First Time In Key West Vacation Guide

Dry Tortugas Beaches

It’s never a dull moment in Key West – it is truly one of a kind. This tiny, 2 x 4 mile sub-tropical island dangling like a charm at the end of the Florida Keys chain is a great escape. Surrounded by crystal clear water, Key West is not a made-up fantasy island just for tourists. It’s a quaint, colorful, quirky historic town, where locals, called Conchs, trace their multi-generational heritage back to the Bahamas and Cuba. Rich history, street after street of quaint, colorful cottages, tangles of tropical foliage leaning in over small lanes, this laid-back island is a place of multiple interesting layers, a magnet to artists, writers, and free spirited thinkers of all kinds.

For first time visitors, it’s important to begin with Key West’s most unique sights and iconic activities. This way, you’ll see what it’s like to live a true island lifestyle.

Catch a Ride
Taking a narrated Conch Tour Train tour or Old Town Trolley tour of the island is absolutely the first thing to do in Key West. It’s a great way to get the feel of the island, see a lot, learn a lot and get your bearings. Similarities between the train and the trolley: Both offer great 90-minute tour, hitting all the highlights and all the train engineers and trolley conductors give terrific, fact-filled, fun tours.

The whimsical open-air, with a canopy top, train winds through Old Town’s narrow street and lanes. It has 3 stops along the loop tour: Mallory Square area, Upper Duval and Historic Seaport. You can get off at the Upper Duval Stop as well as the Historic Seaport to walk around the surrounding area, taking in the sights and ambience and get back on a later train. The trolley goes through Old Town and New Town and along the stretch of island on the Atlantic Ocean side, with hop off/hop on privileges at 13 great stops along the route.

Do the Duval Crawl
Everyone knows Duval Street. Walk all or at least part of the 14 blocks of Key West’s “main street,” stretching from one end of the island to the other – from the Gulf of Mexico to the Atlantic Ocean. Definitely geared towards tourists, especially Lower Duval on the Gulf side, it’s lined with shops, bars, restaurants and museums, many in picturesque homes built in the mid to late 1800s.

Block by block, from the 100 block to the 1400 block, the “nice factor” goes up on the way up Duval. Colorful, quaint historic buildings house a diverse collection of interesting shops and boutiques selling everything – clothing, jewelry, hammocks, hats, cigars and wine. Pleasant restaurants, many with outdoor or open air seating and art galleries round out the attractive mix. Along the walk: Sloppy Joes at the corner of Greene is a Key West institution; Oldest House Museum is a peek into life on the island in the mid-1800s. Hard Rock Café and Grand Café between Caroline and Eaton are both in great old houses; stained glass windows inside historic St. Paul’s Church on the corner of Eaton should not be missed. Margaritaville, a must do for all Parrotheads, is between Fleming and Southard, so is La Trattoria, one of Key West’s fine dining, yet casual, restaurants.

Duval Street Key West

Stroll the Waterfront
This waterfront of Mallory Square is the oldest area in Key West. It’s a bustling place, with an open-air marketplace feel. It’s a great place to find souvenirs – natural sponges and tropical clothing. You can’t leave Key West without a pair of Kinos, Key West’s favorite locally made sandals.

While in Mallory Square, go into Key West Aquarium, a Key West treasure, for an up-close experience with sea creatures from the surrounding waters. Shout out “Wreck Ashore” from the 80 foot tower of the Shipwreck Treasures Museum; enjoy authentic Cuban food at El Meson de Pepe – black beans and yellow rice, Cuban sandwiches, yellowtail snapper, tostones and mojitos.

Celebrate the Sunset
Watching the sun dip down into the turquoise water under a sky streaked in splendid golds, pinks and purples of sunset is a Key West ritual. The best and most fun place to watch it happen is at Sunset Celebration, along the waterfront from Mallory Square to the Westin Resort. About an hour before sunset, the migration towards Mallory Square begins. Street performers line the waterfront to entertain with a variety of acts, stunts and tricks. Glimpse into your future at a Tarot card reading, check out local art and handmade jewelry or grab a drink at the pop up bars at the Westin.

Mallory Square Sunset Celebration

Sail Into the Sunset
There’s nothing like a sail into the sunset! Soft tropical air, gentle waves lapping, Key West’s waterfront bathed in golden light within sight, an ever-changing sky leaving trails of vibrant color – all the while relaxing on deck sipping beer, wine or champagne. This is a true Key West experience. Numerous sunset sails on a variety of vessel types – sailing catamarans, sailing schooners, glass-bottom boat – depart from the Historic Seaport every evening, about an hour before sunset, to head out to the mouth of Key West Harbor and back. Fury Water Adventures’ Champagne Sunset Sail, Sunset Sail on America 2.0, Sunset Watersport’s Sunset Sail, Schooner Appledore Champagne Sunset Sail, Glassbottom Boat Sunset Cruise, Danger Charter’s upscale Wind & Wine – each offers a similar yet different experience. They all serve some version of beer and wine, and sometimes champagne, plus hors d’oeuvres to go accompany the drinks. Two to three delightful hours, on the water, at sunset -the perfect way to begin a Key West evening.

Amp up the Energy
With water all around, getting out on it, or in it, is part of the Key West experience. Choices offered by numerous watersports operations range from peaceful kayaking close to nature in the pristine backcountry waters to the thrill of parasailing. Key West Echo Kayak takes out small groups on a 2.5 hour tour of the backcountry. Lazy Dog offers kayak tours and paddleboard tours. Fury Water Adventures’ 3-hour Dolphin Watch and Snorkel combines two favorites: finding and watching dolphins cruising through the water, occasionally leaping high, and snorkeling in the clear backcountry waters. Key West Snorkel Safari is a private 3 hour trip to the backcountry for two aboard an open fisherman, a comfortable boat, popular in the Keys. With the word “adventure” being the operative, all day water experiences, with all the necessary water toys – wave runners, kayaks, parasails, snorkels, paddleboards – are great fun. Check out Do-It-All Water Adventures; Do – It-All Water Adventures with Parasailing, Power Adventure Water Tour of Key West, Ultimate Water Adventure.

Key West Fury All Day Watersport Activities

Something to Write Home About
The mystique of Ernest Hemingway draws visitors from all over the world to the house where Ernest Hemingway lived and wrote from 1929 until 1939. Lines form at the gate of the brick-walled two-story Spanish colonial house built in 1851, and purchased by Hemingway and his wife Pauline in 1928. Some of the furniture and pieces that were in the house when during their time there are placed throughout the house, and a view of the second floor studio where the legendary author wrote, among others, “For Whom the Bells Toll” and “Death in the Afternoon,” is interesting. The grounds are tropical; lounging 6-toed cats, descendants of Hemingway’s cat, Snowball, are a great photo op.

History of Presidential Proportion
At the Truman Little White House, well-informed tour guides provide wonderful insight into the important people who stayed in this large, simple, wood-sided house built by the Navy in 1890. It was still Navy property when Admiral Nimitz suggested that President Harry Truman stay here for a much-needed get-way from the stresses of Washington. Truman first stayed at the house in 1946, liking it so much he came back 10 more times. These were working vacations during which the nation’s business was conducted. Dignitaries, Senators, Federal Judges, high-ranking military officers made the trip to Key West to meet with Truman in what he once called the Little White House.

The tour goes through all the rooms, which as though in a time warp, are just as they were. Most of the furnishings are original to the house. Those that are not are carefully researched reproductions. Throughout the house, are carefully placed artifacts. Today, the Little White House is more than a museum. It continues to host dignitaries, which have included former presidents, senators, secretaries of state, first ladies, and military leaders. The photos in one of the galleries tell that story.

Truman Little White House

The End of the Line
The red, yellow and black buoy marking the southernmost spot in the United States is an obligatory pilgrimage photo op. Queue up with the crowd, hand your camera or iPhone to the person next in line and ask them to take a photo of you standing by the buoy. While in this southernmost area of town, take the time to walk up South Street to see the Southernmost Mansion, a vision of gingerbread and pink, and have a bite to eat at the Southernmost Café, right out on the beach.

Escape to Another Island Paradise
A 70 mile boat trip aboard Yankee Freedom III, a spacious, comfortable, fast, smooth-riding catamaran skimming over turquoise water to Fort Jefferson in the Dry Tortugas is a once-in-a-lifetime experience. The ride out is wonderful. Seeing the massive Civil War-era red brick fort appear on the horizon, alone in the middle of the vast ocean, and grow in size as it is approached is mind-boggling. Once there, tour the fort, either self-guided or on a ranger led tour; snorkel, enjoy the beach areas, or even hang out on the boat decks. Enjoy a continental breakfast on the way out, lunch at the fort, and drinks from a cash bar and snacks on the relaxing ride back. Definitely memorable.