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Key West Time
April 23rd
7:24am · 73°F

Tips for Surviving the Peak Season in Key West

Waiting in line to shoot selfies at the Southernmost Point Waiting in line to shoot selfies at the Southernmost Point

Surviving the Season in Key West

Crystal clear blue skies. Temperatures mostly in the 70s. Gentle breezes. Nothing can compare to the Winter and Spring months in Key West. So much of the rest of the country is cold and gray, or snowy. There's little wonder so many people eagerly escape to the tropical paradise of Key West for sunshine and warmth. At VHKW - Vacation Homes of Key West, many of our regular guests return to the same vacation rental homes year after year when they escape the cold from the northlands. Of course, with a high number of visitors on the tiny island, traffic gets busier, restaurants and stores become crowded, and service becomes slower.

Those of us 'year-round' locals have lived through this cycle over and over. And we've figured out tricks and short cuts to avoid aggravating crowds and breeze through the peak winter-spring season unscathed. Here we offer five local's tips to help you avoid the crowds during your visit.  Follow these and you can just relax and savor your stay in beautiful Key West.


1.Get Around Without a Car

Most of our vacation rental guests stay in historic Old Town Key West. This end of the island is compact, and pedestrian-friendly. Here you'll find the Historic Key West Seaport, and famous landmarks like Mallory Square, the Hemmingway Home and the Southernmost Point. World famous Duval Street cuts right through the district, from the Gulf of Mexico to the Atlantic, with an enticing array of famous bars, restaurants, entertainment venues and shops.

Truth is, Old Town Key West is as quaint as can because it was founded before there were cars! With all this charm comes narrow streets and lanes and very limited parking. In the commercial areas, parking is expensive, whether in lots or at meters on the streets. Good news is that many of our guests find cars unnecessary and choose to get around by foot, on bicycles or scooters during their stay. (See this earlier post for options.) You'll learn that many places you want to visit are within easy walking distance.

When you need vehicle transport, there are taxicabs as well as ride-share providers (Uber and Lyft) on the island. If you prefer private transportation, there are also rental car companies. If you decide to drive a car into Key West, keep in mind that many of our vacation rental homes have parking.

2.Grocery Shop Locally or Have Food Delivered

When you stay in a VHKW vacation rental, you'll enjoy the wonder feature of your own kitchen to cook in. Shop for groceries in Old Town at the locally owned Fausto's Fine Foods markets. There are two convenient locations. Or, you may choose to have Publix or Winn-Dixie supermarkets on North Roosevelt Boulevard deliver. You can pick up fresh seafood right in Old Town at Eaton Street Seafood Market. If you don't feel like grocery  shopping, our concierge service can arrange to have your groceries delivered to your vacation rental.

3.Make Restaurant Reservations In Advance

When cooking isn't on the agenda, Key West offers an astounding number and variety of first-rate restaurants. You'll find everything from light fare and tapas to multi-course 5-star fine dining options. The local seafood is some of the best on the planet, and often served fresh the very day it is caught. You can choose to sample fare from a variety of international cuisines or go for traditional American, Caribbean and Cuban-inspired offerings. Make a quick online search of Google's Key West Restaurant listings, and you'll see what we mean.

But be forewarned: many of these establishments can get quite busy during high season and waits for seating can be long. If you check their individual websites, you can choose restaurants that accept reservations. We recommend planning ahead and making reservations earlier in the day.

4.Dine at Off-The-Beaten-Path Restaurants

Hogfish Bar, Stock Island Hogfish Bar, Stock Island

A great way to avoid the crowds during the busy times is to enjoy restaurants that are not in  downtown Key West. Restaurants on and around the Seaport, and those located along the Duval-Simonton corridors inevitably fill up during the high winter and spring season. But excellent options are available elsewhere, and not too far away.

Key West locals frequent the restaurants that are out of the hub bub. Why not enjoy some of their favorite places. On South Roosevelt Blvd., near the Key West International Airport, you can visit La Trattoria Italian Restaurant. Right next door is Benihana, offering Japanese Teppanyaki style cuisine with a little show business thrown in. And on North Roosevelt, nestled next to the Cow Key Channel Bridge, Tavern N Town is right off the lobby of the Marriott Hotel. The Tavern offers elevated dining in a sophisticated atmosphere. If you do have a vehicle, there  is generally plenty of parking at these places.

Venture a little further, and cross the Cow Key Bridge, as if you are leaving Key West. Moments later, you'll find yourself on Stock Island. This is a less busy area, but there are several delightful restaurants. For elegant dining on the water, check out Matt's Stock Island Kitchen and Bar, at the Perry Hotel and Marina. Just to the right of the bridge is Hurricane Hole Waterfront Bar and Seafood Grill, featuring casual dining at the marina.

Continue up U.S.1 Highway about 500 yards, and you'll arrive at the local's favorite Mexican restaurant, Chico's Cantina. Bear right and head down Maloney Avenue for wood-fired pizza and superb Italian food at Roostica.

And now for a renowned, but hidden, Key West gem. Over on Stock Island's working waterfront sits Hogfish Bar & Grill. This informal and friendly dining spot offers the freshest local seafood you'll find anywhere on the island, simply but expertly prepared. It is served up at picnic tables in a semi open-air dining area. Local color at its finest, and live music on weekends.

5.Places to Go to Avoid the Crowds

Higgs Beach The less busy end of Higgs Beach at the least busy time of day- around 10AM


Sure, it may be Winter, but if you are visiting from more northerly climes, 75 degrees can feel quite warm. You may choose to bask in the sun and take a dip in the ocean. If you go to  popular Higgs Beach (at the end of Reynolds Street), chances are you'll find it a bit crowded. But if you walk around to the other side of the West Martello Fort, chances are good you'll find some wide-open beach. The stretch of sandy beach between the Fort and the White Street Pier is generally much less busy. Plus, there is free parking along the beach walk.

While you're at the Higgs Beach area, treat yourself to a quiet stroll or a bicycle ride on the White Street Pier. This wide concrete pier extends 320 yds out over the ocean. Enjoy the wide-open sky and limitless ocean vistas. Let the sea breezes embrace you.

Another place to find some quiet or solitude, is Fort Taylor Beach at the Zachary Taylor State Park. This is believed by many to be the nicest beach in Key West. There is a small fee to enter, but this includes your parking. Even though this beach and park can get quite busy during season, it is expansive with trails that lead out toward the Gulf of Mexico. Enjoy a stroll and the unique flora of this area.

If beaches are your thing, you can almost always find some space and solitude at Smathers Beach. Situated along South Roosevelt Blvd., it's nearly a mile long. Since it is such a long stretch, mosey long until you find your spot.

Reynolds Street Pier Enjoying sunset at Reynolds Street Pier


Any regular visitor to Key West will tell you about its world-class sunsets. The Sunset Celebration at Mallory Square is legendary. Fair enough; this daily carnival-like event is something you need to experience once. But, like so many things this time of year, Mallory Square can be a real mob scene, and parking nearby is often out of the question. But there are other options.

Many locals and visitors, seeking quiet, prefer the somewhat Zen-like experience of watching the sun dip below the horizon from one of the piers near Higgs Beach. On the east end, there is the expansive White Street Pier. On the west end, check out the smaller Reynolds Pier, that offers a great vantage point. There is lots of free parking dotted all around the area, so no problem there. The little known John & Mary Spottswood Waterfront Park is a unique seaside enclave park tucked in next to the Casa Marina Hotel at the intersection of Alberta and Seminole Streets. This is another great vantage point for enjoying the sunset, and free on-street parking is usually available nearby.

Key West Garden Club at the West Martello Tower Key West Garden Club at the West Martello Tower


One of the best parts of visiting Key West is visiting the historical, artistic, and natural points of interest. But like the restaurants, favorite attractions can become as busy as beehives during the high season. Getting away from the Old Town epicenter offers some fun and unique alternatives and smaller crowds! Instead of waiting in line to visit the Hemmingway Home or the Key West Aquarium, why not take in the Key West Tropical Forest & Botanical Garden. Here you'll find 15.2 acres of native forest garden to tour and breathe in fresh air.

Another of our favorites is The Fort East Martello Museum, which sits nestled between the Airport and the Atlantic on South Roosevelt Blvd. This museum, housed in an authentic Civil War-era fort, offers a variety of historic and artistic exhibitions which are both educational and entertaining. Including the infamous haunted Robert the Doll. And, just down the shoreline, at Higgs Beach, sits a sister fort, The West Martello Tower. This classic structure is home to the Key West Garden Club. Enjoy a unique opportunity to explore a lush and expertly curated tropical garden perched on the edge of the ocean.

Avoiding crowds is automatic when you book a specialized tour, sail, or excursion, all of which are intrinsically self-limiting. Be sure to check out these Guided Key West Experiences on our VHKW website for some suggestions, or contact our concierge to help you plan one of your own design.

Old Town Key West One of the many quiet lanes in Old Town Key West

On your own

There's no better way to savor and absorb the charm, history and architectural significance of Key West, than to charge out on your own on foot or by bicycle. Wandering the less travelled little residential streets and lanes throughout Old Town will provide you with hours of free entertainment. Take in the unparalleled ambience of the neighborhoods as you bask in the fabulous weather and get some healthy non-strenuous exercise at the same time.

Old Town Key West is the largest historic district of primarily centurion wooden structures in the U.S.A. Many of the houses here date from the early 1800's, and the quirks and distinctions of these hand-crafted houses are astounding. You can't really savor their magnificence when you just drive through. You miss so much when you're in a car.

As you're strolling or biking around, be sure to drop by the Historic Key West Cemetery to visit generations from the past. This cemetery is the largest green space in Key West with beautiful trees and intriguing features. Visit the USS Maine Memorial, a small military plot that was erected  to honor those who died aboard the battleship Maine that as blown up in Havana Cuba Harbor  in 1898. There's also humor to be found with some of the most unique gravestone epitaphs to be found anywhere.

Also worth a visit, just two blocks from the Cemetery, is the Our Lady of Lourdes Shrine Grotto. It stands adjacent to spectacular Saint Mary Star of the Sea Catholic Basilica. The coral rock shrine was built in 1922 by Sister Louis Gabriel and her fellow nuns. Their belief was that it would deflect devastating hurricanes from directly impacting their beloved island of Key West. During impending hurricanes, many locals pray at this shrine..


You have chosen the very best time of the year to visit us here in the Keys. Unless you're in a big hurry (and why would you be?) you're sure to have a pleasant and relaxing stay here. Just plan ahead, go slow, and use our tried-and-true tips and tricks to season like a local!

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