Key West Girls Trip: Plan Your Perfect Girls Weekend In Paradise

Key West Girls Trip

Gather the sisterhood to begin planning the ultimate Key West girl’s trip! Key West’s beauty, history, and reputation for adventure make it the perfect place for a girlfriend getaway. It doesn’t hurt that “golden hour” here makes for some envy-inducing photos!

The best part about this tropical paradise is that it’s year-round sunshine and warm temperatures allow you to plan your Key West girl’s weekend or week-long getaway around your schedule instead of getting boxed in by the weather.

As the southernmost point in the United States, Key West offers Caribbean-like beauty without the need to dust off your passport. In fact, one fun piece of trivia is that Key West is actually closer to Cuba than it is to Miami!

The fun will be had, secrets will be kept, and girlfriend bonds will grow as strong as the midday sun in the Florida Keys! Get the ball rolling by forwarding these seven things to include in a girl’s trip to Key West to your travel crew!


1) Book A Daytime Or Sunset Cruise On A Private Boat In Key West, Florida

You simply have to get out on the water during a Key West girl’s trip! The best way to feel like a VIP while touring the Florida Keys is to book a spot with a company that sails a small-group boat fleet. This gives you the privacy and prestige of a “private boat” even if you’re not quite in the yacht class! You’ll feel like a celebrity as you wave to passengers on larger ferries or tourist boats.

Key West Boat Trips operates a world-class fleet that’s perfect for groups of friends looking for unforgettable experiences on the water. While under the care of an experienced captain, guests enjoy relaxing tours and Key West sunset cruises that include lobster dinners.

After winding through mangroves to dock, passengers can get out to explore breathtaking sandbars in privacy and seclusion away from the tourist crowds. While Key West Boat Trips offers several packages to choose from, common destinations include:

  • Mud Keys

  • Boca Grande

  • Snipe Point

The experience of splashing in shallow turquoise water with your friends is something you’ll never forget! You also never know when you’ll have the opportunity to snap a quick photo of the bottlenose dolphins that frequent the waters around Key West during your voyage. The lively reef environment here is also home to manatees, sea turtles, sea sponges, and tropical fish.

It’s time to make some amazing memories on the water! Grab your girlfriends and book an unforgettable private bout tour with us!

Girls Trip In Key West - Sunset Cruise


2) Plan An Extravagant Pink Shrimp Dinner

The coral sand off of Key West is home to tender sweet pink shrimp that are part of the island’s culinary tradition. The best place to experience fresher-than-fresh Key West pink shrimp for the first time is at a local restaurant right on the island. Here’s a list of top places to get real Key West pink shrimp:

  • Half Shell Raw Bar

  • The Stoned Crab

  • Thirsty Mermaid

  • Alonzo’s Oyster Bar

  • Blue Heaven

  • B.O’s Fish Wagon

While pink shrimp is wonderful as a peel-and-eat appetizer, Key West restaurants offer blackened pink shrimp, pink shrimp skewers, pink shrimp Benedict, coconut pink shrimp, pink shrimp tacos, pink shrimp ceviche, and so much more!

It should be noted that Blue Heaven has exceptional Key Lime pie. You could also head out for dessert at Key Lime Pie Bakery or Kermit’s Key Lime Shoppe.

Sample the most delicious southern delights on this epic Key West girl’s trip. Get ready to indulge in a culinary journey that will leave you craving for more.

Key West Girls Trip - Culinary Journey, Food Tour


3) Book A Key West Girls Weekend At The Southernmost Beach Resort

Located in Historic Old Town Key West on the island’s Atlantic Coast, Southernmost Beach Resort pampers guests with unparalleled luxury on the southernmost point of the United States!

This iconic hotel and resort is located just a short sprint away from the shops, restaurants, and hot nightlife spots of Duval Street. Guests are treated to world-class amenities nestled within a campus peppered with lush garden walkways, beaches, and unending views of the sea.

There are other luxurious resorts and hotels in Key West worth considering:

  • Opal Key Resort & Marina

  • Havana Cabana

  • Pier House Resort & Spa

Opal Key Resort & Marina, Key West, Florida Keys


4) Trace The Steps Of History At The Key West Lighthouse

Offering a great way to get some steps in during a Key West girl’s trip, the Key West Lighthouse invites visitors to climb 88 steps to enjoy views from the top. Along the way, lighthouse visitors can explore photographs, writings, and keepsakes belonging to former keepers and their families.

First lit in 1849, this historic lighthouse that stayed operational through wars, storms, and changing tides in technology now stands as a seaside monument to a way of life that no longer exists.

If you and your girlfriends have a passion for the past, then the Key West Lighthouse is an absolute must-visit. Step back in time and immerse yourselves in the rich history of this iconic landmark.

Visit Key West Lighthouse On Your Girlfriend Road Trip


5) See The Street Performers At Mallory Square During A Girl’s Trip To Key West

A Key West sunset at Mallory Square is magical! While the roster changes slightly from week to week, the famous Mallory Square Sunset Celebration takes place 365 days a year. Fire eaters, jugglers, escape artists, acrobats, preachers, magicians, animal tamers, and live music performers begin showing up a few hours before the sky turns a milky orange.

Key West’s beloved buskers arrive at around the same time that popular food trucks serving conch fritters, chimney cakes, popcorn, smoothies, and pineapple drinks show up!

Get ready to witness the sky transform into a breathtaking masterpiece, surrounded by a vibrant atmosphere. It’s time to soak up the magic and create memories that will last a lifetime.

Street Performers At Mallory Square During A Girl's Trip


6) Experience Live Music, Drag Shows, And More On Duval Street After Dark

Once you’ve soaked in the breathtaking sunset at Mallory Square, it’s time to hit Duval Street with your crew. With nearly 45 bars and clubs to choose from, the Duval Street area is the default “going out” spot on any Key West girl’s trip. The best establishments for getting a little wild during a “Duval crawl” include:

  • Aqua Bar and Nightclub (Aqualex Key West)

  • 801 Bourbon Bar

  • Tiki House

  • The Rum Bar

While mojitos, piña coladas, and daiquiris are all popular, it’s the Rum Runner that serves as the island’s unofficial libation of choice. While you’ll find the Rum Runner at any Key West bar worth its salt, legend says that it was invented by a bartender at Tiki Bar nearly 50 years ago. A proper Rum Runner features rum, fruit juice, banana liqueur, blackberry liqueur, and grenadine.

Your awesome girlfriend crew is about to experience a night filled with laughter, dancing, and unforgettable moments. Conquer Duval Street after the sun goes down! Get ready to paint the town red with your crew!

Key West Live Music, Drag Show, And More On Duval Street After Dark


7) Go Island Hopping

The best way to fit a fun day trip inside your girl’s trip to Key West is to hop to a nearby island for a few magical hours! Depending on how far you want to voyage with your crew, the best picks are Sunset Key (500 yards), Stock Island (3 miles), Big Pine Key (30 miles), and Key Largo (98 miles).

If you’re planning a Key West girl’s trip without a car, you can use a ferry or bus to reach these destinations. Here’s what each one offers:

  • Sunset Key: Million-dollar private homes and luxury resorts

  • Stock Island: Fishing charters and snorkeling excursions

  • Big Pine Key: Theater of the Sea, the National Key Deer Refuge, and one of the clearest reefs on the planet for diving

  • Key Largo: The Dive Capital of the World is home to John Pennekamp Coral Reef State Park, the Florida Keys Wild Bird Rehabilitation Center, the Grecian Rocks, and Island Dolphin Care

Get ready for an epic island-hopping adventure and explore these breathtaking spots surrounding Key West. It’s time to embark on a journey filled with excitement and adventures.

Island Hopping, Florida Keys, South Florida


Start Charting A Course For Your Key West Girls Trip

Key West and the Florida Keys tourism spots unlock paradise during a girl’s trip! You’re going to have so much fun sunbathing by palm trees, jamming out to live music, and snapping photos of restaurant tables covered in slices of Key Lime pie and cocktails.

Of course, no Key West girls’ weekend can be considered official unless you’re setting sail on a daytime or sunset cruise around the Florida Keys. Key West Boat Trips is going to take care of you by offering an elegant experience on the water that you just can’t get with a ferry or public tour boat.

Before you say goodbye to Key West it’s time to head out for some water-filled fun with your girlfriends. Let the good times roll, ladies! Gather your gang and book your group’s voyage in Key West today!

Water Activities On A Girlfriend Getaway With Key West Boat Trips

3 to 4 hours
Group Size
Up to 12

Sandbar Tour For Large Groups

If your group is larger than 6 and you have a hard time finding a boat ride to the sandbars because of the 6 passengers limit, we are here to help. You can book our 2 identical Hurricane 27 foot deck boats and our captains will drive them side by side so you can take cool photos and they will raft up the boats on the sandbars so you can enjoy and share this amazing time together.

3 to 4 hours
Group Size
Up to 6

Hopping Sandbars In Key West

What a perfect day to take a boat ride! You will see not one but several different sandbars on this tour! It will only take 25 minutes to get there on our epic adventure, and we can stop as long as you want at those sandbars that interest you the most. This is something you cannot miss!

Experience the mangrove trails of Mud Keys and hang out with locals at Snipe Point after. You won't want the day to end.

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2 hours
Group Size
Up to 6

Key West Sunset Cruise

Ocean, meet our captain! One of the best things about the backcountry waters is how it’s never too crowded. So jump in and enjoy the peacefulness and remoteness as you stand in the "middle of the ocean" with nothing but water around you. Optionally, bring some champagne to enjoy with the sunset as a backdrop. Then, just sit back and relax as you cruise on out into the middle of nowhere, leaving behind any stress or worries.

2 hours
Group Size
Up to 6

Mud Key Mangrove Safari

It's time for some adventure and excitement with a boat trip through the backcountry. After only a short ride, we'll take you on a leisurely cruise down to Mud Key Sanctuary, where you can enjoy the countryside and take in all the wonders of nature that surround you. Stop by the sandbar for a refreshing dip or just stroll around and soak up the sun. Capture your memories and cherish them forever.