Alaskan Cruise

With how much our community has grown in the past 12 years, we love looking for ways to continue to gather together and socialize, bond, or celebrate. Over 600 community members and over 100 active bowlers on a regular basis, Out! Bowling has become a social force in the Chicago-area. Our bonds last a lifetime. Because of this, we’re inviting all members of the Out! Bowling community, and more broadly, the LGBTQ community we touch, to join us for an Alaskan Cruise in May 2027. See below for all the information you need to know.

If you’re interested in being part of this cruise, please call or text Casey Wooley (the travel planner and Out! Bowling Member) at 734-718-6024 or email him at caseywooley@mainstreetandmoretravel.com. Let him know which cabin type you’re interested in (see below). He’ll work details with you specifically. We are now actively taking deposits and have 6+ confirmed passengers as of August 2026 with more likely to join.

Key Highlights of the Trip

Key Details:

May 19, 2027 to May 27, 2027 (8 Nights, 9 Days)

Travel coordination and booking is being handled by Casey Wooley (league founder) and professional travel agent with Magical Memories by Casey.

We have 6 (or more) confirmed sailors and more are being added until the trip reaching capacity or begins. Here is the run-down of the itinerary:

  • 5/19: Fly into Seattle with Pre-Cruise Stay at Fairfield Inn by Marriott.
  • 5/20: Embarkation Day from Seattle, WA cruise port.
  • 5/20 to 5/26: Inside Passage (Cruising), Ketchikan, Juneau, Tracy Arm Fjord, Prince Rupert British Columbia, Sailing at Sea.
  • 5/27: Arrive back in Seattle, WA and fly back home.

Additional Information:

  • Each traveler responsible for their own flights into/out of Seattle on 5/19 & 5/27.
  • Ground transportation can be handled via RideShare to/from airport and cruise port.
  • Casey will book on the behalf of each traveler: the pre-cruise hotel stay on 5/19, the cruise accommodations 5/20 to 5/27, and optional travel insurance.
  • The Cruise is 5/20 to 5/27 aboard the Virgin Voyages Brilliant Lady.
  • Solo, double, triple, and quadruple occupancy is available depending on room type.
  • Unexpired passports are required due to a stop in British Columbia.
    • For our trans friends: currently the US government requires that new, renewed, or replacement U.S. passports must reflect a person’s biological sex assigned at birth (using only an M or an F). The X marker option has been removed. However, any existing, unexpired passports with an X or updated gender marker remain 100% valid for travel until they expire.

Expected Costs and Deposit Information:

  • Estimated Cost is based on cabin type and fare type. These prices reflect pricing as of August 2026 and may change. Pricing listed is for 2 people per cabin (total cost for the cabin, so divide by 2 to get a per traveler cost). Other options (1 and 3/4 room layouts are also available):
    • Inside Cabin (no windows, comfortable 177 SF great for 2 people who don’t want to be woken up by the Alaskan sun):
      • Base Fare $2424/cabin.
      • Essential Fare: $2520/cabin.
      • Premium Fare: $3150/cabin.
    • Sea View (Port Hole) Cabin (port hole with views of the sea, up to 220 SF for standard layouts. Great for watching the sea and the Alaskan view with your morning coffee):
      • Base Fare: $3354/cabin.
      • Essential Fare: $3500/cabin.
      • Premium Fare: $4130/cabin.
    • Sea Terrace (Balcony option ranging from 185 SF to 225 SF of indoor and outdoor space. Fantastic for lounging in the morning with that crisp Alaskan air):
      • Base Fare: $3688/Cabin.
      • Essential Fare: $3850/Cabin.
      • Premium Fare: $4480/Cabin.
    • Note: other options also available include XL Sea Terrace, and Suites known as Rockstar and Mega Rockstar Quarters if you’re interested. Solo options may be available, capacity dependent.
    • Fare Types:
      • Base Fare (Set in Stone): Low but Non-Refundable and non-changeable (no date or name changes allowed). You do get to choose your exact room number and deck location. Includes basic WIFI (1 device) and 15-day dining window. Flexible with a good value.
      • Essential Fare: A bit higher, but you get some more flexibility with cancellation. If you cancel 120+ days out, your deposit converts to a Future Voyage Credit. Allowed to make date changes, and can change the names of sailors 2 through 4 (just not the primary lead). Full control of your cabin and classic wifi and dining reservation window of 45 days
      • Premium Fare (VIP All Inclusive Option): Maximum freedom. Full cancellation and date change flexibility, and you can change any name on the booking including the primary lead. Full control of room choice. Dining reservations 60 days out and premium WIFI for up to 2 devices with streaming speeds. Built in Bar Tab credit of $15/sailor/night. If you book the Sea Terrace, you get an extra credit of $100 in sailor loot.
  • Flights: Estimated $400 to $500 roundtrip per traveler. Each traveler is responsible for making their own flight arrangements and supplying that information to Casey.
  • Pre-Cruise Hotel Stay: Estimated $300 + tax.
  • Travel Insurance: Optional, but highly recommended. This is based on when you buy it, your age, and total cost of your trip. Approximately 7 to 9% of total trip cost.
  • Deposit: 20% of cruise fare required to secure your reservation. Fare type will determine any cancellation and refund policies. Casey can go over these with you in more detail.

If you’re interested in being part of this cruise, please call or text Casey Wooley (the travel planner and Out! Bowling Member) at 734-718-6024 or email him at caseywooley@mainstreetandmoretravel.com. Let him know which cabin type you’re interested in (see above). He’ll work details with you specifically. We are now actively taking deposits and have 6+ confirmed passengers as of August 2026 with more likely to join.