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Italy in August – Amalfi, Sailing, & Sicily

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I’m traveling to Italy in early August for two weeks. I’ll be with a friend for the first 4 days, then my husband for the rest of the trip. Our trip must include 3 days on the Amalfi coast and sailing (somewhere in Italy) on a boat that my husband can skipper.

LOGISTICS
I leave the U.S. on August 1 and arrive in Rome on the morning of August 2. I will depart from Rome back to California on August 15. I’ll meet my friend in Rome, and we will visit the Amalfi coast. My friend leaves Italy (departing from Naples) on Saturday, August 6. My husband arrives in Rome on Friday, August 5 and may meet me in Amalfi, but we’re flexible. He departs Rome on August 15 (with me).

WHAT WE LIKE
With my friend, we would like to linger, walk, eat, swim, languish, and drink wine on the beautiful stretch of Amalfi with warm and vivacious people. With my husband, we want to explore the outdoors on foot, relax, eat great food in a non-pretentious setting, and stay at 4 and 5 star properties. We would consider renting an apartment in Amalfi or another location. (And we don’t like shopping.)

OUR MUST-HAVES
Amalfi coast with my friend for at least 3 nights. We will either spend the first night in Rome (preferred) or head down to Amalfi right away. After flying 15 hours, does it make sense to stay overnight in Rome, or go directly to Naples?
Sailing trip for two or three days (one to two nights) anywhere in Italy where my husband can co-skipper. We want to hire a skipper who speaks Italian and knows the waters. The city where we rent the boat does not matter. We are thinking about sailing near the Amalfi coast or near Sicily. What are good locations anywhere in Italy to rent a boat with a skipper for 2-3 days? Any recommendations for where to rent the sailboat?

(MANY) QUESTIONS
I don’t want to spend all day on a sailboat, but rather would like to use the boat for transportation (and so my husband can get his sailing fix in). If we rent a sailboat for a week (instead of two days) and want to visit towns, what towns are within an hour (or two) sail from each other (on the Amalfi coast)?
The region of Sicily is high on my list for the food, the laid-back lifestyle, and the history, but I’m open to other suggestions, especially if Sicily will be too hot in the summer. Where (if anywhere) in Sicily would be good to visit in early August? Would sailing in Sicily be a good option instead of sailing in Amalfi?
If we went to Sicily is it better to go by train and stop half way in between to stay overnight, or take a plane from Naples? If we stopped halfway between the two cities, where are good cities/towns to stay?
Does it make sense to rent an apartment in Amalfi, and if so, which town makes the best home base for a week?
Thanks in advance for reading and for any advice you have about my trip!

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