How to Make the Most of a Lifestyle Trip to The Villages, Florida

Today we continue our series on The Villages, Florida.

Last time we discussed the Top Reasons to Move (Or Not Move) to The Villages, Florida.

If you missed that, you may want to check it out.

Today we’re going to cover everything about making the most of a lifestyle trip to The Villages (TV).

What’s a Lifestyle Trip?

Let’s begin with a definition so we’re all on the same page.

A lifestyle trip to The Villages, Florida is a short-term visit designed to let prospective residents experience what it’s like to live there—before making a decision to buy or rent a home. Think of it as a “try before you buy” retirement preview.

A Lifestyle Preview Plan (their official name) is offered by The Villages sales team (you are assigned an agent to be your main contact, get you settled, etc. but you can have as little or as much access to/attention from them as you want — they are pretty chill) and typically includes:

• A fully furnished home or villa for 4–7 nights.
• A golf cart to get around like a true Villager.
• Access to recreation centers, pools, and fitness facilities.
• Free golf on executive courses.
• Resident ID or guest pass, giving you entry to events, clubs, and amenities.
• Option to attend community tours or open houses with a sales rep.
• Live entertainment at the town squares—nightly, no cover charge.

There’s a per night cost, which is unbelievably reasonable for what you get, as follows:

• January $179/night
• February & March $199/night
• April $149/night
• May-September $99/night
• October – December $149/night

You can get more details on it here.

What Does the Trip Accomplish?

The purpose of the trip is as follows:

• Test-drive the lifestyle: See if you enjoy the active, social, golf-cart-driven community vibe.
• Explore neighborhoods and home types: Tour villas, cottages, designer homes, and more.
• Get to know residents: Talk to locals and ask questions about real day-to-day life.
• Try activities: Join a pickleball game, swim, dance at the square, or visit a club meeting.
• Evaluate fit: Ask yourself if this community matches your goals for retirement living.

Basically it’s a trial run and/or sample of what it’s like to live in The Villages.

Anyone (who is 55+) can partake of the visit, but it’s primarily for:

• Retirees or pre-retirees exploring where to relocate.
• Snowbirds seeking a winter home.
• Anyone wanting to see if The Villages’ lifestyle suits their personality, pace, and budget.

What to Do on a Lifestyle Trip

You are free to do whatever you want on a Lifestyle Trip, but if you’re haphazard about it you’ll probably miss a lot.

So it’s smart to experience as much as you can in a planned/structured way so you get to see/experience the things that are most important to you. 

Here are some things I suggest you consider doing during your visit (in order of importance):

1. Explore the Town Squares

• If you have the time, visit all three main town squares: Spanish Springs, Lake Sumter Landing, and Brownwood Paddock Square. Each offers live music nightly, shopping, dining, and a unique theme.
• If you’re an over-achiever, you can visit the mini-square called Sawgrass Grove as well as the newest square, Eastport, which is supposedly going to open in late 2025 (it’s where the newest construction is).
• If you’re pressed for time, just visit Lake Sumter Landing and Brownwood (and Eastport if it’s open and you’re thinking of buying a place near it.) Spanish Springs is older and Sawgrass doesn’t have all the amenities as the others.
• Be sure to check out the boardwalk as well as the Lake Sumter Boat Tour when visiting Lake Sumter landing (which, IMO, is the best town square so far).
• Stay late for the entertainment at least one time—the music and dancing are central to the social life in The Villages. (Every town square has live music every night. You can find out who’s playing each night on TV app.)

2. Try the Recreational Lifestyle (do one or two activities during your stay)

• Golf: Play a round at an executive course. With over 50 executive courses, you can golf almost every day if you want. If you’re not a full-fledged golfer you can try a Pitch and Putt (there’s a good one by the Okahumpka Recreation Center — see below) or a putting course (there’s a good one by the Ezell Recreation Center — see below)
• Pickleball & Tennis: Try your hand at pickleball—it’s wildly popular there.
• Swimming & Fitness: Check out the sports pools and recreation centers. Join a water aerobics or fitness class. Or just hit the pool and relax. You’re bound to find some new friends there!

3. Take a Golf Cart Tour

• Explore the cart paths. It’s pretty easy to navigate as The Villages app has golf cart trail navigation built in. By the way, the “golf cart trails” are almost always (if not always) multi-modal trails which means walkers, bikers, and the like have just as much right to be on the trails as golf carts do.
• Drive through neighborhoods, along scenic paths, and even over special bridges and tunnels built for golf cart traffic.
• I would personally set aside a whole day for this. You’ll knock several things off your list (and on this list I’m providing) if you just get out on your golf cart and go.

4. Visit Recreation Centers

• Each “village” has access to regional (larger) and neighborhood (smaller) recreation (rec) centers.
• Visit major rec centers like Eisenhower, Rohan, or Everglades, each packed with pools, classes, and event spaces. Many feature unique patriotic or local-themed décor.
• If you do visit Sawgrass Grove, it shares a parking lot with Ezell Rec Center, which is a regional rec center (one of the bigger ones like the others above).
• If you can only see a couple, check out Eisenhower or Everglades as a great example of a larger rec center and Lake Okahumpka Rec Center as a very nice mid-sized rec center.

5. Dine and Shop Like a Local

• What is a trip to TV without food? Our favorite places to eat include Willie Jewell’s (BBQ) in Magnolia Plaza (it’s near the Everglades Rec Center and not too far from the Village of Fenney), Piesanos (Italian) in Lake Deaton Plaza (not far from Rohan Rec Center), and the Fenney Grill (good breakfasts/pancakes) in the Village of Fenney (which is beautiful in and of itself with the magnificent trees when you first drive in and the nature walking path in the rear of the rec center there).
• For a very unique eating place try Edna’s which has food and live music in an outdoor setting. Also very close to Hogeye Preserve Trail if you want to check that out.
• For sweets, we liked Island Fin Poke in Brownwood for their Dole Whip (which used to be half price from 3-5 pm…not sure if that’s still the case or not), Peterbrooke Chocolate in Lake Sumter Landing (great chocolate treats), Kilwin’s in Spanish Springs (ice cream, fudge, and treats), and the king of them all, Russell Stover Chocolates (ice cream and more candy and treats than you can handle) just west of highway 301 on state road 44 (near Brownwood).
• Visit local boutiques, markets, and festivals hosted in the town squares. The shops in Lake Sumter Landing are the best in TV IMO. There’s also a weekly farmer’s market in Brownwood every Saturday morning.
• Go into a Publix. If you live there it’s going to be your main grocery store, so you might as well lay down and take it. Hahaha. Pro tip: shop the buy one get one sales each week to make the prices at least closer to decent.

6. Talk to Residents

• Strike up conversations—Villagers are famously friendly.
• Ask what they like (or don’t) about living there. It gives you an honest inside look.
• You can chat them up anywhere — at the pool, in restaurants, at the nightly concerts, etc.

7. Take a Sales Tour

• If this is an official lifestyle preview visit, your rep will be more than willing to schedule a guided tour—take advantage of their knowledge and community access.
• Consider visiting the Street of Dreams — basically a grouping of model homes. You can see many styles of homes in one spot and even if you don’t want to buy, it’s a fun time looking.
• Just half a day for this is all you’ll need.

8. Take a Nature Walk or Visit a Park

• Explore Hogeye Preserve Trail or local walking/biking paths. It’s not just golf—there’s plenty of nature, too.
• I’ve already mentioned Lake Okahumpka Rec Center. There are two very nice walking paths there as well — one outside of the rec center and one behind it on the boardwalk.

9. Attend Clubs & Activities

• Browse the Rec News (weekly insert that comes out every Thursday – they may deliver one at your house as I believe they give you daily delivery of The Villages newspaper, The Daily Sun, and those contain the recreation center inserts) or check online for club schedules.
• Join a club meeting or activity that matches your interest—whether it’s cards, crafts, faith groups, political clubs, or foreign language meetups. There are 3,500+ clubs for everything from photography to genealogy, veterans’ groups to bocce ball. Find your people and your passion.
• I would only spend time doing this if there’s something you are very interested in and it will be part of your decision to live in TV or not. Otherwise, I’d save it for another (second) trip.

10. Catch a Show or Movie

• Attend a live show at The Sharon L. Morse Performing Arts Center or see a movie at the Old Mill Playhouse.
• I’d make this optional and/or for a second visit as well.

11. Attend a Church or Worship Service (Optional)

• If faith is part of your life, try visiting a local church to see how the spiritual community feels.
• If you come from a larger church, you’re going to have to reset your expectations of what your options are.

And finally, a few other tips:

• Dress comfortably: Casual and golf attire is the norm.
• Visit in-season (Jan–April) and off-season (summer) if you can, to get a balanced sense of activity levels. The summer will be a shocker for you if you’re from the north.
• Check out anything else that’s important to you (like a gym or specific types of shopping)

Questions to Ask

Asking the right questions during a lifestyle trip to The Villages, Florida can help you decide whether it’s the right fit for your retirement or seasonal living. 

Here’s a categorized list of key questions to ask residents, staff, and yourself:

1. Questions to Ask Residents

• What do you like most about living here?
• Is there anything you wish you knew before moving here?
• How easy was it to make friends?
• Are the clubs and activities as active as they seem?
• Do you feel safe in your neighborhood and around the community?
• How’s the healthcare access and quality nearby?
• What’s the biggest downside to living in The Villages?
• Do you rent or own? How did you choose your village/home?
• Do you find the cost of living reasonable here?
• What do you do on a typical day?

2. Questions to Ask Sales or Welcome Staff

• What are the main differences between each village or neighborhood?
• What are the monthly fees (amenity fee, property tax, bond, maintenance)?
• Can you explain the bond and how long it lasts?
• Are there age restrictions or rules I should be aware of?
• What options are available if I want to rent before buying?
• How does healthcare work within The Villages? Are there urgent care or hospitals nearby?
• Are there plans for expansion or construction near the area I’m looking at?
• Can I bring my own golf cart or do I need to buy one here?

3. Questions to Ask Yourself

• Can I see myself living here full-time or seasonally?
• Am I more drawn to the active lifestyle or the social aspects?
• Do I want to be near shopping, healthcare, or golf?
• Would I prefer a quieter or more vibrant part of the community?
• How does this compare to other retirement places I’ve visited?
• Is this financially sustainable long-term based on my retirement plan?

4. Questions About Daily Life & Services

• How are grocery stores, restaurants, and shopping options?
• What’s traffic like—by car and golf cart?
• How easy is it to get around without a car?
• How reliable are services like landscaping, pest control, or home maintenance?

5. Questions About Clubs & Activities

• How do I find and join clubs or hobby groups?
• Are the fitness classes and sports facilities easy to access?
• Are there waitlists for golf or popular clubs?
• Is there a central calendar of events and activities?

Remember, you can do multiple Lifestyle Trips or move from your first one to staying longer with a rental home to really check the place out.

So if you miss something, you can hit it on the second trip. lol 

Anyway, that’s a pretty comprehensive overview of how to make the most of a Lifestyle Trip to TV. 

Is there anything you think I missed or do you have any questions for me?