How To Plan A Romantic Key West Vacation

Wondering how to plan a romantic getaway or find some cool experiences to add to your special vacay? In the 305, we celebrate romance 365, and you don’t have to go far to find it. Here are some ideas for you to surprise your loved one during your Key West vacation.

Splurge and get a room with a view!

Surround yourself with beauty when you stay with us!

La Mer & Dewey House is Key West’s best-kept secret. Enjoy Key West charm and luxury decor paired with vintage touches in our adult-only accommodation. This is romance at Southernmost!

How To Plan A Romantic Key West Vacation 1

Guests who stay at La Mer and Dewey begin their day on our oceanfront terrace with a chef-prepared, gourmet continental breakfast. There is also afternoon hors-d’oeuvres on the terrace and an onsite Concierge. Enjoy and explore the surrounding private gardens filled with lush greenery, a courtyard fountain, and stunning views of South Beach. It’s a luxury guest-house experience at Southernmost Beach Resort!

Room suite

Always guaranteed attention to details in your special requests.

Bottle of sparkling with two glasses and card

Photo credit: @brianaleetharp

Learn more about the La Mer and Dewey House Experience.

Cabana for Two, Yes Please!

Pool with cabanas
Get pampered and book a Private Cabana during your stay!  Sit back and relax, rewind, and get in the chill zone with your special someone.  Sip cocktails by the sea and lounge in a poolside cabana or bask in the ocean breeze on our private beach. The choice is yours.

Reserve your private cabana today!

Eat and Drink at the Beach

Key West beach cafe with a view of the ocean
Photo credit: @Zilip

Enjoy breakfast, lunch, and dinner, along with cocktails in between at Southernmost Beach Cafe.  Best view, food, and one of the best beach bars on the island. Even better news is the location is steps from our resort.

Schedule Play Time

A couple in the pool
Photo Credit: @connelltsmith5 at the Shores Bar

Take A Seaplane to the Dry Tortugas

Get ready for an experience of a lifetime and take a seaplane to the Dry Tortugas.

A couple learning against the Key West Seaplane

Photo Credit: @kimberlyyyyy via Key West Seaplane Adventures Facebook Page

Dry Tortugas National Park offers some of the best snorkeling and skin diving in North America, just 70 miles from Key West and the Florida Keys. The shallow waters (5-15 feet) make snorkeling at the Dry Tortugas the best snorkeling and fun for everyone.  This is the trip of a lifetime and the one that you’ll remember forever.  Take time to explore the park’s historic Fort Jefferson; snorkel, dive or swim in the clear waters and enjoy breathtaking birdwatching.

Our experience with Seaplane Adventures was simply a one in a lifetime experience! Kris, our pilot was ahhhmazing! He was so professional, yet super personable.  He was very knowledgeable about the history of Ft. Jefferson and how it came about all. He was also very knowledgeable of the marine life we saw along the ride.  Riding co-pilot is an option and if you can I suggest doing so.  We would def do this again when we return to key west…. every time!
~ Tonya Holland, Key West Seaplane Adventures Facebook Review

Image taken from Key West Seaplane

Photo credit:  Key West Seaplane Adventures

Learn more about Key West Seaplane Adventures.

Visit a Museum

Museum with a furry pet cat

Photo Credit: Rob O’Neal, Florida Keys News Bureau

The Ernest Hemingway Home and Museum

Ernest Hemingway lived and wrote in Key West for ten years. During that time, he wrote seventy percent of his life works. Visit the Hemingway Home and Museum during your visit and take part in one of the guided tours and look out for the world-famous Polydactyl (six-toed cats).  Sometimes we think the cats are just as famous as Papa!

Built-in 1851, home to Ernest Hemingway 1931-1940, Ernest Hemingway Home and Museum is a National Historic Landmark, Literary Landmark, and recognized by Library of Congress for its importance in U.S. History.

I love you for all that you are, all that you have been, all that you’re yet to be.
~ Ernest Hemingway

The Hemingway Home and Museum is also a venue for weddings and special events. When the museum doors close, the property is the backdrop of many celebrations.

The Ernest Hemingway Home and Museum is located at 907 Whitehead Street, Key West.  Open 9 am – 5 pm.

Enjoy the Nightlife and Live Music Scene

Little room jazz club bar shot

You don’t have to go far to hear the sound of music in Key West. It’s everywhere!  You could be walking down the world-famous Duval Street and pass by restaurants, bars, and eclectic cafes with live music.

Little Room Jazz Club

Looking for Jazz, then we recommend the Little Room Jazz Club located at 821 Duval Street.  The music starts at 5:30 and ends at 11 pm.  Monday is a Sing-A-Long Piano Bar Happy Hour from 5:30 – 7:30 – a fun way to start the evening!

Great venue to hear wonderful jazz and blues. Fantastic happy hour, great happy hour food. It is a treat to come hear Larry Smith for happy hour. ~ Rusty Hodgdon recommends Little Room Jazz Club on Facebook.

The best way to enjoy the music scene is just to get lost in paradise.  While taking a nightly stroll, there will be a song, concert, or tune that will grab your attention.  Go with it.

Attend Smokin Tuna Saloon’s Key West Songwriter Sessions!

Smokin Tuna Saloon’s Key West Songwriter Sessions

 “Key West Songwriter Sessions” is yet another creation of Key West’s Charlie Bauer (founder of the world-renowned Key West Songwriters Festival & owner of the Smokin’ Tuna Saloon). Each month, as part of a 6-part series, hit songwriters will entertain attendees in intimate settings built for storytellers! No need to wait for Songwriters Festival to come around in May, get into the show every month.  (Key West Songwriters Festival is May 6 -10, 2020)

Watch the Sunset

Ocean sunset with sailboat

Photo credit: @_whatswrong

Yes, Key West is known for a spectacular Sunset Celebration however today we want to focus on a sunset experience for two.  Skip the crowds and head over to Fort Zachary Taylor Historic State Park.  This is love on the rocks and the only thing missing is you!

Still searching for ideas? Don’t worry, our concierge and our team will be able to give you many more ideas and help you plan something extra special if needed.

We hope you loved today’s blog and encourage you to share your love stories with us!  What places did you love, what were your most memorable moments?  We want to hear all about it!  One last thought, love surrounds the island, and we’re pretty sure you’ve been diagnosed with the island fever and are next in line to say “I love Key West” #somolife