A Starter Charter in The Med

“But everything looks so close together on the map!” exclaimed the forlorn luxury yacht charter guest when advised against a two-week Mediterranean cruise starting in Palma de Mallorca and ending in Venice.

Charterers who are new to the Med want to explore all of it in one go. But, unless you have the whole summer, this is geographically impossible. Capt. Brian Bennett of M/Y Lailanai, a 20-year veteran of summer Med charters, recommends a two-week itinerary with a little bit of everything: shopping, dining, beaches, history and sightseeing.

Day 1: Guests fly into Nice and meet the boat in Port Vauban. They can spend the afternoon walking around, drinking in the sea air and wafting French smells. Don’t forget a visit to the Picasso museum.

Day 2: After, an early morning departure to Saint-Tropez, spend the day anchored off of the beach at Baie de Pampelonne. Later in the afternoon, make for the Basin and send the guests out for  an evening of dockside exploring to check out the restaurants, cafes and clubs.

Day 3: Head straight to the islands off of Cannes for another relaxing day before tying up in the old port. If the guests like bouillabaisse, this is the place.

Day 4: Depart for Villefranche-sur-Mer or Beaulieu sur Mer. Guests can Jet Ski, kayak or paddleboard. From there, take a short jaunt to Port Hercules, Monaco. Make the guests' dinner reservations at Café de Paris and Casino Monte Carlo.

Day 5: After an overnight run to Portofino, your guests will awaken in the old port for a day of shopping, sitting in Italian cafes and sight seeing.

Day 6: Spend a relaxing day off of Portofino beach. Don’t forget to grab the world’s best focaccia. Bennett recommends an early morning trip to the bakery, as they run out of bread by 9 a.m.

Day 7: Another overnight run will put you in Elba. A beautiful island made famous for imprisoning Napoleon, but more recently known for its wine production.

Day 8: Make a short run to Ponza. Throw your guests in the tender to explore the stunning volcanic caves in the area. In the evening, depart for Naples.

Day 9: Your guests will have a full day between visiting Pompeii and Herculaneum, cities destroyed by the eruption of Mt. Vesuvius. The more adventurous can head straight to the volcano.

Day 10: After a day of touring, your guests will be ready for the beach. Anchor off of the south of Ischia to drink in the breathtaking beauty. An evening of cafes, bars and clubs is on the guests' menu.

Day 11: Spend the day anchored in the bay on the southern side of Capri. Your guests can see the renowned sea stacks before returning to port for the evening.

Day 12: Arrange for your guests to visit the town of Anacapri, high on the mountain. In the afternoon, cruise down the Amalfi coast towards Positano. Be sure to point out La Sirena, where Ulysses tied himself to the mast and ordered his men to stuff their ears so he might safely hear the reputed beautiful siren song without harm.

Day 13: Guests can explore more of Amalfi from the marina.

Day 14: Make an early start on the three-hour ride back to Naples where your guests will have time for last minute shopping before departing.

Bennett stresses the importance of mixing up activities. He notices guests get antsy after a day or two on the beach and crave a shore side experience. He also notes that tips increase as crewmembers speak eloquently about where they are, instead of shrugging and saying “I don’t know, I’m just the _______.” So get your Google on and brush up on history, mythology and geography.