April 29 - May 6, 2026
Sicily, Italy
Discover the beauty of Sicily in Palermo and Taormina. Both cities offer two unforgettable sides of the island - vibrant culture and coastal beauty.
Palermo is Sicily's capital, where centuries of history meet bold street life. Explore Arab-Norman architecture, grand cathedrals and bustling markets. Palermo delivers culture and character at every turn.
Taormina is a picture-perfect hill town perched above the Ionian Sea. Stroll charming streets lined with boutiques and cafes, take in sweeping views of Mount Etna from the ancient Greek Theatre, and relax on nearby beaches with crystal-clear water. Taormina is elegant, scenic and timeless.
Together, Palermo and Taormina create the perfect journey - rich history, incredible cuisine, stunning views and the soul of Sicily.
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Thursday, April 30th
Morning:
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Depart home cities (Wednesday, April 29th)
Afternoon:
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Scattered afternoon arrivals Arrive in PMO (40-minute transfer to hotel)
Evening:
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6:30 PM - 8:30 PM Group Dinner on the Ouverture Terrace, set atop the hotel rooftop.
DRESS CODE
Day: Comfortable travel clothes
Evening: Smart Casual - Lightweight, polished attire for mild evenings.
Layer-friendly pieces with breathable fabrics and comfortable, stylish footwear.
Friday, May 1st
Morning:
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7:00 AM - 11:00 AM Breakfast at Neobistrot at the hotel
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8:50 AM Meet in the hotel lobby.
9:00 AM Activity Departure to Erice, a Medieval hilltop town.
10:30 AM - 12:30 PM Guided visit of Erice town starting with a traditional cookie tasting.
Afternoon:
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12:30 PM Free time to wander, shop, and enjoy lunch at your own pace.
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2:30 PM - 4:00 PM Transfer back to hotel
Evening:
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Dinner on own (MEC Restaurant, Gagini, Osteria Ballaro Ingresso)
DRESS CODE
Day: Casual / active wear, comfortable walking shoes
Evening: Smart Casual - Lightweight, polished attire for mild evenings.
Layer-friendly pieces with breathable fabrics and comfortable, stylish footwear.
Saturday, May 2nd
Morning:
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7:00 AM - 11:00 AM Breakfast at Neobistrot at the hotel
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9:20 AM Meet in the hotel lobby.
9:30 AM - 12:00 PM Activity Guided walking tour of historic Palermo.
Afternoon:
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At leisure for shopping, open market, and church visits. Lunch on own.
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Recommendation: Cappadonia (best gelato)
Evening:
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6:00 PM Meet in hotel lobby for a short walk to dinner.
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6:10 PM - 9:15 PM Group Dinner at Palazzo Francavilla, a refined evening inspired by Sicilian nobility and cuisine —where you might just step into the kitchen yourself.
DRESS CODE
Day: Casual / active wear, comfortable walking shoes
Evening: Elevated chic - Dresses, jeans or pants with a dressy blouse, long sleeve button up shirts with slacks.
Sunday, May 3rd - Transfer Day!
Morning:
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7:00 AM - 11:00 AM Breakfast is included, at Neobistrot, at the hotel.
8:30 AM Bag Pull
9:20 AM Meet in the hotel lobby.
9:30 AM Departure for Taormina.
10:45 AM - 12:15 PM Guided Visit of Cefalù.
Afternoon:
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12:15 PM - 12:45 PM Free time for exploration.
12:45 PM - 1:45 PM Group Pizza Lunch
1:45 PM-4:30 PM Transfer to Taormina, arrival and check-in to Hotel Grand San Pietro.
Evening:
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Dine arounds (Arrianchiara, La Capinera, Kist, Nunziantina, Vineria Modi)
DRESS CODE
Day: Comfortable travel attire / casual / active wear, comfortable walking shoes
Evening: Smart Casual - Lightweight, polished attire for mild evenings. Layer-friendly pieces with breathable fabrics and comfortable, stylish footwear.
Monday, May 4th
Morning / Afternoon:
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7:30 AM - 10:30 AM Breakfast is included, at Giardino degli Ulivi, at the hotel.
9:50 AM Meet in the hotel lobby.
10:00 AM - 12:00 PM Activity Walking Tour of Taormina & Greek Theatre -
At leisure for shopping, sightseeing, and exploring at your own pace. Lunch on own.
12:00 PM - 3:30 PM Optional Buy-in Activity: Cooking class with Luisa.
Evening:
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6:20 PM Meet in the hotel lobby to depart for dinner.
6:30 PM - 10:30 PM La Dolce Vita Themed Group Dinner
at Canonica degli Archi, an artist’s private residence. This is and indoor/outdoor venue.
DRESS CODE
Day: Casual / active wear, comfortable walking shoes
Evening: La Dolce Vita, Through Your Own Lens: A modern Sicilian escape blending resort-chic ease, timeless 1940s–50s elegance, and vibrant Mediterranean style—flowy fabrics, linen tailoring, vintage touches, and bold, sun-soaked prints. Visit www.hooplatraveltrips.com/htmg-sicily-theme-night for inspiration and ideas!
Tuesday, May 5th
Morning:
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7:30 AM - 10:30 AM Breakfast is included, at Giardino degli Ulivi, at the hotel.
8:20 AM Meet in the hotel lobby.
8:30 AM Full Day Activity Depart for Mt. Etna & winery lunch.
9:40 AM – 12:10 PM Ascend via cable car and 4x4 minivan — guided visit of Mt. Etna up to 2,900 m (9,500 ft).
Afternoon:
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1:10 PM Lunch & wine tasting at Terre Costantino winery.
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4:00 PM Arrive back to the hotel.
Evening:
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Dinner on own
Day: Casual / active wear, comfortable walking shoes
Evening: Smart Casual - Lightweight, polished attire for mild evenings. Layer-friendly pieces with breathable fabrics and comfortable, stylish footwear.
Wednesday, May 6th
Morning:
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7:30 AM - 10:30 AM Breakfast is included, at Giardino degli Ulivi, at the hotel. Your Bag Bull and Hotel Departure times will be emailed to you the afternoon prior to your departure.
Scattered departures from Hotel
11:30 AM Official hotel check-out.
Evening:
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Arrive in home cities
Dress - Day: Comfortable travel clothes.
Rules and Regulations
This trip is exclusively for the internal use of c-suite executives at the qualifying advertiser’s business and is non-transferable to any other party. Travel will begin and end in the market from which the advertiser qualified (e.g., Charlotte, NC). If travel is required from a different city, Hoopla Travel Partners must be notified as soon as possible. Any flight deviations will be coordinated by Hoopla Travel Partners, and any associated surcharges or fare differences will be the responsibility of the participant. Please see the Transportation section for further details.
Each qualifier may bring one guest. All accommodations are based on double occupancy. Both participants and their guests must be 21 years of age or older to participate in or travel as part of this program.
Trip Communications & Documents
Updates and communications about your trip will be delivered via email up until your trip. If you have any questions, please email Allison Donnahoe at allison@hooplatravel.com. If you are not receiving any communications, please be sure to check that your email is correct on your registration and to check your spam folder. Final trip documents will be mailed approximately two weeks prior to the April 29th departure.
This pre-trip packet will include:
Program Booklet
Includes detailed itinerary, dress codes, guest list, accommodations, and helpful trip info.
Airline Confirmation
Your finalized flight details and ticket information, including record locator numbers and departure times.
Activity Confirmation
A summary of all scheduled activities you and your guest are confirmed to attend and what to wear.
Travel Insurance
Your travel insurance details and coverage info are included and will be emailed to you.
Leave at Home Card
A handy reference card with contact info and your travel schedule to share with family or a contact back home.
Luggage Tags
Custom luggage tags to help identify your bags and ensure smooth handling during group travel.
Program Inclusions
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Luxury Accommodations at Hotel et des Palmes & Grand Hotel San Pietro
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Roundtrip airfare from SAT/AUS to PMO and CTA back to SAT/AUS
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Ground transportation from PMO/CTA
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Group activity (5)
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Daily breakfast at the hotels (6)
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Lunch (1)
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Group Dinners (3)
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All program tips, taxes and gratuities
Passport Requirements
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U.S. Citizens: Must have a valid passport with at least 3 months of validity beyond the planned date of departure from Italy.
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No visa is required for stays under 90 days for tourism.
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A return or onward ticket and proof of sufficient funds may be requested.
Traveler’s Guide to Sicily
In May, Sicily daytime temperatures are between 70-75°F with evenings around 57-59°F.
Sicily operates on Central European Standard Time and is only 7 hours ahead of Central Standard Time. When it's 2:00 PM in San Antonio / Austin, Texas, it is 9:00 PM in Sicily.
The official currency is the Euro (€). It’s a good idea to carry a small amount of cash for tips, small purchases, and places that may not accept. ATMs are widely available, and opt to be charged in euros rather than U.S. dollars for better exchange rates.
U.S. travelers will need a type C plug adapter (two round prongs) or Type L (three round pins) Sicily runs on a 230V / 50Hz power supply so a voltage converter is needed for non-dual voltage appliances such as curling irons and straighteners.
Major credit cards are also accepted in most establishments.
Tipping is appreciated but not required in Sicily. For good service, a 5–15% cash tip (in Euros) is customary. All taxes, tips, and gratuities for bellmen, housekeeping, activities and included meals are already covered in your itinerary.
Sicily is a very safe destination for tourists. Just follow basic precautions—watch for pickpockets in crowded areas and use hotel safes. Tap water is safe to drink. For emergencies, dial 112 for national protection & rescue center or 113 for local police.
In Sicily, the most popular ways to get around are by taxi or Uber, both widely used for ride-hailing services across major cities.
Suggested Packing List
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Passport
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Comfortable travel attire
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Active wear T-shirt / tank top, shorts, leggings, comfortable shoes. See the activities page for more information based on your choice of activity.
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Lightweight clothing: Breathable fabrics like cotton or linen
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Smart / Resort Casual: Men: Collared shirts, dress shorts or slacks, and closed-toe shoes. Women: Sundresses, skirts, blouses, or elegant separates with dress sandals or flats.
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Swimwear
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Cover-up: Sarongs, wraps, or lightweight dresses for the beach or pool.
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Sweater / wrap / jacket for evenings
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Hat: Wide-brimmed or cap for sun protection.
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Sunglasses
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Toiletries
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Personal medications
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Tote bag or beach bag / small backpack or crossbody for excursions
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Chargers / portable battery pack
Activities
Day In Erice
9:00 AM – 4:00 PM
Step back in time as you ascend to Erice, a breathtaking medieval hilltop town perched high above the western coast of Sicily. Wander through ancient cobblestone alleys, discover Norman towers and centuries-old churches, and soak in sweeping panoramic views that stretch all the way to the North African coast on a clear day. A beloved highlight is the traditional cookie tasting — Erice is world-renowned for its exquisite almond sweets and handcrafted pastries lovingly made by local pasticcerie. Enjoy free time to explore, shop, and savor lunch at your leisure in this magical village before returning to the hotel.
Palermo Walking Tour
Discover the soul of Sicily’s capital on a guided walking orientation through historic Palermo. Explore lively piazzas, striking architecture, and colorful streets while learning about the city’s history, culture, and local life. A perfect introduction to help you get your bearings and experience Palermo like a local.
9:30 AM – 1:30 PM
Guided Tour of Taormina
10:00 AM – 12:00 PM
Discover the beauty of Taormina on a guided walking tour that brings history and scenery together. Stroll through charming streets, learn about the town's rich past and visit the famous Greek Theatre, where ancient ruins meet breathtaking views of the sea and Mount Etna.
Cooking Class with Luisa
Buy in Optional
12:00 PM – 3:30 PM
(Follows Taormina Walking Tour)
Enjoy an authentic Sicilian cooking class with Luisa. Learn to prepare traditional Sicilian dishes using fresh, seasonal ingredients. After cooking, sit down to enjoy the meal you've created, paired with local wine and unforgettable views - an intimate, hands-on experience that captures the heart of Sicily.
MT. Etna & Winery Lunch
Full Day
Embark on an extraordinary Land Rover expedition up the slopes of Mt. Etna — Europe's highest and most active volcano. Traverse dramatic lava fields, peer into ancient craters, and journey through otherworldly volcanic landscapes as your expert guide shares the fascinating geology and mythology of this legendary mountain. The adventure culminates with an exclusive winery lunch on Etna's fertile slopes, where the rich volcanic soil gives life to some of Sicily's most celebrated and distinctive wines.
Transportation
Round-trip coach airfare for two from home cities to Palermo (PMO) and returning to home cities from Catania (CTA) is included in this program. Keep an eye out for an email regarding flight information and booking. If you have requested to upgrade, you will need to pay the full cost of any difference in airfare due to upgrading at the time of booking (upgrade prices are subject to availability and may change). Rates are not guaranteed until payment is processed and booking is confirmed. Approximately two weeks before the flight, participants will receive a pre-trip confirmation letter with flight details and record locator number. If considering any type of deviation from the group flight, please let Hoopla Travel Partners know by emailing allison@hooplatravel.com. All flight deviations will be planned by Hoopla Travel Partners and surcharges/fare differences will be assessed directly to the participant.
A participant’s specific itinerary will be provided in the pre-trip confirmation letter.
The Grand Hotel et Des Palmes in Palermo, Italy, is a historic, elegant Art Nouveau luxury hotel known for its opulent interiors with frescoed ceilings, stained glass, and a blend of antique and modern decor, offering fine dining, a library, wellness center with pool, and central location near theaters and historic sites, providing a blend of tradition and modern comfort.
Accommodations
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Via Roma 398, 90139 Palermo, Italy
+39 091 2779600
Check-in: 2:00 PM
Check-out: 12:00 PM
Suspended between sky and sea, in a in a strategic position from which it dominates Taormina, the Grand Hotel San Pietro offers the privilege of an enchanting view of the Ionian Sea, surrounded by the enigmatic majesty of Etna, the poetry of Isola Bella and its cobalt tale, the Blue Grotto.
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Check-in: 2:00 PM
Check-out: 11:30 PM