BOSFL Bears Cruise Hawaiian Islands

BOSFL Bears Cruise Hawaiian Islands

February 27 – March 6, 2027 |  7 Nights |  NCL Pride of America  |  From $4,233/person

Aloha, Bears! Get ready for the adventure of a lifetime as BOSFL sets sail through the breathtaking Hawaiian Islands aboard the NCL Pride of America — the only US-flagged cruise ship sailing year-round through Hawaii. With four stunning island destinations, zero sea days, and an incredible lineup of BOSFL group perks, this is your chance to experience the magic of Aloha surrounded by your Bear family.

Your Home on the Pacific

The Pride of America is a one-of-a-kind floating resort purpose-built for Hawaii. Enjoy world-class amenities including a full-service Mandara Spa, multiple pools and hot tubs, an outdoor jogging track, beach volleyball, and a wide range of dining and entertainment options — all while sailing between some of the most spectacular islands on Earth.

Pre-Cruise: Waikiki Welcome

Arrive early and soak in the spirit of Honolulu! Your BOSFL package includes a pre-cruise night at the Courtyard by Marriott Waikiki Beach (400 Royal Hawaiian Ave), with your choice of King or Queen Balcony room. On Friday, February 26, join the group for a magical evening at the Hilton Hawaiian Village for the weekly Friday Night Music & Fireworks celebration at 7:45 PM — the perfect kick-off to an unforgettable trip.

Island-by-Island Itinerary

Day 1 — Honolulu, Oahu (Departs 5:00 PM, Feb 27) 
Board the Pride of America at the Honolulu Cruise Terminal and settle into your stateroom. Explore the ship, enjoy a welcome sailaway with your BOSFL crew, and watch the Oahu skyline fade as your Pacific adventure begins.

Day 2 — Kailua-Kona, Big Island (Arrives 7:00 AM, Departs 5:00 PM, Feb 28)
Step ashore in Kailua-Kona, the sun-drenched heart of the Big Island’s west coast. Snorkel with manta rays, visit the historic Huliheʼe Palace, explore local coffee farms, or simply relax on the famous black-sand beaches. Kona’s warm, dry climate makes it a paradise for outdoor adventurers and beach lovers alike.

Day 3 — Hilo, Big Island (Arrives 7:00 AM, Departs 5:00 PM, Mar 1)
Hilo is the lush, rainforest side of the Big Island — dramatic and utterly unique. Witness the power of Hawaii Volcanoes National Park, marvel at the thundering Akaka Falls, stroll through the vibrant Hilo Farmers Market, and discover a side of Hawaii most visitors never see.

Days 4–5 — Kahului, Maui (Arrives 7:00 AM Mar 2, Departs 5:00 PM Mar 3)
With a full overnight in Maui, you have maximum time to explore the Valley Isle. Watch the sunrise from the summit of Haleakala Crater, drive the legendary Road to Hana through waterfalls and jungle scenery, windsurf at Hoʻokipa Beach, or browse the boutiques and galleries of Lahaina. Two days on Maui means you can do it all.

Days 6–7 — Nawiliwili, Kauai (Arrives 9:00 AM Mar 4, Departs 2:00 PM Mar 5)
Kauai, the Garden Isle, is Hawaii’s most dramatic and untouched island. Explore the Grand Canyon of the Pacific at Waimea Canyon, glide down the Wailua River to the mystical Fern Grotto, or take a thrilling helicopter flight over the knife-edge Na Pali Coast. Your overnight stay means you can experience Kalapaki Beach at sunset and explore local markets on the final morning. The last evening aboard features a Gala Night, Broadway-style performances, and a grand farewell celebration.

Day 8 — Return to Honolulu (Arrives 7:00 AM, Mar 6)
Savor a farewell breakfast at the Aloha Café as the Honolulu skyline comes into view. Disembark refreshed and full of memories. Your post-cruise night at the Courtyard by Marriott Waikiki Beach gives you one last chance to explore Honolulu before heading home.

What’s Included

• 7-night cruise aboard NCL Pride of America in a BA Mid-Ship Balcony stateroom
• Pre-cruise hotel night at Courtyard by Marriott Waikiki Beach (King or Queen Balcony)
• Post-cruise hotel night at Courtyard by Marriott Waikiki Beach
• Pre-cruise group event: Friday Night Music & Fireworks at Hilton Hawaiian Village (Feb 26)
• Hawaii Beverage Package for two guests
• Specialty Dining — 3 meals for two guests at NCL’s specialty restaurants
• Wi-Fi Package — 150 minutes for two guests
• Shore Excursion Credit to apply toward island adventures
• Prepaid Service Charge for two guests

Pricing & Registration

Starting from $4,233.73/person (BA Mid-Ship Balcony, double occupancy)
Deposit: $125/person to reserve your spot
Booking Deadline: October 30, 2026
Availability: Only 12 spots remaining — don’t wait!

Additional stateroom categories available including Balcony Family Suites and Penthouse with Large Balcony. Contact us for pricing on upgraded staterooms.

Trip Requirements & Details

• Difficulty Level: Easy — suitable for all fitness levels
• Departure City: Honolulu, Hawaii (HNL)
• Trip Leader: BOSFL Travel Committee
• Questions? Contact us at travel@bosfl.org

Book Your Hawaiian Escape Today

This is a bucket-list journey through four of the most spectacular islands in the world — all without unpacking more than once. With only 12 spots available at this price, now is the time to reserve your place in the Aloha spirit. Click Register Now to secure your stateroom and join your BOSFL ʻohana on the adventure of a lifetime!