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Schooner Wharf Bar Wrecker’s Cup Race Series 2026 Experience the Annual Wrecker’s Cup Race a Key West Sailing Tradition! Inspired by Key West’s colorful maritime past, the Wrecker’s Cup Race brings history to life with one of the island’s most exciting on-the-water events. In the 1800s, ships often ran aground on nearby reefs, triggering fast-paced…

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…

How to Spend New Year’s Eve & Day in Key West: Fireworks, Cruises & Island Fun [2025] Planning to celebrate New Year’s Eve in Key West? There’s no better place to ring in the New Year than this laid-back island paradise. From legendary Duval Street ball drops and sunset celebrations to boat cruises, sandbar adventures, and New Year’s Day…

Christmas in Key West: Best Things to Do, Holiday Lights, Sandbars & Festive Tours Ever dreamed of celebrating Christmas in paradise?  Key West is the perfect place to celebrate the holidays with your loved ones. Instead of dreaming of a white Christmas, imagine palm trees adorned with white lights, sailboats sparkling with colorful holiday lights,…

Thanksgiving Dinner in Key West 2025: Best Restaurants, Menus & Reservations Spending Thanksgiving in Key West means warm weather, island flavors, and a variety of places to enjoy a holiday meal. Most Thanksgiving dinners are concentrated in Old Town, the Historic Seaport, Casa Marina, and Stock Island, with options ranging from waterfront fine dining to…

Thanksgiving Sunset Dinner Sail in Key West | Holiday Cruise with Dinner, Drinks & Live Music Thanksgiving Dinner Sail in Key West – Holiday Menu, Live Music & Unlimited Open Well Bar – Very Limited Seating This Thanksgiving, trade the traditional dining room for a Key West catamaran sailing into the sunset. Step aboard and…

Things to do in Key West in November 2025 Experience the Excitement of November in Key West November in Key West brings perfect weather – If you’re wondering what to do in Key West in November, this guide highlights the top events, local tips, and must-do activities for your fall getaway. Warm sunshine, gentle ocean…

Things to do in Key West in October 2025 Looking for the best things to do in Key West in October 2025? This tropical island in the Florida Keys is a vibrant destination known for its lively festivals, world-class boating, and endless sunshine. While much of the U.S. is cooling down with pumpkin spice lattes, Key…

Rainy Day Activities in Key West – Indoor Things to Do When It Rains Don’t let a little rain ruin your Key West vacation! While our island is known for sunshine, there’s still plenty to enjoy when the weather turns. From cozy museums and tropical conservatories to spa days, tiki bar crawls, and even rainy-day-friendly…

Fun Things To Do In Key West In September September in Key West: The Underrated Sweet Spot September is one of the best-kept secrets in Key West. With summer crowds fading and winter season not yet in full swing, this early fall window offers ideal conditions for laid-back adventures and unbeatable travel deals. From snorkeling…

Labor Day Weekend in Key West 2025 – Your Guide to Festivals, Cruises & Sandbar Trips Labor Day Weekend in Key West is the perfect time to experience the island at its liveliest. From sunrise to sunset, the Conch Republic turns into a tropical playground filled with live music, food and drink festivals, waterfront parties, and…

Which Boat Should You Rent in Key West? Deck vs. Pontoon vs. Center Console Choosing the right boat rental in Key West can make or break your day on the water. Whether you’re cruising to a remote sandbar, snorkeling the reef, or hosting a family outing, the type of boat you choose matters. In this guide, we’ll…

Sunday Funday in Key West: Best Boat Rentals, Sandbar Charters & Local Tips Looking for the ultimate Sunday Funday in Key West? There’s no better way to experience island life than on the water – with a boat rental to a remote sandbar or a sandbar charter. Whether you’re visiting for the weekend or a…

Best Things to Do in Key West in August August in Key West: Fewer Crowds, Endless Fun August is the perfect time to experience Key West at a slower, more relaxed pace. With lighter crowds and plenty of sunshine, you can enjoy the island’s best attractions without the wait. Cool off at Dante’s pool, take…

Best Places to Watch the Sunset in Key West Key West is famous for its unforgettable sunsets, with dozens of stunning spots to watch the sky light up in color. From Mallory Square to hidden tiki bars, sunset boat trips, and quiet waterfront parks, no two sunsets in Key West are ever the same –…

Key West’s Mini Lobster Season Guide Contact us ASAP if you need a mini lobster season boat rentals. They book quickly. Key West’s mini lobster season, also known as the sport season, will take place on July 30th and 31st, the last consecutive Wednesday and Thursday of the month. This two-day event allows recreational divers…

Top Things to Do During Womenfest in Key West (2025 Guide) Celebrate Women in Paradise at Key West’s Womenfest 2025 Get ready for five fabulous days of fun, empowerment, and fierce femininity at Womenfest Key West, the island’s iconic celebration designed by women, for women. From September 3-7, 2025, the Conch Republic transforms into a vibrant stage…

7 Best Things to Do in Key West on July 4th: Fireworks, Fun, and Island Vibes Planning to spend Independence Day in Key West? You’re in for a laid-back island celebration filled with sunshine, stunning ocean views, and unforgettable local experiences. Whether you’re traveling with family, cruising in for the day, or just looking to…

Spend a day like a local, on the water! Looking to experience the real Key West? Spend your day on the water – just like the locals do. Cruise to the local sandbars and remote islands with a sandbar charter, tiki bar boat charter, slide boat charter, or custom sandbar charter – perfect for bachelorette…