Let’s talk best Key West weekend getaways! There’s nothing quite like the feeling you get watching the sun dip while listening to live music at Sunset Pier, feeling the sand between your toes at the Southernmost Point, or bar hopping along Duval Street with an obligatory stop for a frozen Rum Runner at Sloppy Joe’s.
With its laid-back island energy, colorful streets, gorgeous sunsets, fresh seafood, vibrant bar scene, and plenty of places to explore, vacations in Key West are always a good idea.
South Floridians are lucky to have the Florida Keys in our backyard. It is incredibly easy to switch right into vacation mode the moment you set foot in The Conch Republic. Whether you’re road-tripping down from South Florida or flying in for a short escape, a couple of days is just enough time to soak up the best of the island. Here’s how to make the most of a quick Key West vacation.
Where to Stay: Margaritaville Beach House Key West
As you plan your Key West weekend getaways, where you stay can make a big difference. I recently stayed at Margaritaville Beach House Key West. Its located right across from one of Key West’s most popular stretches of sand, Smathers Beach, which makes it an easy choice for a laid-back island escape. It’s a great home base when you want to explore and go out on the town, but also have a comfortable and quiet spot to come back to and truly unwind.
The 186-room resort brings that signature ‘it’s 5 o’clock somewhere‘ state of mind to the southernmost point of Florida, with spacious guest rooms and one- and two-bedroom suites, a lagoon-style pool with tropical surroundings, lawn games and hammocks scattered throughout the property.
Following the Jimmy Buffet theme, you know there are cheeseburgers and margaritas available at the resort! The Tin Cup Chalice Bar & Chill offers full-service dining for breakfast, lunch and dinner right on property, so you don’t have to go far for a bite or a cocktail. Happy hour is every day from 5-7 pm featuring food and drink specials, and room service is available daily from 7:30 am to 10 pm.
There’s also a 24-hour fitness center, an on-site provision shop, kids’ activities, and plenty of open-air spaces for soaking up the Key West sunshine. It’s definitely an ideal location for a family trip, but I also recommend it for Key West weekend getaways for couples. If you happen to be by the pool around 2 pm, you can cool down with fruit smoothie samples and popsicles. In the lobby, treat yourself to fruit-infused water and freshly baked cookies every day from 5-7 pm. I highly recommend making it a point to swing through the lobby in the afternoon for one of those cookies…
Oh, and the complimentary shuttle to Downtown Seaport Harbor and Key West International Airport is a major bonus! We used the shuttle multiple times throughout the weekend to get into town and to and from the airport.
Yes, I know most people drive if they live in South Florida, but a flight from Miami is much easier and way less tiring. Trust me; this is probably one of my biggest travel tips for Key West! Try flying once and you’ll never look back.
Margaritaville Beach House offers everything you need for your Key West vacations: beach and pool time, food and cocktails, and easy access to the action of Old Town. Plus, there are plenty of vacation packages available throughout the year, especially if you are a Florida resident.
Address: 2001 S Roosevelt Blvd., Key West, FL33040
Phone: 305-292-9800
Things to Do During Key West Weekend Getaways
You can pack a surprising amount into a Key West weekend, but my favorite way to experience the island is to mix a few must-do activities with plenty of time to wander, check out live music and entertainment, and enjoy cocktails with a stunning view. Here are a few things worth adding to your Key West Florida itinerary.
Key West Butterfly and Nature Conservatory
This is Roger’s and my favorite thing to do in Key West! The Key West Butterfly and Nature Conservatory is a colorful little escape home to hundreds of free-flying butterflies and beautiful lush greenery. Walking through the tropical conservatory with butterflies and birds fluttering all around you, and sometimes even landing on you, is such a fun experience. You really only need about 15-20 minutes here, so it’s a quick stop, but well worth it. It’s a great change of pace from the typical beach-and-bar Key West itinerary. Don’t forget to stop and say hi to Rhett and Scarlett, the conservatory’s resident flamingos!
Address: 1316 Duval St., Key West, FL 33040
Phone: 305-296-2988
Sunset Sail with Sebago Watersports
No Key West Florida vacation feels complete without getting out on the water, and a sunset cruise is the perfect way to do it. We spent the evening sailing on board a catamaran with Sebago Watersports as the sun dipped toward the horizon. Light appetizers were served and a full bar was available, included in the ticket price. An acoustic guitarist set the mood singing great songs throughout the ride. Roger and I have been on quite a few sunset sails during our travels, and this one exceeded my expectations. The Sebago Watersports Sunset Sail is a must-do during your Key West weekend getaways. It’s truly one of those experiences that allows you to slow down and savor the moment.
Address: 205 Elizabeth St., Unit 1, Key West, FL 33040
Phone: 786-841-9109
Sunset Pier
If you’re looking for that quintessential Keys Florida combination of cold drinks, live music, casual and lively atmosphere, and a front-row seat to the sunset, Sunset Pier is the spot. Grab a cocktail, find a spot overlooking the water, and settle in as the music plays and the sky starts changing colors. This is the place where you’ll say you’re only stopping for one drink, and somehow end up staying for a few hours.
Address: 0 Duval St., Key West, FL 33040
Dinner at Opal Key Resort and Marina
For another waterfront stop, head to Lolita’s Coastal Cocina at Opal Key Resort & Marina. The open-air setting and harbor views make it a great spot to settle in for an early dinner before a night out on Duval. The menu features a variety of shareable plates, handcrafted cocktails, and a full tequila and mezcal menu. If you’re a tequila fan, you will love the drinks. My favorite was the Guava Island with Milagro Silver tequila, guava syrup, coconut egg white foam, and pressed lime. For food, I recommend the Gulf shrimp ceviche with plantain chips and Acapulco jumbo crab cake coated in a blue corn tortilla crust with avocado, roasted red pepper aioli, and cilantro lime crema.
Address: 245 Front St., Key West, FL 33040
Phone: 305-294-4000
A few additional Key West highlights to note include the Ernest Hemingway Home and Museum, Mallory Square, and Fort Zachary Taylor Historic State Park Beach. Make time to stop in these local favorites for food and drinks: Blue Heaven, Sloppy Joe’s, Capt. Tony’s Saloon, Half Shell Raw Bar, and for a fine dining experience, Cafe Marquesa.
Plan Your Key West Weekend Getaways
The beauty of a Key West weekend is that you really don’t need to over-plan it. All you need is a few main activities planned, which I’ve helped you out with here, and then it’s better to simply go with the flow.
As long as you’ve got a good place to stay, food and drinks, time on the water and at one of the beaches, live music, and sunset views, you’re golden. That’s more than enough to make your Key West FL vacation one to remember.
Disclosure: This is a sponsored post by Margaritaville Beach House Key West and The Florida Keys
Looking for more weekend getaway ideas in Florida? Check out this Palm Beach vacation resort and this hotel in Vero Beach.
FAQs
Two to three days is just enough to experience many of Key West’s highlights without feeling like you’re rushing around. A long weekend gives you plenty of time for the beach, sightseeing activities, sunset on the water, great food and drinks, and time left over to simply wander.
If you want to be in the middle of all the action, stay somewhere on Duval Street. However, if you want to go home at the end of the night to somewhere a bit quieter, Margaritaville Beach House Key West is a great option, especially because of its proximity to Smathers Beach and complimentary transportation to the Downtown Seaport Harbor.
Although Key West is a year-round destination, summer can be brutally hot and humid. November through April are much cooler, but this time of year is also especially popular, so you may run into crowded areas and higher prices for travel and hotels. If you’re visiting during the warmer months, there will be less crowd, but expect higher humidity and the possibility of afternoon rain showers.
