Insignia itinerary map for October 27, 2025 (16 nights)
Insignia itinerary map for October 27, 2025 (16 nights)
16 nights · 12 ports
Round-trip · Boston, Massachusetts
OceaniaInsignia

Insignia
October 27, 2025

16-Night Island Inspiration aboard Insignia · Departing October 27, 2025 from the Port of Boston, Massachusetts.

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// AT A GLANCE

This 16-night cruise aboard the Insignia departs from Boston, Massachusetts on Monday, October 27, 2025 and returns on Wednesday, Nov 12th. October weather across this route averages 85°/67°F.

The itinerary safety score for this sailing is 7.8 out of 10, averaged across 12 ports.

ITINERARY SAFETY SCORE
7.8OUT OF 10
MODERATE TIER
Safer than 78% of all cruises
Ranked across every sailing in our database.
LEAST SAFESAFEST
01
16
night cruise
Mon → Wed
02
Boston
departure port
Massachusetts
03
12
port stops
Inspiration
04
5
sea days
Day 3
// ON THIS PAGE07 SECTIONS
// 02 · CRUISE PRICE

Insignia October 27, 2025 Price & Tracking

INSIGNIA·OCTOBER 27, 2025

The graph below tracks historic price of the Insignia cruise ship departing October 27, 2025. The most recent price for this sailing starts at $3,120 ($195 per night) for an Inside Cabin. Compared to the average price of $3,555 ($223 per night), this represents a recent decrease of 12%.

Insignia cruise departing October 27, 202516-night itinerary. Current Inside Cabin price: $3,120 ($195 per night). Average price: $3,555.

// PRICE HISTORY · INSIDE
Last 6 months · refreshes daily
This cabin
Avg $3,223
LIVE RATE
INSIDE CABIN
Insignia · October 27, 2025
$3,120
$195 per night · 16 nights
3% below average
Avg $3,223 · You save $103

Prices change often and may differ at checkout. Click to see the latest available price.

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// 03 · ITINERARY

16 Night Island Inspiration (Boston To Miami) Cruise Map

Interactive Itinerary MapOCTOBER 27, 2025
The Insignia sails on October 27, 2025 for a 16 Night Island Inspiration (Boston To Miami) (Boston Roundtrip). The ship will depart the port of Boston, Massachusetts at 6:00 PM and will return to the port of Miami, Florida on Nov 12th at 7:00 AM. During the 18-day journey, the Insignia will visit 11 additional ports and will spend 5 days at sea.
// CRUISE PORT SCHEDULE
Insignia
OCTOBER 27, 2025
18 STOPSSCROLL FOR ALL ↓
Loading map...
16 NIGHTS · 11 PORTS
ROUND-TRIP · BOSTON
// 04 · PORTS

16 Night Island Inspiration (Boston To Miami) Port List

Insignia·October 27, 2025
Boston, Massachusetts — Day 1 of Insignia October 27, 2025 cruise
DAY
1
EMBARKATION
MONDAY·OCT 27

Boston

Massachusetts
ARRIVAL
DEPARTURE
6:00 PM

Boston, Massachusetts, offers docking at Black Falcon Terminal. Travelers explore Freedom Trail and Boston Common. Excursions visit Salem’s Witch Museum. Local markets sell clam chowder. The peak season, May to September, brings mild weather for city tours. Photography captures colonial landmarks and Charles River vistas. Dining onboard includes lobster rolls, a New England favorite. Souvenirs, like patriot crafts, are sold in ship shops. Briefings cover Revolutionary history. Light layers suit the temperate climate, while comfortable shoes enhance historic walks. Boston’s cultural charm offers a vibrant American stop. Cruise travelers enjoy a mix of historic trails and scenic harbors, making Boston an engaging destination for exploration.

Newport, Rhode Island — Day 2 of Insignia October 27, 2025 cruise
DAY
2
PORT 1
TUESDAY·OCT 28

Newport

Rhode Island
ARRIVAL
DEPARTURE
8:00 AM
5:00 PM

Newport, Rhode Island, offers docking at Newport Port. Travelers explore The Breakers and Cliff Walk. Excursions visit Providence’s RISD Museum. Local markets sell clam chowder. The peak season, June to September, brings mild weather for coastal tours. Photography captures Gilded Age mansions and Atlantic vistas. Dining onboard includes lobster rolls, a Rhode Island favorite. Souvenirs, like nautical crafts, are sold in ship shops. Briefings cover Narragansett history. Light layers and waterproof boots suit the temperate climate, while sturdy shoes enhance cliff walks. Newport’s historic charm offers a vibrant American stop. Cruise travelers enjoy a mix of opulent estates and scenic coasts, making Newport an engaging destination.

Hamilton, Bermuda — Day 4 of Insignia October 27, 2025 cruise
DAY
4
PORT 3
THURSDAY·OCT 30

Hamilton

Bermuda
ARRIVAL
DEPARTURE
10:00 AM

Hamilton, Bermuda, offers docking at Hamilton Port. Travelers explore Front Street and Bermuda National Gallery. Excursions include snorkeling at Tobacco Bay. Local markets sell fish chowder. The peak season, May to September, brings warm weather for coastal tours. Photography captures pastel buildings and Atlantic vistas. Dining onboard includes spiny lobster, a Bermudian favorite. Souvenirs, like cedar crafts, are sold in ship shops. Briefings cover Bermuda Triangle history. Light clothing and sun protection suit the subtropical climate, while water shoes enhance reef exploration. Hamilton’s vibrant charm offers a lively Bermudian stop. Cruise travelers enjoy a mix of historic streets and scenic beaches, making Hamilton an engaging destination for exploration.

St. George's, Bermuda — Day 5 of Insignia October 27, 2025 cruise
DAY
5
PORT 5
FRIDAY·OCT 31

St. George's

Bermuda
ARRIVAL
DEPARTURE
8:00 AM
4:00 PM

St. George’s, Bermuda, offers docking at St. George’s Port. Travelers explore Tobacco Bay and Fort St. Catherine. Excursions include snorkeling at Achilles Bay. Local markets sell fish chowder. The peak season, May to September, brings warm weather for coastal tours. Photography captures colonial streets and Atlantic vistas. Dining onboard includes spiny lobster, a Bermudian favorite. Souvenirs, like cedar crafts, are sold in ship shops. Briefings cover Bermuda Triangle history. Light clothing and sun protection suit the subtropical climate, while water shoes enhance reef exploration. St. George’s historic charm offers a vibrant Bermudian stop. Cruise travelers enjoy a mix of UNESCO landmarks and scenic beaches, making St. George’s an engaging destination.

Gustavia, St. Barthelemy — Day 8 of Insignia October 27, 2025 cruise
DAY
8
PORT 8
MONDAY·NOV 3

Gustavia

St. Barthelemy
ARRIVAL
DEPARTURE
7:00 AM
5:00 PM

Gustavia, St. Barthelemy, has docking at Gustavia Port. Travelers explore chic boutiques and Shell Beach. Excursions visit Colombier’s secluded coves. Local markets sell French pastries. The peak season, December to April, brings warm weather. Photography captures yacht-filled harbors and turquoise seas. Dining onboard includes bouillabaisse, a French Caribbean dish. Souvenirs, like coral jewelry, are sold in ship shops. Briefings cover island glamour. Light clothing and sun protection suit the tropical climate. Snorkeling gear enhances reef exploration. Gustavia’s luxurious vibe offers a stylish Caribbean stop, blending French elegance with tropical allure.

St. John's, Antigua — Day 9 of Insignia October 27, 2025 cruise
DAY
9
PORT 9
TUESDAY·NOV 4

St. John's

Antigua
ARRIVAL
DEPARTURE
6:00 AM
4:00 PM

St. John’s, Antigua, offers docking at St. John’s Port. Travelers explore Nelson’s Dockyard and Shirley Heights. Excursions include snorkeling at Cades Reef. Local markets sell fungi. The peak season, December to April, brings warm weather for coastal tours. Photography captures colonial docks and Caribbean vistas. Dining onboard includes pepperpot, an Antiguan favorite. Souvenirs, like batik crafts, are sold in ship shops. Briefings cover Carib history. Light clothing and sun protection suit the tropical climate, while water shoes enhance reef exploration. St. John’s vibrant charm offers a lively Antiguan stop. Cruise travelers enjoy a mix of historic dockyards and scenic beaches, making St. John’s an engaging destination for exploration.

Castries, St. Lucia — Day 10 of Insignia October 27, 2025 cruise
DAY
10
PORT 10
WEDNESDAY·NOV 5

Castries

St. Lucia
ARRIVAL
DEPARTURE
8:00 AM
7:00 PM

Castries, St. Lucia, offers docking at Castries Port. Travelers explore Pigeon Island and Sulphur Springs. Excursions include snorkeling at Anse Chastanet. Local markets sell green fig salad. The peak season, December to April, brings warm weather for coastal tours. Photography captures Piton peaks and Caribbean vistas. Dining onboard includes callaloo soup, a St. Lucian favorite. Souvenirs, like cocoa crafts, are sold in ship shops. Briefings cover Carib history. Light clothing and sun protection suit the tropical climate, while water shoes enhance reef exploration. Castries’ vibrant charm offers a lively St. Lucian stop. Cruise travelers enjoy a mix of volcanic landscapes and marine adventures, making Castries an engaging destination for exploration.

Bridgetown, Barbados — Day 11 of Insignia October 27, 2025 cruise
DAY
11
PORT 11
THURSDAY·NOV 6

Bridgetown

Barbados
ARRIVAL
DEPARTURE
7:00 AM
6:00 PM

Bridgetown, Barbados, offers docking at Bridgetown Port. Travelers explore Harrison’s Cave and Bathsheba Beach. Excursions include snorkeling at Carlisle Bay. Local markets sell flying fish cutters. The peak season, December to April, brings warm weather for coastal tours. Photography captures limestone caves and Caribbean vistas. Dining onboard includes cou-cou, a Bajan favorite. Souvenirs, like rum crafts, are sold in ship shops. Briefings cover Bajan history. Light clothing and sun protection suit the tropical climate, while water shoes enhance reef exploration. Bridgetown’s vibrant charm offers a lively Barbadian stop. Cruise travelers enjoy a mix of natural wonders and scenic beaches, making Bridgetown an engaging destination for exploration.

St. George's, Grenada — Day 12 of Insignia October 27, 2025 cruise
DAY
12
PORT 12
FRIDAY·NOV 7

St. George's

Grenada
ARRIVAL
DEPARTURE
6:00 AM
12:00 PM

St. George’s, Grenada, offers docking at St. George’s Port. Travelers explore Grand Anse Beach and Fort George. Excursions include snorkeling at Moliniere Sculpture Park. Local markets sell oil down. The peak season, December to April, brings warm weather for coastal tours. Photography captures spice markets and Caribbean vistas. Dining onboard includes callaloo soup, a Grenadian favorite. Souvenirs, like nutmeg crafts, are sold in ship shops. Briefings cover Carib history. Light clothing and sun protection suit the tropical climate, while water shoes enhance reef exploration. St. George’s vibrant charm offers a lively Grenadian stop. Cruise travelers enjoy a mix of scenic beaches and cultural heritage, making St. George’s an engaging destination.

Kralendijk, Bonaire — Day 13 of Insignia October 27, 2025 cruise
DAY
13
PORT 13
SATURDAY·NOV 8

Kralendijk

Bonaire
ARRIVAL
DEPARTURE
12:00 PM
9:00 PM

Kralendijk, Bonaire, offers docking at Kralendijk Port. Travelers explore Washington Slagbaai Park and Klein Bonaire. Excursions include snorkeling at Bari Reef. Local markets sell kadushi soup. The peak season, December to April, brings warm weather for coastal tours. Photography captures flamingos and Caribbean vistas. Dining onboard includes keshi yena, a Bonairean favorite. Souvenirs, like salt crafts, are sold in ship shops. Briefings cover Arawak history. Light clothing and sun protection suit the tropical climate, while water shoes enhance reef exploration. Kralendijk’s coastal allure offers a vibrant Bonairean stop. Cruise travelers enjoy a mix of marine biodiversity and scenic islands, making Kralendijk an engaging destination for exploration.

Oranjestad, Aruba — Day 14 of Insignia October 27, 2025 cruise
DAY
14
PORT 14
SUNDAY·NOV 9

Oranjestad

Aruba
ARRIVAL
DEPARTURE
6:00 AM
3:00 PM

Oranjestad, Aruba, offers docking at Oranjestad Port. Travelers explore Arikok National Park and California Lighthouse. Excursions include snorkeling at Baby Beach. Local markets sell keshi yena. The peak season, December to April, brings warm weather for coastal tours. Photography captures cacti landscapes and Caribbean vistas. Dining onboard includes funchi, an Aruban favorite. Souvenirs, like aloe crafts, are sold in ship shops. Briefings cover Arawak history. Light clothing and sun protection suit the tropical climate, while water shoes enhance reef exploration. Oranjestad’s vibrant charm offers a lively Aruban stop. Cruise travelers enjoy a mix of natural parks and scenic beaches, making Oranjestad an engaging destination for exploration.

Miami, Florida — Day 17 of Insignia October 27, 2025 cruise
DAY
17
DISEMBARKATION
WEDNESDAY·NOV 12

Miami

Florida
ARRIVAL
DEPARTURE
7:00 AM

Miami, Florida, offers docking at PortMiami. Travelers explore South Beach and Wynwood Walls. Excursions visit Everglades National Park. Local markets sell Cuban sandwiches. The peak season, December to April, brings warm weather for coastal tours. Photography captures art deco and Atlantic vistas. Dining onboard includes stone crab, a Floridian favorite. Souvenirs, like seashell crafts, are sold in ship shops. Briefings cover Seminole history. Light clothing and sun protection suit the subtropical climate, while comfortable shoes enhance city walks. Miami’s urban charm offers a vibrant American stop. Cruise travelers enjoy a mix of vibrant nightlife and scenic wetlands, making Miami an engaging destination for exploring Florida’s southern coast.

// 05 · WEATHER

16 Night Island Inspiration (Boston To Miami) Weather Forecast

Insignia·October 27, 2025
OCT FORECAST · BOSTON
Historical monthly averages for travelers visiting this port.
54°
AVG · °F
Mostly sunny days
AVG HIGH
86°
AVG LOW
22°
AVG RAINFALL
4.8"
Source: 30-year historical climate averages via Open-Meteo
// YEAR-ROUND AT BOSTON
Average monthly temperature and rainfall. Your sail month is highlighted.
AVG TEMP °FRAINFALL IN
54°JANFEBMARAPRMAYJUNJULAUGSEPOCTNOVDEC12-MONTH AVERAGE · DATA: 30-YEAR HISTORICAL
// 06 · SHORE EXCURSIONS

Insignia October 27, 2025 Excursions

Insignia·October 27, 2025

From beach breaks and snorkeling to local food tours and cultural landmarks, these shore excursions help you make the most of every stop. Browse by port below to compare top-rated options and plan your day before you board.

// BROWSE BY PORT
EMBEDDED · POWERED BY VIATOR

Browse shore excursions for each port on this Insignia itinerary. Tours, activities, and transfers are provided by Viator.

Pricing & availability provided by Viator. Book directly from listing.
See all Boston excursions
// 07 · SAFETY SCORE

Itinerary Safety Score

16 Night Island Inspiration (Boston To Miami)

Based on comprehensive research of cruise port safety information, including recent crime reports, travel advisories, Global Peace Index rankings, and specific port security concerns, we've created a "safety score" for each cruise port stop. The overall rating below represents a combined score for your specific cruise itinerary.

ITINERARY AVERAGE
MODERATE TIER
0OUT OF 100
LOWHIGH
Safer than 78% of all cruises
7.8/10 itinerary average · ranked across every sailing in our database.
LEAST SAFESAFEST
// HOW WE SCORE
Four signals, weighted by recency.

Scores combine recent crime reports, government travel advisories, Global Peace Index rankings, and port-specific security incidents. Refreshed monthly.

8.0 – 10.0
Safe — Low-risk; standard precautions apply.
6.5 – 7.9
Moderate — Generally safe with normal vigilance.
5.0 – 6.4
Caution — Stay alert; avoid certain areas after dark.
0 – 4.9
High caution — Significant risk; book guided excursions.
REFRESHED MONTHLY
// PORT-BY-PORT BREAKDOWN12 PORTS
01

Boston 🇺🇸

Massachusetts · United StatesSAFE

Boston is a safe port for cruise travelers, but standard urban caution is advised in crowded areas to avoid petty theft.

0.0/10
SAFETY SCORE
02

Newport 🇺🇸

Rhode Island · United StatesSAFE

Newport, Rhode Island, is a safe destination for cruise travelers with low crime rates, though standard precautions are recommended.

0.0/10
SAFETY SCORE
03

Hamilton 🇧🇲

Bermuda · BermudaMODERATE

Hamilton, Bermuda, is generally safe for cruise travelers, but vigilance is advised in less populated areas due to occasional petty theft.

0.0/10
SAFETY SCORE
04

St. George's 🇧🇲

Bermuda · BermudaSAFE

St. George's, Bermuda, is safe for travelers, but they should remain vigilant against rare opportunistic theft and follow local transport guidelines.

0.0/10
SAFETY SCORE
05

Gustavia 🇬🇵

St. Barthelemy · GuadeloupeSAFE

Gustavia is a safe cruise destination with a low crime rate and strong security presence, ensuring a secure experience for visitors.

0.0/10
SAFETY SCORE
06

St. John's 🌍

Antigua · AntiguaMODERATE

St. John's is generally safe for travelers, but vigilance is advised due to potential petty theft and risks in certain neighborhoods after dark.

0.0/10
SAFETY SCORE
07

Castries 🌍

St. Lucia · St LuciaMODERATE

Castries is generally safe for tourists, but visitors should stay vigilant in crowded areas to avoid petty theft and protect belongings.

0.0/10
SAFETY SCORE
08

Bridgetown 🇧🇧

Barbados · BarbadosMODERATE

Travelers should stay vigilant in busy areas of Bridgetown, as petty crime and scams can occur, and secure personal belongings.

0.0/10
SAFETY SCORE
09

St. George's 🇬🇩

Grenada · GrenadaMODERATE

St. George's, Grenada, is safe for cruise travelers, but vigilance against petty theft is advised in busy tourist areas.

0.0/10
SAFETY SCORE
10

Kralendijk 🌍

Bonaire · Netherlands AntillesMODERATE

Kralendijk is a safe cruise destination with low crime rates, but travelers should remain vigilant against petty theft and secure belongings.

0.0/10
SAFETY SCORE
11

Oranjestad 🌍

Aruba · Netherlands AntillesSAFE

Oranjestad is a safe cruise destination, but travelers should remain vigilant in crowded areas to avoid petty theft.

0.0/10
SAFETY SCORE
12

Miami 🇺🇸

Florida · United StatesMODERATE

Travelers should remain vigilant and safeguard belongings in Miami, as certain neighborhoods may have higher crime rates, especially after dark.

0.0/10
SAFETY SCORE
// 08 · CRUISE SHIP

Insignia Ship Overview

Specs & DetailsOCEANIA
Insignia
OCEANIA · REGATTA
CHRISTENED
1998
STATEROOMS
0
TONNAGE
30,300GT
28.2% BELOW AVG· vs avg 42,200 GT
YEAR BUILT
1998
5 YEARS OLDER· vs avg 2003
LENGTH
594ft
11.4% BELOW AVG· vs avg 671 ft
PASSENGER COUNT
698cruisers
20.9% BELOW AVG· vs avg 882 cruisers
// ABOUT THE SHIP

The Insignia has a construction date of 1998 and a total size of 30,300 gross tons. The ship measures 594 feet in length. Insignia is included in Oceania's Regatta class. At full capacity, the Insignia holds 698 passengers. That includes 298 cruise vacationers and 400 staff members. The Insignia total number of staterooms is 0.

// INSIDE THE FULL SHIP PAGE
Dive deeper into the
Insignia
  • Size comparison chart against other ships
  • Bars, restaurants, and venue highlights
  • Renovation and dry-dock schedule
  • FAQs about Insignia
Full Insignia Ship Info
// 09 · FAQ

Frequently Asked Questions

FAQs for yourInsignia·October 27, 2025sailing
  • Live pricing is not currently available for this sailing. Sign up for price-drop alerts above to be notified when fares appear.

    PRICING
Researched and assembled by Gangwaze Cruise Editorial using daily-refreshed itinerary, pricing, weather, and safety data.
LAST UPDATED · MAY 22, 2026