New Shoreham’s coastal access frames one of southern New England’s most rewarding choices for on-water luxury: private charters, hands-on sail training, and performance rentals that turn a day trip into something cinematic.
Whether you want a fully private seven-hour charter with BYO provisions and a dedicated captain, a multi-day live-aboard ASA certification to unlock global bareboat rentals, or a high-powered center-console for fishing and watersports, the operators below represent a concentrated set of premium options reachable from New Shoreham by short transit.
This guide groups each curated experience by style—private charter, instructional course, or performance rental—so you can match craft and format to the day you want: refined relaxation, technical sailing skills, or action-packed watersports. Booking links and operator details are preserved verbatim from provider listings to make reservation quick and transparent.
The six experiences at a glance
| Experience | Format | Duration | Strongest fit |
|---|---|---|---|
| Full Day CharterPrivate 7-hour charter — BYOB, captain provided | Private full-day charter | 7 Hours | A private, relaxed day on the water for small groups up to six. |
| ASA 104: Bareboat Cruising3-day liveaboard course to certify bareboat cruising | Live-aboard sailing course | Live Aboard, 3 days 2 nights | Aspiring skippers who want a certification and multi-day, hands-on training. |
| ASA 101 - 15 HourWeekend keelboat course — beginner-friendly | Weekend sailing course | 15 Hours (3 days, partial days) | Beginners seeking a concentrated introduction to keelboat sailing. |
| 26' Boston WhalerCenter-console Outrage — best for fishing, twin 225HP | Powerboat rental (center-console) | Half Day (4 hrs) · Full Day (8 hrs) | Groups who prioritize fishing performance and open-water speed. |
| 26' XR7Spacious deck for watersports and cruising | Performance day rental | Half Day (4 hrs) · Full Day (8 hrs) | Watersports and social cruising for mid-size groups. |
| 21' BaylinerBow rider ideal for waterskiing and tubing | Bow rider day rental | Half Day (4 hrs) · Full Day (8 hrs) | Active days on the water—skiing, tubing, and quick cruising. |
01 · Best private day
Full Day Charter — a private, all-inclusive escape on the water
For travelers based in New Shoreham seeking a singular day afloat, this private Full Day Charter presents a controlled, luxurious option: the boat, fuel, and captain’s fee are included, soft drinks and ice are provided, and you’re welcome to bring your own beverages and snacks. Operator notes emphasize privacy—no outside guests are added to your booking—so the rhythm of the day is set entirely by your party.
Operational details to note: occasional fuel surcharges may apply for trips leaving local waters, and any temporary dockage or transient fees are the responsibility of the party. Gratuities for the captain and crew are customary and appreciated. With capacity for up to six passengers, this charter suits small groups or families who want a curated, low-interruption day on the water with a professional at the helm.
View the full experience details02 · Best for certification
ASA 104 Bareboat Cruising — live-aboard training that unlocks independent chartering
This three-day live-aboard ASA 104 course is structured like a compact cruise: students spend two nights aboard while practicing docking, anchoring, navigation, and systems management. The curriculum blends on-deck instruction with practical application at sea, enabling candidates to handle a 35–45-foot boat and work toward an International Proficiency Certificate. The operator frames the experience as a progression from ASA 103 and recommends preparatory study with the provided textbook.
Beyond mechanics it’s a practical immersion: mornings and evenings are used for theory while underway or at anchor, and students complete chart work, man-overboard drills, and an exam at the conclusion. The course is recommended for those 16 and older, runs with small groups to maximize instructor attention, and is ideal for travelers who want the independence to bareboat charter worldwide after certification.
View the full experience details03 · Best beginner course
ASA 101 — a concentrated 15-hour weekend to get you sailing
If your goal is to move from spectator to active sailor quickly, ASA 101 compresses basic keelboat instruction into 15 hours across a Friday–Sunday schedule. The course focuses on fundamental sail handling, safety, and maneuvering under sail, delivering a baseline certification and practical confidence for day sailing.
Pricing and student logistics are outlined by the operator, and the format is ideal for travelers who want an intensive, hands-on introduction without a prolonged commitment. After completing ASA 101 some students choose subsequent courses like ASA 103 and ASA 104 to extend skills toward bareboat competence.
View the full experience details04 · Best for fishing groups
26' Boston Whaler — a high-performance center-console for anglers
Uihlein's Marina offers a Boston Whaler Outrage configured for fishing and offshore performance: twin 225HP engines, a T-top, and a layout that accommodates large groups. Rates and duration options vary by half- or full-day, and captains are available upon request (licensed to charter groups up to six). This craft is built for anglers who want range and reliability on open water.
The operator’s rate structure separates vessel rental from fuel, and captain hire carries an hourly fee. For a luxury-minded fishing trip, the Whaler balances rugged capability with passenger comfort, making it a strong choice for a social group focused on sport fishing and offshore cruising.
View the full experience details05 · Best for watersports
26' XR7 — spacious deck and flexible layout for tubing and cruising
The XR7 is positioned as a multi-use platform: roomy deck, open social spaces, and enough power to tow tubes or support waterskiing. Uihlein's Marina offers half- and full-day rentals with the option to add a licensed captain for parties under certain group-size restrictions. Fuel is separate from the rental rate, and captains, when engaged, are charged hourly.
This boat is for groups that value on-deck comfort and flexibility—ideal for families or friends mixing relaxed cruising with activity. If you plan to include watersports in your itinerary, allow for extra time to rig gear and discuss captain support when you reserve.
View the full experience details06 · Best budget-conscious luxury
21' Bayliner — nimble bow rider for active days on the water
The Bayliner offers quick acceleration and a deep V hull that makes it a reliable option for waterskiing, wake sports, or a brisk cruise. Half- and full-day options give flexibility for shorter excursions or full-day itineraries; fuel is additional. Captains can be provided for an hourly fee, and operator notes advise confirming captain availability for smaller groups.
This craft suits travelers who want the feel of a premium day on the water without the scale and expense of larger vessels. It’s straightforward to operate with a licensed captain and delivers what many active groups seek: responsiveness and easy rigging for tow sports.
View the full experience detailsHow to choose
Match the trip to the story you want from the destination
Pick the experience that best serves the mood you want—slow and private, technically focused, or fast and social. Below, match intent to the right craft and format.
Before you go
Four practical planning checks
Several operators offer licensed captains for an hourly fee and may limit captained charters to smaller groups—verify availability when booking.
Quotes often exclude fuel and any transient or dockage fees; factor these into your daily budget to avoid surprises.
If booking ASA courses, verify prerequisites (ASA 101/103 recommended) and minimum ages—ASA 104 specifies a 16+ minimum.
Bring layered clothing, sun protection, and any personal items. Operators typically provide life jackets and basic safety equipment, but confirm inclusions.
Frequently asked questions
Planning a luxury experience
Can I bring my own food and drinks on a private charter?+
Yes. The Full Day Charter notes soft drinks and ice are provided and expressly allows BYOB and personal snacks or lunches.
What age is required for the ASA 104 course?+
ASA 104 lists a minimum age of 16; the course is a three-day live-aboard designed to develop bareboat competencies.
Are captains included with Montauk boat rentals?+
Captains are available by request for the Montauk rentals but may be limited to charters of six people or fewer and are charged hourly.
Do rental rates include fuel?+
Generally no—several operators list fuel as excluded and may apply additional fuel surcharges for extended trips.
How this guide was prepared
We compiled and edited operator-supplied descriptions, images, and booking links to present a concise, curated set of premium on-water options accessible from New Shoreham. Selections reflect a balance of private charter, instructional sailing, and high-performance rentals. Readers should consult provider pages for live availability and operator policies.
New Shoreham is a convenient launching point for premium maritime experiences: private charters for relaxed days, live-aboard courses that accelerate competence, and performance rentals for active outings. Each operator’s listing includes direct booking pages for immediate confirmation.
Use this guide to match the right craft and format to your travel story, and confirm logistics—fuel, captain fees, and dockage—directly with providers. Safe travels and smooth water ahead.