The Ultimate Way to Experience America’s Cup 2027: on an Italian Sailing Holiday

Naples offers something quite different from recent editions of the America's Cup. Rather than on a wide, exposed stretch of coastline, the racing will take place in a relatively compact and sheltered bay that's surrounded by islands, historic towns and one of the most celebrated coastlines in the world. 

Naples will deliver a racecourse made for viewing from the water, even though the large superyachts will be blocking the best views. The atmosphere on the water - the buzz of being involved and observing these boats is what it's all about. It's an experience to be lived as part of a broader sailing journey. And on board, the tv screens can be tuned to the prime race view as needed! 

A Natural Theatre for Sailing and Spectating

What makes the Bay of Naples so appealing is the way everything sits within easy reach (check out the Location Guide on our Naples destination page).

From a yacht you will never be far from the action, but equally you are never confined to it. You can spend the day following the racing—watching the AC75 foiling monohulls lift and accelerate across the bay in ideal summer conditions—then move on in the late afternoon to a completely different setting for the evening.

That might be a quiet harbour steeped in history, a lively waterfront town, or a secluded anchorage with views back toward Mount Vesuvius. The transitions are short, the options varied, and the overall experience far more fluid than anything land based.

This is where Naples stands apart. The geography allows you to combine a world-class sporting event with genuine cruising, rather than having to choose between the two.

Sailing Through the Heart of Southern Italy

Within a relatively small cruising radius, you have access to an extraordinary range of destinations.

To the south lies Capri, instantly recognisable for its dramatic coastline and refined atmosphere. It’s a place of sheer cliffs, hidden coves, and its famous limestone formations rising out of the sea. Arriving by yacht, particularly early or late in the day, offers a very different perspective from the bustling day-visit crowds.

To the north and west, Ischia provides a softer contrast. This island is bigger, greener, and known for its thermal springs and relaxed pace. Harbours here feel more lived-in, less polished, and often more welcoming for an extended stay.

Beyond that, the Pontine Islands offer something quieter again. Less visited, more traditional, and ideal if you want to step away from the main flow and experience a more authentic slice of Italian coastal life.

What ties all of this together is distance, or more accurately the lack of it. These are not long passages. They are short, manageable sails that allow you to explore without pressure, adjusting your plans day by day.

Capri sunset

The Aragonese Castle at Ischia

Naples under Vesuvius

Colourful Procida

The Amalfi Coast Within Easy Reach

Then there is the Amalfi Coast.

Stretching along and beyond the southern side of the Sorrento Peninsula, it’s one of those places that genuinely lives up to its reputation. Towns like Positano and Amalfi seem to rise straight out of the water, layered in colour and history. Back on the northern Bay of Naples side, Sorrento offers a natural gateway between Naples and the coast itself.

From a charter yacht, you’re not tied to busy road access or fixed accommodation, and so the experience is far more flexible.  You can arrive early in the morning before the day visitors, linger into the evening when things quieten down, and move on when it suits you.

It’s this freedom, subtle but significant, that completely recasts the nature of touring this destination.

Why a Yacht Makes Sense During the AC38 Event

Major events like the America’s Cup inevitably place pressure on local accommodation. Teams, media, sponsors, and spectators all converge at once, and availability ashore becomes both limited and expensive.

A charter yacht offers a different approach entirely.

Rather than competing for space on land, you create your own base on the water. Your accommodation, transport, and vantage point are all combined in one. For groups, particularly those travelling together, it often works out to be not just more flexible, but surprisingly cost-effective.

We see this regularly in places like Capri, where groups attending weddings or events find that a modern catamaran—complete with comfortable cabins, shared living spaces and the option of a skipper—can deliver both better value and a far more memorable experience than staying ashore.

For the America’s Cup, the same logic applies.

Timing the Market: Why Early Planning Matters

At this stage of 2026, there are signs that charter pricing has not yet fully adjusted to the significance of the AC38 event.

It's always the way with forward planning a year out, that most operators begin listing their full fleets only as the current season ends. Therefore their pricing still reflects 2026 rates. By the time October 2026 rolls around, and maybe sooner, forward bookings will have started in earnest. Therefore it's to be expected that all remaining boats will steadily see increased pricing in response to demand.

From experience, the best boats in the best locations are always the first to go. By securing your charter yacht early, you not only get more choice. You also get ahead of  any late upward pricing pressures. 

It’s not about rushing into a decision, it's about understanding the timing.

Peaceful Positano evening

Sorrento street scene

The Value of Experience and Access

This is where working with an experienced charter specialist makes a real difference.

At Sail Connections, our role is to look beyond what’s immediately visible online. Most public booking platforms draw from a single database, which means they only ever show part of the available market.

Our approach is broader. We work across multiple global databases and maintain long-standing relationships with operators in the Mediterranean and beyond. In practical terms, that allows us to:

• Identify boats that may not yet be publicly listed
• Understand which fleets will be operating in and around Naples
• Secure options before demand peaks
• Compare across the full market, not just a subset

We have a more complete view of what’s available, and that can make all the difference between simply finding a boat and finding the right one.

Just as importantly, our service comes at no additional cost to you. It’s about adding clarity and confidence to the process, not complexity.

More Than an Event: A Complete Sailing Experience

The America’s Cup in Naples is not just something to attend for a day or two. In this setting, it becomes part of a wider experience.

You can follow the racing from the water, move between some of Italy’s most iconic destinations, and shape the journey to suit your own pace and interests. Some days will be about the spectacle of the event; others will be about quiet anchorages, local food, and the simple pleasure of being on the water.

That balance is what makes this opportunity stand out.

It’s the difference between being a spectator, and being part of it.

FAQs

Is it too early to plan for 2027?
Not at all. Early planning typically means better choice of boats and more favourable pricing, particularly for high-demand periods.

Do I need sailing experience?
No. Options range from fully bareboat charters for experienced sailors through to skippered and fully crewed yachts, depending on how hands-on you want to be.

How long should I allow?
A one-week charter will give you time to combine race watching with exploring the surrounding islands of the Bay Of Naples and a quick look at the Amalfi Coast. Two weeks will allow you to do the Amalfi Coast justice, and look at sailing further afield - north or south to enjoy more of stunning coastal Italy.

Start Planning

If the idea of experiencing the Naples America’s Cup from the water appeals, it’s worth starting the conversation early.

At this stage the format and racing arrangements are not confirmed, nor is the final number of challengers. We will be watching with interest as more announcements are made, and updating our information as the event approaches.

We can help you explore the full range of options and shape a charter that fits your plans. Whether that’s focused on the racing, the cruising, or some of both.

Photo credits all from Unsplash:

Capri sunset photo by Sam Ferrara

Capri banner photo by Julia Worthington

Positano photo by Dimitry B

Naples photo by Aversa Taxion

Ischia photo by Pronto Ischia

Procida photo by Vincenzo Godono

Sorrento photo by Chalo Gallardoon