation experience to new heights.
Reserve early – November is prime season for scooter rentals in Key West. Call or text us today to secure your ride.
Historic Key West Cemetery Stroll
During the stroll, small groups of visitors will be escorted to gravesites where interpreters will tell the stories of the deceased in brief monologues. Among the gravesites to be visited are those of the Los Martires de Cuba, the Figueredo plot, the Benjamin Albury family restoration, the Otto plot, and Piedad Ayala. Learn more
Insider Tips for Visiting Key West in January
- Plan outdoor activities for mid-day.
January mornings and evenings can feel cool on the water, so boating, sandbar trips, and sightseeing are most comfortable between late morning and mid-afternoon. - Pack layers – even in paradise.
While daytime temperatures are warm, ocean breezes and evening events can feel chilly. A light jacket or hoodie makes a big difference. - Book popular tours early.
January festivals and races attract visitors, and boat tours often fill up faster during these dates – even outside peak season. - Choose boating days based on wind, not temperature.
January weather is mild, but breezy days can affect water conditions. Flexible scheduling helps ensure the smoothest boat experience. - Use scooters or golf carts.
Parking is limited in popular areas, and alternative transportation makes it easier to hop between Old Town, the waterfront, and event venues. See this Self-Guided Golf Cart Tour for great info. - Check sunset times when planning cruises.
January sunsets arrive earlier than in summer, which is perfect for evening cruises without late nights. - Expect clearer skies and lower humidity.
January’s dry season conditions are ideal for photography, sightseeing, and long days outdoors.
January in Key West FAQs
Is January a good time to visit Key West?
Yes – January is one of the best months to visit Key West. The weather is warm and dry compared to most of the U.S., crowds are smaller than peak spring season, and the island hosts major festivals, races, and outdoor events.
What is the weather like in Key West in January?
January weather in Key West is typically mild and sunny, with daytime temperatures in the low to mid-70s°F and cooler evenings in the 60s. Humidity is low, making it ideal for sightseeing, boating, and outdoor activities.
Is January a good month for boating in Key West?
Yes. January offers excellent boating conditions, especially on calmer days. Cooler temperatures make time on the water comfortable, and visibility is often good for sandbar trips, island hopping, and sightseeing cruises.
Can families with kids visit Key West in January?
Absolutely. January is a great time for families visiting Key West. Popular family-friendly activities include boat tours, sandbar trips, festivals, outdoor races, historic attractions, and easy island transportation like scooters and golf carts.
Are boat tours and sandbar trips available in January?
Yes, boat tours and sandbar trips run year-round in January, weather permitting. Many visitors prefer January boating because of the cooler temperatures, less crowded waters, and comfortable conditions for longer trips. Be sure to reserve your boat day as trips can sell-out.
What should tourists pack for a January trip to Key West?
Pack light layers. Bring shorts and t-shirts for daytime, a light jacket or sweater for evenings, comfortable walking shoes, sunscreen, sunglasses, and swimwear for boating or beach days. See our guide for packing for your boat rental or sandbar day.
Is January busy or crowded in Key West?
January is considered a high-quality travel month rather than a peak-crowd month after the business of New Year’s Eve. While popular events draw visitors, it’s generally less crowded than spring break or summer, making it easier to enjoy tours, restaurants, and attractions.
Are January events suitable for first-time visitors?
Yes. January events in Key West are ideal for first-time visitors because they showcase the island’s culture, food, history, and outdoor lifestyle without overwhelming crowds.
