Trip Overview
Delight in an eight-night private charter circumnavigation of Sicily aboard the iconic Sea Cloud II. Beginning and ending in Malta, the journey includes one night in Valletta, the capital of the island nation and one of the most concentrated historic areas in the world. Visit Sicily’s treasures with stops in Trapani, Palermo, Giardini Naxos, and Syracuse. Marvel at archaeological and architectural wonders, including the ancient city of Segesta, the riches of Palermo’s Norman Palace, and the Greek amphitheater of Taormina.
The itinerary also features a full day in the Aeolian Islands, one of six UNESCO World Heritage sites visited, along with a specially timed sunset sailing through the Strait of Messina. Sample the rich flavors of Marsala with a guided tasting. Life aboard combines the romance of classic sailing with the highest standards of modern comfort.
An optional two-night pre-trip extension is available, offering an unforgettable introduction to Malta and Gozo.

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Schedule by Day
Click each drop-down below to view a detailed itinerary. For a full view, please select "print page".

Pricing
More information on the cabin categories can be found on the ship webpage here.
Cabin Category | Double Occupancy | Single Occupancy |
|---|---|---|
Category 1 | $8,990 per person | $13,990 |
Category 2 | $11,990 per person | $18,590 |
Category 3 | $13,490 per person | $20,790 |
Category 4 | $13,990 per person | Inquire |
Category 5 | $14,990 per person | Inquire |
Category 6 | $15,990 per person | Inquire |
Category 7 | $18,990 per person | Inquire |
To reserve a space on this program, a $2,000 deposit is required per person. Final payment is due 120 days before departure (January 24, 2027) payable by check, wire transfer, or credit card (credit card payments will incur a processing fee of 2%). Participants will receive an invoice directly from the tour operator, Criterion Travel for all subsequent payments after the initial deposit.
Notification of cancellation must be received in writing by HAA from the participant. Cancellations received within 14 days of booking are eligible for a full refund, provided that initial deposits were made 121 days or more prior to departure. After 14 days, $1,000 per person becomes non-refundable.
The program terms and conditions can be found here and must be acknowledged upon registration.
Accommodations
- 8 nights aboard Sea Cloud II
Optional Pre-Tour Extension: Malta
May 22 - 25, 2027
This two-night pre-trip extension offers an unforgettable introduction to Malta beyond its capital. Discover the island’s stunning landscapes and local charm, including a day trip to the idyllic island of Gozo to see the world’s oldest megalithic temples. Explore the south coast, starting with the awe-inspiring Haġar Qim complex, then visit the colorful fishing village of Marsaxlokk. Dine within the ancient walls of M’dina, and spend two nights at the centrally located Excelsior Hotel. Cross to Gozo to visit the UNESCO World Heritage Site of Ġgantija and the charming city of Victoria, then return to Valletta to join the main Sea Cloud II tour with the rest of the group.
Overnight: Excelsior Hotel (2 nights)
Meals:
- $1,690 per person, double occupancy
- $2,190 single occupancy
The opportunity to register for the extension will be provided directly from the tour operator following the participants confirmation on the program
What to Expect
This promises to be a memorable journey, but as with all travel, a flexible attitude, a spirit of adventure, and a willingness to explore new areas will enhance your enjoyment of this program. We are sure you will be pleased with the exciting educational program provided, but we want you to be aware of the pace and activity level. This is a moderately strenuous program, at times physically demanding and busy, with considerable walking at some sites. You do not have to participate in all the scheduled activities, except when traveling to the next destination. Daily activities can involve up to two miles of walking, often on uneven surfaces; elevators may not be available and stairs may not have handrails. The ship does not have an elevator, so you will need to navigate stairs, possibly while on choppy seas. You will need to climb into and out of tenders for two shore excursions (staff and crew will be on hand to assist). Participants should be fit and in active good health. Limited medical facilities are available on board the Sea Cloud II. Any physical condition requiring special attention, diet, or treatment must be reported. All reasonable efforts will be made to accommodate special diets and treatment, but medical service and treatment is generally not at the level found in the U.S. Participants must be in good physical and mental health to keep up with the group's pace. Those requiring extraordinary assistance must bring someone to provide the necessary help. This program ranges from moderately active to very active, depending on your chosen activities. Travel will be by private motorcoaches or vans. We suggest to all participants to obtain a medical evacuation insurance policy.