Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

South Portland, Maine Boat Rentals & Yacht Charters

Page 1 of 124 listings

Day and term sailing charters out New Bedford, Massachusetts and Cape Cod.
Sailing in Portland · 6 guests

Day and term sailing charters out New Bedford, Massachusetts and Cape Cod.

New
$850/day
Scenic Cruises & Fishing Charters out of Casco Bay
Tours in Portland · 6 guests

Scenic Cruises & Fishing Charters out of Casco Bay

5.0
$150+/hour
Cruise Casco Bay aboard the 32ft Flye Point Trawler!
Powerboats in Falmouth · 6 guests

Cruise Casco Bay aboard the 32ft Flye Point Trawler!

5.0
$155+/hour
Experience Beautiful Sebago Lake with a Pontoon Rental!
Powerboats in Standish · 8 guests

Experience Beautiful Sebago Lake with a Pontoon Rental!

New
Snoozed - Active 28 Jun 2026
19’ Classic ski boat - day cruiser 225hp
Powerboats in Maine · 8 guests

19’ Classic ski boat - day cruiser 225hp

5.0
$100/hour
Private charter offers an intimate, customizable sailing experience.
Sailing in Maine · 6 guests

Private charter offers an intimate, customizable sailing experience.

New
$80+/hour
Private Intimate Charter on 21' Eastern Center Console - Casco Bay Outing
Powerboats in Maine · 6 guests

Private Intimate Charter on 21' Eastern Center Console - Casco Bay Outing

New
$100/hour
24ft Sebago Lake Cruise with Southbay Pontoon!
Powerboats in Casco · 6 guests

24ft Sebago Lake Cruise with Southbay Pontoon!

5.0
$150+/hour
Saltwater Charter, Sightseeing and Family Mackerel Trips in Southern Maine
Fishing in Wells · 4 guests

Saltwater Charter, Sightseeing and Family Mackerel Trips in Southern Maine

New
Snoozed - Active 02 Oct 2026
Wells Harbor Fishing Charter on 25ft C-Hawk Pilot House
Fishing in Wells · 6 guests

Wells Harbor Fishing Charter on 25ft C-Hawk Pilot House

5.0
$75+/hour
Hatteras 50ft Motor Yacht for Cruise or Sightseeing in Boothbay Harbor, Maine
Events in Boothbay Harbor · 6 guests

Hatteras 50ft Motor Yacht for Cruise or Sightseeing in Boothbay Harbor, Maine

New
$350/hour
17ft Starcraft Bowrider on Moose Pond in Denmark, Maine
Powerboats in Denmark · 6 guests

17ft Starcraft Bowrider on Moose Pond in Denmark, Maine

5.0
$750/day
Discover the Damariscotta River where 80% of Maine oysters are farmed
Events in Damariscotta · 49 guests

Discover the Damariscotta River where 80% of Maine oysters are farmed

New
$600/hour
Discover the Damariscotta River with a local captain!
Powerboats in Damariscotta · 6 guests

Discover the Damariscotta River with a local captain!

New
$325/hour
Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0
$175+/hour
Enjoy beautiful Maine at Damariscotta Lake with Mariah SX19 Bowrider!
Powerboats in Nobleboro · 8 guests

Enjoy beautiful Maine at Damariscotta Lake with Mariah SX19 Bowrider!

New
$260+/day
Bennington 22' Pontoon on Merrymeeting Lake, New Hampshire
Powerboats in New Durham · 8 guests

Bennington 22' Pontoon on Merrymeeting Lake, New Hampshire

5.0
$215+/hour
Sunfish Sailboat on Merrymeeting Lake in New Hampshire
Sailing in New Durham · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

5.0
$61+/day
Fishing - Cruising - Swimming- Tubing on Silver Lake OR Conway Lake
Powerboats in Conway · 10 guests

Fishing - Cruising - Swimming- Tubing on Silver Lake OR Conway Lake

5.0
$125/hour
21' Bass Boat Charter in Nobleboro, Maine
Fishing in Nobleboro · 2 guests

21' Bass Boat Charter in Nobleboro, Maine

New
$50+/hour
22ft Massimo Pontoon Boat with 150hp outboard
Powerboats in Readfield · 10 guests

22ft Massimo Pontoon Boat with 150hp outboard

5.0
$350/day
Sweetwater Pontoon 20ft
Powerboats in Readfield · 10 guests

Sweetwater Pontoon 20ft

5.0
$280+/day
24ft Manitou Pontoon
Powerboats in Readfield · 10 guests

24ft Manitou Pontoon

5.0
$280+/day
24ft Crestliner Bass Boat Rental in Sidney, Maine
Powerboats in Sidney · 3 guests

24ft Crestliner Bass Boat Rental in Sidney, Maine

New
$81/hour

South Portland Reviews

  1. ML

    Marc

    Fishing - Cruising - Swimming- Tubing on Silver Lake OR Conway Lake

    Clay was a great host! Our bachelor party was supposed to hit Silver Lake; unfortunately the boat ramp was closed due to rain. Clay reached out and offered another location that would be available. Clay was a helpful guide, filling us in on tid bits of historical information while bringing us to different areas of the lake.

  2. NJ

    Nathan

    22ft Massimo Pontoon Boat with 150hp outboard

    The entire experience was perfect. Brett was very flexible with drop off and pick up for the boat. The communication between myself and Brett was also great as he was prompt to respond. Would definitely rent from Brett again!

  3. NK

    Nancy

    Sunfish Sailboat on Merrymeeting Lake in New Hampshire

    All round really fun, easy and pleasant experience! Fabulous day sailing!

  4. SP

    Swapnil

    Scenic Cruises & Fishing Charters out of Casco Bay

    We had a great trip out with Anthony. The boat was comfortable, clean and itinerary was ideal for the time with the trip around the islands ending with a beautiful sunset. Saw some seals along the way. We also learned interesting historical and ecological tidbits about the surrounding islands. Thanks for everything!

  5. James

    James

    Scenic Cruises & Fishing Charters out of Casco Bay

    Anthony and Alyssa were great! They told us about the history and stories behind places we saw and we’re really nice without being overbearing. They took us by the lighthouses, islands and even stopped at a bar restaurant for lunch/drinks. Would highly recommend them for any kind of boating or fishing day off Portland-wonderful people!

  6. Stephanie

    Stephanie

    24ft Sebago Lake Cruise with Southbay Pontoon!

    We had an exceptional day with Anthony! He was prompt, very quick to respond via messaging, and overall a very helpful guy. He made our day extremely easy. He was fun to interact with and very personable. The boat was extremely clean and Anthony was very prepared, anticipating all of our needs. He was knowledgeable about the area and easy to talk to. Overall a great day!