Trip Itinerary

Naples & Fort Myers

April 18 – 23, 2026
Alex Demo & Jordan Demo  ·  United First  ·  6 days
Key Drives
RSW Airport → Realtor Meeting
Sat Apr 18 · ~30 min · NV Realty, 42091 Cypress Pkwy, Babcock Ranch
Babcock Ranch → Ritz-Carlton Naples
Sat Apr 18 · ~1 hr · via I-75 South
Ritz-Carlton → Captain & Krewe
Sun Apr 19 · ~15 min · 629 8th St S, Naples
Ritz-Carlton → Hogfish Harry's
Mon Apr 20 · 6:30 PM · 600 Neapolitan Way, Naples
Ritz-Carlton → Truluck's
Tue Apr 21 · 6:30 PM · 698 4th Ave S, Naples
Ritz-Carlton → Residence Inn Fort Myers
Wed Apr 22 · ~45 min · 10054 Gulf Center Dr
Residence Inn → RSW Airport
Thu Apr 23 · ~15 min · Hertz drop-off, then Terminal
Outbound Flight
UA1115 · Sat Apr 18
EWR 6:45 AM → RSW 9:49 AM
United First · Seats 02E / 02F
Return Flight
UA2461 · Thu Apr 23
RSW 11:01 AM → EWR 2:00 PM
United First · Seats 01E / 01F
Confirmation Number
XXXXXX
Hertz Rental Car
Volvo XC90 Hybrid PRESTIGE
Conf: XXXXXXXXXXX
Pickup Sat Apr 18 · Drop-off Thu Apr 23 · 9 AM
RSW Rental Center · Modify at hertz.com →
EWR Newark — Outbound (Apr 18, ~5:00 AM arrival)
United uses both Terminal A and Terminal C at EWR. Gate assignments vary and aren't posted until ~24 hrs before departure. Plan for either terminal.
United Club (United/Star Alliance boarding pass required)
• Terminal A — near gate A27 · opens 5:00 AM
• Terminal C — upper level near gate C74 · opens 5:00 AM
• Terminal C — near gate C123 · opens 5:00 AM · showers available
Amex Centurion Lounge
• Terminal A — near gate A34 · opening 2026 (check status before trip)
Priority Pass
• No traditional lounge at EWR. Be Relax Spa (Terminal A) and Minute Suites (Terminal C) accept Priority Pass for select services.
RSW Fort Myers — Return (Apr 23, ~9:00 AM arrival)
United operates from Concourse C (gates C1–C9).
No lounges at RSW — no airline lounges, no Amex Centurion, no Priority Pass. The airport is mid-expansion ($1.1B) but lounges are not yet part of the plan.
• Concourse C has a Starbucks and Great American Bagel after security.
Saturday · April 18, 2026
6:45 AM
✈ UA1115 Departs EWR — United First
Seat 02E (Traveler 1) · 02F (Traveler 2) · Non-stop to Fort Myers (RSW)
9:49 AM
Arrive Fort Myers (RSW)
Baggage included (Premier Silver). Hertz counter in RSW rental car facility.
9:00 AM
🚗 Hertz Pickup — Volvo XC90 Hybrid
⚠ Reservation says 9:00 AM but flight lands 9:49 AM — update pickup time
~11:00 AM
🏘 Babcock Ranch Self-Tour (90 min)
~30 min drive from RSW. See Babcock Ranch tab for stops & realtor contact.
~12:30 PM
Depart Babcock Ranch → Naples
📍 Navigate to Ritz-Carlton Naples
~1 hour drive south to Naples via I-75.
4:00 PM
🏨 Check-in: The Ritz-Carlton Naples, Tiburón
Sunday · April 19, 2026
Evening
🍽 Dinner: Captain & Krewe Seafood Market & Raw Bar
Walk-in only (no reservations). Open until 8 PM.
📍 Navigate to Captain & Krewe · (239) 263-1976 · cknaples.com
Monday · April 20, 2026
6:30 PM
🍽 Dinner: Hogfish Harry's Restaurant + Bar
OpenTable confirmed — party of 2.
📍 Navigate to Hogfish Harry's · (239) 776-7623 · hogfishharrys.com
Tuesday · April 21, 2026
6:30 PM
🍽 Dinner: Truluck's Ocean's Finest Seafood & Crab
OpenTable confirmed — party of 2. Business casual. Live piano nightly.
📍 Navigate to Truluck's · (239) 530-3131 · trulucks.com
Wednesday · April 22, 2026
11:00 AM
🏨 Check-out: Ritz-Carlton Naples
4:00 PM
🏨 Check-in: Residence Inn Fort Myers
Evening
🍽 Dinner Option: Backwater Jack's
Waterfront casual dining at Bonita Bay Marina. American & seafood — tiki bar vibe with elevated food. Indoor, screened porch & bar seating. Wed–Sun 3–9 PM. Happy Hour 3–5 PM & 8–9 PM. $$–$$$.
⚠ Non-residents must call ahead — you'll be cleared through the Bonita Bay gate. Cashless (cards only). 20% auto-gratuity.
📋 Reserve on OpenTable · 📍 Directions · (239) 992-3010 · backwaterjacksbonita.com
Thursday · April 23, 2026
Early AM
🏨 Check-out: Residence Inn Fort Myers
⚠ Flight departs 11:01 AM — check out early and head to RSW
~9:00 AM
🚗 Hertz Drop-off — Volvo XC90 Hybrid
11:01 AM
✈ UA2461 Departs RSW — United First
Seat 01E (Traveler 1) · 01F (Traveler 2) · Non-stop to Newark (EWR)
2:00 PM
Arrive Newark Liberty (EWR)
Detail Traveler 1 Traveler 2
eTicket016XXXXXXX001016XXXXXXX002
MileagePlusPremier SilverMember
Miles Earned8,640 award · 1,080 PQP · 2 PQF5,400 award · 1,080 PQP · 2 PQF
Outbound Seat02E (EWR→RSW)02F (EWR→RSW)
Return Seat01E (RSW→EWR)01F (RSW→EWR)

~30 min drive from RSW. Lennar golf community comparison. Discovery Center → Babcock National → Webb's Reserve.

🧑‍💼 Sample Realtor — NV Realty Group

Babcock Ranch resident · 13 yrs experience · 118 sales · 5.0★ reviews

Stop 1: Discovery Center

~11:00 AM · Founder's Square

Speak with a Town Ambassador, pick up community map. Request directions to Babcock National & Webb's Reserve Lennar models.

📍 Navigate to Founder's Square
42850 Crescent Loop, Punta Gorda, FL 33982

↓ Drive ~5 min south on Babcock Ranch Rd

Stop 2: Babcock National

~11:15 AM · Guard-gated · Lennar estates $750K+

Established premier golf neighborhood. 18-hole Gordon Lewis course. Tell gate guard you're visiting the Lennar Sales Center. Focus on luxury estate models. Park near clubhouse.

📍 Navigate to Babcock National
43101 Greenway Blvd, Punta Gorda, FL 33982

↓ Drive ~5 min to Webb's Reserve

Stop 3: Webb's Reserve

~11:55 AM · Flagship luxury · Lennar mid-$700s–$1M+

18-hole Jack Nicklaus course, aqua driving range & putt-putt. Newer construction. High-end finishes and customizable features.

📍 Navigate to Webb's Reserve
44500 Webb's Reserve Blvd, Punta Gorda, FL 33982

↓ Depart ~12:30 PM → ~1 hr drive to Naples via I-75

Three communities, all in your price band ($750K–$1.2M), all with bundled or amenity-rich golf, large resort clubhouses, and zero-entry pools.

Total time: ~90 min (65 min on-site + ~25 min driving). Gated access requires a licensed realtor — engage your realtor first.

🧑‍💼 Sample Realtor — Lakewood Ranch

Licensed realtor required for gated access. Start with a 15-min discovery call before the trip; meet them at Stop 1.

Stop 1: Del Webb Lakewood Ranch

20 min · $600K–$1.1M · Massive amenity campus · Resort + lap pools · 55+

Del Webb's 30,000+ sq ft clubhouse is the amenity benchmark — resort pool, lap pool, fitness center, pickleball, and a full social calendar. Tour the clubhouse and one model. Note: 55+ active adult community.

Realtor Guidance: Ask about resale vs. new build trade-offs and whether the 55+ restriction works for your situation. Your realtor can confirm current sub-$1.1M resale inventory.

📍 Navigate to Del Webb
17501 E State Road 70, Lakewood Ranch, FL 34202

↓ Drive ~10 min north on Lorraine Rd to Asolo Blvd

Stop 2: Esplanade at Azario

20 min · $750K–$1.3M · Bundled golf (deeded homes) · Culinary Center · Spa

Newer Esplanade with a distinctive rolling 18-hole course (rare for SW Florida). Signature Culinary Center, wellness spa, resort pools, Bahama Bar. The flagship for "Esplanade Lifestyle."

Realtor Guidance: Critical — verify which specific homes have deeded bundled golf (not every home does). Also ask about CDD fees: newer villages can add $1,500–$3,000+ annually on top of taxes. Have your realtor flag worthwhile builder upgrades.

📍 Navigate to Esplanade at Azario
4016 Santa Caterina Blvd, Lakewood Ranch, FL 34211

↓ Drive ~12 min north via Uihlein Rd to The Masters Ave

Stop 3: Lakewood National Golf Club

25 min · $500K–$1.1M · Best value · Bundled golf (all homes) · 36 holes

The powerhouse of bundled golf: 36 holes (Commander & Piper courses), grand clubhouse, full-service spa, tiki bar, zero-entry resort pool. Strongest amenity-to-price ratio of the day.

Realtor Guidance: Have your realtor break down the full monthly carrying cost — HOA fees can run $500+/mo but cover golf, amenities, and lawn care. Understand exactly what's bundled before falling for the lifestyle.

📍 Navigate to Lakewood National
17605 Lakewood National Pkwy, Lakewood Ranch, FL 34211