Special Events Tours
uNIQUE cRUISE eXPERIENCES DURING sPECIAL EVENTS IN PORTLAND
SpecIal Events Tours
Experience Portland’S Festivities – Celebrate on the Water
This month we’re featuring local wineries for our Sips & Sights Wine Tasting Cruises. We also have a really fun lineup of Halloween Events in Portland that you won’t want to miss including costume contests and disco dancing on our Tiki Nights!
There’s always something to celebrate aboard Island Style Charters! Our Portland cruises bring people together for birthdays, anniversaries, family gatherings, vacations, milestones, and those days when you simply want to make an ordinary weekend feel special.
Throughout the year, we also add limited-time cruises and special experiences inspired by Portland events, holidays, local flavors, and the seasons. From wine tasting cruises and waterfront festivals to Halloween fun and holiday lights, there’s always something new happening on the Willamette River
Sips and sights wine tasting cruises
Fall Feature: Wine tasting meets Portland cruising!
Spend a fall afternoon cruising the Willamette while discovering wines from some of our favorite local wineries listed below. Our Sips & Sights Tasting Cruises pair a relaxed two-hour cruise with featured wine tastings, beautiful Portland views and the chance to hear directly from the people behind the wines.
Each featured tasting cruise includes three wine tastings, light bites, a full glass of select wine, and more! There will be plenty of time to relax, mingle and take in the scenery as we cruise beneath Portland’s bridges and see the incredible fall foliage. Our onboard bar is also available throughout the cruise, along with a little Island Style fun along the way.
FALL 2026 SCHEDULE
October 4 | Love & Squalor
Featured wine tasting cruise
October 11 | Hip Chicks Do Wine
Featured wine tasting cruise
October 18 | Fall Colors Sunset Cruise
We’re switching things up this Sunday with a scenic fall sunset cruise! Enjoy the changing colors, Portland skyline and beautiful evening views along the Willamette. No featured wine tasting is currently scheduled for this date.
October 25 | Stoller Family Estate
Featured wine tasting cruise
Featured wineries and cruise details vary by date, so be sure to check your selected cruise for that day’s complete experience.
Come for the wine, the views, or simply a fun new way to spend a fall afternoon on the water!
Looking for fun events in portland in October
Things get a little spooky aboard Island Style Charters in October! From pirates and pumpkins to haunted happy hours, we’ve got some frightfully fun ways to celebrate Halloween on the Willamette River.
- Tiki Nights & City Lights is getting a Halloween makeover! 🎃🪩 Join us for our final October cruises featuring disco vibes, costumes, dancing, city lights and plenty of Island Style fun on the Willamette. Costumes encouraged!
- Tiki Boat Party Float BOO’s Cruises — Kick back with a fall cider in hand on one of our Tiki Boat Party Float Happy Hour Events. These typically start around 5pm or 6pm, but happy hour can happen anytime you’re on the island!
- Fall Colors Sunset Cruises — Experience Portland in its fall colors! Cruise the Willamette as changing leaves frame the river, bridges and city skyline, then watch the scenery glow as the sun sets over the water.
- Book a Private Charter — There’s still time to get your team on the water! Celebrate your crew, gather the company, or squeeze in that team outing before our cruising season wraps up in early November.
every cruise is a celebration
There’s always something to celebrate aboard Island Style Charters! Our Portland cruises bring people together for birthdays, anniversaries, family gatherings, vacations, milestones, and those days when you simply want to make an ordinary weekend feel special.
Throughout the year, we also add limited-time cruises and special experiences inspired by Portland events, holidays, local flavors, and the seasons. From wine tasting cruises and waterfront festivals to Halloween fun and holiday lights, there’s always something new happening on the Willamette River
You don’t need a holiday on the calendar to celebrate. Every week we welcome guests aboard for:
- Birthdays & Anniversaries
- Family Gatherings & Portland Vacations
- Date Nights & Nights Out with Friends
- Engagements, Promotions & Personal Milestones
- Private Parties & Group Celebrations
- Or Just Because!
What Makes our Tours Special
Our Portland river cruises and special events offer:
- Portland from the Water: See the city, bridges, skyline, and Willamette River from a whole new perspective
- Island-Style Atmosphere: Relaxed, welcoming cruises designed around having fun together
- Seasonal Experiences: Special cruises inspired by holidays, local events, wine, and Portland’s changing seasons
- Something Worth Celebrating: Come for a special occasion—or turn an ordinary day into one
- Limited Availability: Special event cruises have limited capacity, so advance reservations are recommended
Whether you’re visiting Portland or looking for something different to do in your own backyard, Island Style Charters offers a fun, laid-back way to experience the city and the Willamette River.
BookIng InformatIon
Boarding Location: South Waterfront Park
Address: 2001 S River Drive, Portland, OR 97201 (use Google, not Maps)
Important Notes:
- Special Events Tours have specific departure times noted in your booking documents
- These tours often sell out weeks in advance – early booking is strongly recommended
- Schedule and availability are updated regularly as new events are announced
Contact us at 504-754-9569 or aloha@islandstylecharters.com
