Croatia coastal old town — engineer your PTO around US holidays for longer voyages

PTO Maximizer

Work Smart.
Sail Longer.

Be Strategic. Be a PTO Maximizer.

4 days off. 9 nights at sea.

Your Hidden Advantage

Work smarter.
Sail longer.

Most people treat federal holidays as long weekends. PTO Maximizers treat them as departure days.

Built for teachers stacking school breaks, federal employees with 11 guaranteed holidays, and anyone with a few PTO days saved — read the calendar better and book 60–90 days out.

Pick a holiday anchor

The U.S. has 11 federal holidays — each one is a paid day you don't have to spend. They become your cruise anchor; build the voyage around them and the calendar works for you.

Bridge with PTO

Use a few strategically placed PTO days before or after to extend the bridge. 1–4 days off can unlock 4–9 nights at sea — without burning your entire leave balance.

Paolo books it

Tell Paolo your holiday window, your preferred line, and your budget. He finds the voyage, stacks the perks, and handles every detail — including perks the booking engine won't surface.

Line

Duration

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Pricing for

Solo prices reflect Virgin Voyages' actual single supplement (varies by voyage)

New York to Bermuda & Back — Valiant Lady — Holiday sailing curated by Off The Grid Getaways

🧭 Columbus Day

31% OFF

3 PTO days → 6 nights

PTO Pivot No. 01

New York to Bermuda & Back

✦ Valiant Lady ✦ New York ✦ 6 nights

Oct 7 – 13, 2026

💡 Depart Wed · Columbus Day (Mon) = 1 free day mid-week · 3 PTO = 6 nights

Sea View

Starting at $1,039 $714 per sailor · 2 adults

31% off · double occupancy

$119 per sailor / night · 6 nights

$1,428 cabin total · 2 adults share one cabin

Book This Sailing →

Caribbean Holiday Escape — Scarlet Lady — Holiday sailing curated by Off The Grid Getaways

🎄 Christmas

35% OFF

4 PTO days → 5 nights

PTO Pivot No. 02

Caribbean Holiday Escape

✦ Scarlet Lady ✦ Miami ✦ 5 nights

Dec 21 – 26, 2026

💡 Depart Mon · Christmas (Fri) = 1 free day · 4 PTO covers the workweek

Sea View

Starting at $1,168 $795 per sailor · 2 adults

32% off · double occupancy

$159 per sailor / night · 5 nights

$1,590 cabin total · 2 adults share one cabin

Book This Sailing →

New Year's Caribbean Celebration — Resilient Lady — Holiday sailing curated by Off The Grid Getaways

🥂 New Year's Day

49% OFF

4 PTO days → 7 nights

PTO Pivot No. 03

New Year's Caribbean Celebration

✦ Resilient Lady ✦ Miami ✦ 7 nights

Dec 27 – Jan 3, 2027

💡 Depart Sun Dec 27 · New Year's Day (Fri) = 1 free day · 4 PTO = 7 nights

Insider

Starting at $2,364 $1,463 per sailor · 2 adults

38% off · double occupancy

$209 per sailor / night · 7 nights

$2,926 cabin total · 2 adults share one cabin

Book This Sailing →

Caribbean Escape — Resilient Lady — Holiday sailing curated by Off The Grid Getaways

✊🏾 MLK Day

39% OFF

4 PTO days → 8 nights

PTO Pivot No. 04

Caribbean Escape

✦ Resilient Lady ✦ Miami ✦ 8 nights

Jan 16 – 24, 2027

💡 Depart Sat · MLK Day (Mon) = 1 free day · 4 PTO = 8 nights at sea

Insider

Starting at $1,593 $1,032 per sailor · 2 adults

35% off · double occupancy

$129 per sailor / night · 8 nights

$2,064 cabin total · 2 adults share one cabin

Book This Sailing →

Mediterranean Valentine's Voyage — Resilient Lady — Holiday sailing curated by Off The Grid Getaways

🇺🇸 Presidents Day

47% OFF

4 PTO days → 7 nights

PTO Pivot No. 05

Mediterranean Valentine's Voyage

✦ Resilient Lady ✦ Barcelona ✦ 7 nights

Feb 14 – 21, 2027

💡 Set sail Valentine's Day · Presidents Day (Mon) = 1 free day · 4 PTO = 7 nights

Insider

Starting at $1,810 $1,253 per sailor · 2 adults

31% off · double occupancy

$179 per sailor / night · 7 nights

$2,506 cabin total · 2 adults share one cabin

Book This Sailing →

Caribbean Summer Escape — Resilient Lady — Holiday sailing curated by Off The Grid Getaways

🇺🇸 Memorial Day

36% OFF

4 PTO days → 7 nights

PTO Pivot No. 06

Caribbean Summer Escape

✦ Resilient Lady ✦ Miami ✦ 7 nights

May 30 – Jun 6, 2027

💡 Depart Sun · Memorial Day (Mon) = 1 free day · 4 PTO takes Tue–Fri

Insider

Starting at $2,016 $1,323 per sailor · 2 adults

34% off · double occupancy

$189 per sailor / night · 7 nights

$2,646 cabin total · 2 adults share one cabin

Book This Sailing →

Fire & Sunset Soirées — Valiant Lady — Holiday sailing curated by Off The Grid Getaways

✊🏾 Juneteenth

32% OFF

1 PTO days → 4 nights

PTO Pivot No. 07

Fire & Sunset Soirées

✦ Valiant Lady ✦ Miami ✦ 4 nights

Jun 17 – 21, 2027

💡 Depart Thu · Juneteenth (Fri) = free · Just 1 PTO day = 4 nights at sea

Insider

Starting at $942 $636 per sailor · 2 adults

32% off · double occupancy

$159 per sailor / night · 4 nights

$1,272 cabin total · 2 adults share one cabin

Book This Sailing →

Grand Cayman & Bahamas — Valiant Lady — Holiday sailing curated by Off The Grid Getaways

🎆 Independence Day

36% OFF

4 PTO days → 5 nights

PTO Pivot No. 08

Grand Cayman & Bahamas

✦ Valiant Lady ✦ Miami ✦ 5 nights

Jul 5 – 10, 2027

💡 Depart Mon Jul 4 · Holiday = 1 free day · 4 PTO = 5 nights total

Insider

Starting at $1,189 $795 per sailor · 2 adults

33% off · double occupancy

$159 per sailor / night · 5 nights

$1,590 cabin total · 2 adults share one cabin

Book This Sailing →

Bahamas & Atlantic Ports — Resilient Lady — Holiday sailing curated by Off The Grid Getaways

🎆 Independence Day

42% OFF

4 PTO days → 7 nights

PTO Pivot No. 09

Bahamas & Atlantic Ports

✦ Resilient Lady ✦ Miami ✦ 7 nights

Jul 4 – 11, 2027

💡 Depart Sun Jul 4 · Holiday = 1 free day · 4 PTO = 7 full nights

Insider

Starting at $2,090 $1,442 per sailor · 2 adults

31% off · double occupancy

$206 per sailor / night · 7 nights

$2,884 cabin total · 2 adults share one cabin

Book This Sailing →

The Caribbean — Valiant Lady — Holiday sailing curated by Off The Grid Getaways

⚓ Labor Day

35% OFF

2 PTO days → 5 nights

PTO Pivot No. 10

The Caribbean

✦ Valiant Lady ✦ Miami ✦ 5 nights

Sep 4 – 9, 2027

💡 Depart Sat · Labor Day (Mon) = 1 free day · Only 2 PTO = 5 nights

Insider

Starting at $1,167 $795 per sailor · 2 adults

32% off · double occupancy

$159 per sailor / night · 5 nights

$1,590 cabin total · 2 adults share one cabin

Book This Sailing →

Dominican Daze — Valiant Lady — Holiday sailing curated by Off The Grid Getaways

🧭 Columbus Day

37% OFF

4 PTO days → 5 nights

PTO Pivot No. 11

Dominican Daze

✦ Valiant Lady ✦ Miami ✦ 5 nights

Oct 11 – 16, 2027

💡 Depart Mon (Columbus Day = free) · 4 PTO closes the week · 5 nights total

Insider

Starting at $1,039 $695 per sailor · 2 adults

33% off · double occupancy

$139 per sailor / night · 5 nights

$1,390 cabin total · 2 adults share one cabin

Book This Sailing →

Caribbean Getaway — Resilient Lady — Holiday sailing curated by Off The Grid Getaways

🎖️ Veterans Day

40% OFF

4 PTO days → 7 nights

PTO Pivot No. 12

Caribbean Getaway

✦ Resilient Lady ✦ Miami ✦ 7 nights

Nov 7 – 14, 2027

💡 Depart Sun · Veterans Day (Thu) = 1 free day mid-trip · 4 PTO = 7 nights

Insider

Starting at $1,309 $903 per sailor · 2 adults

31% off · double occupancy

$129 per sailor / night · 7 nights

$1,806 cabin total · 2 adults share one cabin

Book This Sailing →

Rates subject to change. Daily gratuities excluded unless noted.

VV rates sourced via First Mate booking link — refreshed on a rolling schedule. NCL rates sourced independently — not pulled live from NCL.com. Ponant rates from us.ponant.com. Celebrity rates pulled live from celebritycruises.com (Solo Infinite Veranda where available, otherwise the lowest available cabin tier). All subject to change without notice. Message Paolo to confirm availability before booking. PTO calculations based on a standard US Mon–Fri schedule. Federal holidays subject to your employer's policy. All Sailors must be 18+.

From the English Channel to the Irish Sea — L'Austral — Holiday sailing curated by Off The Grid Getaways

🇺🇸 Memorial Day

5 PTO days → 8 nights

PTO Pivot No. 01

From the English Channel to the Irish Sea

✦ L'Austral ✦ Honfleur (France) ✦ 8 nights

May 19 – 27, 2026

💡 Depart Tue · Memorial Day (05/25) = 1 free day · 5 PTO covers the rest

Deluxe Stateroom Lowest Available

Starting at $5,460 per sailor

$10,920 per cabin · 2 sailors · double occupancy

$683 per sailor / night · 8 nights

Work Smart.Sail Longer.

Be Strategic. Be a PTO Maximizer.

Work smarter.Sail longer.

Pick a holiday anchor

Bridge with PTO

Paolo books it

Your Pivot Windows.Adults-only luxury.

New York to Bermuda & Back

Caribbean Holiday Escape

New Year's Caribbean Celebration

Caribbean Escape

Mediterranean Valentine's Voyage

Caribbean Summer Escape

Fire & Sunset Soirées

Grand Cayman & Bahamas

Bahamas & Atlantic Ports

The Caribbean

Dominican Daze

Caribbean Getaway

Ponant Pivot Windows.Expedition luxury.

From the English Channel to the Irish Sea

A Celebration of Art Featuring the 61st Venice Biennale

Baffin Bay secrets

Cities and splendours of the Adriatic

From the English Channel to the Irish Sea

A Celebration of Art Featuring the 61st Venice Biennale

Ancient Wonders and Culinary Delights: Cruising Southern Italy and Sicily – with Smithsonian Journeys

NCL Pivot Windows.Inside & studio rates.

Bermuda from New York

Eastern Caribbean from Port Canaveral

Bermuda from New York

Bahamas from Port Canaveral

Bahamas from Port Canaveral

Western Caribbean from Galveston

Bahamas from Jacksonville

Bahamas from Jacksonville

Bahamas from Miami

Bahamas from Jacksonville

Western Caribbean from Galveston

Bahamas from Jacksonville

Bahamas from Port Canaveral

Bahamas from Miami

Bahamas from Miami

Bermuda from Philadelphia

Bermuda from New York

Eastern Caribbean from Miami

Western Caribbean from Port Canaveral

Bermuda from New York

Eastern Caribbean from Miami

Bahamas from Jacksonville

Bahamas from Miami

Bahamas from Miami

Tell Paoloyour dates.

Work Smart.
Sail Longer.

Work smarter.
Sail longer.

Your Pivot Windows.
Adults-only luxury.

Ponant Pivot Windows.
Expedition luxury.

NCL Pivot Windows.
Inside & studio rates.

Tell Paolo
your dates.