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How to Spend 3 Days in Key West

How to Spend 3 Days in Key West

From juicy sunsets to coral reefs, three days in Key West mean time to soak up the quirky charm of the island escape. Come to join the party crowd, watch ocean sunsets, and take in historical sites, then head offshore to see the Gulf of Mexico’s castaway islands and mangroves. Here’s how to make the most of your time in the Conch Republic.

 

Day 1: Island Orientation

Find the high points of Key West’s tree-shaded streets and waterfront on a tour through the heart of town by trolley or train. In the afternoon, visit some of the stops in-depth, whether you’re following in Hemingway’s footsteps, browsing the shops at Mallory Square, or gazing out from the southernmost point in the United States. In the evening, snag a coveted spot on a sunset cruise from the waterfront; it’s worth booking in advance to ensure your spot. Since the trips range from sails aboard historical vessels to party boats with free-flowing drinks, you can make the night as relaxing or wild as you want.

 

Day 2: Offshore Explorer

With a full day to explore you can head as far as Dry Tortugas National Park, a cluster of islands with powdery beaches, coral reefs, and a historical military fort. Alternatively, simply snag a kayak, paddleboard, Jet Ski, or cruise boat to see everything from mangrove forests to the surrounding reefs. For an up-close look at the bright corals of the Florida Reef, choose a tour that goes beneath the waves: glass-bottom boat cruises and snorkeling trips give you perfect views, and beginner-friendly dive trips mean you don’t need certification to try scuba diving in Key West.

 

Day 3: Conch Republic Relaxation

Start your last day with a slow walk on the sand of Higgs Beach, known for catching the best morning light on the island. Instead of committing to lunch in a single restaurant, explore the best of Key West food, from fresh-caught seafood to Key Lime pie, on a food tour of downtown. It’s a shortcut to finding the best bites on the island, with plenty of themed options that offer a delicious take on the history and culture of the Florida Keys. As daylight fades, head to Mallory Square to catch one final Key West sunset alongside celebrating crowds and oddball buskers. Toast your final night with a drink in one of Key West’s many bars—they range from wild daiquiri joints to historic Hemingway hangouts perfect for a leisurely cocktail.

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14 Tours and Activities | All Key West Tours

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Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

star-5
Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$63.00
From
$63.00
Taking safety measures

Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

star-4.5
Jam to island beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Unlimited drinks and appetizers included; multiple departure times available to suit your schedule.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$63.00
From
$63.00
Taking safety measures

Key West Hop-On Hop-Off Trolley Tour

Key West Hop-On Hop-Off Trolley Tour

star-4.5
Explore the best that Key West has to offer on this narrated, hop-on hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Select from an unlimited 1- or 2-day pass to suit your schedule.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$47.20
From
$47.20
Taking safety measures

Small-Group Key West Food Tasting and Cultural Walking Tour

Small-Group Key West Food Tasting and Cultural Walking Tour

star-5
Eat your way around Key West on this food tour with a guide who introduces you to 'mom and pop' eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and, of course, key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
Taking safety measures

Key West Full-Day Island T'ing Eco-Tour: Sail, Snorkel and Kayak

Key West Full-Day Island T'ing Eco-Tour: Sail, Snorkel and Kayak

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Enjoy a day of fun in the sun on the Island T’ing adventure off the coast of Key West. Sail away from the island city of Key West to the beautiful blue waters of the Gulf of Mexico on a large catamaran. Hop in a kayak and enjoy a paddle around a natural stand of mangrove. Snorkel above a coral reef. Look for dolphins, stingrays, sea turtles, manatees and more on this full-day adventure. A full breakfast and buffet lunch, plus beer, wine, soft drinks and homemade sangria are included.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$119.95
From
$119.95
Taking safety measures

Key West Mangrove Kayak Eco Tour

Key West Mangrove Kayak Eco Tour

star-5
Paddle a kayak through mangrove creeks and shallow water on a Key West kayaking tour that offers an up-close look that this unique coastal environment. This guided tour is the perfect way to spot Florida wildlife in a natural habitat.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$50.00
From
$50.00
Taking safety measures

Key West Glass-Bottom Boat Tour with Sunset Option

Key West Glass-Bottom Boat Tour with Sunset Option

star-4
For the aquatic adventure of a lifetime, take this cruise to North America's only living coral barrier reef. No need to go scuba diving or snorkeling for this great view — from the deck of a glass-bottom catamaran boat, see more than 600 species of tropical fish, sharks, turtles, lobsters and crabs, plus colorful coral and a vast collection of other sea life. Upgrade to a sunset cruise to enjoy Champagne and soft drinks as the sun settles into the Gulf of Mexico.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$49.77
From
$49.77
Taking safety measures

Key West Pub Crawl

Key West Pub Crawl

star-4.5
Get ready to party in paradise on this guided, 2.5-hour Key West pub crawl. The beautiful island city of Key West is famous for its raucous bar scene. Visit some of its most popular and entertaining establishments, beginning downtown and then traveling to the historic seaport and back to busy Duval Street. Enjoy a domestic beer or mixed drink at each of the five locations and receive a free souvenir t-shirt to commemorate the event. Guests must be at least 21 years old to participate.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$34.99
From
$34.99
Taking safety measures

Key West Wild Dolphin Sail and Shallow-Water Snorkel

Key West Wild Dolphin Sail and Shallow-Water Snorkel

star-4.5
Take a half-day sailing adventure off the coast of Key West, Florida and observe wildlife. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.
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  • 4 hours
  • Taking safety measures
From
$95.59
From
$95.59
Taking safety measures

Key West Living Coral Reef Snorkel Adventure

Key West Living Coral Reef Snorkel Adventure

star-4
Explore the only living coral reef in North America during this snorkeling adventure from Key West. Sail aboard a state-of-the-art catamaran as you voyage toward the reef. Receive snorkeling guidance from your knowledgable crew, making this experience perfect for first-time snorkelers. Use of sanitized snorkel gear and beer, water, and margaritas (afternoon trip only) provided.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$45.49
From
$45.49
Taking safety measures

Ultimate Jet Ski Tour of Key West

Ultimate Jet Ski Tour of Key West

star-4.5
Experience Key West’s tropical blue waterways on this Jet Ski tour along the Atlantic Ocean and/or the Gulf of Mexico. Enjoy panoramic island views and watch for dolphins, stingrays, sea turtles, manatees and more while gliding over warm ocean water. Bring a waterproof camera to capture this southernmost point in the continental United States.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$149.00
per group
From
$149.00
per group
Taking safety measures

Key West Conch Tour Train

Key West Conch Tour Train

star-4
Explore the best that Key West has to offer on this narrated, Conch Tour Train excursion. Visit Key West’s top attractions and learn about the Conch Republic’s history and residents, past and present. See where Ernest Hemingway used to hang out and find out why Harry Truman used to spend so much time here. Get to know Old Town Key West, from the Front Street Depot to Mallory Square and everything in between, including live onboard commentary from a professional tour conductor. It’s Key West’s original sightseeing tour.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$36.70
From
$36.70
Taking safety measures

All-Inclusive Water Adventure Excursion in Key West

All-Inclusive Water Adventure Excursion in Key West

star-5
Save time and money in Key West on this all-inclusive, full-day excursion. Enjoy a day of sailing, snorkeling, and kayaking off the coast. Visit the Key West National Wildlife Refuge and explore an underwater world full of colorful fish and coral. Includes a buffet lunch with unlimited beer, wine, and soft drinks.
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  • 6 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$129.00
From
$129.00
Taking safety measures

Scuba Diving Guided Tour from Big Pine Key

Scuba Diving Guided Tour from Big Pine Key

star-4.5
Go scuba diving at a Key West reef without any required certification. Under the supervision of a certified dive instructor, spend your vacation time exploring the underwater world of one of the earth's largest reefs. This is a perfect opportunity to learn the basics of scuba; all instruction and equipment included means even beginners can give it a try.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
  • Taking safety measures
From
$115.00
From
$115.00
Taking safety measures