Days to Italy·17 June 2026
Blue Deer Sea Lodge
Blue Deer under sail

The Pontine Islands
& the Amalfi Coast

17 — 25 June 2026

Dear friends,

Eight days at sea with three couples we are privileged to call friends. Through the Pontine Islands, on to Capri, and along the Amalfi Coast. Long days on the water, longer dinners at anchor, and the kind of slow company we don’t make enough time for.

Erika has put this together so you have everything in one place: the journey day by day, the boat, and every phone number that matters. Please feel free to reach out to her if you have any questions.

See you in Italy.

Grazie!
Dean & Tawney

Eight days · Four couples · Five islands · One boat

Positano from the sea
The Four Couples
Antoinette & Barry
Davis
Paul & Kelly
Gittemeier
Dean & Tawney
Macfarlan
Bill & Yvette
Smith
The Route

From Gaeta south through the Pontine Islands, across the Gulf of Naples to Capri, and home along the Amalfi Coast.

GAETA PALMAROLA PONZA VENTOTENE ISCHIA CAPRI POSITANO CASTELLAMMARE N TYRRHENIAN SEA
Day by Day

The Voyage

Weather reflects typical June conditions. A real forecast will follow closer to departure.

Hotel San Pietro, Positano
Wednesday · 17 June

Arrival in Positano

Hotel San Pietro
High · Low
79° / 66°
Sunrise
5:30 AM
Sunset
8:35 PM
Typical for Positano
Sunny, light breeze

Most of the party arrives in Naples today and travels together by private car to Hotel San Pietro.

  • Around 10:00 AM
    Davises & Gittemeiers · Naples Airport

    Flying in via Chicago. American 180 touches down around ten.

  • 10:28 AM
    Macfarlans · Naples Centrale

    Arriving from Florence on Frecciarossa 9505.

  • Late Morning
    Private Transfer to Positano

    The driver will collect both parties and take the group along the Amalfi Coast to Hotel San Pietro.About ninety minutes by road. The drive is extraordinary — and very winding. If anyone’s prone to motion sickness, best to come prepared.

  • Evening
    At Leisure

    Dinner plans to follow. The terrace at San Pietro is incomparable at sunset.

A Few Phrases +
Buongiorno
bwon-JOR-noh
Good morning · hello
Buonasera
bwoh-nah-SEH-rah
Good evening
Grazie mille
GRAH-tsee-eh MEE-leh
Thanks very much
Un caffè, per favore
oon kah-FEH, per fah-VOH-reh
A coffee, please
Quanto costa?
KWAHN-toh KOH-stah
How much?
Dov’è il bagno?
doh-VEH eel BAHN-yoh
Where’s the bathroom?
About Positano +

Once a humble fishing village, Positano became the darling of artists and writers after John Steinbeck’s 1953 Harper’s Bazaar essay, which opened with: “Positano bites deep. It is a dream place that isn’t quite real when you are there and becomes beckoningly real after you have gone.” The pastel houses cascading down the cliff are now part of the UNESCO-listed Amalfi Coast.

Its roots run deeper. The Greeks called this bay Sireneo, after the sirens Odysseus was warned against. The yellow-and-green-tiled dome of Santa Maria Assunta, at the heart of town, is said to shelter a Byzantine icon of the Madonna that washed ashore in the 13th century, bearing the command “Posa, posa” — put me down. The town took its name from hers.

A Taste of the Amalfi Coast +

The Amalfi Coast’s wines come from terraces above the sea: Fiano di Avellino (honeyed, floral whites) and Falanghina (brighter, more saline). For dinner, try scialatielli ai frutti di mare — hand-cut pasta with mixed seafood — or spaghetti with the famous alici di Cetara anchovies. End with limoncello and a slice of delizia al limone, the region’s signature lemon cake.

Hotel San Pietro guestroom
Thursday · 18 June

A Slow Day on the Coast

The Smiths Arrive
High · Low
80° / 67°
Sunrise
5:31 AM
Sunset
8:35 PM
Typical for Positano
Clear

Bill and Yvette join the party today. Everyone else: linger.

  • 10:35 AM
    Depart Rome

    The Smiths board the Frecciarossa 9403 at Roma Termini for Naples.

  • 11:48 AM
    Arrive Naples Centrale

    A private driver will be waiting at the station.

  • Around 1:30 PM
    Arrive Hotel San Pietro

    Lunch at the hotel or in town. The party whole again by evening.

  • Evening
    Dinner Together

    Reservations to follow.

A Few Phrases +
Salve
SAHL-veh
Polite hello, any time
Vorrei…
voh-RAY
I’d like…
Un tavolo per due
oon TAH-voh-loh per DOO-eh
A table for two
Il conto, per favore
eel KOHN-toh, per fah-VOH-reh
The check, please
Squisito!
skwee-ZEE-toh
Exquisite!
Un altro, per favore
oon AHL-troh, per fah-VOH-reh
Another, please
About Hotel San Pietro +

Il San Pietro di Positano was built into the cliff by Carlino Cinque in 1970. The 17th-century chapel at its entrance gave the hotel its name. The Cinque family still runs it — Humphrey Bogart, Audrey Hepburn, and Mick Jagger have all stayed.

The hotel is nearly invisible from the road. Cinque built it downward into the rock, so its rooms step down the cliff face on a promontory his family had owned for generations. Guests reach the private beach ninety meters below by an elevator cut through the stone. When it opened, critics said a hotel outside the town center would never succeed. A half-century later, it is considered one of the most beautiful hotels in the world.

A Taste of Positano +

The Sfusato Amalfitano — Positano’s prized thin-skinned lemon — gives more than limoncello. Look for granita al limone at midday, pollo al limone on dinner menus. At aperitivo, a Negroni Sbagliato (Campari, sweet vermouth, prosecco) or a chilled Greco di Tufo. For anyone with a sweet tooth: bab’a al limoncello, the rum-soaked sponge cake served with its own lemon syrup.

Palmarola, Pontine Islands
Friday · 19 June

Gaeta to Palmarola

Boarding Day · Four Hours at Sea
High · Low
78° / 68°
Sunrise
5:36 AM
Sunset
8:43 PM
Typical for Palmarola
Sunny, moderate breeze

Aboard by noon. South to Palmarola — the wildest of the Pontines. Fishing lines out.

  • Morning
    Positano to Gaeta

    A private transfer for the full party from Hotel San Pietro to the marina at Gaeta.A note from Captain Lorenzo — soft or foldable luggage is far easier to stow aboard.

  • Around 12:00 PM
    All Aboard · Depart Gaeta

    A welcome aperitivo. The crew will orient the party to the boat.

  • Afternoon
    Four Hours to Palmarola

    Roughly four and a half hours under sail. Rods and reels out along the way.

  • Evening
    At Anchor · Dinner Aboard

    Uninhabited, dramatic, and entirely our own. The chef’s first proper dinner on board.

A Few Phrases +
Andiamo!
ahn-DYAH-moh
Let’s go!
A bordo
ah BOR-doh
Aboard
Salpare
sahl-PAH-reh
To set sail
Il capitano
eel kah-pee-TAH-noh
The captain
Alla salute!
AH-lah sah-LOO-teh
To your health! (toast)
Che vista
keh VEE-stah
What a view
About Palmarola +

The wildest and most remote of the Pontine Islands. Volcanic, uninhabited except for a few summer houses, and once called “one of the most beautiful islands in the world” by National Geographic. The Romans used Palmarola as a place of exile; today it’s more likely you’ll have the anchorage to yourselves.

Geologically, Palmarola is the remains of a volcano that went dormant a million years ago. Its cliffs rise in cathedral-like columns — the tallest is known as the Cattedrale — and the seabed below is scattered with Roman anchors from wrecked grain ships once making their way to the imperial warehouses at Puteoli.

A Taste of the Pontines +

The Pontines produce Biancolella and Forastera — crisp, mineral whites shaped by volcanic soil and sea breeze. The local catch is pesce azzurro (bluefish, mackerel, anchovies) grilled simply, dressed with lemon and island olive oil. Fave e cicoria — mashed broad beans with wild chicory — is a Pontine staple.

Snorkelling at anchor
Saturday · 20 June

Palmarola to Ponza

Watersports & the Pink Cliffs
High · Low
79° / 68°
Sunrise
5:36 AM
Sunset
8:42 PM
Typical for Ponza
Mostly sunny

A short sail to the most celebrated of the Pontine Islands. The day belongs to the water.

  • Morning
    Short Cruise to Ponza

    Half an hour from Palmarola by sea.

  • Midday
    At Anchor · Watersports

    Paddleboards, seabobs, kayaks, snorkelling. All the gear is aboard.

  • Evening
    Dinner Aboard · Ponza

    Sunset over the pink-streaked cliffs of Chiaia di Luna.

A Few Phrases +
Andiamo a nuotare
ahn-DYAH-moh ah nwoh-TAH-reh
Let’s go swimming
L’acqua è perfetta
LAH-kwah eh pehr-FEH-tah
The water’s perfect
Che meraviglia
keh meh-rah-VEE-lyah
How wonderful
Che giornata
keh johr-NAH-tah
What a day
Un po’ di più?
oon poh dee PYOO
A little more?
Passami l’asciugamano
PAH-sah-mee lah-shoo-gah-MAH-noh
Pass the towel
About Ponza +

The largest of the Pontines, Ponza has served as a place of exile since Roman times — Nero banished his first wife Octavia here in AD 62. The dramatic pink-streaked cliffs of Chiaia di Luna beach and the Grotte di Pilato (Pilate’s Caves) — Roman fish farms carved into the rock two thousand years ago — are the island’s defining sights.

The town’s arched seaside promenade and the pastel cluster of houses around the port date to a Bourbon rebuilding in the 1770s; before that, most of the island lay abandoned. At Cala Feola, natural saltwater pools reachable only by tender or on foot hold their warmth through summer better than the sea that surrounds them.

A Taste of Ponza +

Ponza’s Biancolella is the definitive wine: vines have grown on these terraces since Roman hands planted them. On land, look for zuppa di lenticchie, pesce al limone, and the island’s ricotta di pecora. Meals commonly close with a grappa or a small glass of limoncello, chilled to just above freezing.

Blue Deer at anchor by cliffs
Sunday · 21 June

Ponza to Ventotene

Twenty Miles South
High · Low
80° / 69°
Sunrise
5:35 AM
Sunset
8:40 PM
Typical for Ventotene
Clear · summer solstice

Roman, tiny, unhurried. If the party wishes, a good local trattoria for dinner ashore.

  • Morning
    Cruise to Ventotene

    Roughly two hours at sea.

  • Afternoon
    Explore the Island

    The Roman harbor — hand-cut into the tuff stone — is one of a kind. Small, wanderable, uncrowded.

  • Evening
    Dinner · Ashore or Aboard

    The Captain knows a trattoria on the island. Decide day-of.

A Few Phrases +
Buona giornata!
BWOH-nah johr-NAH-tah
Have a good day!
Permesso?
pehr-MEH-soh
May I? / excuse me
Mi scusi
mee SKOO-zee
Pardon me (formal)
Un cappuccino, grazie
oon kah-poo-CHEE-noh, GRAH-tsee-eh
A cappuccino, thanks
Delizioso!
deh-lee-TSYOH-zoh
Delicious!
Ancora un po’
ahn-KOH-rah oon POH
A little more
About Ventotene +

Tiny, ancient, and quietly consequential. Ventotene’s Porto Romano — the Roman harbor hand-cut from volcanic tuff in the 1st century BC — is still in use today. Augustus banished his own daughter Julia to this island in 2 BC for sexual scandal; she spent five years here before being moved to the mainland.

The neighboring islet of Santo Stefano, visible from the harbor, was built into a Bourbon panopticon prison in 1797 and held Sandro Pertini — later president of Italy — for years before the war.

In 1941, anti-fascists Altiero Spinelli and Ernesto Rossi, imprisoned on Ventotene, drafted the Ventotene Manifesto — one of the founding documents of the idea of a united Europe. It is still read aloud in Strasbourg when the European Parliament seats new members.

A Taste of Ventotene +

The island’s lenticchie di Ventotene — small, firm, earthy — are a Slow Food Presidium, grown in volcanic soil since Roman times. The kitchen pairs them with fish just off the boat. Wine: local Biancolella, or a glass of Falanghina from the mainland. A passito or Moscato closes the evening.

The Faraglioni, Capri
Monday · 22 June

Ventotene to Capri

Via Ischia · A Pause for Pizza
High · Low
82° / 69°
Sunrise
5:33 AM
Sunset
8:37 PM
Typical for Capri
Sunny

The longest passage of the week. Forty-eight miles south, a midday stop at Ischia, and on to Capri by late afternoon.

  • Morning
    Depart Ventotene

    Heading south toward the Gulf of Naples.

  • Midday
    Lunch Stop · Ischia

    Pizza where it was invented. A proper break before the last leg.

  • Afternoon
    Arrival in Capri

    At anchor near the Faraglioni. Ashore for a walk through town and some shopping.

  • Evening
    Dinner at Da Paolino

    The famous lemon-tree restaurant. A Capri institution. Reservation in progress. paolinocapri.com

  • Night
    Anchor off Capri

    Back aboard, the Faraglioni lit below.

Da Paolino, Capri
Da Paolino · Capri
A Few Phrases +
Un tavolo per otto
oon TAH-voh-loh per OH-toh
A table for eight
Cin cin!
CHEEN CHEEN
Cheers!
I limoni di Capri
ee lee-MOH-nee dee KAH-pree
The lemons of Capri
Un limoncello
oon lee-mohn-CHEH-loh
A limoncello
Molto buono
MOHL-toh BWOH-noh
Very good
Dov’è la Piazzetta?
doh-VEH lah pyah-TSEH-tah
Where’s the Piazzetta?
About Capri & Da Paolino +

The Emperor Tiberius ruled Rome from Capri for the last decade of his life (AD 27–37); his Villa Jovis still crowns the eastern cliff. The island has drawn artists and writers ever since — Axel Munthe, Graham Greene, Jackie Onassis. Da Paolino opened in 1977 as a family trattoria under a canopy of lemon trees. The same trees still hang over the tables tonight.

The Faraglioni — the three sea stacks that anchor Capri’s silhouette — are named Stella (attached to the island), Faraglione di Mezzo (pierced by a tunnel tall enough for a tender to pass through), and Scopolo (the farthest, home to a blue-throated lizard found nowhere else on earth). Da Paolino’s signature dish is hand-rolled lemon-ricotta ravioli; a welcome limoncello arrives at every table. Photographing other parties is quietly frowned upon — the clientele tends to prefer it that way.

A Taste of Capri +

Capri’s table: insalata caprese (invented here — tomato, mozzarella, basil), ravioli capresi (cheese-stuffed pasta, which you’ll meet at Da Paolino), and torta caprese, the island’s famous flourless chocolate-almond cake. For drinks: Capri DOC wines, the crisp Falanghina, or a limoncello made from i limoni di Capri.

Positano at dusk
Tuesday · 23 June

Capri to Positano

Lunch at Le Sirenuse di Mare
High · Low
83° / 70°
Sunrise
5:32 AM
Sunset
8:36 PM
Typical for Positano
Clear

The final full day. Lunch seaside at Le Sirenuse’s new Nerano restaurant. A last dinner at anchor off Positano — and nightcaps ashore at Le Sirenuse.

  • Morning
    Depart Capri

    A short crossing toward the Amalfi Coast.

  • 12:00 PM
    Lunch · Le Sirenuse di Mare, Nerano

    A table of eight at noon. This is the Le Sirenuse family’s new seaside outpost — their first summer open. sirenuse.it Reservation in progress. Written confirmation to follow.

  • Afternoon
    On to Positano

    At anchor offshore with that postcard view of the cliffs.

  • Evening
    Final Dinner Aboard

    A proper send-off from the chef.

  • Later
    Nightcaps at Le Sirenuse

    Tender ashore for drinks on the iconic terrace.

A Few Phrases +
Che tramonto
keh trah-MOHN-toh
What a sunset
Grazie di cuore
GRAH-tsee-eh dee KWOH-reh
Heartfelt thanks
È stato meraviglioso
eh STAH-toh meh-rah-vee-LYOH-zoh
It’s been wonderful
Alla nostra!
AH-lah NOH-strah
To us!
Un brindisi
oon BREEN-dee-zee
A toast
Che serata
keh seh-RAH-tah
What an evening
About Le Sirenuse, Positano +

The Sersale family opened Le Sirenuse as a hotel in 1951, turning their summer home into Positano’s first proper resort. Jacqueline Kennedy, Dustin Hoffman, and Franco Zeffirelli were among its early guests. Le Sirenuse di Mare — their seaside outpost at Nerano — opened in summer 2025. You’ll be among the first to dine there.

The hotel takes its name from the sirens who, in Greek myth, lured sailors onto the rocks at the tip of the Sorrento peninsula. Odysseus had himself lashed to the mast to hear their song and live; lesser captains didn’t. The sirens were said to live on Li Galli, the three islets visible on clear days from the hotel’s terrace — Rudolf Nureyev bought them in 1988 and died there in 1993. The Sersales still run the hotel, four generations on; Carla Sersale designs the ceramics and linens and the house fragrance, Eau d’Italie, bottled in a laboratory upstairs.

A Taste of Nerano & Positano +

At Nerano, the dish is spaghetti alla Nerano — pasta tossed with zucchini, aged provolone, and basil, invented here in the 1950s at the Maria Grazia restaurant. Back aboard off Positano, the chef’s final dinner may feature linguine al cartoccio (seafood baked in parchment) with a bottle of Greco di Tufo. At Le Sirenuse’s terrace afterwards: Franco’s Gin Sour, the bar’s signature.

Hotel San Pietro pool
Wednesday · 24 June

Disembark · Castellammare

Disembarkation
High · Low
84° / 70°
Sunrise
5:32 AM
Sunset
8:36 PM
Typical for Castellammare
Sunny

A last breakfast aboard. Disembark by ten. Macfarlans and Smiths to Rome; Davises and Gittemeiers to Naples.

  • Morning
    Breakfast Aboard

    A quiet final morning on the boat.

  • 10:00 AM
    Disembark at Castellammare di Stabia

    Drivers meeting at the marina. Under an hour to Naples; about two and a half hours to Rome.

  • Midday
    Private Transfers

    Macfarlans & Smiths — private car to Rome for the flight the 25th.
    Davises & Gittemeiers — private car to Naples.

  • Overnight
    A Night Ashore

    One night in Rome or Naples before the flight home.

A Few Phrases +
Arrivederci
ah-ree-veh-DEHR-chee
Goodbye (lasting)
A presto
ah PREH-stoh
See you soon
Ci vediamo
chee veh-DYAH-moh
See you
Grazie per tutto
GRAH-tsee-eh per TOO-toh
Thanks for everything
Buon viaggio
bwon VYAH-joh
Safe travels
About Arrivederci +

From the Italian “a rivederci” — “until we see each other again.” The word carries the assumption of return. Italians rarely say a hard goodbye.

They prefer “a presto” (until soon), “ci vediamo” (we’ll see each other), or “a dopo” (until later). All carry the same quiet optimism: this isn’t over. Ciao — the word that circled the world — derives from the Venetian “s’ciavo,” I am your servant. Even a casual Italian hello is a small promise.

A Taste of Naples +

Before catching transport, a last Neapolitan taste: pizza margherita (invented in Naples in 1889), sfogliatella (the shell-shaped ricotta pastry), and mozzarella di bufala campana from the region’s water buffalo herds. The regional wine is Lacryma Christi del Vesuvio, grown on Vesuvius’ slopes — said in local legend to be Christ’s tears when he wept over the fall of Satan.

Thursday · 25 June

Homeward

Flights from Naples & Rome

Safe travels home. Grazie per tutto.

  • 12:00 PM
    Davises & Gittemeiers · Naples → Philadelphia

    American 781 from Naples, connecting through PHL to DFW on American 2947 (departs 5:30 PM, arrives DFW 8:21 PM).

  • 1:10 PM
    Macfarlans & Smiths · Rome → Dallas

    American 239, direct FCO to DFW. Arrives 6:25 PM.

Getting There & Home

Passage

Flights, trains, and the drivers waiting on the other side.

Davis & Gittemeier
Via Naples · 17 June
Outbound
DFW → ORD · American 2988
connecting in Chicago
Transatlantic
ORD → Naples · American 180
arriving around 10:00 AM, 17 June
Night Ashore
Naples · hotel to follow
24 June
Homeward
Naples → PHL · American 781
departing 12:00 PM, 25 June
Final Leg
PHL → DFW · American 2947
departs 5:30 PM · arrives DFW 8:21 PM
Macfarlan
Via Rail · 17 June
To Naples
Frecciarossa 9505 · Florence → Naples
arriving Naples Centrale 10:28 AM, 17 June
Night Ashore
Hotel de la Ville · Rome
24 June
Homeward
FCO → DFW · American 239
departs Rome 1:10 PM · arrives DFW 6:25 PM, 25 June
Smith
Via Rome · 18 June
To Naples
Frecciarossa 9403 · Roma Termini → Naples
arriving Naples Centrale 11:48 AM, 18 June
Private Transfer
Driver at the station to Positano
arriving Hotel San Pietro around 1:30 PM
Night Ashore
Hotel de la Ville · Rome
24 June
Homeward
FCO → DFW · American 239
departs Rome 1:10 PM · arrives DFW 6:25 PM, 25 June
Private Transfers Arranged
  • Naples → Positano · 17 June
  • Naples → Positano (Smiths) · 18 June
  • Positano → Gaeta · 19 June
  • Castellammare di Stabia → Rome · 24 June
  • Castellammare di Stabia → Naples · 24 June (pending confirmation)

Davises & Gittemeiers — a transfer to Naples on the 24th can be arranged. Let me know.

Blue Deer from above
Aboard

The Boat

Sunreef 74 · San Lorenzo Sea Lodge · built 2015

The Blue Deer is one half of a story. Her owners — Giorgia and Stefano Barbini — also keep the White Deer, a lodge high in the Dolomites. The same sensibility runs through both: fine Italian fabrics in blue, grey, and white; food from farms rather than brands; and the unhurried, convivial pace that the Italians long ago perfected.

Sailing beyond ordinary horizons
74 ft
Length
8+2
Guests
Four
Cabins
Four
Crew
The lounge
Dining interior
A cabin
The galley
Your Crew
Captain
Lorenzo
First Mate
— to follow
Chef
— to follow
Stewardess
— to follow
Onboard

A welcome aperitivo. Daily cleaning. Bed-linen and towels changed across the week. Up to six sailing hours each day — though most will be fewer. The water toys live on deck:

Aperitivo aboard
Small Things. They Matter.

Good to Know

1
Luggage

Soft or foldable luggage rather than hard cases — far easier for the crew to stow. The cabins have generous wardrobes.

2
Wi-Fi at Sea

Internet aboard is compatible with on-board signal and is not guaranteed. Download your music, podcasts, and reading before leaving home.

3
Gratuity for the Crew

Not included in the charter. Customary is ten to twenty percent of the charter fee, given at the end of the week — entirely at your discretion.

4
Flexibility

Stefano has noted that the route can be adjusted day-of with Captain Lorenzo. A longer stop, a different bay, a quieter evening — just say the word.

5
The Pace

Up to six sailing hours a day. Most days will be far fewer. Plan to slow down.

Initial Payment
$4,987.95
Amount owed per couple · wire instructions on file
Who to Call

Contacts

Erika
Chief of Staff to Dean Macfarlan
Macfarlan Capital Partners
Happy to help with trip questions, last-minute changes, and logistics.
Manuel
Ground Transfers in Italy
All Italian drivers — Naples and Rome airports, port transfers, Positano.
Stefano Barbini
San Lorenzo Sea Lodge · Owner
For questions about the boat, the route, or special requests.
Captain Lorenzo
Aboard the Blue Deer
Itinerary adjustments day-of are made directly with the Captain.
Hotel San Pietro
Positano · 17 — 19 June
Via Laurito 2, Positano
In an Emergency
In Italy, dial
112
Buon Viaggio.