Skip to content
sail portland maine logo
  • Home
  • Charters
    • Sunset Charters
    • Crown Jewel Charters
    • Dolphin Marina Charters
    • Culinary Cruises
    • Weddings & Elopements
  • Book Trip
  • About
    • Our Boats
    • FAQs
    • Reviews
  • Blog
  • Contact Us

Author: Ian Glass

friends on private charter | maine marathon

Run, Relax, Repeat: Your Guide to the 2025 Maine Marathon Weekend

September 17, 2025 Ian Glass

The Maine Community Bank Maine Marathon, Half Marathon, and Marathon Relay is returning to Portland on Sunday, October 5, 2025,…

Continue Reading →

Posted in: Day Cruises, Local Guides
boat charters in portland maine

Why a Chartered Cruise in Casco Bay is the Best Way to See Maine’s Lighthouses

August 5, 2025 Ian Glass

There’s something timeless and awe-inspiring about Maine’s coastal lighthouses. Perched on rocky outcroppings or tucked away on windswept islands, these…

Continue Reading →

Posted in: Day Cruises, Maine Trips, Private Charters
cruising aboard calista ann | date night ideas Portland Maine

Sunset Sail & Dinner: 5 Romantic Date Night Spots in Portland, Maine

July 9, 2025 Ian Glass

Looking for unique and unforgettable date night ideas in Portland, Maine? Whether you’re celebrating an anniversary, planning a surprise proposal,…

Continue Reading →

Posted in: Local Guides, Private Charters, Sunset Cruises
portland head light | scenic Casco Bay cruises

Sail Portland Maine Named One of the “Top 10 Things to Check Off Your Maine Bucket List”

Ian Glass

We’re excited to share that Sail Portland Maine has been featured in Visit Portland’s latest blog, “Top 10 Things to…

Continue Reading →

Posted in: Maine Trips, Press Releases
dinner party private cruise | old port half marathon

Making the Most of Your Shipyard Old Port Half Marathon & 5K

May 27, 2025 Ian Glass

Crossing the finish line at the Old Port Half Marathon & 5K (coming up on Saturday, June 7, 2025) is no…

Continue Reading →

Posted in: Private Charters, Special Events
small business discount

Portland Businesses, This One’s for You: Private Charters with a Local Rate

May 6, 2025 Ian Glass

At Sail Portland Maine, we believe Portland’s small businesses deserve a break — the kind with sea breeze, harbor views,…

Continue Reading →

Posted in: Local Guides, Maine Trips, Private Charters, Special Offers
things to do in Portland Maine cruise stop

A Cruise Ship Stop You Won’t Forget: How to Elevate Your Portland, Maine Visit

April 23, 2025 Ian Glass

Portland, Maine, is a city brimming with history, charm, and breathtaking natural beauty. Known for its vibrant arts scene, award-winning…

Continue Reading →

Posted in: Day Cruises, Local Guides, Sunset Cruises
party boat portland maine

Why a Private Boat Charter is the Ultimate Bachelor or Bachelorette Party Experience

March 25, 2025 Ian Glass

If you’re planning a bachelor or bachelorette party, you’re likely looking for something beyond (or in addition to!) the traditional…

Continue Reading →

Posted in: Bachelor/Bachelorette Parties, Private Charters, Special Events
private sunset cruise Portland Maine

Set Sail for Romance: The Perfect Private Sunset Cruise in Portland, Maine

March 17, 2025 Ian Glass

Looking for a romantic way to spend an evening in Portland, Maine? A private sunset cruise on Casco Bay with…

Continue Reading →

Posted in: Private Charters, Special Events, Sunset Cruises
couple enjoying a sunny sail | things to do in Portland Maine for couples

An Unforgettable Day in Portland, Maine for Couples Arriving by Cruise Ship

July 20, 2024 Ian Glass

If you’re visiting Portland, Maine this summer as one of your cruise ship travel destinations, you’re in luck! We’ve crafted…

Continue Reading →

Posted in: Day Cruises, Local Guides, Sunset Cruises

Post navigation

Page 1 of 4
1 2 … 4 Next →

Recent Posts

  • Run, Relax, Repeat: Your Guide to the 2025 Maine Marathon Weekend
  • Why a Chartered Cruise in Casco Bay is the Best Way to See Maine’s Lighthouses
  • Sunset Sail & Dinner: 5 Romantic Date Night Spots in Portland, Maine

Recent Comments

  • Casco Bay Sunset Cruise: 5 Reasons to Book with Sail Portland Maine on 5 of the Most Romantic Spots to Get Married in Maine
  • Why Book a Private Boat Charter in Portland, Maine for Your Celebration on Maine Trips for an Instagram-Worthy Weekend
  • Events to Host on a Harbor Cruise in Portland, Maine | Sail Portland Maine on Why You Should Book a Private Casco Bay Sunset Cruise for Your Next Celebration

Contact Us

  • Email
    sailportlandmaine@gmail.com
  • Phone
    207-200-6650
  • Address
    Fore Points Marina
    1 Marina Way
    Portland, ME 04101
  • Home
  • Charters
  • Book Trip
  • About
  • Blog
  • Contact Us
Copyright © 2025 Sail Portland Maine