When Hurricane Irma hit the Florida Keys in September of 2017, many feared the worst for Key West. Thankfully, Key West largely rebounded within a month of the storm! So, I updated my Key West travel guide for 2018, “Key West 2018: One Perfect Trip Travel Guide,” on Amazon and Kindle. Key West attractions, as well as hotels, restaurants, bars, sunset cruises, kayaking, jet ski tours, entertainment experiences, and activity choices are included in the book. For this article, I have selected three days of recommended itineraries from the book to highlight. For even more of my personal thoughts, click on the audio bar at the end of this post to hear my accompanying podcast.
Key West Day 1 of 3 – Suggested Itinerary
Highlights: Trolley Tour, Beach Time, Rum Distillery, Sunset Cruise
8:30 am – Have breakfast in or near your hotel. Note: If you don’t want to return to the hotel to change clothes after lunch, you may want to put on your bathing suit under your casual clothes if you plan to swim at Simonton Beach at Lagerhead’s Beach Bar after lunch. (See lunch section below for more information.)
Between 9:00-9:45 am and 11:15 am (depending on start time and stops) – Take the 90 minute Key West Trolley Tour from Mallory Square to get an overview of Key West.
Adult ticket prices are $31.45. There are discounts available for military and seniors over age 62 and children under 12. If you wish to add a second consecutive day, your two-day ticket will cost only about $10 more than a one-day ticket. If you buy your tickets online, there is a $3.00 adult ticket discount. Online tickets are good for any day within six months of purchase.
The Conch Tour Train is another option for an overview tour of Key West. This tour has only three stops. You can get off at a stop and get back on at a later time if seats are available. You can only make one loop over the course of your day. The entire loop takes about 90 minutes. The first stop is at the Front Street Depot, and the tour ends right behind it in Mallory Square. Learn more about the Conch Tour Train check out their website below.
Between 10:30 am and 11:15 am – Either stay on the Key West Trolley Tour and repeat Stops 1 – 3 or get off at Stop 1 and walk to Lagerhead’s Beach Bar for lunch and some beach time.
11:15 am – 2:45 pm – Enjoy some beach time and a casual lunch at Lagerhead’s Beach Bar. The burgers and fish tacos are excellent. Quesadillas are great, too! Alcoholic drinks are available. Breakfast is served all day, as well. Lounge chairs are available to rent for $10 a day. Lagerhead’s is open daily from 9 am until after sunset.
Directions from Key West Trolley Tour, Stop 1, 401 Wall Street – near Mallory Square: Walk away from Mallory Square on Tifts Street or Exchange Street to Front Street and turn left. Walk about 0.2 mile to Simonton Street and turn left. Walk about a block to the water. Lagerhead’s Beach Bar will be on your left at the ocean. (This walk is about 0.3 mile from Key West Trolley Stop 1.)
Directions from Key West Trolley Tour, Stop 3, 150 Simonton Street: Walk toward Front Street and toward the water on Simonton Street for about 0.1 mile. Lagerhead’s Beach Bar will be on your left at the ocean. (This walk is about 0.1 mile from Key West Trolley Stop 3.)
2:45 pm – 4:00 pm – Walk about 0.1 mile from Lagerhead’s Beach Bar to take the free 3 pm tour of the Key West First Legal Rum Distillery (except Sunday) at 105 Simonton Street. There is a rum tasting option, too. The cost is $10 for a large souvenir shot glass that you will use to taste eight different types of rum. While you are there, take a look at some of the interesting and historic artifacts. The free distillery tours are offered at 1:00 pm, 3:00 pm and 5:00 pm Monday through Friday and at 1:00 pm and 3:00 pm on Saturday. Self-guided tours are allowed at other times and days, Monday through Sunday 10 am – 8:30 pm.
4:00 pm – Head back to your hotel to change for your Sunset Cruise.
Before 6:00 pm – Walk or take a taxi/Uber to arrive at the check in counter for your 6:30 pm Sunset Cruise.
Check in for your Sunset Cruise at 6:00 pm – Trade in the voucher you purchased online for discounted tickets for your boarding pass. Two options that I recommend are Commotion on the Ocean (about $52) and Danger Charters Wind and Wine Sunset Cruise (about $85).
Commotion on the Ocean sunset cruise leaves from the Key West seaport, located on the corner of Greene St. and Elizabeth St. next to The Conch Republic Seafood Company. Get tickets through Fury Water Adventures.
Danger Charters Wind and Wine Sunset Cruise leaves from the dock at the Margaritaville Key West Resort Marina.
6:30 – 8:30 pm – Sunset cruise
8:30 pm – or after the Sunset Cruise – either make your way back to your hotel, or have dinner or snacks or dessert or drinks at the dock as you exit your cruise. Below are some choices near each of the two cruise recommendations.
(1) If you took the Commotion on the Ocean cruise, you will be at the Key West Historic Seaport. Right in front of you as you exit the catamaran, you will see the Conch Republic Seafood Company. You can enjoy dinner as you listen to live music there or to your left as you exit the cruise at the Schooner Wharf Bar.
The Conch Republic Seafood Company is located at the marina at the Key West Historic Seaport at the entrance to the Commotion on the Ocean sunset cruise at 631 Greene Street. The reasonably priced menu includes fresh seafood brought in daily from the adjacent dock, a raw bar, conch chowder, salads, and chicken fingers. There is a late night snack menu, too. Open daily from 11:30 am until around midnight. There is usually live music from 6 pm to 10 pm daily and from 1 pm to 5 pm on Friday and Saturday. Check the live entertainment calendar on the website for more details.
The Schooner Wharf Bar is located at the marina at the Key West Historic Seaport to the left of the exit from the Commotion on the Ocean sunset cruise at 202 William Street. The legendary establishment is more of a bar than a restaurant, but it does offer a full, reasonably priced menu at breakfast, lunch, and dinner. It is open daily from 8 am to 4 am. Schooner Wharf has been acclaimed in such diverse publications as the New York Times for its unique nautical decor, music and food, and open-air proximity to ocean breezes. The menu includes stone crab claws, peel-and-eat shrimp, fresh-shucked oysters, conch chowder and fritters, as well as chicken wings and burgers. There is live entertainment daily from noon to 5 pm and again from 7 pm until 11 pm or midnight.
The Key West Pub Crawl usually makes a stop here, so you may want to choose another option if you are planning to do the pub crawl. (See Chapter 4 for information about the pub crawl.)
(2) If you took the Wind and Wine cruise, you will be at the Margaritaville Key West Resort Marina when you exit the cruise. If you walk to your left as exit the sailboat, you will see Bistro 245 on the water at the Margaritaville Key West Resort. You can enjoy dinner outdoors or indoors there or for a casual, less expensive dinner walk about a quarter mile to Garbo’s Grill. Following is some information about each of these choices.
Bistro 245 is located in the Margaritaville Key West Resort overlooking the water at 245 Front Street. There are times during the day when there could be a cruise ship docked right in front of you. Menu highlights include shrimp and lobster fettuccini, seafood mixed grill, truffle crusted grouper, and steak dishes. Most entrees are in the $25 to $40 range. The lobster quesadilla and flat bread appetizers make a great meal, too! The restaurant is open for breakfast, lunch, and dinner daily.
Garbo’s Grill is located at 409 Caroline Street between the Margaritaville Key West Resort and Duval Street. This casual eatery is one of the most highly rated dining options in Key West by reviewers. Once featured on Guy Fierri’s “Diners, Drive-Ins and Dives,” it is a former food truck location that now has actual seating! Menu items include fish tacos, burgers, hot dogs, Korean BBQ, and Yum Yum Shrimp. The restaurant is open for lunch and dinner daily, except Sunday.
Key West Day 2 of 3 – Suggested Itinerary
Highlights: Truman Little White House, Latitudes lunch on Sunset Key, Fort Zachary Taylor State Park, Sunset Celebration at Mallory Square, Sloppy Joe’s Bar
9:00 am – Have breakfast in or near your hotel.
10:00 am – 11:00 am – Take the guided tour of the Harry S. Truman Little White House and/or visit the two free exhibit rooms. If you take the guided tour, you will learn about the Little White House and the importance of Key West as a naval base for the United States. The two free exhibit rooms are worth your time even if you do not take the guided tour. Displays in the free exhibit rooms have included Easter eggs from the White House annual egg roll and historical artifacts from Harry S. Truman and other presidents who have visited the Little White House.
In recent times, President Bill Clinton and Hillary Clinton stayed at the Little White House the night before attending Donald Trump’s wedding to Melania. President Jimmy Carter visited with his grandchildren before taking all of them to Margaritaville restaurant for burgers.
Museum hours: 9 am – 4:30 pm daily. To check out current ticket prices and for more information check the official website:
11:15 am – 12:45 pm – Have lunch at Latitudes on Sunset Key. Latitudes is the premier restaurant of the Sunset Key Cottages resort. It was named the number 1 Best Overall Restaurant in Key West by Open Table in 2016 and one of the 100 Most Romantic Restaurants in America for 2017. It is open for breakfast, lunch, and dinner. Lunch prices are reasonable for a restaurant of this caliber and the views are unparalleled. Menu items include salads, including their famous lobster salad (worth the $24!), fish tacos, flatbread, and burgers.(Be sure to book reservations in advance through www.OpenTable.com in order to be able to board the free ferry from the Margaritaville Resort dock to the restaurant.)
1:00 pm – 5:00 pm – Head back to your hotel, perhaps stopping to shop a bit, to change and chill out by the pool. Or, walk, ride a rental bike, or taxi/Uber to the amazing Fort Zachary Taylor State Park.
At Fort Zachary Taylor State Park, you will find the crystal clear waters of Key West’s most untouched beach, located at the southern end of the park. You will find it hard to believe that you are anywhere near the hustle and bustle of restaurants, shopping, and bars. You can rent an umbrella and two lounge chairs. The park provides opportunities for picnicking, swimming, snorkeling (rental equipment available), and fishing, as well. There is a short nature trail and bicycling within the park. The beachfront Cayo Hueso Café offers snacks, cold beverages, beach sundries, and souvenirs.
There is really a fort, too! Designated a National Historic Landmark in 1973, Fort Zachary Taylor was one of a series built in the mid-1800s to defend the nation’s southeastern coastline. Completed in 1866, it played important roles in the Civil War and Spanish-American War. Guided tours of the fort are available daily at 11 am. The park is open from 8:00 a.m. until sundown, 365 days a year. The fort closes at 5:00 p.m. The cost to enter is $2.50 for pedestrians and bicyclists. The entrance fee for visitors arriving in vehicles is $4.50 for one person, $7.00 for two people, and $0.50 for each additional person in the vehicle. Taxis will take you all the way to the beach, about 0.3 mile from the park entrance. Bring water shoes, because Key West beaches are a little rocky due to all the shells and coral.
5:00 pm – Head back to your hotel to change for the nightly Mallory Square sunset celebration and dinner.
6:30 pm (or about an hour before sunset) – Sunset – Walk or take a taxi/Uber to Mallory Square for the nightly sunset celebration, the quintessential Key West experience. About an hour before sunset each night, the crowds start building to enjoy the nightly street performers and local magicians and just to be together with people from all over the world to celebrate the sunset. The exact time of sunset is listed daily on the website. Be sure to see this at least once while you are in Key West!
8:00 pm – or after the Sunset Celebration – Have a casual dinner or appetizers on the pier looking over the water while you listen to live music at the Sunset Pier at Ocean Key Resort just a 5-minute walk of Mallory Square at 0 Duval Street overlooking the water.
At Sunset Pier at Ocean Key Resort and Spa, the live band will most likely still be playing at the entrance to the pier even after the sun sets at this lively outdoor restaurant on the pier at the wonderful Ocean Key Resort and Spa. The small lights above you twinkle on the water below as you enjoy drinks, small plates or a full meal after a fun day in Key West. The burger, lobster grilled cheese sandwich, and the coconut shrimp are especially delicious! The restaurant is open 11 am to 11 pm daily (weather permitting).
After dinner – Walk 2 blocks away from the ocean on Duval Street to Sloppy Joe’s Bar at 201 Duval. Sloppy Joe’s was a favorite of Ernest Hemingway. It was Hemingway who encouraged the original bar run by Joe Russell to change its name to Sloppy Joe’s because the floor of Joe’s bar was always sloppy wet from melted ice. The bar opened the day Prohibition was repealed, and it celebrated 80 years in its current location at the corner of Duval and Green Streets in 2017! There is live music daily from noon until 2:00 a.m.
Key West Day 3 of 3 – Suggested Itinerary
Highlights: Jet Ski Tour, Hemingway House, Blue Heaven Restaurant, Key West Lighthouse, Southernmost Point, Dinner in Old Town, Pub Crawl
8:30 am – Have breakfast in or near your hotel.
9:30 am – 11:00 am – Take the guided jet ski tour of the island. (Or, get up an hour earlier and take the 8:30 am tour for a lower priced tour.) Fury Water Sport’s Jet Ski tour around the island is a Key West is a 90-minute tour around the waters of Key West. Tours run from 8:30 am – 3:30 pm. The first tour at 8:30 am is $109.95 per jet ski, and other tours are $130.95. Two or three people will share one jet ski, not to exceed 460 lbs (208 KG). Note: Depending on how choppy the water is on your day, you may get tossed around a good bit! Tours are available from the following locations: Margaritaville Key West Resort, Hyatt Centric, Marriott Beachside Hotel, Galleon Marina, and 0 Duval Street.
11:00 am – 12:00 pm – Change for lunch and make your way to Blue Heaven restaurant.
12:00 pm – 1:30 pm – Have lunch at Blue Heaven restaurant at 729 Thomas Street in the middle of Old Town Key West, near the Hemingway House and the Key West Lighthouse. Blue Heaven is one of the most well-known restaurants in Key West. The roosters roaming the premises are almost as famous as the food. Breakfast is served until 2 pm daily, so you may want to try the famous blueberry pancakes, even if you come for lunch. Other highlights are shrimp and grits, Jamaican jerk chicken, and pan-sautéed yellowtail with citrus beurre blanc. Blue Heaven features casual indoor & outdoor dining, live music most days 11 am – 1 pm and 7 pm – 9 pm, and a great gift shop to peruse while you wait if there are crowds when you arrive.
1:30 pm – 1:45 pm – Walk about 10 minutes to 907 Whitehead Street to the Ernest Hemingway Home and Museum.
1:45 pm – 2:30 pm – Tour the Ernest Hemingway Home and Museum. Author Ernest Hemingway lived and wrote in this home for about 10 years, beginning in 1931, when he was married to his second wife, Pauline. The home is a National Historical Landmark. One highlight of the tour is the in-ground pool, the first in Key West. The exorbitant cost of the pool prompted Hemingway to take a penny from his pocket, press it into the wet cement of the surrounding patio, and joke, “Here, take the last penny I’ve got!” Look for the penny, embedded between flagstones at the north end of the pool. Also, look for descendants of Hemingway’s famous six-toes cats walking around the property. Thirty-minute guided tours are $14 for adults, $6 for children ages 6-12, cash only, 9 am – 5 pm daily, with no advance booking option.
2:30 pm – 3:15 pm – Walk across Whitehead Street to the Key West Lighthouse. The current lighthouse dates to 1848. At that time, it had a woman as its Keeper; nearly unheard of during the 19th century. In 1969, the U.S. Coast Guard decommissioned the Key West Lighthouse, since there was no longer a need for a full-time Keeper due to technological advancements.
Today, the lighthouse serves as a museum dedicated to Key West’s maritime heritage and to the men and women who were Keepers. Visitors can walk up the 88 steps to the top of the light as well as explore the belongings, photographs, and words of the lighthouse Keepers and their families. Hours: 9:30 am – 4:30 pm daily, except December 25. Admission: adults $10, children ages 6 and up $5.
3:15 pm – 6:00 pm – Either return to your hotel or head to the beach for some relaxation, shop your way down Duval Street, or walk to the Southernmost Point to take some pictures at this icon of Key West.
6:00 pm – 6:15 pm – Make your way to Bagatelle restaurant in the heart of the action at 115 Duval Street.
6:15 pm – 7:45 pm – Bagatelle is set in a large two-story 1884 home with wraparound balconies, this seafood-focused American restaurant was a 2016 Open Table Diner’s Choice Winner. Menu items include swordfish, seafood linguini, lobster tail, and steak offerings. Entrée prices at dinner range from $28 to $55. The restaurant is open for Breakfast and Lunch, as well. It serves brunch daily until 4 pm. Book on OpenTable.com in advance. Ask to sit on an upstairs balcony for a great view of Duval Street below.
7:45 pm – 8:00 pm – Make your way to the starting point of the Key West Pub Crawl at 218 Whitehead Street #2. Following is information about two Pub Crawl options.
Key West Pub Crawl
8:00 pm – 10:30 pm – 2½ hour Pub Crawl on Tuesday, Thursday, and Saturday (Also Thursdays at 1 pm) $34.95 with $5 discount for online booking with code “5OFF” includes five cocktails and a souvenir T-shirt. Must be 21 or over. Must show ID.
8:30 pm – 10:30 pm – Two-hour Haunted Pub Crawl on Monday, Wednesday, and Sunday, $24.95 with $5 discount for online booking with code “5OFF” includes a souvenir T-shirt. The tour stops at three pubs, but drinks must be purchased separately. 21 and over only. Must show ID.
Don’t Forget the Pie! – Just one block off Duval Street on Greene Street, near Sloppy Joe’s bar, be sure to stop by for a piece of pie at the Key Lime Pie Company at 511 Greene Street. Choose from Key Lime pie slices, bars, or a variety of other ways to taste or take home the famous treat from the island.
For the complete itineraries of my Key West vacation recommendations, a special “Key West in a Day” chapter, hotel recommendations, and many more restaurant and attraction recommendations, check out my “Key West 2018” $8.99 USD Amazon paperback book here or my $5.99 Kindle book by the same name here.
You may also be interested in my earlier podcast, “15 Things to Do in Key West,” where I discuss some of the things to see and do in Key West with my millennial age daughter and son-in-law and my husband. The blog and podcast are both available at this link:
Note that in a December 2017 “State of the Florida Keys Tourism Industry” report detailing the ongoing impact of Hurricane Irma, it indicates that the Parrot Key Resort on Key West will open on June 1, 2018, and the Inn at Key West and Key West Bayside Inn & Suites will open in summer of 2018. To access the report and to review the impact of Hurricane Irma on the rest of the Florida keys, check out that report here:
Until next time, I hope all of your travel days are just perfect!