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How to Spend 2 Days in Key West

How to Spend 2 Days in Key West

With two days in Key West, you can relax into the pace of life in the Conch Republic. Whether you’re a lifelong sailor or a devoted landlubber, come to explore mangroves, spot native dolphins, and check out local landmarks, with time left over for island sunsets and umbrella drinks. Here’s what you need to know when planning your escape.

 

Day 1: Conch Republic Essentials

**Morning:**Snag tickets for the hop-on, hop-off bus or open-sided trolley that make the rounds of Key West to get your bearings. If you’re going to continue sightseeing in the afternoon, consider an option with all-day access, which is a convenient way to avoid driving and parking.

 

**Afternoon:**Tune into the parts of Key West that interest you most by choosing a guided walking tour focused on food, drinks, or history. Key West has plenty of hidden foodie hot spots, and the tree-lined streets are packed with ghost stories and colorful characters that you’ll encounter along the way.

 

**Night:**Kick off the night with a Key West sunset; there’s always a crowd at Mallory Square, or you can board a sunset cruise to catch last light on the water. Sunset cruises in Key West range from laid-back sailing trips to parties with free-flowing drinks, so choose your boat accordingly.

 

Day 2: Natural Wonders

**Morning:**Get a salt-water start with an active morning of fishing, paddling among the mangroves, or parasailing. Back on land, fuel up for an afternoon of exploring with a Key West seafood lunch followed by chilled Key lime pie.

 

**Afternoon:**Now that you’ve seen Key West from above water, it’s time to peek beneath the waves. Snorkeling and scuba trips feature coral reefs just off the coast—there are even scuba options for noncertified divers—or you can skip the wet hair altogether by hopping a glass-bottom boat.  

**Night:**Finish your Key West adventure with a taste of the local bar scene, which goes from rustic Hemingway haunts to theme bars with a rainbow of tropical drinks. Pub crawls and bar tours are a fun way to meet fellow travelers while getting a feel for the town’s colorful nightlife.

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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
$58.72
From
$58.72
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

Adults only Champagne Celebration Sunset Cruise from Key West

Adults only Champagne Celebration Sunset Cruise from Key West

star-5
Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
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  • 2 hours
  • Taking safety measures
From
$79.49
From
$79.49
Taking safety measures

Key West Mangrove Kayak Eco Tour in Small-Group

Key West Mangrove Kayak Eco Tour in Small-Group

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 Fishing Day Trip

Key West Fishing Day Trip

star-4.5
Going fishing while in Key West is a must, and this deep-sea fishing tour takes you on a comfortable boat that can fit up to 60 passengers. Whether you’re a beginner or an experienced fisherman, your captain and crew helps you with your skills. Try to catch snapper, grouper, mackerel, or shark. A license and all bait are included, and restrooms are on board for convenience.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$71.42
From
$71.42
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 Historical Seaport Food Tasting and Cultural Walking Tour

Key West Historical Seaport Food Tasting and Cultural Walking Tour

star-5
Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the beach and docks into some of the most colorful neighborhoods in Key West, pausing to sample locally-caught fish tacos, Key West pink shrimp, conch ceviche, spiny lobster, or other just-as-delicious non-seafood options, learning about Key West history along the way. Don't forget to save room for homemade sangria and our famous key lime pie! Exploring Key West on foot is an ideal way to soak up the vibrant atmosphere, and group size is limited to 10 people to ensure personal service from your guide.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
Taking safety measures

Parasailing in Key West with Professional Guide

Parasailing in Key West with Professional Guide

star-5
Get a bird’s-eye view of Key West from high above the crystal blue waters of the Atlantic Ocean on this parasailing tour. Experience the thrill of flying while watching the bustling activity along the coastline and the abundance of marine life below. See dolphins, turtles, fish, and more from 300 feet in the air. Enjoy gentle, dry takeoffs and landings.
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$79.95
From
$79.95
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

Scuba Diving Guided Tour

Scuba Diving Guided Tour

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