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Key West

As the southernmost point in the continental United States, Key West offers guests an eclectic mix of options for all couples. You can enjoy thrilling days and nights filled with bustling wild adventures or a quiet and relaxing time of warm sand, lush garden strolls, and island history.

Nicholas Fabbri
Scenset travel curator
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Trip Overview

May 18 - May 25

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Weather

In May, Key West, Florida, experiences warm and pleasant weather, making it an ideal time to visit. Temperatures typically range from the mid-70s to the mid-80s Fahrenheit (around 24-29Β°C), providing a comfortable environment for outdoor activities. Rainfall is light, with occasional showers or thunderstorms, mostly in the afternoons or evenings. The warm sea breezes and clear skies make May a great time for enjoying the beaches and exploring the island's natural beauty.

Sunday, 18 May, 2025
Day 1: Arrival in Key West

Key West, steeped in history and famed for its picturesque sunsets and laid-back charm, is an idyllic destination for celebrating a honeymoon. With romantic walks through the Old Town and serene beach outings, it combines cultural richness with tropical bliss. This enchanting island promises a memorable getaway with its vibrant nightlife and diverse dining options.

Once you land, collect your luggage and pick up your rental car from the airport.

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The drive time from the airport to Casa Marina is approximately 10 minutes.

Your Stay: Casa Marina

Why we love it for you? Enjoy luxury resort recreation and relaxation at the legendary Casa Marina Key West. Nestled along the southern edge of the island – overlooking more than 1,100 feet of beach reserved exclusively for hotel guests – their Key West accommodations provide an elegant yet refreshingly simple hideaway for travelers.

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Casa Marina

  • Ocean View - King
  • Adults
  • This room features ocean and pool views
  • Breakfast included
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Casa Marina

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Settle into your hotel and pamper yourself poolside by getting a cocktail or take a stroll on the largest private beach in Key West.

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Dining Options

Louie's Backyard: A waterfront restaurant with a beautiful oceanfront deck, serving contemporary American cuisine with Caribbean influences.

The Flaming Buoy Filet Co.: A cozy and intimate restaurant offering an eclectic menu with creative twists on classic dishes, such as lobster mac and cheese and filet mignon.

Blue Heaven: Known for its relaxed atmosphere and delicious Caribbean-inspired cuisine, Blue Heaven is a great spot for a casual yet flavorful dinner. Try their famous lobster and shrimp dishes, or enjoy a hearty breakfast-for-dinner option.

The rest of the afternoon/evening has been left for you to explore at your own pace.

Monday, 19 May, 2025
Day 2: Food and Walking Tour

Head into town today for a wonderful food tour followed by a relaxing afternoon and evening on the beach.

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Key West Food Tour

Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the docks into some of the most colorful neighborhoods in Key West, pausing to sample locally-caught fish tacos, Key West pink shrimp, 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 a refreshing glass of white wine and their famous key lime pie!

  • Small Group Tour


Booked by someone

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Please wear comfortable shoes. Moderate amount of walking is involved.

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Scenset is happy to book dinner reservations for you at any of the amazing local restaurants after booking.

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Casa Marina

  • Ocean View - King
  • Adults
  • This room features ocean and pool views
  • Breakfast included
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Casa Marina

Tuesday, 20 May, 2025
Day 3: Dolphin Watch and Snorkel Tour

Enjoy the morning at your own pace (perhaps with invigorating sunrise yoga) before setting out for an exciting afternoon of dolphin watching and snorkeling.

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Sandbar Private Charter

A 4-hour private charter in Key West offers an unforgettable day on the water, perfect for exploring the island's stunning marine environment at your own pace.

You can book a sandbar charter in Key West for mornings or afternoons. It’s a half-day private charter, so times are somewhat flexible to meet the needs of your group.

Generally, we leave the dock in the morning or afternoon. The entire trip lasts about four hours.

  • Sand bar tours start and end at The Perry Hotel and Marina.
  • Load up and leave the marina (morning, midday, or afternoon)
  • Head out into the backcountry (around 45 min)
  • Sand bar time! We usually visit a few different sand bars each trip (around 2.5 hours)
  • Head back in (around 45 min)

Once you've made it back to the resort, take the rest of the evening to freshen up before going to dinner.

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Scenset is happy to book dinner reservations for you at any of the amazing local restaurants after booking.

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Casa Marina

  • Ocean View - King
  • Adults
  • This room features ocean and pool views
  • Breakfast included
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Casa Marina

Wednesday, 21 May, 2025
Day 4: Relax and Sailboat Sunset Cruise

Enjoy a morning and afternoon at your own tempo, strolling through Old Town or indulging in the luxury offerings at Spa Al MarΓ©, before embarking on a spectacular sunset sailing experience.

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Find everything you need for a relaxing day in the sun. Whether you’re lounging by one of the two tropical pools or on the resort’s private beach, the pool and beach concierge has you covered with chaises, umbrellas and towels.

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Spa al MarΓ© offers indoor and outdoor treatments that will leave you feeling rejuvenated and refreshed. Relax and unwind with a therapeutic massage by experienced therapists, recharge and balance with an extensive collection of aromatherapy treatments.

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Sunset Sail

Sunset Sail Key West boasts a fleet of unique classic sailboats that strive to wow you without the crowds. Sit back while the captain and mate raise the sails, shut off the engine and sail you and your family off into sunset.

Take the wheel or take in the sights as we sail you through a tour of Key West harbor, sail past the crowds at Mallory square and cross the line of the Gulf of Mexico into the Atlantic Ocean.

Beverage is included, food is not

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Casa Marina

  • Ocean View - King
  • Adults
  • This room features ocean and pool views
  • Breakfast included
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Casa Marina

Thursday, 22 May, 2025
Day 5: Half-day Fishing Adventure

Enjoy some time relaxing on the beach or by the pool in the morning, and then hit the water for a private fishing charter.

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Private Fishing Charter

As you spend the day out on the water, you'll take in the stunning natural beauty of the Keys, with its crystal clear waters and picturesque islands. Trolling the open waters can produce hard-fighting species like Amberjacks, Sailfish, and Mahi. Trolling trips are great because the boat and the knowledge of your captain take care of half the work for you. You get to sit back, relax, enjoy the sweet sea breeze, and rest your arms while you wait for the reel to start screaming and your work to begin.

Bottom fishing changes the target species to an entirely different set of fish. You can expect delicious and hard-fighting reef species like Snapper, Grouper, Cobia, Kingfish, and even Sharks!

Included by Scenset

After the tour, head back to your hotel and spend the rest of the afternoon relaxing poolside with a tropical drink in hand or however you see fit. Whenever you are ready, make your way to the beach to enjoy an oceanside fire.

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Scenset is happy to book dinner reservations for you at any of the amazing local restaurants after booking.

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Casa Marina

  • Ocean View - King
  • Adults
  • This room features ocean and pool views
  • Breakfast included
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Casa Marina

Friday, 23 May, 2025
Day 6: Kayak Through the Keys

Start your morning off at your own pace. Get breakfast, lay by the pool, take a swim in the ocean. Then, get ready for an afternoon gliding through the Keys!

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Kayak Tour

A Key West kayaking tour offers a tranquil and immersive experience in the island's unique natural environment. Paddling through the serene waters, you'll navigate winding mangrove creeks and shallow flats, surrounded by lush greenery and crystal-clear water.

These eco-friendly tours are often guided by knowledgeable naturalists who provide insights into the diverse ecosystems and wildlife that inhabit the area. Along the way, you may encounter various species of birds, fish, and even marine life like rays and small sharks. The gentle pace of kayaking allows for a closer look at the intricate root systems of the mangroves and the vibrant marine life below.

It's a perfect excursion for nature enthusiasts, photographers, and anyone looking to escape the hustle and bustle for a peaceful connection with Key West's natural beauty.

As you wrap up your trip, make sure to get all your belongings together before heading out one last time at an amazing dinner of your choosing.

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Scenset is happy to book dinner reservations for you at any of the amazing local restaurants after booking.

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More Dining Options

Latitudes: Located on Sunset Key, Latitudes provides a refined dining experience with stunning waterfront views. The menu features fresh seafood and gourmet dishes, perfect for a special occasion or a romantic evening.

A&B Lobster House: For a classic seafood dining experience, A&B Lobster House is a top choice. Known for its fresh lobster, oysters, and fine dining service, it provides an upscale atmosphere with beautiful marina views.

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Casa Marina

  • Ocean View - King
  • Adults
  • This room features ocean and pool views
  • Breakfast included
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Casa Marina

Saturday, 24 May, 2025
Day 7: Relax and Toes in the Sand Dinner

Spend a gorgeous day relaxing poolside, lounging on the beach, or luxuriating at a spa before a delicious dinner on the beach.

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Beaches Close By
  • Casa Marina Beach: The resort's very own private beach, providing direct access to pristine sands and clear waters.
  • Higgs Beach: A short walk from Casa Marina, Higgs Beach is a popular public beach with a pier, picnic tables, and volleyball courts.
  • Smathers Beach: Long stretch of sandy shoreline, palm trees, and calm waters ideal for swimming.

Once you've had enough fun in the sun, go back to your accommodation to freshen up before dinner.

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Tide to Table

Kick off your sandals and enjoy an unforgettable toes-in-the-sand dinner. With live music and incredible vibes, you and your family will be in full relaxation mode while enjoying astonishing dining options. While the food may be amazing, the ambiance can't be beaten while you watch a stunning sunset and cherish the moments from your trip.

Reservation Made By a Guest, Paid Locally

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Casa Marina

  • Ocean View - King
  • Adults
  • This room features ocean and pool views
  • Breakfast included
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Casa Marina

Sunday, 25 May, 2025
Day 8: Departure Day

Soak in the last minute sun before you depart for your flight home!

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11:00 - Check-Out

Check-out this morning is at 11am.

You are welcome to store your luggage and use the hotel facilities until your departure (if applicable).

Thank you for travelling with us. We hope you had a fantastic trip and we wish you a safe flight home!

Trip Pricing

While on the trip, you can access your support team if any need arises to make your trip as smooth as possible. We are here to support you.

Booking Your Trip

If you like what you read and are ready to pull the trigger on this once-in-a-lifetime adventure, please send a message in the app or an email to let us know.

We would be thrilled to secure all the reservations and make sure everything is taken care of, including special surprises along the way.

Scenset: Travel Greener
Scenset: Travel Greener
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Scenset invests in making the world a better place. Scenset will offset the fuel used during the trip. On top of that, we will offset an extra 10% to make your trip a carbon-positive experience.

Currently, we support Gold Standard Climate+ Projects from the Gold Standard Foundation.