Posted in North American Travel

How to Have a Romantic and Affordable Weekend in Key West

“Affordable” is not a word that’s usually associated with the Florida star of drunken nights and steamy days (prepare for an endless amount of romance puns in this one). I debated calling this weekend “affordable”, because, compared to my other adventures, this was definitely not on the cheaper end.

One of the most expensive parts of visiting Key West is the steep cost of accommodations. Even during the off-season, a weekend in a hotel within walking distance of Duval Street will run about $300-500 a night. But if you’re willing to accept that most of your expenses will come from where you sleep (or at least rest between bar hopping), then the rest of the weekend can be easy on your wallet without skimping on the romance or experience.

Cheers to going big for the weekend!

So, join me, your self-appointed Romance Connoisseur, on my top tips for How To Have a Romantic and Affordable Weekend in Key West, Florida.

Tip 1: Drive

Nothing says romance more than driving past palm trees and blue water with the windows down, especially when you get to hear that motor purr at 45 mph (the top speed on the US 1 from Key Largo to Key West).

Two lanes, the whole way. Photo credit:

I currently live in Fort Myers, so driving to Key West is usually the easiest option for me. However, even if you’re visiting from the Great North, flying into Miami or Fort Lauderdale and renting a car is still your best bet. The Florida Keys are scattered with small airports, including a commercial airport located in Key West. While this may seem convenient, a quick Google Flights search shows that not only is Key West airport typically very expensive to fly into, it is also coupled with multiple layovers and connections. (If you’re located near a major airport hub for Frontier, Spirit, or JetBlue, you have much better prices and connections. These airlines provide multiple nonstop services to Key West at a reasonable rate, but are very limited.)

Nonstop flight options for a random weekend in November.

Opting to drive Highway 1 through the Keys comes with additional bonuses. As mentioned above, accommodation in Key West is extremely pricey, regardless of the season. If you’re looking to book an extended weekend with that special someone (or yourself! #treatyoself), renting a car gives you the option of staying in the Upper Keys for some of your stay. While they aren’t cheap, the Upper Keys offer a wider area of hotels, Airbnbs, and campgrounds, bringing costs down to as low at $100 a night, depending on where you stay. The Upper Keys are also less crowded than Key West, granting you a bit more serenity and privacy if you want to take a dip into the ocean with your lady lover under a full moon (just don’t watch Jaws before this trip).

Bahia Honda is a great stop to spend a half a day enjoying the “beach”. Heads up, if you’re looking for the typical white sand beaches, these don’t exist in the Keys. Photo credit: Nicholas Larghi Photography

The Upper Keys also provide some great stops for sightseeing along the way that shouldn’t be skipped over. Some of my favorites include:

  • Keys Chocolate and Ice Cream on Key Largo- Best stop for key lime pie on a stick, ice cream, and gourmet sweets. If you go at night, you get the added bonus of enjoying their delicacies under a patio of twinkle lights, and what says romance more than twinkle lights? Nothing.
Aw, sweet diabetes.
  • The History of Diving Museum on Islamorada- Okay, so this one may not get you a lot of romance points, but history can be sexy, right? Regardless, this is a great stop for any dive, ocean, or history enthusiasts, and is also a great option to escape the rain. Tickets are $15 a person, but you can easily spend a couple hours here.
Gotta love that 60’s vibe. Photo credit:
  • Bahia Honda State Park on Big Pine Key- You can think me later when this stop pays off in your favor (insert winky face). This park is definitely a major reason for driving. Located just under a hour from Key West, this park provides one of the best beaches in the Keys, as well as a great place for snorkeling, boat tours, paddle boarding, and kayaking. The old railroad bridge at the park also offers one of the highest vantage points in this area, so you can get sweeping views of the ocean as a backdrop for the cute couple photo that will be your phone’s background for the next 7-10 months. You can also reserve a campsite here if you want to see the bridge under the Milky Way. Nothing says “eternal love” like 10,000 no-see-ums and 10 billion stars.
Insert cheesy romance line here. Photo credit: Nicholas Larghi Photography
  • Florida Keys Cafe on Big Pine Key- If you’re driving into Key West in the morning, this is a definite stop to grab a much needed coffee and delicious breakfast. Not only is the food divine, but this family-owned and operated restaurant is also very affordable (under $15 a plate, which is affordable in this territory). It’s not much to look at on the outside, but the inside is full of charm, sweet servers, and the nice aroma of salty fishermen. No one is feeling very loving when they’re hangry, so be sure to stop in here, pack in some grub, and continue on to the Southern Capitol of Debauchery.
Beauty is on the inside for this one.

Tip 2: Opt for the Nice Hotel

Now that you’ve made it to your destination, picking out the perfect place to call home for the weekend is going to impact the rest of this lovecation. Hotels in Key West are pricey (if I haven’t said this enough), but if you’re smart in your selection, then the cost will be worth the experience. Hotels are the most expensive close to Duval Street; however, if you’re banking on getting your plus one hammered with frozen cocktails, it works in you favor to stay within walking distance of the bars and attractions. Anything over half a mile from Sloppy Joe’s, and you’re officially too far to stumble your way home.

The Old Town Manor. This used to be a doctor’s residence and office. If you stay inside the house, it is supposedly haunted. I did not stay in the house.

We stayed at the Old Town Manor, just around the corner from the main road. At $400 a night, this hotel was one of the most expensive I’ve ever stayed in, but it was more than worth the price (and still on the cheaper end of Key West accommodations). This B&B offered everything required for a weekend of romance, and relaxation. A converted residence from 1886, we had the option to stay inside the main house or in the converted carriage house outside (we chose the carriage house). Because we weren’t right on Duval, we were able to enjoy the party scene, but retreat to the quiet serenity of our own garden. Breakfast included a buffet of salmon, homemade jams, fruits, and a variety of bagels and freshly-pressed orange juice (with the added bonus of baby chicks running around). We stayed in the Jarcada Room, and we had our own patio overlooking the beautiful gardens and breakfast area. The house was also available if we wanted to pop in for some refreshing fruit-infused water, chat with the incredibly helpful staff, or escape the heat in the charming parlor or on the front porch. If you’re trying to convince your significant other that you need a trip here pronto, I will provide some extra photos to seal the deal.

Tip 3: Find Free Activities for the Day Time

Because you might be experiencing sticker shock over the price of your hotel, spend the day enjoying the town without opting for the expensive excursions. Key West has a lot of offer to the hardy traveler who isn’t afraid to brave the heat and put some miles on their shoes. The neighborhoods spanning out from Duval Street are filled with colorful, historic homes and Spanish-moss draped avenues. You can easily spend a lazy morning strolling down the sidewalks and just taking in the sights.

Just don’t check Zillow. It will make you feel poor.

If you’re more of a destination person, check out the West Martello Tower and Garden. This Civil-War era fort turned botanical garden is free to the public (open 9:30am-5:00pm, 7 days a week).

Not featured: the hoards of chickens running around. Photo credit: Nicholas Larghi Photography

Ferns, trees, flowers, butterflies, chickens, and beautiful views of the ocean make this a great place to spend an hour or two. Most of the paths are shady, so it is also a good place to escape Florida’s oppressive heat. Pack your sunhat, sunscreen, and skip the cute shoes for something more comfortable as this spot is about a 30 minute walk from Duval Street. However, it brings you closer to the Southernmost Point of the US marker, so you can knock off two things on your “must-see” list.

Just a small sample of all the beautiful flowers to see here. Photo credit: Nicholas Larghi Photography

From here, you can make the short 10-minute walk to the Southernmost Point of the US. This marker is a fan-favorite for all visitors, and your trip wouldn’t be complete without a quick selfie. Try to get here early, as a line does form for pictures and the heat can be rather dreadful. There’s a great little grocery story just across the street where you can pick up some key lime pie on a stick or a cold drink to make up for the long jaunt.

This is not a diet-friendly destination.

At the end of the day, head over to Mallory Square for the daily sunset celebration, courtesy of the more colorful residents of Key West. An hour or so before sunset, this square starts to fill up with visitors, exhibitionists, and the occasional chicken. This is one of the better places on the island to catch the sunset over the ocean, and there’s plenty of places to grab a delicious cocktail to sip on while you wait. (While a lot of people watch the sunset right at Mallory Square, if you walk Harbour Place Condos, you can get a better view and a bit more privacy).

I like pretty views next to boats I can’t afford.

The real attraction though comes from the assortment of freelance performers who put on free shows around the square. You can catch everything from an old guy walking a tightrope to a kid spinning fire– it just depends on the day. Be sure to bring some cash to show your appreciation for your favorite performers.

Be careful. You might be volun-told to join the show.

Tip 4: Splurge on Food and Drinks

If you’re in Key West, chances are very high that you’re here to have a drink or two. Since you’ve opted for a hotel with breakfast and skipped the expensive tours, you have a bit more room in your budget to splurge on some yummy drinks and food. Restaurants can get pricey here, so it helps to do a bit of research if you want to be more strategic in your approach. One of our favorites was Garbo’s Grill at Hank’s Bar. This low-key, outdoor bar offers free, live music and an affordable happy hour ($5 beer in Key West, anyone?).

Nothing like beer in a plastic cup to get the romance flowing.

The best part of this place though is the food truck behind the bar, named Garbo’s Grill. They feature a variety of bar food, including fish tacos, beef tacos, hamburgers, hotdogs, and poke bowls. However, the true winner of the show (and the reason we kept coming back to it the entire weekend) is the Korean Bulgogi Burrito. Unless you’re a monster, you love Korean Bulgogi as much as the rest of the world, and this place does not disappoint. Food costs $10-$15 a plate, which is much cheaper than many of the sit-down restaurants in the area.

Marry me, sweet burrito from heaven.

Spend your evening checking out the colorful and unique bars that fill Duval Street. Like everything else here, drinks aren’t cheap in Key West (most cocktails will cost around $10-$15, depending on how fancy you are), but you’re here for the experience. To save some money, check with your hotel to see if they have coupon cards for some of the bars. We were able to snag a couple Buy One, Get One coupons for some places, which saved us about $10 for each order.

Nighttime, when Duval comes alive. Just remember to hydrate.

Tip 5: Opt for the Off-Season

Key West shines when the rest of the country is buried under ten feet of snow. December through April is peak tourist season for this tiny town, meaning prices for hotels skyrocket and everything gets a bit too crowded for comfort. Remember, there is only one road leading down to the keys, and it can quickly turn into a traffic nightmare on a busy Friday evening.

Starting in May, the tourists start to disappear, as temperatures in the rest of the country start to rise and those poor, pale Northerners get to peak out their front doors and see the sun for the first time in months. While it is hotter and way more humid in the summer, hotels get to be a bit more reasonable and you won’t feel like you’re fighting crowds everywhere you go.

If you are visiting during the summer months, be sure to pack clothes that breathe easily, a good sun hat, and lots of sunscreen. It is also smart to do most of your exploring in the early morning and late afternoon, spending the hottest part of the day by the pool of that adorable hotel you opted for.

I come, I insta, I leave.

Final Thoughts

Key West is definitely one of America’s more unique destinations, but it is also definitely not for everyone. I’m spinning this to be a weekend for couples, because this really isn’t the best destination for kids. Girls weekend, Lonely Boys Days Out, and romantic escapades are all great fits for this colorful destination, but Key West lacks the beaches and kid-friendly attractions that are typical in the rest of Southern Florida. Not to mention the hoards of drunken debauchery that descends upon this town once the sun goes down…

The face of drunken debauchery.

While it doesn’t fit the tune of our normal, budget-friendly destinations, Key West can still be done on a rather affordable budget. It is a great destination for a long weekend with your amore of the hour (or life, whatever floats your boat). Just be smart in your planning, be willing to cough up a bit more for a nice hotel, and most of all, get drunk, make-out in public, and have a great time.

Happy trails, everyone!

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