Cruising the Greek Isles with Dan O’Donnell
Embark on an unforgettable cruise through the enchanting Greek Isles, visiting some of the most iconic destinations in the Mediterranean. Begin in Athens, where ancient history and vibrant city life await. Explore the stunning caldera views of Santorini, the rich history of Crete, and the ancient ruins of Rhodes. Discover the medieval wonder of Monemvasia and the spiritual charm of Patmos. This journey offers a perfect blend of culture, history, and breathtaking landscapes, making it a must for any traveler seeking the beauty and history of Greece.

Dan O’Donnell has more than a decade of experience as a radio news anchor, reporter, and news and sports talk show host. He is a two-time winner of broadcast journalism’s prestigious national Edward R. Murrow Award and has won nearly 20 regional Murrow Awards and Wisconsin Broadcasters’ Awards for excellence. Dan has worked as a Wisconsin correspondent for FOX News Radio, CBS News Radio, ABC News Radio, In Session TV, and HLN’s “Nancy Grace.”
A lifelong Wisconsinite who grew up just four miles from WISN’s studio, Dan is a graduate of both Marquette University and The University of Wisconsin Law School. He is a licensed (but thankfully non-practicing) attorney, so please try not to hold that against him. Dan now lives in Milwaukee with his wife Megan and their three children.
Itinerary
Depart
Your adventure begins with an overnight flight to Athens, the capital city of Greece.
Arrive in Athens, Greece
Welcome to Athens, a treasure trove of antiquities where the beauty of the Acropolis, outstanding museums, charming cafés, sidewalk markets, and stunning views come together in a cultural mosaic for all to enjoy. Upon arrival in this vibrant city, we’ll head straight to one of Athens’ most popular neighborhoods—a perfect place to stretch your legs, soak in the atmosphere, and ease into Greek culture. You’ll have free time to explore at your own pace: browse local shops, people-watch from a shady café, or enjoy a delicious lunch featuring fresh Mediterranean flavors. Afterward, our group will head to the hotel to check in and relax. Later this evening, we’ll come together for a welcome dinner—a chance to get to know your fellow travelers and toast to the exciting journey ahead! (D)
Athens
Your day begins with a panoramic tour showcasing the city’s numerous highlights and monuments, including a photo stop at the Panathenaic Stadium, one of the first modern Olympic Games venues. Then, travel back in time to Ancient Greece and ascend the steep hill of the Acropolis. Greek for “highest city,” this site was an ancient religious center and powerful military fortress. Soak in the gorgeous panoramic views of Athens. Afterward, the remainder of the day is yours to enjoy at leisure. Take this opportunity to explore the vibrant city surrounding the Divani Palace Acropolis. Stroll through the charming streets of Plaka, known for its traditional family-run tavernas, local boutiques, and neoclassical architecture. Whether you’re interested in history, culture, or simply soaking up the local atmosphere, you’re perfectly situated to make the most of your time in Athens. (B)
Athens – Embark the Azamara Onward
Enjoy a leisurely breakfast at the hotel and take some time to soak in your final moments in Athens. Later, we’ll gather for a late-morning departure and transfer to the port of Piraeus—the historic harbor that has served Athens since 482 BC. There, you’ll board the luxurious Azamara Onward to begin your extraordinary cruise through the enchanting waters of Greece and its islands. (B, D)
Syros, Greece
Today, your cruise docks in the captivating island of Syros, the capital of the Cyclades and one of Greece’s best-kept secrets. Far from the crowds of its more famous neighbors, Syros enchants with its neoclassical charm, vibrant culture, and authentic island atmosphere. Step ashore in Ermoupoli, the elegant port town known for its grand mansions, marble-paved squares, and pastel-hued buildings that reflect its rich Venetian and neoclassical heritage. Whether you explore Syros on your own or opt for a guided excursion, today offers a perfect blend of culture, history, and leisurely island charm. (B, L, D)
Patmos, Greece
Your time in Patmos offers a perfect mix of history, spirituality, and natural beauty. After disembarking, explore Skala, the charming port town with its narrow streets and seaside cafés. Visit the Monastery of St. John the Theologian, a UNESCO World Heritage site with stunning views and historical significance. Then, head to the Cave of the Apocalypse, where St. John is believed to have written the Book of Revelation. Finish your day with a delicious meal at a local taverna, enjoying fresh seafood and the sunset. Patmos is a peaceful and memorable stop on your cruise. (B, L, D)
Rhodes, Greece
Get off the ship in Rhodes and step into a world of rich history, stunning architecture, and breathtaking landscapes. Start by exploring the UNESCO-listed Rhodes Town, with its medieval Old Town, cobblestone streets, and sites like the Palace of the Grand Master and the Archaeological Museum. Then, visit the Acropolis of Rhodes, which features ancient ruins and stunning views. In the afternoon, head to Lindos, a picturesque village known for its whitewashed buildings and beautiful beaches. You can explore or simply relax by the sea. Rhodes combines rich history with a peaceful coastal experience for a perfect day. (B, L, D)
Marmaris, Turkey
Today, you’ll arrive in the stunning coastal town of Marmaris, nestled between pine-covered mountains and the sparkling turquoise waters of the Turkish Riviera. A popular destination for its natural beauty and lively atmosphere, Marmaris offers a fascinating mix of ancient history, Ottoman architecture, and modern-day vibrance.
Spend the day exploring the Old Town, where cobbled streets wind past whitewashed houses, bustling bazaars, and the impressive Marmaris Castle, originally built by the Ionians and later rebuilt by Suleiman the Magnificent. The castle offers sweeping views over the harbor and is home to a small museum showcasing local artifacts. For a taste of local culture, browse the Grand Bazaar for Turkish carpets, spices, and hand-crafted souvenirs, or sample traditional dishes like meze and freshly grilled seafood. (B, L, D)
Agios Nikolaos (Crete), Greece
When your cruise ship, the Onward, tenders in Agios Nikolaos, you’ll have the entire day to soak in the essence of this charming coastal town filled with picturesque views and a relaxed atmosphere. Start by strolling along the waterfront promenade, enjoying views of Lake Voulismeni and the surrounding hills. History buffs can visit the nearby archaeological site of Lato, offering ancient ruins and stunning views. For relaxation, head to one of the nearby beaches to swim or sunbathe. You may choose to finish your day with a leisurely meal at a seaside taverna, enjoying fresh seafood and traditional Cretan dishes. Agios Nikolaos offers a perfect mix of culture, history, and natural beauty. (B, L, D)
Santorini, Greece
An unforgettable day in the port of Santorini offers the perfect balance of exploration and relaxation. Upon tendering to Santorini’s shore, take the cable car to the island’s bustling capital, Fira, and wander through its charming streets. The ride offers stunning views of the caldera and takes only a few minutes. Alternatively, you can head to Oia, a village renowned for its iconic, whitewashed buildings, blue-domed churches, and picture-perfect streets. As the day draws to a close, make your way back to the port—but not before witnessing one of the most magical moments in Santorini: the sunset. Watching the sun dip below the horizon, casting a golden glow over the caldera is an unforgettable experience that perfectly wraps up your day in this breathtaking Greek paradise. (B, L, D)
Monemvasia, Greece
Today, your voyage brings you to the final island stop on this unforgettable journey—the captivating, cliffside town of Monemvasia, Greece. As your ship anchors just offshore, you’ll tender to a hidden medieval wonder, dramatically carved into the side of a massive rock formation and lovingly preserved through the centuries. Often called the “Gibraltar of the East,” Monemvasia offers a truly timeless experience. Within its ancient stone walls, you’ll find Byzantine churches, Venetian-era mansions, and cobblestone lanes that whisper stories of the past. As the last island on your cruise through the Greek waters, Monemvasia invites you to slow down and savor the moment—whether you’re enjoying a quiet coffee in a local café, browsing artisanal shops, or simply soaking in the history and sea-swept beauty that surrounds you. It’s the perfect setting to reflect on the journey you’ve taken—filled with discovery, wonder, and the unforgettable magic of the Aegean. (B, L, D)
Athens – Depart for Home
Azamara Onward sails into Piraeus Port in Athens early this morning, marking the end of our cruise. Begin your journey home, carrying memories and experiences that will last a lifetime. (B)
Inclusions
- Economy Class Roundtrip Airfare from Chicago (ORD)
- Roundtrip Airport Transfers from Milwaukee to Chicago (ORD)
- Premium Hotel Accommodations in Athens for Two Nights
- 8 Nights Onboard the Azamara Onward: Select Standard Spirits, International Beers, and Wines Served in Public Areas; Bottled Water, Soft Drinks, Specialty Coffees and Teas; Self-Service Laundry; Concierge Services for Personal Guidance and Reservations; $100 Onboard Credit (Per Stateroom); One Night Specialty Dining Per Person (certain specialty menu items are not included)
- All Ground Transportation
- Expert English-Speaking Guides
- 26 Meals (10 Breakfasts, 7 Lunches, 9 Dinners)
- Gratuities for Cruise Staff, Drivers, Local Guides, and Tour Director
- Taxes and Fees as of April 8, 2025
- Complete Services of Cruise & Tour, Including Tour Director
Extraordinary Experiences
- Connect with Dan O’Donnell at a private cocktail gathering.
- Engage directly with Dan O’Donnell during an exclusive Q&A session.
- Journey through ancient history and culture as you visit the Acropolis in Athens, a timeless symbol of Greek civilization.
- Delight in an unforgettable AzAmazing Evening, where local culture comes alive and reveals the soul of the destination — a once-in-a-lifetime experience only Azamara can deliver.
Not Included
- Increases in Taxes, Fees, or Surcharges after April 8, 2025
- Travel Insurance
- Air Upgrades
- Airline Baggage Fees
- Shore Excursions Booked with Azamara
- Gratuities For Guides, Drivers, or Tour Operations Staff on your Booked Shore Excursions
- Items of a Personal Nature
Please Note:
- Other gateways may be available upon request. Additional charges may apply.
- Hotels may be substituted due to unforeseen circumstances.
- Suggested activities in the ports of call are not included unless otherwise noted. In some cases, additional costs may apply for transportation to ensure easy access to key attractions or the heart of the city. If this is the case, Azamara offers an “On Your Own Excursion,” which provides transportation to and from the city center at specific times, allowing you to explore the destination independently. These excursions can be purchased through your Voyage Planner in your Guest Account.
- If you purchase Premium Economy or Business Class, the upgraded class may only apply to the international long-haul portion of your journey and may be confirmed on alternate flights from the group.
- Cruise & Tour reserves the right to modify this itinerary, and the days of features are interchangeable.
Activity Level
This tour requires moderate physical activity. Participants should be in overall good health and able to walk over both level and uneven surfaces, climb stairs, and walk uphill during the land portion of the tour. The Acropolis visit specifically includes walking uphill. Activities onboard the ship cover an array of interests with various levels of activity to fit your lifestyle. Ship-sponsored shore excursions are designed to accommodate all activity levels. Consider purchasing shore excursions that match your preferences and physical abilities.
Testimonials
Rates
| Oceanview (Cat 6) | $6,499 | Per Person Double Occupancy |
| Oceanview (Cat 6) Single Supplement (Limited Availability) | $2,199 | Per Single |
| Oceanview (Cat 5) | $6,799 | Per Person Double Occupancy |
| Veranda (Cat V3) | $6,999 | Per Person Double Occupancy |
| Veranda (Cat V3) Single Supplement (Limited Availability) | $2,399 | Per Single |
| Veranda (Cat V2) | $7,399 | Per Person Double Occupancy |
| Veranda (Cat V1) | $7,699 | Per Person Double Occupancy |
| Veranda Plus (Cat P1) | $7,999 | Per Person Double Occupancy |
| Club Continent (Cat N2) | $8,999 | Per Person Double Occupancy |
| Club Continent (Cat N1) | $9,199 | Per Person Double Occupancy |
| Business Class Air Upgrade | Inquire at Time of Booking | Per Person |
Travel Insurance will be available, and a quote will be provided following the receipt of the initial deposit for your reservation.
Per Person Double Occupancy Price is based on two people sharing one room.
Single Occupancies are limited and subject to availability.
Deposit / Payment
A deposit of $1,500 per person is required when making your reservation.
A second deposit of $2,000 is due on November 14, 2025.
The final payment is due on February 27, 2026. Payments can be made by credit card or check.
Cancellation / Refund
Your initial deposit of $1,500 is refundable until November 14, 2025, minus a cancellation fee of $750 per person.
From November 14, 2025, to February 27, 2026, the cancellation fee will be 50% of the total deposits paid.
After February 27, 2026, or in the case of non-appearance on the departure day, 100% of the cost of your travel arrangements will be forfeited.

How to Book
Book Online: Click “Book Now” to reserve your spot in just a few steps.
Prefer to talk to us? Call (800) 383-3131 or Request a Call to book by phone and place your initial deposit.
Travel Insurance: A travel insurance quote from Travel Insured International will be emailed to you.
It’s that simple—book online or call us, and you’re all set!
Please Note:
• Platinum Plan: Pre-Existing Condition Exclusion will be waived if you purchase the Platinum protection plan within 21 days of the date of your initial trip payment. Options such as Cancel for Any Reason or Interrupt for Any Reason must also be purchased within 21 days of the date of your initial trip payment.
• Deluxe Plan: Pre-Existing Condition Exclusion will be waived if you purchase the Deluxe protection plan within 14 days of the date of your initial trip payment. Options such as Cancel for Any Reason or Interrupt for Any Reason must also be purchased within 14 days of the date of your initial trip payment.

Travel Insured International Worldwide Trip Protector
Cruise & Tour recommends that you purchase travel insurance.
To purchase travel protection insurance:
View & Print the Travel Insured International Brochure which has a brief summary of coverage.
After making your travel reservation and deposit, a Cruise & Tour representative will create an insurance quote for you. You will receive that travel insurance quote from Travel Insured International Customer Care.
You will then be able to view the quote, add additional coverage options, such as Cancel for Any Reason, and purchase your policy all in the Travel Insured International Portal.
Covered Events for Trip Cancellation/Interruption
Sickness; Accidental Injury or Death of You, Your Travel Companion, Family Member, or Business Partner; Job Loss or Lay Off; Traffic Accident en Route to Departure; Weather; Natural Disaster at Destination; Extension of School Year; Terrorist Attack; Revoked Military Leave; Strike; Bankruptcy of Travel Supplier; Being Hijacked; Quarantined; Subpoenaed; or Asked to Serve on Jury Duty











