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ISSIMO’s Travel Guide to Boat-Tripping Around the Tuscan Archipelago

June 11, 2025

ISSIMO’s Travel Guide to Boat-Tripping Around the Tuscan Archipelago

Where sun-drenched coves, secret islands, and seaside lunches await

There are few better ways to experience the Tuscan archipelago than from the deck of a boat, skin kissed by the sun and crystalline waters glittering below. Spanning from Elba to Giannutri, with wild Monte Argentario as its gateway, this scattering of islands is the stuff of coastal dreams: hidden coves, quaint fishing towns, and the kind of water that needs no filter.

And if you’re staying at Hotel Il Pellicano, you’re already at the heart of it all.

Whether you’re after a lazy day of sun-soaked swims and barefoot lunches, or a maritime adventure with aperitivo on the rocks, we have put together three perfect itineraries for boat-tripping around the Tuscan archipelago, with a little help from captain extraordinaire Alfredo Ballerano, who takes the Il Pellicano guests out at sea daily. All you need is a wide-brimmed hat, sunblock, and the perfect playlist. Ready?

1. The Hidden Coves Circuit

Il Pellicano

Cala del Bove

Cala dei Santi

Cala Piazzoni

This is the route for the sea-dreamers – the ones who want to spend the entire day barefoot, half-salty, and in and out of the water with no sense of time.

Start your morning by gliding past Cala del Bove, a dramatic, untouched bay with emerald water and sea caves carved into the cliffside. It’s wild, remote, and often deserted – a true swim-in-silence moment.

Next, anchor at Cala dei Santi, a narrow inlet surrounded by dense Mediterranean scrub. The water here is otherworldly: clear, still, and impossibly inviting. Slip in, float, repeat.

Your final stop is Cala Piazzoni, a local favourite tucked just beyond the beaten path. Bring a picnic from Il Pellicano—fresh focaccia, burrata, sun-warmed tomatoes, a chilled bottle of rosato—and savour it slowly on deck. This route is about nothing but sea, sun, and softness.

2. The Wild Island Escape

Il Pellicano

Isola del Giglio

Cala dell'Allume

Giglio Castello

Sail westward into open water, toward Isola del Giglio, a Tuscan island that feels suspended in time – crystalline bays, pastel-hued harbours, and medieval hilltop streets that beg to be wandered.

The coastline here is rugged and cinematic, but nothing quite compares to Cala dell’Allume. This deep, rocky cove is wrapped in stone and stillness – accessible only by sea. Anchor here and take your time. Swim through sea caves, explore by snorkel, or simply lie on the deck and watch the light dance on the water.

In the afternoon, head inland for a change of pace. Climb up to Giglio Castello, a fortified hilltop town with cobbled lanes, 13th-century charm, and sweeping views of the archipelago. Grab a table at Ristorante La Margherita back in Giglio Porto before returning to the boat – order the spaghetti alle vongole or catch of the day, and linger as long as you like.

This is the itinerary for those who want it all: wild swims, quiet beauty, and just a touch of old-world adventure.

3. The Portside Glamour Cruise

Il Pellicano

Porto Ercole

Le Viste

La Rocca

For those who like their boat days with a side of Aperol and architecture, this is your route. Hug the coastline and arrive in Porto Ercole, the prettier, quieter twin of Santo Stefano. Moor your boat and head inland for a leisurely morning espresso or a browse through local galleries and boutiques.

For a mid-day dip, cruise around the bend to Le Viste, a tiny, secluded beach with some of the clearest water on the coast. There’s a barefoot-elegance restaurant here too – Ristorante Le Viste – where tables overlook the sea and the grilled octopus comes straight off the boat.

On your way back, stop at La Rocca Spagnola, a 16th-century Spanish fortress that towers above the coast. It’s pure history meets sea air, and makes for one of the best panoramic viewpoints around.

Finish with an aperitivo on board, golden light bouncing off the water, and the hotel lights of Il Pellicano just starting to twinkle in the distance. Chic, slow, and completely unforgettable.

ISSIMO Tips for Boat Days

What to wear

A flowing kaftan from Loretta Caponi, oversized shades, and an ISSIMO x Rivolta Carmignani beach towel.

What to bring

SPF, a vintage Polaroid, a book, and something salty to snack on.

Who to call

The concierge at Hotel Il Pellicano can arrange private boat charters, captains, and packed lunches that rival most restaurants.

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