TravelAge West
Intel and Insights for Today's Travel Advisor

Explore TravelAge West

Destinations

Back
  • Africa & Middle East
  • Asia & South Pacific
  • Caribbean
  • Central & South America
  • Europe
  • Hawaii
  • Mexico
  • USA & Canada

Travel Types

Back
  • Family
  • Adventure
  • Cruise
  • River Cruise
  • Tour Operators
  • Luxury
  • Hotels
  • Culinary
  • Romance
  • Wellness
  • Sustainability

Directories

Back
  • Hotels
  • Cruise

Interactive

Back
  • Click & Win
  • Geo Quiz
  • Slideshows & Video
  • Wave Winner Videos

Professional Development

Back

Industry Insight

  • Business Features
  • Interviews
  • Events
  • Opinion
  • Tech
  • Podcasts
  • Coronavirus and Travel
  • Need to Know Research

Education

  • Certifications
  • Digital Guides
  • Fams
  • Thought Leadership
  • Advertiser Spotlight
  • Webinars
  • Quick Q's

Events

  • Global Travel Marketplace
  • GTM West
  • WAVE Awards
  • GTM by Northstar

Sign Up for Our Monthly Family Getaways Newsletter

I accept the T&C and Privacy Policy.

Search TravelAge West

Clear Field
Samantha Davis-Friedman
Samantha Davis-FriedmanEditorial Associate

Share

  1. Home
  2. Travel
  3. Family Travel

Family Travel in Key West

Dec 07, 2014
Key West is the southernmost point in the U.S. // © 2014 Key West BusTour 2
Key West is the southernmost point in the U.S. // © 2014 Key West BusTour 2

There’s something for everyone in the southernmost U.S. city of Key West, Fla. This family-friendly destination offers waterfront activities such as kayaking, stand-up paddleboarding, snorkeling and glass-bottom boat rides; historical sights like Hemingway House and Truman’s Little White House; and vibrant nightlife along Duval Street and in Mallory Square.

A Scenic Drive and Great Stops
Considered to be one of the top scenic drives in the U.S., the Overseas Highway stretches 113 miles from the Florida mainland all the way to Key West. The picturesque roadway is built on what remains of Henry’s Flagler’s Florida East Coast Railway. Dubbed “Flagler’s Folly” by critics at the time, the completed project later became known as “The 8th Wonder of the World.” 

The railway was built from 1905 to 1912, but in 1935, a hurricane destroyed more than 30 miles of track. During the repairs, much of the rails were converted to highways, but ruins of the railroad can still be seen along the drive.

A great midway stop between Miami and Key West is Islamorada. Depending on the time of day, families can check out the “best breakfast in the Keys” at Mangrove Mike’s or enjoy a delicious lunch on the waterside deck of Hungry Tarpon Restaurant. In addition, kids and adults can feed the 100 or more giant tarpons that gather around the dock at Robbie’s Marina. A highly prized Florida Keys game fish, the tarpon dates back to prehistoric times.

Sign Up for Our Monthly Family Getaways Newsletter

I accept the T&C and Privacy Policy.

Another interesting stop on the way to Key West is Pigeon Key. One of the most historically significant islands in the chain, this is where the 400 workers who built the Overseas Railway were housed in the early 1900s. Today, the island boasts a museum that holds artifacts from Flagler’s Railroad and offers daily guided historic tours.

Noteworthy Sights
Key West offers families two ideal photo opportunities: the buoy marking the exact southernmost spot and the mile marker zero sign where U.S. Route 1 both begins and ends, depending on which way one is traveling.

Between these two sights is the Hemingway House and Museum. Visitors can see where iconic American writer Ernest Hemingway lived and worked and spot the famous polydactyl (six-toed) cats that roam the house and gardens; many of the animals are descendants of a six-toed cat given to Hemingway by a ship’s captain.

A few blocks from Hemingway House is Harry S. Truman Little White House. It was originally the naval command headquarters during the Spanish-American War, World War I and World War II, and the building later served as the winter White House of President Harry S. Truman. 

Today, Truman Little White House is a museum as well as a retreat and place of government business for our nation’s leaders. Both the Hemingway home and Little White House are open seven days a week, 365 days a year.

Extraordinary Excursion
For Key West travelers who want a unique experience, the day trip to Dry Tortugas National Park and Fort Jefferson should not be missed. Departing from Key West onboard the high-speed catamaran Yankee Freedom, visitors travel 70 miles across open water to one of the most unique and spectacular national parks in the U.S. 

Once at Dry Tortugas National Park, tourists can explore historic Fort Jefferson, a 19th century fort, and enjoy swimming and snorkeling in the crystal blue water surrounding the island. Agents should note that this is a full-day excursion that departs at 7:30 a.m. and returns at 5:30 p.m.

When the Sun Goes Down
At the end of each day, Key West hosts a lively Sunset Celebration at Mallory Square Dock. Here, local artists and street performers gather with tourists to watch the sun sink into the Gulf of Mexico. After dark, families can walk to Key West’s “main drag,” Duval Street. Running shore to shore from the Gulf of Mexico to the Atlantic Ocean, the street is just over a mile in length and is lined with shops, bars and restaurants.

The saying goes that good things come in small packages. With a laid-back attitude and a place in American history, Key West offers sun, fun, the beauty of the Caribbean and even a little bit of education. For such a small package, this family vacation is hard to beat.


DESTINATION RESOURCES

Getting There: The trip to Key West along the 120-mile long Florida Keys by car takes about four hours from Miami along the scenic Overseas Highway. In addition, direct flights or connections to Key West International Airport are available from many Florida cities, or visitors can take the Key West Express, which offers high-speed passenger ferries from Fort Myers Beach and Marco Island.

When to Go: The weather in Key West is beautiful all year. In the summer, the average high is 89 degrees. During winter months, it rarely rains, but thundershowers can occur beginning in late May. The official hurricane season begins June 1 and ends Nov. 30, with the highest chance for storms between Aug. 15 and Oct. 15.

The Details

Casa Marina Resort
www.casamarinaresort.com

Dry Tortugas National Park
www.drytortugas.com

Fogarty’s
www.fogartysofkeywest.com

Harry S. Truman Little White House
www.trumanlittlewhitehouse.com

Hungry Tarpon Restaurant
www.hungrytarpon.com

Mangrove Mike’s
www.mangrovemikes.com

Pigeon Key Foundation
www.pigeonkey.net

Robbie’s of Islamorada
www.robbies.com/tarpon

Sunset Celebration
www.sunsetcelebration.org

The Ernest Hemingway Home and Museum
www.hemingwayhome.com

The Southernmost Point
www.southernmostpointusa.com

Tell Us What You Think! forum

Related Content

Read about three great stops for boys in Miami.
  • Most Read
  • Most Shared
  1. The U.S. Passport Is Continuing to Fall in Global Rankings
  2. Top Summer Travel Trends for 2026
  3. Carnival Glory and Carnival Magic Return to Service After Upgrades
  4. The 10 Best Luxury Golf Resorts in California
  5. These 12 Cruise Lines Are Offering Epic World Cruises

From Our Partners

More From TravelAge West

Hotel Solea is the result of a multimillion-dollar makeover.

Carlsbad for Families: Where to Eat, Sleep and Play

The USS Arizona Memorial continues be one of Hawaii’s most sought-after visitor experiences.

A Travel Advisor's Guide to Pearl Harbor

Resting inside the catacombs at the Basilica of St. Patrick’s is a who’s who of prominent New Yorkers.

Review: Catacombs by Candlelight, a Unique New York City Tour

Sponsored Video: New Orleans on Cruises and Advisor Perks

Sponsored Video: New Orleans on Cruises and Advisor Perks

It’s no surprise that Bleecker Street Pizza was named best pizza in New York City three years in a row.

Review: Greenwich Village Walking and Food Tasting Tour

The event featured 14-minute meetings between suppliers and advisors.

VisitBritain Connects Advisors and Suppliers in Los Angeles

Park Hyatt Aviara’s stunning 18th hole

The 10 Best Luxury Golf Resorts in California

The iconic W New York – Union Square building is a New York City landmark.

Review: W New York – Union Square

Tourism stakeholders say the Islands of Hawaii are ready to welcome visitors.

Here's What Hawaii Bookings Look Like Right Now, According to Tourism Stakeholders

More Stories Like This

Halloween festivities at many U.S. theme parks now start months ahead of the holiday.

Here’s How Theme Parks Will Celebrate Halloween in 2026

Read The Story
Snow Canyon State Park near St. George, Utah, offers hiking, biking, sand dunes to play in and even an easy-to-access slot canyon kids will love.

Adventures in Greater Zion With Kids

Read The Story
Hotel Solea is the result of a multimillion-dollar makeover.

Carlsbad for Families: Where to Eat, Sleep and Play

Read The Story
Port Orleans Resort – Riverside and Port Orleans Resort – French Quarter capture the charm of New Orleans.

First Look: Renovations at Disney’s Port Orleans Resorts

Read The Story
Universal Kids Resort will offer kid-friendly rides, interactive play areas, live shows and character meet-and-greets.

Here’s What We Know About Universal Kids Resort

Read The Story
Clients can look forward to new and reimagined attractions and experiences at Walt Disney World Resort.

What’s Happening at Walt Disney World in 2026

Read The Story
Disney and Universal theme parks offer attractions that hit the sweet spot for teens and tweens.

Best Theme Park Attractions for Teens and Tweens

Read The Story
Disneyland Resort's $50 park-hopper deal for kids, ages 3-9, is now live for families who reserve their tickets in advance.

Disneyland Is Prioritizing Families This Summer — And There’s Still Time to Book at a Great Value

Read The Story
Clients could help the gang from the Scooby Doo cartoons solve a mystery during Universal Fan Fest Nights.

How Clients Can Visit Theme Parks After Hours

Read The Story
At The Ranch at Rock Creek, teens can enjoy bowling, shuffle boarding, a private movie theater and more.

Beyond Kids' Clubs: 7 All-Inclusives Tailor-Made for Teens

Read The Story
TravelAge West

About TravelAge West

  • About Us
  • Contributors
  • Sales Team
  • Contact Us
  • My Profile
  • Terms of Use
  • Privacy Policy
  • Do Not Sell or Share My Data

Advertise

  • Advertise With Us
  • Write For US
  • Media Kit
  • Upload Ad Material
  • Digital Ad Specifications
  • Reprints
  • Subscribe to Print

Stay Connected to TravelAge West

Get Us in Your Inbox

I accept the T&C and Privacy Policy.


Northstar Travel Group

Northstar Travel Group

  • Travel Weekly
  • Travel Weekly Asia
  • TravelPulse
  • TravelPulse Canada
  • TravelPulse Quebec
  • Meetings & Incentives
  • Travel Technology
  • Corporate Travel
  • Hotel Investment
  • Data Products
  • AGENTatHOME

Copyright © 2026 Northstar Travel Media, LLC. All Rights Reserved. 301 Route 17 N, Suite 1150, Rutherford, NJ 07070 USA | Telephone: (201) 902-2000

Load Carousel Here
Load Video Here