10 Top Activities To Enjoy In The Key West During Winter

In some US cities, the winter months are marked by blizzards, horrible road conditions, and freezing temperatures. One warm and sunny vacation spot that is immune to these freezing features is the beautiful island city of Key West. Key West, the southernmost point of Florida, features desirable and warm temperatures year-round.

The perfect escape during the winter months, many guests seek out the top-rated resorts in Key West. Those vacationing as a family enjoy booking at one of the ten most family-friendly Key West resorts. This lovely island city also contains several romantic hotels perfect for a couples’ getaway to Key West.

Key West is filled with plenty of fun and exciting activities for guests to embark on while on vacation. From sandy beaches to water activities to exhilarating tours, there is no shortage of enjoyable activities in this island paradise.

Related: 10 Best Florida Resorts To Visit This Winter

10 Snap Some Pictures Of The Florida Keys Overseas Heritage Trail

A unique Key West attraction to visit and snap some photos of is the Florida Keys Overseas Heritage Trail. American industrialist Henry Flagler had the vision to expand his railroad network from Miami to the Florida Keys. This was an ambitious project, especially for the early 1900s, and the railroad took seven years to complete. During construction, there were thousands of men working at a time. Unfortunately, a 1935 hurricane destroyed numerous portions of the bridge. The railroad was eventually turned into a highway and now serves as a historic landmark and multi-use trail for locals and travelers.

9 Explore Key West Lighthouse & Keeper’s Quarters

Fight the winter blues by exploring the tall white Key West Lighthouse and the luscious surrounding flora and fauna. The Key West Lighthouse possesses a unique history, first beginning operation in 1848 with a female keeper (a very rare occurrence for the 1800s). As the lighthouse is no longer in operation, guests can ascend to the top of the lighthouse to enjoy the beautiful views and learn about this landmark.

This must-see attraction is only a one-minute walk from the Ernest Hemingway House, another cool spot to visit and one of the best spots to visit in Key West in winter.

  • Address:
    938 Whitehead St, Key West, FL 33040

  • Hours:
    10 am-5 pm daily

  • Cost:
    Adult- $17, senior/student- $13, child (7-18)- $9, 6 and under free

8 Go Scuba Diving

When considering unique Key West tours that are worth the money, look into booking a scuba diving or snorkeling expedition. Key West is home to a spectacular barrier reef, perfect for exploring via scuba trip. The incredible reef stretches over 350 miles and contains brightly colored parrotfish, a variety of sea turtles, and stingrays.

Key West Scuba Diving offers an afternoon scuba package, allowing guests to explore two coral reef sites. Reservations are required.

  • Duration:
    ~4.5 hours

  • Cost:
    From $95 per person

7 Visit The Key West Aquarium

Travelers who are unable or do not want to embark on a scuba diving trip can still admire Florida’s unique marine life at the Key West Aquarium. This aquarium features exciting live presentations, including feeding sharks and a touch tank experience where guests can interact with conchs, sea stars, horseshoe crabs, and more. Key West Aquarium is dedicated to the conservation of Florida’s ecosystem and sharing information on conservation practices and local wildlife.

  • Address:
    1 Whitehead St, Key West, FL 33040

  • Hours:
    9 am-5pm daily

  • Cost:
    Adult- $22.65, child (4-12)- $12.89, 3 and under free

6 Dine And Shop Along Duval Street

No trip is complete without a bit of souvenir shopping and trying out the local restaurants. Key West’s Duval Street is known for its vast selection of restaurants, bars, shops, and art galleries. In fact, there are over 40 bars to choose from when visiting Duval Street.

Stretching just over 1.25 miles, this street is also perfect for travelers looking for a free afternoon activity, as strolling along the sidewalks and window shopping does not cost a penny.

  • Address:
    Key West, FL 33040

Related: Uncover The Charm Of Key West: Your Guide To Duval Street & Beyond

5 Unwind At Higgs Beach

Arguably the best part of a Key West vacation is soaking up the sun. Vacationers craving a relaxing day at the beach should explore Higgs Memorial Beach Park. Visitors enjoy tanning on the beach, swimming in the blue waters, and walking along the nearby White Street Pier. Pack a picnic lunch to eat on the beach or enjoy a meal at Salute! On The Beach, an on-site restaurant.

This area is also the site of an 1880s African slave cemetery, a National Register of Historic Places site worth visiting.

  • Address:
    1000 Atlantic Blvd, Key West, FL 33040

  • Hours:
    6 am-11 pm daily

4 Enjoy A Spooky Ghost Tour

There are plenty of terrifyingly haunted US destinations to visit, and sometimes getting scared can be fun! When vacationing in Key West, be sure to embark on a spooky ghost or cemetery tour. With a speculated number of around 100,000 people buried in Key West Cemetery, there are bound to be a few ghosts hanging around. Explore these haunted grounds yourself and embark on a self-guided tour.

  • Address:
    701 Passover Ln, Key West, FL 33040

  • Hours:
    7 am-7 pm

Craving a guided tour experience? Enjoy Ghost and Gravestones’ eerie trolly tour of Key West’s most haunted sites.

  • Cost:
    Adult- $39.85, child (0-12)- $39.85

3 Take A Submarine Tour

Another outdoor adventure to be had in Key West is a submarine tour. Billy Ocean Underwater Adventures offers a unique underwater experience where guests can explore the ocean via special underwater submarine scooters. No scuba certification is needed, and guests enjoy swimming alongside the colorful and unique fish. This underwater activity also makes for some stellar and unique photographs.

As of February 2023, Billy Ocean Underwater Adventures is closed for the season, but check Billy Ocean’s website for updates.

  • Cost:
    From $55 per person

2 Swim With Dolphins

Another exciting water activity to try in Key West is swimming with dolphins. Captain Sheri’s WILD about DOLPHINS excursions are perfect for travelers wanting to encounter dolphins in the wild rather than at an aquarium. With over 20 years of experience, the company is passionate about spreading knowledge about dolphins and protecting the beautiful species. This exciting tour includes a boat journey, dolphin encounter, snorkeling experience, and picnic lunch. Guests are also taught plenty of facts about dolphins and their habits. Both half-day and full-day private charters are available.

  • Duration:
    3-7 hours

  • Cost:

1 Embark On A Sunset Cruise

The perfect way to end a day in Key West is by unwinding on a sunset cruise. Sebago Key West Watersports offers a wonderful sunset sail, complete with appetizers, a full bar, and live music. The spacious catamaran measures 70 feet in length, and guests enjoy gliding along the glistening water as the sky turns beautiful shades of pink and orange. Guests also enjoy sipping wine, beer, or sangria while relaxing and taking in the serene view.

  • Meeting point:
    205 Elizabeth St #205, Key West, FL 33040

  • Duration:
    ~2 hours

  • Cost:
    From $79.95 per person