Sicily: A Tapestry of Time
April 14-20, 2027
From: $5595
Activity Level — Moderate
This tour is not suitable for those in a wheelchair or with mobility issues.
Trip Overview
Travel solo—but never feel alone—on this welcoming small-group journey to Sicily designed especially for women who love to explore and connect with others along the way.
This trip brings together a small circle of curious, adventurous women who enjoy discovering new places, sharing great meals, and forming friendships through travel.
With experienced local tour leaders guiding the way, you’ll explore Sicily at a relaxed pace while enjoying the camaraderie that comes from traveling with like-minded women.
Along the journey, we’ll visit some of Sicily’s most memorable places together:
The charming historic island of Ortigia
Lively markets and historic streets in Palermo
The remarkable ancient ruins of the Valley of the Temples
The elegant Baroque beauty of Noto
Sicily’s long history—shaped by Greeks, Romans, Arabs, and Normans—means every town has stories to share.
From the stunning mosaics of Villa Romana del Casale to the seaside lanes of Ortigia, each day brings something new to discover together (while enjoying a granita?).
This Bold Spirit journey is about more than seeing beautiful places. It’s about enjoying meaningful conversations, laughter over long dinners, and the simple joy of exploring the world with a supportive group of women.
We’ll take care of the logistics so you can relax, connect, and fully revel in your spring adventure in Sicily.
MAIN ATTRACTIONS
Relax as your expert tour leader manages all the logistics
Explore fascinating Palermo, once the most powerful city in the Medieval world
Stroll amongst the Ancient Greek Temples of Agrigento
Embrace your inner oenophile at a wine-tasting lunch
Wander the charming streets of seaside Ortigia
Shop for treasures at local markets
Walk Ortigia and try local sweet treats with your guide
Visit the spectacular Roman mosaics of Villa del Casale
Indulge in the Sicilian answer to the snow cone, the granita
Sample formaggi at an award-winning cheese producer’ s farm
Learn the secret ingredients to Sicilian cooking at a hands-on culinary class
Browse the boutiques in Palermo, Ortigia, and Noto
Delight in excellent Sicilian meals with the group
Admire the golden-hued Baroque buildings of Noto
Stay in a historic country inn with lush gardens
Meet a local artisan and learn about “carri” (hand-painted festival carts)
Meet other bold women who love travel as much as you do!
Activity Highlights
Historical sites
Wine tasting
Cooking class
Roman & Greek ruins exploration
Local market visits
Walking tours
Local cheese maker visit
Relaxing in charming cafes
Connecting with other Bold Spirit women
DETAILED Itinerary
Day 1: Ciao! Welcome to Palermo
Arrive at Palermo Airport (PMO) and enjoy a private transfer to your hotel in the heart of the old town.
Check-in is at 3:00 PM, but if you arrive earlier, feel free to drop off your luggage and take a stroll through the lively streets nearby.
In the afternoon, meet your guide and fellow travelers for a brief orientation, followed by a guided walking tour to discover Palermo’s rich history and vibrant culture.
Later, join the group for a welcome dinner and savor your first delicious Sicilian meal—perfect for connecting with your new Bold Spirit travel companions and kicking off your adventure together.
Meals: Welcome dinner & orientation cocktail
Hotel: Palazzo Brunaccini in Palermo or similar
Day 2: A Taste of Palermo
It’s OK to eat granita siciliana everyday; you’re on vacation.
Start the morning exploring one of Palermo’s lively markets with a local chef, selecting fresh ingredients for a hands-on Sicilian cooking class.
Enjoy the meal you prepare for lunch, then spend the afternoon at leisure browsing shops or join an optional visit to the Norman Palace and the dazzling Palatine Chapel, famous for golden mosaics and historic role as the seat of Sicily’s parliament.
Dinner on your own this evening. Our tour leader will have restaurant recommendations for you.
Meals: Breakfast, Lunch cooking class
Hotel: Palazzo Brunaccini in Palermo or similar
Day 3: Sicilian Heartland
In Sicily, life unfolds deliciously slowly—with late-night dinners, sun-soaked markets, and a culinary heritage shaped by centuries of Mediterranean trade and conquest. This is one of the best places to try cannoli and all manner of pistachio-flavored delicacies.
Today we travel south, leaving bustling Palermo behind for the peaceful Sicilian countryside.
Along the way, we’ll stop at an award-winning local cheese farm to see how fresh ricotta is made, watch the traditional art of shaping cheese into festive animal figures, and enjoy a tasting.
After lunch together at the farm, we’ll continue to our charming countryside hotel.
Take time to relax in the gardens or stroll to the nearby coast before dinner at the hotel’s restaurant.
Meals: Breakfast, Lunch at cheese producer, Dinner
Hotel: Countryside historic inn near seaside
Day 4: Valley of the Temples
This morning, meet a local artisan and marvel at the skill that goes into creating Sicily’s famous “carri” (hand-painted festival carts).
Then, wander Agrigento’s charming main street, peek into pastry shops, browse local crafts, and stop for a leisurely lunch at a trattoria.
In the afternoon, get ready for one of the trip’s highlights: the UNESCO World Heritage Valley of the Temples. Walk among some of the Mediterranean’s best-preserved Greek temples and imagine life back in ancient times—no toga required!
Later this evening, enjoy a group dinner back at our hotel.
Meals: Breakfast, Dinner
Hotel: Countryside historic inn near seaside
Day 5: Roman Mosaics of the Villa del Casale
Ciao for now to our countryside hotel — we are headed to Ortigia.
Today we travel to Sicily’s east coast, stopping to admire the spectacular Roman mosaics of Villa del Casale—perfectly preserved under a landslide for a thousand years, including the first-ever “bikini” depicted on a weightlifting woman.
Continue onward to Ortigia, a small island rich with Greek history.
Enjoy a casual orientation walk with your tour leader, sample local treats like granita and cannoli, and settle in for two nights at your charming waterfront hotel.
Dinner on your own this evening.
Meals: Breakfast, Mini Sweets Tasting Tour in Ortigia
Hotel: Small boutique hotel on the Ortigia waterfront
Day 6: Baroque Beauty in Noto
This morning, your driver will take you to the charming Baroque town of Noto, where golden limestone buildings and ornate balconies sparkle in the sun.
Stop for a cappuccino before heading into Sicily’s wine country to visit a small, organic, locally-focused winery.
Enjoy a wine tasting and light lunch, then return to Ortigia to relax, explore, or do some shopping in the city’s many tempting boutiques. Ortigia is a great place to purchase ceramics.
Later, our Bold Spirit group will gather for a farewell dinner. Raise a glass and say cheers to a wonderful Sicilian adventure and new friendships!
Meals: Breakfast, Winery Lunch, Farewell Dinner
Hotel: Small boutique hotel on the Ortigia waterfront
Day 7: Ciao for now
Alas, our adventure has come to an end.
After breakfast at the hotel, it’s time to say farewell to all your Bold Spirit friends before you head to the Catania airport (note that you met us at the Palermo airport at the start of this trip).
There will be one private group transfer to the airport in Catania (CTA). The transfer will be for flights after 12:30PM on this day.
Your tour leader can also help you arrange a private transfer at your own expense for earlier / later departures, or for those who plan to stay on another day or two in Ortigia or Catania.
Our hotel in Ortigia is about 1 hour from the Catania airport.
If you have the time, consider spending two nights in Catania before flying home. We can recommend a great hotel for you.
Want to see more of Italy? Think about flying to Rome or to Naples to extend your adventure
*There are many international international flights out of Catania to North America and to Rome.
Meals: Breakfast
What’s Included:
Seven days and six nights at beautiful hotels and inns
An English-speaking Bold Spirit tour leader accompanying you every step of the way
All meals as indicated in the detailed itinerary (lunches and dinners include one glass of wine)
Private land transfers for the Bold Spirit group throughout the entire adventure
A small group experience—no more than 15 Bold Spirit women travelers
Local expert guides showing you the best of the region
All equipment needed for activities
A session over Zoom to get you ready for this Bold Spirit adventure (1 month or so before the trip to meet other guests)
A packing list
A WhatsApp group to connect with your travel buddies
What’s Not Included:
Round-trip airfare
Cost for additional activities
Taxis to the airport or train station on departure day if you do not travel with the group transfer on Day 7
Meals not outlined in the detailed itinerary
Alcoholic beverages (lunches and dinners do include wine, but not cocktails)
Personal expenses, such as souvenirs
Travel insurance
Private room upgrade (only a few available)
Early hotel check-in
Room service/minibar
Laundry
Tips for guides and drivers
What to Bring on This Adventure:
Comfortable walking shoes
Dressy attire for nights out to dinner
Day pack or bag
Reusable water bottle
You will receive a detailed packing list upon registering
Travel Insurance
Insurance is strongly recommended for your Bold Spirit trip.
We highly recommend that you obtain adequate coverage for cancellation, curtailment, and loss of luggage and personal effects.
Your deposit and final trip balance can then be recovered via a claim to your insurance provider in the event that you must cancel your adventure due to unforeseen circumstances.
No refunds are issued 90 days or fewer from departure.
Check out travel insurance options at Tinleg, Squaremouth, and WorldNomads.
Read all about travel insurance here on our site.
Other Considerations
Our itinerary is subject to change based on availability and unforeseen conditions.
Get ready to do plenty of walking on this trip.
Some paths will take us over rough ground at archaeological sites and across cobbled or uneven streets in town centers. A good level of fitness and confident footing will help you make the most of the adventure. Bring a walking stick if you have balance issues. Wear comfortable, good walking shoes.
The minimum group number for this trip to run is six participants. Do not purchase your flights until the tour is confirmed.
Payment dates:
Deposit: $700 upon registering
2 subsequent payments
You must abide by Italian rules and COVID protocols. Bold Spirit Travel is not responsible if you cannot enter the country due to lack of vaccination or other entry requirements.
Refund amounts are determined as follows:
Upon registration: non-refundable deposit *
120+ days before trip: Full refund minus non-refundable deposit
120–90 days before trip: 50% of balance minus non-refundable deposit
90 days or fewer before trip: No refund
*We use your deposit to secure your hotel room and guides. This is why it is not refundable. Please get travel insurance to cover this cost if you think you may need to cancel the trip for some reason (see above).
Luggage:
1 wheel-on bag no more than 50lbs (you need to be able to handle your luggage on your own — can you lift what you packed?)
1 day pack
1 purse
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