Sun, sand, and adventure await in the wonderful Key West. This summer travel destination is in high demand, especially in May and June. Located at the southern tip of the Florida Keys, this island offers diverse outdoor activities. Expect unlimited beach time, snorkeling, scuba diving, picturesque sunsets, and vibrant nightlife. While the island caters to visitors of all ages, we have tailored this 5-Day Key West Itinerary for couples. Join us as we list out romantic activities to do in your couple’s getaway.
👉 Bonus: We even made a free downloadable 5-day Key West Itinerary for Couples PDF to make your planning super easy. [Get it here👇🏻]
Budgeting For A Two-Person Trip In Key West
Don’t let your fears stop you from visiting Key West. Since the island is one of the top travel destinations, travelers worry about draining their bank balance with a single trip. While there are expenses, you don’t have to finish all your savings with one Key West trip. Draft a budget plan considering all necessary factors, such as food, accommodation, transportation, and activities.
Food
Eat as a local in Key West. The island offers diverse dining options, from local eateries to upscale restaurants and cute cafes. Budget travelers can expect to spend $200 per person on food. If you buy drinks and local snacks, such as Key Lime Pie, the budget might exceed.
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Transportation
One way to manage your budget is to take public transportation in Key West. City bus fares start from $2 for a one-way ride and $4 for a one-day pass. Taxis, pedi-cabs, and ride-shares are pricier, with pedi-cabs charging $1.50 per minute. You can also explore the island on foot to save money.
Accommodation
Key West featured a wide range of accommodations, from condos and Airbnbs to luxury hotels and adults-only all-inclusive resorts. You will find hostels at the lowest price, starting from $90 per night. Inns and bed & breakfasts charge around $244 to $255 per night. Expect to pay over $400 for a single-night stay in a resort.
5-Day Key West Itinerary For Couples: Day 1: Arrival & Sunset Relaxation
Morning: Explore Duval Street☕
- Address: Key West, FL 33040, USA; Google Map
- Things To Do: Dining, Shopping, Nightlife
Upon arrival, check into your cozy accommodation and freshen up. Your first destination will be Duval Street, Key West’s main street, stretching over one mile. It features cafes, restaurants, bars, boutique shops, museums, and art galleries. Walk hand-in-hand and stop by any place that attracts your interest. Then, have coffee and snacks at a cafe. This street is best known for its vibrant nightlife, featuring many bars and pubs.
Afternoon: Mallory Square🌅
- Address: 420 Wall St, Key West, FL 33040, United States; Google Map
- Opening Hours: 24 hours
- Social Media: Official Website, Official Facebook, Official Instagram
What could be more romantic than watching a sunset with your other half? Head to Mallory Square for the famous sunset celebration. This is one of Key West’s main tourist attractions, drawing hundreds of visitors at night to witness the sunset. The celebration takes place two hours before sunset and features street performers, local artists, craft exhibitors, and food carts. You can also buy Key West treasures, souvenirs, or novelty gifts to bring back home.
Also Read: 10 Best Key West’s Most Popular Sunset Spots
Evening: Dinner At A Waterfront Restaurant🍽️
End your first day in Key West with a romantic dinner at a waterfront restaurant. The island has many top-notch seaside dining establishments offering delicious seafood and other cuisines. Choose any one from the following list:
- Sunset Pier: 0 Duval St, Key West, FL 33040, United States; 11:30 AM – 9 PM (Opening Hours)
- Hot Tin Roof: 0 Duval St, Key West, FL 33040, United States; 8-11:30 AM, 6-9 PM
- Louie’s Backyard: 700 Waddell Ave, Key West, FL 33040, United States; 11:30 AM – 2:30 PM, 5 PM – 9:30 PM
- Latitudes – Sunset Key Cottages: 245 Front St, Key West, FL 33040, United States; 7 AM – 2:15 PM, 5 PM – 10 PM
- Blue Heaven: 729 Thomas St, Key West, FL 33040, United States; 8 AM – 2:30 PM, 5 PM – 10 PM
If you want more details, check out this blog on the 10 Best Seafood Restaurants in Key West, Florida.
Day 2: History & Culture
Morning: Visit The Ernest Hemingway Home & Museum🏛️
- Address: 907 Whitehead St, Key West, FL 33040, United States; Google Map
- Opening Hours: 9 AM – 5 PM
- Social Media: Official Website, Official Instagram
Walk the path of legendary Ernest Hemingway on The Ernest Hemingway Home & Museum. It was a private residence of Hemingway and his wife, Pauline Pfeiffer, from 1931 until 1939. Now, as a museum, it receives many visitors daily who come to explore the house’s rooms, garden, and the in-ground swimming pool. The latter was the first of its kind in the Florida Keys and required extensive construction. Meet the museum’s six-toed cats, who are the descendants of Ernest’s original cat, Snow White.
Afternoon: Key West Butterfly And Nature Conservatory🦋
- Address: 1316 Duval St, Key West, FL 33040, United States; Google Map
- Opening Hours: 9 AM – 5 PM
- Social Media: Official Website, Official Facebook, Official Instagram
Spend your afternoon in Key West’s best attraction. Experience the magic as you walk among hundreds of free-flying butterflies at Key West Butterfly and Nature Conservatory. Check out the conservatory’s impressive collection of flowering plants, trees, and waterfalls while you admire 50 to 60 species of butterflies. It will also be an educational experience, as the venue offers a 15-minute film that describes the life cycle and provides basic facts of interest about butterflies. You will also see exotic birds and two glorious flamingos. Later, take a leisurely stroll through the Old Town historic district.
Evening: Romantic Sunset Sailboat Cruise⛵️
- Duration: 1.5 to 2 hours
- Price: $70 to $100+
- Inclusions: Alcoholic/Non-alcoholic beverages, appetizers, live entertainment
Experience a romantic evening on the water. Book a sunset sailboat cruise and sail across the island’s calm waters. These sunset cruises are usually 1.5 to 2 hours long and feature a professional staff onboard. Some offer complimentary non-alcoholic or alcoholic drinks, such as wine, beer, or champagne. You may have to pay extra for appetizers and drinks on some cruises. Book the one that has an open bar, live music, and good food.
Day 3: Beach & Water Activities
Morning: Smathers Beach⛱️
- Address: 2601 S Roosevelt Blvd, Key West, FL 33040, United States; Google Map
- Opening Hours: 7 AM – 11 PM
- Things To Do: Swimming, Parasailing, Jet Skiing, Sunbathing
Bask under the morning sun at Smathers Beach. This is the largest public beach on the island and is a local favorite, especially during the spring and summer months. It is approximately half a mile long and features pristine sands, towering palm trees, and clean waters. Sunbathe, swim, or rent jet skis and traverse through the seas. Alternative: Visit the Fort Zachary Taylor Beach in the Fort Zachary Taylor State Park, which allows swimming, snorkeling, and other beach activities.
Also Read: The Best Beaches in Key West for Swimming and Snorkeling
Midday: Snorkeling or Paddleboarding🤿
- Where to Snorkel in Key West: Fort Zachary Taylor Historic State Park, Smathers Beach, Higgs Beach, White Street Pier
- Cost: $35 to $80 per person
You can’t miss out on water activities on the Florida islands like Key West. It is a haven for watersports lovers, featuring a variety of water activities, from swimming to paddleboarding, scuba diving, and snorkeling. Key West is among the best snorkeling spots, as it is the home to North America’s only living coral barrier reef, the Florida Keys Reef Tract. It boasts a rich biodiversity, featuring diverse species of tropical fish, sponges, and corals, making snorkeling a must-do activity. Alternative: Book a paddleboarding tour and explore the Key West Backcountry.
Also Read: Best Water Activities in Key West, from Jet skiing to Parasailing.
Afternoon: The Mel Fisher Maritime Museum⚓️
- Address: 200 Greene St, Key West, FL 33040, United States; Google Map
- Opening Hours: 10 AM – 4 PM
- Social Media: Official Website, Official Facebook
After all the activities, take a break inside the Mel Fisher Maritime Museum. This century-old Neoclassical building was initially a storehouse for supplies and accounts for the US Navy. It now houses an extensive collection of artifacts from 17th-century shipwrecks, including Santa Margarita, Nuestra Señora de Atocha, and Henrietta Marie. In addition to watching exhibitions, visitors can book a private lab tour, where they can touch the artifacts. Alternative: Visit Key West Shipwreck Treasure Museum to learn about the island’s shipwrecking past.
Evening: Enjoy a lovely dinner at a cozy, intimate restaurant with live music.
Day 4: Adventure & Exploration
Full Day: Dry Tortugas National Park🦜
- Address: Florida, United States; Google Map
- Things To Do: Boating, Snorkeling, Diving, Swimming, Camping, Fishing, Paddleboarding
- Social Media: Official Facebook, Official Instagram
We have a busy day ahead on this fourth day of this 5-day Key West Itinerary for couples. Spend the better half of this day at Dry Tortugas National Park. This 100-square-mile remote park is mostly open water with seven small islands. Its must-renowned feature is a 19th-century Fort Jefferson, a former US military coastal fortress covering 16 acres. It is also renowned for its picturesque blue waters, which are home to rich coral reefs and diverse marine life. Snorkeling and diving are highly recommended. You can also enjoy fishing, wildlife viewing, and camping.
Late Afternoon: Couples’ Spa Treatment💆🏻♀️
Return to Key West and relax with a couple’s spa treatment. Book a couples massage and relax under the hands of talented masseurs. You will enjoy a massage side by side from two professionals in the same room. This experience will help you relax and relieve stress. Ocean Wellness Spa & Salon offers the best couples massage. You can also get a complete spa treatment with facials, pedicures, manicures, and other revitalizing body treatments.
Evening: Nightlife Experience🥂
As the evening approaches, walk along the Key West Harbor hand-in-hand. This port boasts a diverse range of restaurants, shops, bars, hotels, and art galleries. You can stop by any local bar for some drinks before calling it a day. Toast each other with champagne or wine and revisit beautiful memories made throughout this five-day trip. Alternative: Enjoy a quiet night in after dinner.
Also Read: The Best Key West Bars and Nightlife Spots
Day 5: Local Flavors & Departure
Brunch At A Popular Cafe🥐
- Recommended Place: Hard Rock Cafe Key West
- Address: 313 Duval St, Key West, FL 33040, United States; Google Map
- Opening Hours: 11 AM – 11 PM
- Social Media: Official Facebook
Sleep in on your last day in Key West. After you wake up, head to any local cafes for brunch. If you’re looking for a recommendation, the Hard Rock Cafe Key West is renowned for its casual dining and live entertainment. It is conveniently located in the heart of Duval Street and serves authentic American fare, including its island-famous cheeseburgers. You can also check out the cafe’s rock n’roll memorabilia.
Last-Minute Shopping For Souvenirs🛍️
Shop for knick-knacks or trinkets before departure. Mallory Square and Suval Street feature many local artisan shops, boutiques, and shopping centers, where you can buy local crafts, clothing, and unique items. Some recommendations include Besame Mucho (unique gifts), Peppers of Key West (spicy food), Kino Sandals (custom handcrafted sandals), and Wyland Galleries (art).
If time allows, visit the Key West Lighthouse & Keeper’s Quarters or Key West Aquarium. Depart with wonderful memories!
Also Read:
- Best Pet-Friendly Hotels and Resorts in Key West
- Ultimate 15 Best Things to Do in Key West
- The Most Luxurious Hotels & Resorts in Key West, Florida
This 5-Day Key West Itinerary For Couples primarily includes must-see and must-do romantic activities on the island. You can alter, add, or remove any activity based on your preferences. Book guided experiences to enjoy a hassle-free trip in Key West. Choose TourTeller, where we have tallied up hundreds of activities from the top OTAs. You can see a summary, inclusions, and AI review analysis, and even compare similar tours with just a click.
