Key West—a name that conjures up images of crystal-clear waters, swaying palm trees, and a laid-back island atmosphere. It’s a place where the sun seems to shine a little brighter, and the air carries a sense of adventure. But for the Jewish traveler, the question always arises: Can this destination accommodate a frum lifestyle?

The answer is yes—with the right preparation. What many don’t realize is that Key West has a rich Jewish history stretching back over a century. From Jewish merchants who helped build the island’s economy to a historic cemetery that tells the story of early Sephardic settlers, Key West is more than just a beach getaway—it’s a place with a unique Jewish past.

Of course, no trip is complete without knowing where to eat, where to daven, and what to see through a Torah lens. Whether you’re looking for kosher-friendly food options, historical sites, or breathtaking attractions that remind you of Hashem’s beautiful creation, this guide will help you plan a trip that is both relaxing and meaningful.

The Jewish History of Key West

The Early Jewish Settlers

In the late 1800s, Jewish immigrants arrived in Key West seeking economic opportunities. Many were merchants and traders who opened general stores, supplying goods to sailors, fishermen, and local residents. Unlike many Jewish immigrants who settled in bustling cities like New York and Baltimore, these pioneers chose a life in a tropical port town, making their mark in a place very different from the traditional centers of Jewish life.

Key West’s Sephardic Roots

A significant number of the early Jewish settlers were of Sephardic descent, particularly from Cuba and the Caribbean. Their influence can still be seen in some of the historical sites around the island. During the early 20th century, Key West even served as a stopover for Jews fleeing persecution in Europe and seeking new beginnings in the Americas.

Historic Synagogues & Jewish Institutions

While the Jewish community of Key West is much smaller today, remnants of its past remain. The historic Jewish cemetery, one of the oldest in Florida, holds the stories of Jewish families who played a role in shaping the island.

Kosher Food & Dining Options

Before heading to Key West, it’s a good idea to stop at a major supermarket in Miami, where kosher food is abundant. Once on the island, several grocery stores, including Publix and Winn-Dixie, carry basic kosher items like snacks, dairy products with reliable hechsherim, and some frozen meals.

Bringing Your Own Food

Many frum travelers opt to bring their own supply of kosher food, particularly for longer stays. A portable travel burner, disposable utensils, and ready-made meals can make the trip much easier. Some hotels offer kitchenettes, which can be useful for those who prefer to prepare their own meals.

Kosher-Friendly Dining Options

For those looking to enjoy a restaurant experience, vegetarian and seafood establishments can sometimes accommodate kosher travelers who bring their own double-wrapped food to be heated in an oven. Always check with a halachic authority before relying on this option.

Must-See Attractions

The Historic Jewish Cemetery

Tucked away in a quiet part of the island, the Jewish cemetery is a fascinating stop for those interested in history. Many of the gravestones feature inscriptions in Hebrew and Spanish, a reminder of the island’s Sephardic roots. The cemetery tells the story of Jewish immigrants who made their home in Key West, contributing to the community while maintaining their traditions.

Ernest Hemingway’s House

One of Key West’s most famous landmarks, the Ernest Hemingway House, holds an unexpected Jewish connection. Hemingway, known for his literary works, had close friendships with several Jewish writers and intellectuals, and his works often touched on themes of displacement and identity that resonate deeply within Jewish history.

The Key West Lighthouse

A climb to the top of the Key West Lighthouse offers a breathtaking view of the island and its surrounding waters. Looking out at the vast ocean, one cannot help but reflect on the words of Tehillim: “מה רבו מעשיך ה’.” The grandeur of the sea, the vibrant coral reefs, and the endless horizon are all reminders of Hashem’s greatness in creation.

The Southernmost Point

Standing at the Southernmost Point of the United States, one is reminded of the journeys Jews have taken throughout history. Key West was a place of transit for many Jewish immigrants seeking a new life in America. Just as our ancestors traveled across oceans in search of a better future, standing at the Southernmost Point offers a moment to reflect on the resilience of the Jewish people.

Outdoor Adventures & Nature in Key West

Boat Tours & Sunset Cruises

One of the best ways to experience the island’s beauty is by taking a boat tour. Whether it’s a Key West boat trip showcasing the vibrant coral reefs or a sunset cruise on the open water, these experiences provide a chance to marvel at Hashem’s world from a unique perspective. Watching the sun dip below the horizon, painting the sky with fiery colors, is an awe-inspiring moment that brings to mind the words of “מה רבו מעשיך ה’.”

Snorkeling & Exploring Coral Reefs

The coral reefs surrounding Key West are some of the most stunning in the world. While snorkeling is an incredible way to experience marine life up close, it’s important to be mindful of halachic considerations, such as proper swimwear and separating from mixed-gender groups.

Dolphin Watching & Wildlife Experiences

Observing dolphins in their natural habitat is an experience unlike any other. The intelligence and beauty of these creatures are yet another example of Hashem’s intricate design in the world.

Travel Tips

Shabbos in Key West

Key West is a peaceful place for a relaxing and uplifting Shabbos. However, one should plan ahead by booking accommodations within walking distance of the places they wish to be on Shabbos. Bringing an eiruv chatzeros kit can also be helpful.

Davening & Keeping a Torah-Focused Experience

Finding a quiet spot to daven while surrounded by nature can be an incredible experience. Whether it’s at the beach in the early morning or on a secluded walking path, maintaining a connection to Hashem while traveling is essential.

Best Times to Visit

The ideal time to visit Key West is between December and May, when the weather is pleasant, and hurricane season is not a concern. Visiting during off-peak times also makes for a more relaxing experience, avoiding large tourist crowds.

A Journey That Balances Relaxation & Kedusha

Key West may not be the first place that comes to mind for a Jewish traveler, but with the right preparation, it can be an unforgettable experience. Beyond the stunning scenery and relaxed atmosphere, the island offers a glimpse into Jewish history and a chance to reflect on the beauty of Hashem’s world.

A well-planned trip allows for a balance between adventure and kedusha, making it possible to enjoy the wonders of the world while staying connected to Torah and mitzvos. Whether exploring the Jewish history of the island, marveling at the coral reefs, or simply watching the sun set over the ocean, Key West is a destination that offers both relaxation and inspiration.