sicily

& the aeolian islands

11 nights/12 days: June 13-24, 2025

Detour with Nina & Randy

None of Italy’s wondrous corners enchants us quite so much as Sicily and her Aeolian islands. Coveted by the Phoenicians, Greeks, Romans, Arabs, Normans, French, Germans, Spanish, Italians, and even the British, sensuous Sicily blends the best of African flavors with Greek architecture and Italian fashion. Her Aeolian islands are gems cast amid expansive blue waters, white sands, and volcanic pumice, offering a respite from the frenzied pace of mainland life. Count yourself among the lucky and detour with us to this layered island and her mythical archipelago!

highlights include

  • Explore the world’s best preserved Greek temples

  • Indulge in a Sicilian cooking class

  • Unpack for 5 nights in the enchanting Aeolian Islands

  • Savor a farm fresh caper lunch and wine tasting

  • Island hop by private boat from Salina to Panarea, Stromboli, Alicudi & Filicudi

  • Discover the myths rooted in Sicily over Mythological Happy Hours with a classics expert

Sunset Pollara Salina Aeolian Islands

itinerary

Join us on a mythical odyssey around the Mediterranean’s most intriguing island and her fabled Aeolian archipelago. We’ll voyage from the ancient island of Ortygia to the green heart of Salina; walk among Agrigento’s Valley of the Temples and stand suspended above the pristine Roman mosaics of Villa Casale. From our base on sumptuous Salina, we’ll steep in the Tyrrhenian’s crystal seas, island hopping between Stromboli, Panarea, Alicudi & Filicudi. We’ll feast on the fruit of the caper flower and savor the nectar of the grape vine. We’ll summit Mt. Etna, home of Hephaestus, and sink into elegant Taormina, watching the sun fade over a sea sailed by Odysseus.

To have seen Italy without having seen Sicily is not to have seen Italy at all, for Sicily is the clue to everything.
— Goethe

Day 1: benvenuti in sicilia!

Ortygia Syracuse Sicily Italy

Friday, June 13, 2025

Our journey begins on the ancient isle of Ortygia-the historic heart of Syracuse-where we’ll gather around 6 p.m. at our hotel for a welcome reception, followed by a passegiatta (stroll) through the island to enjoy a dinner of exotic Sicilian delights.

From Catania’s Fontanarossa Airport, it is a quick, 60-minute bus or taxi ride to reach Syracuse.  We’ll meet at the hotel around 6 p.m.

Hotel: Hotel Gutkowski | Activity Level: Moderate | Meals: D

day 2: ortygia & Neapolis

Ortygia Island Syracuse Sicily Italy

Saturday, June 14, 2025

Today we peel back layers of history on a guided tour of Ortygia and the Neapolis archeological park (film location of Indiana Jones and the Dial of Destiny!). We’ll whisper in the Ear of Dionysius, explore newly opened caverns (in thanks to the filming of the movie), imagine ourselves as ancient Greeks enjoying a theatrical performance in the 2,500 year-old theater, and conclude our morning with a stroll through Ortygia’s historic center. The afternoon and evening are yours to explore Ortygia’s open air market, partake in the evening passegiatta along the yacht-filled promenade, and sample Ortygia’s delectable seafood offerings.

Hotel: Hotel Gutkowski | Activity Level: Strenuous | Meals: B

day 3: roman mosaics

Cupid & Psyche Roman Mosaics Villa Romana del Casale

Sunday, June 15, 2025

We bid Ortygia farewell and head west by private coach to the Roman hunting lodge of Villa Romana del Casale. This UNESCO World Heritage site boasts the most extensive and beautifully preserved collection of Roman mosaics in the world, offering a vivid glimpse into the opulent lifestyle of the ancient Roman elite. Inspired by this opulence, we’ll indulge in a farm fresh lunch at a nearby agriturismo before we settle into our own country retreat set among thousand year-old olive trees where we’ll enjoy dinner al fresco.

Hotel: Mandranova | Activity Level: Moderate | Meals: B, L, D

day 4: the craft of la cucina

Sicilian Cooking Class Mandranova Sicily

Monday, June 16, 2025

We’ll devote today to la cucina Siciliana, savoring the olive oils made from our hosts’ farm, discovering the exotic and refreshing flavor combinations that comprise Sicilian cooking, and even donning our own chef aprons in the kitchen—be careful, we eat what we cook!  The rest of the day is yours to doze in the shade of the olive trees, soak in the pool, or start writing your own cookbook!  We will gather this evening for a happy hour and olive oil tasting before enjoying dinner together, family style

Hotel: Mandranova | Activity Level: Light | Meals: B, L, D

day 5: valley of the (greek) temples

Valley of the Temples Agrigento in Spring

Tuesday, June 17, 2025

This morning we time travel to ancient Greek Arkagas, or Agrigento, one of the leading cities in the ancient Mediterranean. We devote our morning to the UNESCO World Heritage site of the Valley of the Temples-one of the largest and best-preserved collection of Greek temples in the world. After lunch, we’ll follow in Odysseus’ wake as we set sail (or rather, hydrofoil) for Salina, the green gem of the Aeolian Islands. Tucking into our hotel in Malfa’s historic center, we will enjoy views of chic Panarea and smoky Stromboli as we toast to Aeolus from our panoramic patio.

Hotel: Hotel Ravesi | Activity Level: Strenuous | Meals: B, L, D

day 6: giro di salina

Pollara Salina Aeolian Islands

Wednesday, June 18, 2025

Today we circle the island on a guided giro (tour) that will introduce us to Salina’s immigration history, take us to the island’s cinematic side in Il Postino’s Pollara, savor a farm fresh caper lunch and Malvasia wine tasting in Leni, linger on RInealla’s black sand beach, and set sail to explore Lingua’s salt pans. We’ll cap our tour with a refreshing granita before returning to Malfa. A happy hour overlooking the Tyrrhenian Sea concludes our day together. The evening is yours to relish Malfa’s calm, contemplating Stromboli’s smoke from our infinity pool…perhaps with a passion fruit mojito in hand!

Hotel: Hotel Ravesi | Activity Level: Moderate | Meals: B, L

day 7: chic panarea, smokin’ stromboli

Sailing Aeilian Islands with Stromboli

Thursday, June 19, 2025

This morning we embark by private boat to glitzy Panarea and explosive Stromboli. We’ll linger along the way to swim in the effervescent waters of a submerged volcano and explore nature’s geologic artistry amid towering cliffs and hidden coves. We’ll enjoy free time to get lost in Panarea’s whitewashed wandering streets before heading to Stromboli, where we’ll explore black sand beaches and enjoy an aperitivo in the shadow of the active volcano. Our day concludes admiring the Sciara del Fuoco (live eruption) of Stromboli’s volcano at sunset over dinner together on our boat, sailing back to Salina under star studded skies.

Hotel: Hotel Ravesi | Activity Level: Moderate | Meals: B, D

day 8: Lipari & Vulcano

Friday, June 20, 2025

Our odyssey continues, sailing to the archipelago’s largest and smelliest islands. We’ll bathe at the foot of Lipari’s chalky pumice quarry before proceeding to Marina Corta, where we’ll be free to explore its vibrant shops, restaurants, ruins, and museums. After lunch we continue to the sulphuric island of Vulcano with its unique moonscape, black sand beaches, and panoramic views. We return to Salina with a swim in the Piscina di Venere, where according to legend, the Goddess of Beauty came to swim before joining her husband Vulcan. The evening is yours to enjoy Malfa’s charming shops and gastronomy.

Hotel: Hotel Ravesi | Activity Level: Moderate | Meals: B

day 9: savoring salina

Mediterranean Swim at Pollara Salina Sicily

Saturday, June 21, 2025

Enjoy a vacation from your vacation today, savoring Salina in whatever style you choose. Get your shopping on in Santa Marina Salina, lounge on the black sands of Rinella, explore the island’s winding roads on e-bike or scooter, swim at Malfa’s Scaria beach, summit Salina’s highest peak of Monte Fossa delle Felici, or enjoy la dolce far niente poolside. Want to top off all seven islands? Join an excursion to elegant Lipari or sulphurous Vulcano.

Hotel: Hotel Ravesi | Activity Level: Your Choice | Meals: B

day 10: Mt. Etna, A’ Mutagna

Sylvester Crater on Mt. Etna Sicily

Sunday, June 22, 2025

Today we bid our beloved archipelago assabinirica (until we meet again) and direct our attention to one of the world’s most storied mountains, Mt. Etna, or in Sicilian, A’ Mutagna (the mountain). We will explore this mythical land of Hephaestus and the great Cyclopes, with plenty of free time to circumnavigate a crater (or more) of your choosing. We end our day in elegant Taormina, where gardens, villas, and vistas seduce travel-weary adventurers

Hotel: Splendid Hotel | Activity Level: Moderate | Meals: B

day 11: tempting taormina

Piazza IX Aprile Taormina Sicily

Monday, June 23, 2025

Perched on the clifftops overlooking the Ionian Sea, Taormina captivates with its timeless charm and breathtaking vistas. We’ll spend our morning on a guided tour, wandering cobblestone streets adorned with vibrant bougainvillea, discovering the ancient grandeur of the Greek Theater, and indulging in refreshing granita against the backdrop of smoking Mount Etna. The afternoon is yours to wander the elegant gardens, people watch from posh cafés; hike to the hilltop town of Castelmola; ride a cable car down to Isola Bella; or fulfill your White Lotus fantasy on a scooter ride. Tonight, we will enjoy a final happy hour before savoring our last dinner together. 

Hotel: Splendid Hotel | Activity Level: Light | Meals: B, D

day 12: Assabinirica sicilia!

Isola Bella Sicily with Lemons

Tueesday, June 24, 2025

Our journey together ends after breakfast.  Catania’s Fontanarossa Airport is a 45-minute shuttle or taxi ride away and we will help organize the transfer.  Whether you decide to add a few more days to your stay, or to continue your odyssey elsewhere in Europe, we will say “ni viremu prestu” (see you soon), for we know this won’t be our last detour together!

Blood Oranges Sicily
Caper Flower Salina Sicily
Aeolian Islands Sunset
Granita Salina Sicily
Temple of Concordia Valley of the Temples Agrigento Sicily

$5,895 per person (double/triple occupancy)

$6,895 per person (singe occupancy)

10% deposit

$300 early pay discount until October 13, 2024 with coupon: EARLYPAY

What our travelers are saying

  • "A highlight of the trip was the opportunity to view Stromboli's active lava flow from the boat at night. Stunning! The mythology happy hours in a beautiful outdoor setting were especially informative and fun."

    -Darla G.

  • "It was the best trip I have ever taken in MY LIFE. Doing a tour on our own wouldn’t even come close to the Sicily tour. Taunya and Randy were a great team and they made this a once in a lifetime awesome experience."

    -Sue F.

  • "This was truly a ‘dream trip’ and delivered on every detail promised. Our ‘mythological happy hours’ with Randy were so much fun and instructive on how these islands shared the spotlight on mythological stories written in past millennia."

    -Kent D.

FAQs

  • Each detour includes the price of all admissions to sights seen as a group; tours by local guides, meals as listed in the trip itinerary; accommodations each night of the detour including breakfasts; all domestic flights; all transportation required for group activities from the first hotel to the last hotel of the detour including in er-country flights (transportation for optional group activities and independent travel during the detour is not included), travel consultations and advice from our staff, guides, and vendors including suggestions, tips, and directions, and all trip leader, local guide, driver, and hotel tips. Prices do not include airfare to and from the detour, nor ground transportation to/from airports.

  • Detour prices do not include international airfare or ground transportation to/from the airport.

  • Each detour includes all breakfasts and about half of your lunches and dinners as indicated in the meal guide included in each itinerary: B=breakfast, L=lunch, D=dinner.

  • Yes! Our detours are the perfect way for children (and adults) to learn in action. We welcome and celebrate multi-generational travel. History class was never so fun!

  • Our detour begins in Ortygia (Syracuse) at our first hotel, where we will meet for a welcome reception around 6 pm. Our trip ends in Taormina, which is a 45-minute taxi ride to the Catania airport.

  • While this varies by detour, we generally plan to meet between 5-6 pm at our hotel on Day 1. If you plan to arrive a day early and want to stay in our trip hotel, please make arrangements with the hotel directly, indicating that you are part of our group.

  • Please plan to fly into and out of Catania’s Vincenzo Bellini Airport.

  • Each trip page has a “book now” button that links to our online registration and payment system. There you can pay the 10% per person deposit and choose to pay in installments or to pay the full amount.

  • Deposits are refundable for 30 days from receipt. After 30 days they are nonrefundable.

  • Final payment is due 90 days prior to detour commencement but you may pau in full any time prior to this.

  • Cancellations are allowed without penalty (excepting deposit) until the final payment deadline. After the final payment deadline 100% of funds paid are nonrefundable.

  • Each trip page has a “book now” button that links to our online registration and payment system. There you can pay the 10% per person deposit and choose to pay in installments or to pay the full amount.

  • Yes, all published prices are per person, based on double occupancy, or when available, single occupancy. Please contact us for triple occupancy pricing.

  • During the registration process you will have the opportunity to request single occupancy, if it is offered. Due to the boutique nature of our hotels, we are not always able to offer single accommodations, but are happy to pair you with another single traveler.

  • Yes. You must be able to carry your own luggage up at least three flights of stairs and on uneven ground for up to a quarter mile.

  • Dressler Detours are physically demanding. To enjoy the experience, you must be in good walking shape. The most active days may average 5 miles of walking (often over uneven surfaces and including lots of climbing/steps), lots of standing while listening to your guide during group sightseeing, and possibly stair-climbing while carrying your own bag up to your hotel room. This detour includes boat travel as well. We’ve included an activity guide for each day of our itinerary: light=mostly sedentary, moderate=walking 1-3 miles on mostly even ground, strenuous=walking 3+ miles on hills/uneven ground.