Thinking of a longer stay

Question

Have been coming regularly for over almost 40 years . Have stayed a few days to a week , most recently 4-5 days annually over new years .

My wife and I are discussing a longer stay next year 2-3 weeks maybe a month. Just curious for those who have made the transition from a vacation to a longer stay , if it was as expected , better or perhaps different/ too long ? Thanks

Answer

Transitioning from a short vacation to a longer stay in the Florida Keys can be a very rewarding experience, but it does come with some differences and considerations. Many long-time visitors find that extending their stay allows them to explore the islands more deeply, relax at a slower pace, and enjoy the Keys’ lifestyle more fully.

One of the biggest benefits is the opportunity to experience the Keys beyond the typical tourist activities. Instead of rushing to see the main attractions in a few days, you can spend mornings on the beach, afternoons snorkeling or kayaking, and evenings sampling local restaurants at leisure. The slower pace often leads to a more immersive and less stressful experience.

However, there are a few practical considerations to keep in mind:

Accommodation: For stays of 2-3 weeks or longer, renting a vacation home, condo, or apartment is usually more comfortable and cost-effective than staying in a hotel. This also gives you access to a kitchen, which is convenient for longer stays.
Weather and Season: Consider the time of year. Winter and spring are more popular, so long-term rentals may be in high demand and more expensive. Summer and early fall can be quieter and more affordable, but also hotter and more humid.
Supplies and groceries: Unlike a short trip where dining out is easy, longer stays may require grocery shopping and meal planning. Having a car is usually essential to access larger stores and explore different parts of the Keys.
Activities: For a longer stay, it’s easy to mix in new activities such as fishing trips, diving excursions, paddleboarding, or visiting less-traveled islands, which you may skip on shorter visits.
Social and community aspects: Extended stays can give you a chance to connect with locals or seasonal residents, which often enriches the experience. Some people join classes, tours, or community events, making the Keys feel like a temporary home rather than just a vacation spot.

Most people who have made the shift from a 4-5 day vacation to 2-3 weeks report that the experience is better than expected. You get to enjoy the laid-back lifestyle, explore beyond the usual tourist spots, and feel more at ease with a slower schedule. However, some find that a full month might feel too long if they don’t plan activities or have the flexibility to explore, so pacing yourself and having a plan is recommended.

Overall, a longer stay allows for a richer, more relaxed experience of the Keys. It’s often described as “more like living than vacationing,” which many longtime visitors enjoy immensely.

Thinking of a longer stay

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