Private Half Day Sailing Charter in Portland Maine
Overview
A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.
What's Included
- Snacks Light refreshments including locally inspired, chef-curated charcuterie
- Alcoholic beverages A post-swim digestif, including crisp, refreshing glass of wine or local beer, and non-alcoholic options such as sparkling waters and sodas
- Option to take the helm or brush up on your sailing skills
- Beautifully outfitted sailing yacht, coast guard certified captain + crew
- Snorkelling masks and fins and wetsuits available
- A flexible route based on conditions and your vibe
- Time to swim or relax at anchor
- Onshore stops for exploring (like Peaks Island). For onshore stops, check out full-day options.
Meeting Location
1 Cutter Street
Portland, ME 04101, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
A half-day sail is one of the easiest (and best) ways to get out on the water and experience the Maine coast from a completely different perspective. This private sailing charter is designed for a relaxed few hours—cruising through Casco Bay, taking in the views, stopping for a refreshing swim, and enjoying the best view of Maine from the deck with refreshments in hand.
Each trip is tailored to your group and the wind conditions that day, but a frequently requested, guest favorite sailing route begins in downtown Portland before heading out into Casco Bay. From there, we'll pass Portland Head Light for a close-up view from the water and weave through the classic rocky islands that make this stretch of coast so unique. When the timing feels right, we’ll drop anchor so you can swim, relax, or just soak it all in before a peaceful sail back toward the harbor.
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
Frequently Asked Questions (9)
Q: Will I get seasick on Private Half Day Sailing Charter in Portland Maine?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-5657622P1
Traveler Photos
Reviews
Average 5.00 out of 5 stars based on 1 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (9)
The answers provided below were previously given in response to questions from City Sky Diving customers.
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If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy.
Feb 2023- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (EST).
- Snacks. Light refreshments including locally inspired, chef-curated charcuterie.
- Alcoholic beverages. A post-swim digestif, including crisp, refreshing glass of wine or local beer, and non-alcoholic options such as sparkling waters and sodas.
- Option to take the helm or brush up on your sailing skills.
- Beautifully outfitted sailing yacht, coast guard certified captain + crew.
- Snorkelling masks and fins and wetsuits available.
- A flexible route based on conditions and your vibe.
- Time to swim or relax at anchor.
- Onshore stops for exploring (like Peaks Island). For onshore stops, check out full-day options.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Private Half Day Sailing Charter in Portland Maine is as follows:
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Private Half Day Sailing Charter in Portland Maine will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- SnacksLight refreshments including locally inspired, chef-curated charcuterie
- Alcoholic beveragesA post-swim digestif, including crisp, refreshing glass of wine or local beer, and non-alcoholic options such as sparkling waters and sodas
- Option to take the helm or brush up on your sailing skills
- Beautifully outfitted sailing yacht, coast guard certified captain + crew
- Snorkelling masks and fins and wetsuits available
- A flexible route based on conditions and your vibe
- Time to swim or relax at anchor
- Onshore stops for exploring (like Peaks Island). For onshore stops, check out full-day options.
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
