✈️ DD Travel

Simple · Fun · Memorable

Las Vegas

Thursday, October 22 – Monday, October 26, 2026

Travel party: Dan & Elaine DiMaggio · Gentry & Lynn Ganote

Home base: Wynn Las Vegas — four nights

Trip Photos

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Top 10 Things to Do

Ten things to do in Las Vegas, with where to find each one.

  1. “O” by Cirque du Soleil — Bellagio, center Strip
  2. Michael Jackson ONE — Mandalay Bay, south Strip
  3. Grand Canyon helicopter tour — Maverick terminal, 6075 S. LV Strip
  4. Red Rock Canyon scenic drive — approx. 17 miles west of the Strip
  5. Hoover Dam tour — Boulder City, approx. 35 miles southeast of LV
  6. High Roller observation wheel — LINQ Promenade, center Strip
  7. Mob Museum — 300 Stewart Avenue, downtown Las Vegas
  8. Italian cooking class at Eataly — Park MGM, center Strip
  9. The Magician’s Study — Park MGM, center Strip
  10. Dig This Las Vegas — 800 W. Roban Avenue, south of the Strip

Upcoming Trips

Where we're headed, in the order they arrive.

The Las Vegas Strip lit up at night

Las Vegas

Thursday, October 22 – Monday, October 26, 2026

Four nights at the Wynn with Gentry & Lynn — golf at Cascata, Earth, Wind & Fire at the Venetian, and the Raiders at Allegiant Stadium.

Naples Pier stretching into the Gulf of Mexico from a white sand beach

Naples, Florida

Saturday, February 20 – Saturday, March 6, 2027

Gulf Coast sunsets, soft sand, and the landmark Naples Pier. A relaxed beach fortnight with unhurried mornings and easy strolls along Fifth Avenue South.

Turquoise water and white sand at Grace Bay, Turks and Caicos

Turks & Caicos Spring Break

Sunday, April 5 – Sunday, April 12, 2027

Grace Bay's turquoise water and powder-white sand over spring break. A full week on the beach with boat days and fresh seafood.

🌲

Maine

July 2027

Pine woods, cold clear water and long northern evenings. A summer week built around the coast, the lakes and unhurried days outdoors.

🌺

Hawaii

Monday, October 5 – Wednesday, October 20, 2027

Two full weeks in the islands — volcanic landscapes, warm water, and sunsets worth planning the day around.

Turquoise water and white sand at Grace Bay, Turks and Caicos

Turks & Caicos

April 2 – 9, 2028

A return to Grace Bay. A quiet island escape built around the beach, boat days, and fresh seafood.

🏰

Paris to Prague

May / June 2028

A journey across the heart of Europe, from Parisian boulevards to the spires of Prague, with classic cities and countryside in between.

🛳️

Western Caribbean Cruise

September 2028

Warm water, easy sea days and a new port each morning. All the unpacking done once.

🚗

Maine Coastal Road Trip

October 2028 · Portland to Bar Harbor

Autumn color along the Down East coast, from Portland's waterfront north through harbor towns to Bar Harbor and Acadia.

Photos: Las Vegas by Frank Schulenburg (CC BY-SA 4.0) · Naples Pier by Marc Ryckaert (CC BY 4.0) · Grace Bay by Csouthard (CC BY-SA 3.0), via Wikimedia Commons.

Daily Plan

Travel Day

Day 1 — Thursday, October 22 (TRAVEL DAY)

  • ~6:30aCarey Limousine to Atlanta airport — not yet booked
  • 11:02aDelta DL 466 — Atlanta to Las Vegas
  • 12:21pArrive Harry Reid International (LAS)
  • ~1:30pCab to the Wynn
  • ~2:30pCheck in at the Wynn — Panoramic View Room
  • ~5:00pMeet up with Gentry & Lynn — hospitality hour
  • 6:00pDinner at Sinatra
  • AfterNightcap somewhere in the Wynn — spot to be chosen
Golf Day

Day 2 — Friday, October 23 (GOLF DAY)

  • EarlyBreakfast at the Wynn — several options
  • ~8:20aDan & Gentry depart the Wynn for Cascata
  • 10:06aTee time at Cascata — Dan & Gentry
  • ~10:00aElaine & Lynn — spa, tasting or workshop, to be decided
  • EveningDinner with “The Jimmy Whale” at The Poodle Room — time to be confirmed
Football & Show Day

Day 3 — Saturday, October 24 (COLLEGE FOOTBALL & SHOW)

  • MorningBreakfast — to be decided
  • DayCollege football at a sports book — Wynn or Circa
  • ~6:00pDinner at the Venetian or Palazzo — restaurant to be chosen
  • 8:30pEarth, Wind & Fire at the Venetian
Raiders Day

Day 4 — Sunday, October 25 (RAIDERS DAY)

  • 9:45aLimo pickup to Mandalay Bay — tentative
  • 10:30aPregame brunch at Flanker, early NFL games on
  • 11:45aWalk to Allegiant Stadium with the crowd
  • ~NoonEnter the stadium — premium areas and warmups
  • 1:25pRaiders vs. Rams kickoff
  • EveningDinner back at the Wynn — restaurant to be chosen
Travel Home Day

Day 5 — Monday, October 26 (TRAVEL HOME DAY)

  • ~9:30aCab to Harry Reid International (LAS)
  • AirportBreakfast at the airport or the Delta Sky Club
  • 12:31pDelta DL 748 — Las Vegas to Atlanta
  • 7:25pArrive Atlanta
  • ~7:25pCarey Limousine home — not yet booked

Hotel

One hotel for the whole trip. Stay dates and guests up front, then Show Details for contacts, the room, the open upgrade question and your own notes.

Wynn Las Vegas

Las Vegas, Nevada · Days 1–5 · Panoramic View Room

Check-inThu, Oct 22~2:30 PM
Check-outMon, Oct 26Depart ~9:30 AM
Nights4Oct 22 – 26, 2026
Conf # 32779131

Guests: Dan & Elaine

Also staying in Las Vegas: Gentry & Lynn

Dining

Every meal in the master itinerary, in travel-day order. Booked restaurants carry their reservation number; the rest are the shortlists still to be chosen from.

Day 1 · Thu, Oct 22 · Travel Day

Sinatra

Dinner · 6:00 PM · Booked

Address: 3130 S Las Vegas Blvd — at the Wynn

Phone: 1-888-320-7110

Reservation #: 9FUJ9T4NJC37

Getting there: On property. Walk from the room.

After Dinner — Wynn Late-Night Bars

After dinner · Spot to be chosen

Overlook Lounge: Best scenery.

Aft Cocktail Deck: Open-air deck.

Tower Suite Bar: Quiet upscale nightcap.

Eastside Lounge: Live music and dueling pianos.

Little Bubble Bar at Delilah: Old Vegas glamour.

Getting there: All of them are inside the Wynn.

Day 2 · Fri, Oct 23 · Golf Day

Breakfast At The Wynn

Early morning · Place to be chosen

Tableau: Best upscale breakfast. Beautiful, quiet room by the Tower Suites pool and gardens.

Terrace Pointe Café: Best everyday breakfast. More casual, overlooking the pool and gardens.

The Buffet at Wynn Las Vegas: Best big Vegas breakfast and brunch.

Sunrise at Sinatra: Newer full-service breakfast and lunch at Encore, more elegant.

Caffè Al Teatro: Best quick breakfast and open 24 hours — coffee, croissants, breakfast sandwiches, smoked-salmon bagels, fruit and pastries.

Urth Caffé: Casual coffee-shop breakfast with lighter options.

Note: Dan and Gentry leave for Cascata around 8:20 AM, so breakfast needs to be early.

The Poodle Room

Dinner with “The Jimmy Whale” · Time to be confirmed

Address: 2777 S Las Vegas Blvd — top of the Fontainebleau

Phone: Poodle Club concierge, 702-678-0560

Reservation: Gentry made it. Time still to be confirmed.

Getting there: Allow about 20 minutes for travel from the Wynn.

Dress: High-end and upscale — dress nicely. There is a cigar lounge.

Day 3 · Sat, Oct 24 · Football & Show Day

Breakfast

Morning · To be decided

Nothing planned yet. The Wynn breakfast list from Friday all still applies.

Dinner At The Venetian

Dinner · ~6:00 PM · Restaurant to be chosen

Why here: Convenience — Earth, Wind & Fire is at the Venetian at 8:30 PM.

Bazaar Meat by José Andrés: Palazzo. Upscale, memorable and different; called one of Vegas's best steakhouses.

CUT by Wolfgang Puck: Palazzo. Beautiful room, excellent beef and polished service.

Delmonico Steakhouse: Venetian. Emeril Lagasse's steakhouse — less flashy, extremely well regarded.

Mott 32: Palazzo. The choice for something other than steak — high-end Cantonese in a spectacular room, known for Peking duck.

Day 4 · Sun, Oct 25 · Raiders Day

Flanker — Pregame Brunch

10:30 – 11:45 AM · Tentative

Address: Mandalay Bay, Las Vegas

Reservation: Online inquiry submitted August 12 — not yet confirmed.

What it is: Pregame brunch and lunch with Bloody Marys and cocktails, watching the early NFL games. Flanker opens at 9 AM on Sundays.

Getting there: Limo from the Wynn at 9:45–10:00 AM, then walk to Allegiant Stadium at 11:45 AM with the crowd.

Dinner At The Wynn

Evening · Restaurant to be chosen

SW Steakhouse: Excellent steaks, real Japanese Wagyu, polished service, and the Lake of Dreams setting. Classic high-end Vegas dinner.

Sinatra: Elegant and quieter, old-school Vegas feel with osso buco, pastas and Italian-American classics.

Mizumi: Sushi, sashimi, robata and teppanyaki beside the waterfall and gardens.

Getting there: All on property, after the game.

Day 5 · Mon, Oct 26 · Travel Home Day

Breakfast At The Airport

Morning · At LAS

Breakfast at the airport or in the Delta Sky Club before the 12:31 PM flight.

Transportation

Every flight, limo and cab in the master itinerary, in travel-day order. Departure time and the from → to leg sit at the top of each card, with the confirmation number right below. Anything not yet booked says so.

Day 1 · Thursday, October 22 · Travel Day

Limo to Atlanta, the midday Delta flight west, then a cab up the Strip.

Carey Limousine — Home to Atlanta Airport

Day 1 · Thu, Oct 22 · ~6:30 AM pickup

Departs~6:30 AMThu, Oct 22
FromHomeCurbside pickup
ToAtlanta AirportATL

Status: Not yet booked — to do.

Type: Private car service

Passengers: Dan & Elaine

Phone: 404-223-2000

Delta Air Lines — Flight DL 466

Day 1 · Thu, Oct 22 · 11:02 AM departure

Departs11:02 AMThu, Oct 22
FromAtlantaATL
ToLas VegasLAS
Conf # G7MGX

Arrives Las Vegas: Thursday, October 22 at 12:21 PM local time

Seats: 2A & 2B — Dan & Elaine

Cab — Airport to the Wynn

Day 1 · Thu, Oct 22 · ~1:30 PM

Departs~1:30 PMAfter baggage
FromLASTaxi stand
ToWynnCheck-in ~2:30 PM

Type: Taxi from the airport rank — no booking needed

Journey: About 15–20 minutes up the Strip

Day 2 · Friday, October 23 · Golf Day

Out to Boulder City for the morning round, then across to the Fontainebleau for dinner.

Wynn ⇄ Cascata Golf Course

Day 2 · Fri, Oct 23 · Departs ~8:20 AM

Departs~8:20 AMFri, Oct 23
FromWynnDan & Gentry
ToCascataBoulder City · ~9:00 AM

Status: Transportation to and from Cascata still to be arranged.

Distance: About 30 miles southeast of the Wynn — allow roughly 40 minutes

Tee time: 10:06 AM

Course phone: 702-294-2005

Wynn to the Fontainebleau

Day 2 · Fri, Oct 23 · Evening

DepartsEveningTime TBC
FromWynn3131 Las Vegas Blvd S
ToFontainebleau2777 S Las Vegas Blvd

Type: Cab or rideshare — no booking needed

Journey: Allow about 20 minutes

Notes: Departure time depends on the Poodle Room reservation, which Gentry is confirming.

Day 3 · Saturday, October 24 · Football & Show Day

Nothing booked. The Wynn sports book is on property; Circa is downtown on Fremont Street, and the Venetian is a short cab or a walk up the Strip.

Around the Strip

Day 3 · Sat, Oct 24 · As needed

Type: Cabs and rideshare — no booking needed

Wynn to the Venetian: A few minutes by cab, or about a 15-minute walk south along the Strip

Wynn to Circa, downtown: About 15 minutes by cab to 8 Fremont St

Day 4 · Sunday, October 25 · Raiders Day

One limo down to Mandalay Bay in the morning; the walk to Allegiant Stadium happens on foot with the crowd.

Limo — Wynn to Mandalay Bay

Day 4 · Sun, Oct 25 · 9:45–10:00 AM pickup

Departs9:45 AMSun, Oct 25
FromWynnLimo pickup
ToMandalay BayFlanker · 10:20–10:30

Status: Tentative — part of the Flanker pregame plan still to be confirmed.

Onward: Leave Flanker at 11:45 AM and walk to Allegiant Stadium with the crowd; enter around noon.

Day 5 · Monday, October 26 · Travel Home Day

Cab to the airport, the early-afternoon flight east, then the limo home.

Cab — Wynn to the Airport

Day 5 · Mon, Oct 26 · ~9:30 AM

Departs~9:30 AMMon, Oct 26
FromWynnAfter check-out
ToLASHarry Reid Intl

Type: Taxi from the hotel — no booking needed

Notes: Breakfast at the airport or in the Delta Sky Club.

Delta Air Lines — Flight DL 748

Day 5 · Mon, Oct 26 · 12:31 PM departure

Departs12:31 PMMon, Oct 26
FromLas VegasLAS
ToAtlantaATL
Conf # G7MGX

Arrives Atlanta: Monday, October 26 at 7:25 PM local time

Seats: 2C & 2D — Dan & Elaine

Carey Limousine — Atlanta Airport to Home

Day 5 · Mon, Oct 26 · ~7:25 PM

Departs~7:25 PMAfter landing
FromAtlanta AirportATL
ToHome—

Status: Not yet booked — to do.

Phone: 404-223-2000

Tickets

Everything that needs a ticket, a tee time or a reservation held in someone's name, in the order you'll use it. Tick each one off as it lands.

Cascata Golf Course — Tee Time

Morning round for Dan and Gentry at Cascata in Boulder City, about 30 miles southeast of the Strip. Rental clubs requested and forecaddies are included.

Date & TimeDay 2 · Friday, October 23, 2026 · 10:06 AM tee time
Website To Acquire Ticketsgolfcascata.com
Date Tickets Should Be AcquiredBooked — confirmation code 068515, confirmed by reply email

The Poodle Room — Dinner Reservation

Dinner with “The Jimmy Whale” at the top of the Fontainebleau. High-end and upscale, with a cigar lounge — dress nicely.

Date & TimeDay 2 · Friday, October 23, 2026 · time still to be confirmed
Website To Acquire Ticketsfontainebleaulasvegas.com
Date Tickets Should Be AcquiredGentry made the reservation — confirm the time with him

Sports Book Seating — College Football

A seat for the Saturday college football slate. The Wynn Race & Sports Book is on property; Circa Sports downtown is the bigger room and takes reservations.

Date & TimeDay 3 · Saturday, October 24, 2026 · daytime
Website To Acquire Ticketscircalasvegas.com
Date Tickets Should Be AcquiredIn advance — investigate reserved seating. Wynn 702-770-3075 · Circa reservations@circasports.com

Earth, Wind & Fire — The Venetian

Saturday night headline show at the Venetian, following dinner on the same property.

Date & TimeDay 3 · Saturday, October 24, 2026 · 8:30 PM
Website To Acquire Ticketsvenetianlasvegas.com
Date Tickets Should Be AcquiredElaine has the tickets — seat details still to come

Flanker — Pregame Reservation

Pregame brunch table at Flanker in Mandalay Bay before the walk over to Allegiant Stadium. Flanker opens at 9 AM on Sundays.

Date & TimeDay 4 · Sunday, October 25, 2026 · 10:30 – 11:45 AM
Website To Acquire TicketsOnline inquiry submitted August 12, 2026
Date Tickets Should Be AcquiredChase the reply — the whole Sunday morning plan depends on it

Raiders vs. Rams — Allegiant Stadium

Sunday afternoon NFL at Allegiant Stadium, a short walk from Mandalay Bay. Premium areas, then kickoff at 1:25 PM.

Date & TimeDay 4 · Sunday, October 25, 2026 · 1:25 PM kickoff
Website To Acquire TicketsGentry is acquiring the tickets
Date Tickets Should Be AcquiredBefore the trip — confirm with Gentry

Still To Do

Everything in the master itinerary still marked TBD or to-do, gathered in one list so nothing gets lost between now and October.

Notes

Naples, Florida

Saturday, February 20 – Saturday, March 6, 2027 · Four adults, ages 64–76. Sixteen things to do, each with its location, telephone number and website.

Things To Do · 1–16

1 · Boston Red Sox Spring Training

Baseball · Fort Myers

Watch the Red Sox at JetBlue Park in Fort Myers.

Location: JetBlue Park, 11500 Fenway South Drive, Fort Myers, FL 33913

Telephone: (239) 226-4700 · Tickets: (877) 733-7699

2 · Naples Sunset Or Dinner Cruise

Boat cruise · Naples Bay

The Naples Princess offers sightseeing, sunset and dinner cruises with climate-controlled indoor seating.

Location: 550 Port O Call Way, Naples, FL 34102

Telephone: (239) 649-2275

3 · Delnor-Wiggins Pass State Park

Gulf beach · North Naples

A beautiful Gulf beach conveniently located near North Naples.

Location: 11135 Gulf Shore Drive, Naples, FL 34108

Telephone: (239) 409-0637

4 · Naples Botanical Garden And Tram Tour

Gardens · Naples

Tour the garden’s scenic areas by tram to reduce the amount of walking.

Location: 4820 Bayshore Drive, Naples, FL 34112

Telephone: (239) 643-7275

5 · Fifth Avenue South And Third Street South

Shopping & dining · Old Naples

Spend an afternoon shopping, visiting galleries and enjoying cocktails or dinner. Valet parking is recommended.

Fifth Avenue South: 837 Fifth Avenue South, Naples, FL 34102

Telephone: (239) 692-8436

Third Street South: 1207 Third Street South, Naples, FL 34102

Telephone: (239) 649-6707

6 · Dolphin And Wildlife Cruise

Boat cruise · Tin City

Pure Florida offers narrated dolphin-watching cruises through Naples Bay, the mangroves and nearby coastal waters.

Location: Tin City, 1200 Fifth Avenue South, Naples, FL 34102

Telephone: (239) 263-4949

7 · Golf At Tiburón Golf Club

Golf · North Naples

Play either the Gold or Black course, both designed by Greg Norman. Request a tee time and rental clubs well in advance.

Location: 2620 Tiburón Drive, Naples, FL 34109

Telephone: (239) 593-2200 · Golf shop: (239) 593-2201

8 · Artis—Naples And The Baker Museum

Museum & performance · Pelican Bay

Visit the museum and combine it with a Naples Philharmonic concert, Broadway production or other evening performance.

Location: 5833 Pelican Bay Boulevard, Naples, FL 34108

Telephone: (239) 597-1900

9 · Corkscrew Swamp Sanctuary

Boardwalk nature walk · East Collier

Explore the elevated boardwalk through an old-growth cypress forest. You can turn around before completing the entire 2¼-mile route.

Location: 375 Sanctuary Road West, Naples, FL 34120

Telephone: (239) 348-9151

10 · Everglades City Airboat Adventure

Airboat tour · Everglades City

Captain Jack’s offers narrated mangrove airboat tours. Request a smaller boat and ask about ride intensity before booking.

Location: 905 Dupont Street, Everglades City, FL 34139

Telephone: (239) 695-4400

11 · Sur La Table Cooking Class

Cooking class · Mercato

Participate in a hands-on cooking class and eat the meal you prepare. This is particularly convenient from North Naples.

Location: Mercato, 9105 Strada Place, Suite 3105, Naples, FL 34108

Telephone: (239) 598-3586

12 · Naples Wine Collection Tasting

Wine tasting · Vanderbilt Beach

Sample boutique and limited-production wines. Call to determine whether a scheduled tasting or private tasting is available during your visit.

Location: 2343 Vanderbilt Beach Road, Suite 604, Naples, FL 34109

Telephone: (239) 513-0095

13 · Glassblowing In The Garden

Studio workshop · Olde Naples

Create a handblown ornament, bowl or decorative glass piece with artist Conrad Williams. Visits are by appointment only.

Location: 525 Yucca Road, Naples, FL 34102

Telephone: (239) 285-1101

14 · Fifth Avenue Culinary Tasting Tour

Walking food tour · Old Naples

Visit several restaurants and taste chef-selected dishes while learning about Old Naples. Confirm the walking distance before booking.

Meeting location: Fifth Avenue South — the precise meeting point is provided after booking

Telephone: (866) 328-7935

15 · Shelling And Dolphin Expedition

Boat cruise · Keewaydin Island

Cruise to Keewaydin Island for dolphin watching, wildlife viewing and shell collecting. Ask about boarding ease and shaded seating.

Location: Pure Florida at Tin City, 1200 Fifth Avenue South, Naples, FL 34102

Telephone: (239) 263-4949

16 · Edison And Ford Winter Estates

Historic homes & gardens · Fort Myers

Tour the historic winter homes, Edison’s laboratory, museum and botanical gardens. Allow approximately 2½–3 hours.

Location: 2350 McGregor Boulevard, Fort Myers, FL 33901

Telephone: (239) 334-7419

Before Booking

February and March are peak season, so reserve the Red Sox game, the cruises, the cooking class, the wine tasting, the glassblowing session and the Artis—Naples performance well in advance.

Confirm all 2027 schedules and operating details before booking.

Turks & Caicos Spring Break

🧭

Trip Planning In Progress

This destination is being developed and will be available in a future DD Travel update.

Maine

🧭

Trip Planning In Progress

This destination is being developed and will be available in a future DD Travel update.

Hawaii

🧭

Trip Planning In Progress

This destination is being developed and will be available in a future DD Travel update.

Turks & Caicos

🧭

Trip Planning In Progress

This destination is being developed and will be available in a future DD Travel update.

Paris to Prague

🧭

Trip Planning In Progress

This destination is being developed and will be available in a future DD Travel update.

Western Caribbean Cruise

🧭

Trip Planning In Progress

This destination is being developed and will be available in a future DD Travel update.

Maine Coastal Road Trip

🧭

Trip Planning In Progress

This destination is being developed and will be available in a future DD Travel update.